entrepreneurship

The $100M Journey: Turning Setbacks Into Triumphs With John St. Pierre

The $100M journey is a testament to the power of persistence and vision in achieving extraordinary success. Join Mark Cox as he sits down with John St. Pierre, author of The $100M Journey. John shares his inspiring journey from college student to successful entrepreneur in this insightful conversation. Discover the secrets behind his success, including valuable lessons on building and scaling businesses, overcoming setbacks, and achieving massive goals. Learn how John turned adversity into opportunity, navigated the challenges of rapid growth, and ultimately realized his $100M dream. Don't miss this inspiring story of entrepreneurial triumph!

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The $100M Journey: Turning Setbacks Into Triumphs With John St. Pierre

John, welcome to the show. It's so great to meet you.

Thanks for having me, Mark.

We got a bit of a shared history, certainly with your College Pro experience. I was so excited to speak to you, John. First of all, I loved the book The $100 Million Journey. I love the transparency of the book in terms of the successes and failures. One of the things I haven't ever seen before was that I loved it when you were referencing another book. It's not just a footnote, but you actually do a blurb on the book and a summary of the book. It is just so interesting.

The Journey Of Building And Growing A Business

I was super excited to talk to you because I’ve always seen that connection between entrepreneurs and selling, it is very important for any entrepreneurial organization, and the behaviors and the approach are very similar to the two groups of people. Maybe just for context to get things properly started, tell us a little bit maybe the short story of your journey to get you here.

Mark, I think we have a lot in common. I'm from Montreal. I played hockey growing up. My kids still play hockey. I started my entrepreneurial roots in the college painting business. There's probably a lot more that we have similar. Excited to jump into this conversation. I think, for me, the journey of an entrepreneur, and you mentioned it very well, a lot of entrepreneurs first start by learning to sell.

If you go really right back to that first job out of college, I had a really interesting twist, Mark, which was, I was a Canadian going to school in the United States Who had a student visa, but I didn't have a work visa, so I couldn't go bartend like my roommates were in the summertime. My first summer, I went back and planted trees in Northern Ontario as my summer job. I vowed I was never going to do that again.

I found this loophole, which was that you can own an LLC, a limited liability company in the United States, without being on a work visa. I was like, “That's interesting. I don't have to go on payroll. I can actually own a company.” With that, I became a franchisee for College Pro Painters as a junior in college and going back to sales. It's like, “Let us teach you how to paint and now go convince homeowners to pay you $3,000 to $5,000 per paint job and you don't even have any painters yet.”

Being thrown into the sales realm was really interesting. I can remember walking away from my first estimate and getting that first deposit check, $500 or so, and I just sold these homeowners on trusting me in painting their home and the responsibility that came with that sale and then going, “I can do this. Let me go get the next one and the next one.”

Here we are 30-some years later and taking all the learnings from those experiences, and they were plentiful, to where I am now, which is now, I'm the chairperson of a holding company. We have five small union-sized businesses the largest being a $100 million national facilities, maintenance and construction company down here in the US. We also provide services in Canada as well. Taking all that learning over that journey has just been quite the ride.

I lived that same world of the student painters. I worked for the main competitor to College Pro, which was called Student Works. I can still remember that first estimate with my general manager, when I was in front of a homeowner and starting the sales process of trying to give them an estimate on painting their home. By the way, I’ve sold a billion-dollar deal. I’ve sold large corporate deals. It is pretty difficult to extract $5,000 from a homeowner, much different than the corporate world because this is money out of their wallet.

John, you'll appreciate this. We painted interiors during my first year in the painting company. Now we're in somebody's house, we're painting their dining room, we're spilling paint on their dining room table or expensive rug. There were some difficult times, but there was some great learning there, for sure. Your journey was just incredible.

How John Helps Entrepreneurs Today

After starting multiple businesses that surpassed the $50 million in revenue point, and then eventually the $100 million in revenue point. The ups and downs of those journeys where you had ownership in some cases, not as much ownership in some cases, and had some hard lessons learned. Given what you do and how do you help entrepreneurs, John? You do a lot of this type of thing and coach a lot of entrepreneurs as well.

I think, Mark, through that story of being an entrepreneur and growing, I learned a lot about what I help entrepreneurs through my failure. Not that I had one failure, I had many failures, but my biggest failure was I cofounded a company. We grew it for over fifteen years to $55 million in global revenues. I was the CEO of the business, and we were a humming. We wanted to take the next step to grow up from $55 million to North of $100 million. We brought on $20 million of private equity funding. Seven months later, I was fired.

I was fired from the very company that I not only founded, but I poured fifteen years of heart and soul into, and everything that I had, and I had the logo tattooed on my forehead. My kids had nothing but that company's apparel. It was in the industry. I wanted to spend the rest of my life. It was devastating. I woke up in the aftermath of that and go, “Where did I go wrong? What were some of the keys introspectively that I contributed to this situation?” It's not what somebody did to me. It was what did I do? Where did I miss? It's in those learnings that I came up with seven principles of entrepreneurial success that I now work with entrepreneurs.

I actually took those principles that I had learned. I applied them to my other business that I had, and we successfully grew that from around $15 million of revenues to North of $100 million the right way. What I really work with entrepreneurs now, Mark, is how do you grow your lifestyle-size business? I call lifestyle a $5 million to $20 million business, not the startup phase.

As someone who's built a nice lifestyle business, how do you grow that to become a high performing business where you, as the owner, can build something of significance that you don't have to run every day and be there managing every day? In that journey from lifestyle to high performance, there are cliffs and pitfalls there. There are tons of opportunities for you to fail just like I did. I help entrepreneurs overcome that growth paradox or that messy middle stage of growth.

By the way, the other reason I was so excited, John, because I'm in that boat. Of course, In The Funnel is my entrepreneurial venture. We're a sales training company, and we are in that stage of lifestyle from the, as you said, the $500,000 to $4 million, $5 million we're in that stage now and so we're this lifestyle business trying to get to the next level. One of the things I found very comforting, at least for me as I was reading the book, whether it's you or Verne from Gazelle's and the Growth Institute talking about, everybody thinks that as you grow, things get easier and easier. You're sitting back and it's quite the opposite. You have to have your true North or this conscious decision that says, “I'm trying to get to the next level and here's why, but I’ve got to embrace the fact that everything's going to get harder.”

There's no doubt. Growth is painful. Growth is costly. Growth takes cash. Growth can be strenuous. I think the biggest problem I’ve found, Mark, is this concept of you want to grow so fast. We all, as entrepreneurs, want to grow so fast. We want to get our business to a certain destination so quickly that we lack the patient ambition to make the right decisions.

To really go at it in a calculated and strategic manner that can preserve your equity that you have in the business that can help your company and the team within your business grow along with you at the right pace. That's a lot of the things that I see with entrepreneurs is just that lack of patient ambition to grow their businesses the right way versus just grow it as quickly as they can. When you do that, you can run it right off the cliff like I did.

John, certainly in the world nowadays, there have been years of SaaS growth models where with the exponential returns that against revenue or multiples against revenue or EBITDA, but mostly it was against revenue and venture capital pound pushing money into those firms. It was really this growth at whatever cost model. There were two groups of people, I think, that were most affected by that.

First, the clients and the prospects. I think as we exploded sales teams in SaaS businesses trying to scale rapidly, we had massive farms of sales development reps and business development reps reaching out to clients and prospects, but they didn't know what they were doing. They hadn't received the same training you'd received with College Pro. Then the second thing that really gets impacted are those salespeople themselves because so many of them fail or they don't stay. There's a third of every professional sales organization turns over every year.

What I think people don't realize is the impact on a young person, if they start a new job, they're so proud to come out of college or university, they got that first sales job, maybe with a known brand in some capacity. Seven months later, if they're no longer working for that firm, or they were fired because it wasn't proper training, there weren't proper patient growth expectations, I think it has this major impact on a young person. That kind of failure stings. I could feel the sting of all of your ups and downs in the book as I was reading it. It's really well written, but it's so authentic and transparent.

It's very true. Back to that growth, what happens when people growth for growth’s sake or growth at all costs, what ends up happening is your business starts taking on customers you don't even want. They don't even fit your port portfolio. They start taking you in different directions. Now you start diversifying in all these different verticals your business wasn't intended to go in, and then you start consuming cash. The problem starts amplifying.

Having that focus on how you're trying to grow exactly, where you're trying to grow and being super targeted, like the riches are in the niches, like go after specifically what you do and do best speaks a little bit to that growth for growth's sake. When you growth for growth's sake, you just take everything that comes on. You say yes to everything. It never works.

The Most Important Sales Skills For Entrepreneurs

It's a quick path to burnout. Your clients aren't as happy. You're not as happy and it's a quick path to burnout. When we look at all of your experience and all of the teams that you had, you had these businesses scaling so rapidly. What are the most important sales skills for these entrepreneurs that you're working with? When you start to think about them and their businesses, what do you think are the most important sales skills for them to cultivate?

This may not be a sales skill, but I want to double down on what I just said, which is the shiny object syndrome. As an entrepreneur, you most likely were the top salesperson in your company before you hired your first salesperson. You knew how to do it. You knew how to sell the paint job, or you knew how to sell the product or the software, and then you built people around it to help you sell it going forward.

What ends up happening is you get bored and you're like, “They're selling that product now or that service, so why don't we start this new line or why don't we do these new things?” You start diversifying yourself all over the place without really getting what you have to its max capability. You start burning a lot of time, energy investment and all these different side things that don't play to the core of what your business is.

I think that focus to double down on what your company does and does well, until which point you've achieved a high performing company. Your company's making $1 million in net operating cashflow a year. That company can go on without you, and you want to start a new venture. Go for it. It gets that real core focus to not deviate from the plan.

Focus on doubling down on what your company does and does well until you’ve achieved a high-performing company.

I think to put it maybe a little bit differently as well, I remember my first sales training and they were talking about the vacuum salesperson who comes in and puts some dirt on the floor, vacuums it up and says, “Do you want to buy a vacuum?” They say, “Sure,” then they buy one. They train somebody that exact same way, and a year later, the person does not make any sales because he's trying to oversell the vacuum cleaner. How do you focus in on your core business and in the sales realm is really most important trait that I think entrepreneurs lack.

Just that ideal client profile and sticking to the knitting. I think it's almost in the nature of an entrepreneur, I think amazing entrepreneurs generally are about adding value into the universe. The challenge is they're always on the lookout for other ways that they can be helping clients and prospects. It seems so obvious. “We're going to do this and we're going to do this.”

One of the things is, it's not always sexy, but it's like exercise. Part of it is just the core discipline of showing up and doing the same thing, just staying with it and just staying focused because we're all curious and we're all intellectually challenged. Sometimes, we're always zipping all over the place. Frankly, we have that problem a lot here at In The Funnel. I think if our team was running this show and I wasn't on it they'd say, “Every once in a while, Mark comes in on a Tuesday and has this vision of something to do. Three weeks from now, it doesn't seem like such a great idea.”

That's the concept of patient ambition as well. It comes back full circle, which is to continue to go down the road. Go more aggressive, maybe down the same road, but not deviate. When I did find myself deviating as an entrepreneur, for example, we were in the sporting industry. We were running sporting events, hockey events, lacrosse events and all these different events. We're like, “We're running these events. These people need to wear jerseys. Let's make some jerseys. Let's open a manufacturing facility to make jerseys.”

The next thing you know, we're trying to sell a new product we knew nothing about and gassing millions of dollars a year to try and provide jerseys to our customers because we thought it was just a natural idea as opposed to just grow your core business, grow your core product or service. That lack of patient ambition plays into the sales component. Mark, that brings it me to other elements, which is what is the strategic plan of the business. The core strategic business plan that you're following, so when John or Mark walk in on a Tuesday and say, “We're going to paint the walls yellow,” everybody's like, “Where's that in the strategic plan?” They can hold you accountable to a plan as well.

Building A Sales Team For Entrepreneurs

In the early days, John, we had an informal advisory group, and it was a little bit helpful for that just forcing me to come up with the plan and then on a quarterly basis, go back to the plan. It just added a little discipline, but still more work to do on our side, for sure. You talked about those early-stage entrepreneurs and some of those really important sales skills and staying focused.

You aptly point out we've had the same experience with our clients. We see entrepreneurs. They are very good at selling the vision and the outcomes from the offering. At what point do you typically try and counsel your clients to actually try and build a sales team where other people can actually sell? It's quite interesting. We're in a lot of mid-size organizations. Let's call it a $25 million to $50 million SaaS organization selling into an enterprise client where the founder or 1 or 2 people are still doing the vast majority of the new client acquisition. How and when do you counsel your clients to start trying to build the sales organization? How do they actually ramp it up so other people outside the visionary can sell?

In the seven principles of entrepreneurial success I talk about in the book, principle seven is how do you move from CEO to chairperson? Your number one job as an entrepreneur CEO is to replace yourself in every single role you fulfill in that business. That is your job. Otherwise, you just bought yourself a job. You are the job. That's the key role. My answer to that question is as soon as possible. That's where I typically lean.

What I’ve learned is that a lot of entrepreneurs that initially start their business because they're the best sales rep are not necessarily the best sales manager because they look at their team go, “I could do that better. I could do this better.” They don't know how to effectively manage their sales team effectively. They have a lack of control in their minds if they give up the sales management.

There's a very interesting transition where I see a lot of entrepreneurs will want to hire their first salesperson and they'll become the sales manager, but then they suck at being a sales manager. They're too distracted. There’s not enough focus. They've never been a sales manager before. They lack in those skillsets that are the next frontier is how do you replace yourself as the sales manager to bring in a professional sales manager can manage your sales team based on KPIs and metrics and focus on the numbers and the growth of the salespeople and leadership of the salespeople and development of the salespeople accordingly?

I think it's that stairstep. How do you replace yourself as soon as possible? From a sales perspective, then you become the sales manager. How do you replace yourself as soon as possible from a sales management perspective so you can be the visionary and not necessarily the integrator of the sales processes in the business? Your vision should still be present and just be trained on, but just because you're the best sales rep doesn't make you the best sales manager. You have to replace yourself for your business to grow.

Just because you're the best sales rep doesn't make you the best sales manager, and you have to replace yourself for your business to grow.

That principle, John, is so true, not just in the entrepreneurial world. It's true in the corporate world. You ran an amateur sports business. It's true in athletics. The best person on our hockey team was not someone who was the best leader on the hockey team. The best players, Gretzky's a good example, he always said he couldn't coach. They often do it. Wayne Rooney, British soccer, we get a lot of British folks reading, your best fantastic player, but can't move into that role. Those are different roles.

I’ll go back to those painting route every once in a while. I was amazed at the amount of personal development that I experienced in a 4 or 6-month period of time going from being a university student who drank way too much for somebody 140 pounds and then suddenly getting focused in on running the business. When I look back, the general manager who worked with me for that business, I still see that person as a major coach or leader in my world. In fact, in my case, that individual still running the painting company, they're called Student Works Painting. His name is Chris Thompson. He's still out there. He was named by Deloitte as one of the top entrepreneurs in Canada.

That's fantastic.

It really is. The essence of what I thought was so interesting about coaching was that it is such a critical challenge in B2B sales. The coaching in those days was very interesting because the franchisee understood they were running their own business. They were in control. They weren't being told what to do, but they had someone coaching them on trying to make them better. Who had a vested interest in trying to make them better? Franchisee was the hero of the story.

Somehow, in B2B sales, it's changed to the point where the sales leader is now the hero of the story. In many cases, seeing the sales team is just tools for them to achieve their goal or objective. Nobody wants to be the tool. Everybody wants to be the hero of their story. Whether it's small, medium enterprise, or even a large enterprise, we're seeing the same thing across the board where this coaching or management is the X factor of B2B sales nowadays. Are you seeing that as well?

I’ll tell you what I'm seeing that brings the parallel as you were saying that and same as you. The pure coaching and mentorship that I had in my first role with College Pro led me to read more. It led me to be a sponge for how do I do this better, evaluating how I did stuff and giving me feedback so I could perform at a higher level. I think as we've gotten away from that period of time, I even look at young entrepreneurs now and they don't have the mentorship and coaching I had in that environment. They just don't. One of the things I like to look at is, are you a manager, a leader, or a mentor? I look at that spectrum.

I think what you're saying a lot too is that what you're finding is a lot of the sales management are becoming managers to try and get these people to execute the kpis that I need to hit for my goal so I can go up to my boss and say, “I'm the hero. Look what I just did,” as opposed to mentoring their team. I think that's a little bit of a Corporate America issue where when you get to the boardroom, you want to show all your wins and what you did so you can get the promotion. There's a lack of that. In the small, medium-sized business world, Mark, I don't see that as much. I don't play a lot in the corporate boardrooms, but I do know that there's a lot of problems there regarding backstabbing and, “I did this and I did this,” because they want to be seen on that front line.

Whereas in the small, medium-sized business, if you don't develop a team of intrapreneurs, I call them a team, of people that act like entrepreneurs within your business, from the salespeople to the sales management, to the ops people, to find everybody. If you don't build this culture of entrepreneurship where you're mentoring and developing them, still holding them accountable to the goals and responsibilities, and providing them leadership so they can grow, you will never get out of your business. You'll never be able to enjoy the fruits of your business because you'll just turn and churn through people as they come in and out of your business seeking mentorship and seeking a place they love to get, be developed and grow. To me, that plays to the sales group as much as any other group. As a leader, if you are not mentoring your people, you're on a dangerous path.

If you don't develop a team of entrepreneurs within your business, you will never get out of your business.

Managing Ups And Downs In The Entrepreneurial Journey

John, I’ve always seen this alignment between entrepreneurs and salespeople. At the highest level, I guess, it's just the simplicity of any day, week, or month, you've actually got to go out into the universe and make something happen to create attention and interest and then demand and close a deal to bring revenue into the business. As salespeople, they're feeling that ongoing cadence because they're worried about success and hitting their goals and keeping a job.

With entrepreneurs, they're worried about keeping the lights on. The same thing happens, but it's a very unique world where the outside world is going to define our success in some ways because we've got to get that money coming in. A lot of the other roles, frankly, are backstage for companies, whether it's finance or HR and some of these other things.

One of the topics that come up a lot on this show in professional sales is just mental health and being in the right mindset as you're traveling this journey and maybe managing those ups and downs where we're not going euphoric happy, we're not going into the valleys too much. We try and maintain an even keel. Tell me a little bit about what you see in the entrepreneurial world where that same cadence to perform is so vital. Are you noticing some challenges or opportunities there as well? How do you coach entrepreneurs on managing those ups and downs?

I believe that's my mission and probably yours as well.

In many ways it is.

Mental health is a big problem. It's a big problem. It's been amplified by COVID. It's been amplified by different things going on in the world. As an entrepreneur, and sometimes much like a sales rep, you're in business sometimes by yourself, trying to run your business. You can't necessarily bring your problems home every night to the family because that doesn't help that situation. You don't really want to bring it to your team when you're scared and something's going on.

The same thing happens to a sales rep. You may not be having a good quarter, and your sales manager's expecting this from you, so you have to try to present that face there, and you want to look good in front of your colleagues. You don't want to go home and say, “I'm going to miss my big bonuses,” or whatever the situation may be.

That pressure that just keeps accumulating, where is the valve? Where is the release valve to be able to have a conversation with a mentor, with a coach to help guide you along the right path and reinforce some of your maybe beliefs or do away with your limiting beliefs of, “I can't do this,” or whatever you're saying to yourself as you go through this path. I look at it as a transition curve as well of life. From uninformed optimism to crisis of meaning to back to informed optimism, that is the life of ups and downs. When you have the right mentorship, whether that be the leader in your organization or the entrepreneur running your business, or a coach on the side, it doesn't really matter. That coach can minimize ups and downs.

Yes, you do have successes, and yes, you don't win deal once in a while, but you know how to manage it. You know how to manage your emotions, you know how to manage your subconscious mindset and how you're talking to yourself and how you're performing each and every day. That is a major component of sales, entrepreneurship and everything. It's basically a life code in general for everybody now. Are you seeking the right guidance, whether it be books you're reading, the videos you're watching, the people you're talking to? Are you surrounding yourself with the right information to guide you in the right way?

On the side, one of my hobbies is I'm in a bar band that I jumped back into after twenty years of not doing it. I jumped back in a few years ago, and we play in Toronto with a bunch of executives and core who are on boards, and we do charity gigs for different associations. One year, we donated all the money to CAMH, which is the Center for Addiction and Mental Health. It was a real wake-up call for me. This was post-COVID, but in advance of the gigs, our lead singer who is on the board of CAMH, which share stats on mental health and issues, and it was flabbergasting. One of the things that's interesting, the way they look at it is there's this spectrum.

In the past, you might have looked at it and said, if you cross this aspect, you've got a mental health issue. There are a lot of steps along the path to that where you're just not yourself or you're just not feeling good. One of the things we've constantly coached on this program is trying to focus on those things that you can control. There are a lot of things that are outside of our control. If I am short on revenue as an entrepreneur, if I'm short on qualified deals as a salesperson, that's not going to change overnight. Over the next 2 or 3 days, I can certainly trigger some live conversations that are eventually going to lead me in the right direction. Zoning in on those things that we can control most.

Just as a reminder for our readers, just while we're on this topic, one book I picked up, which I thought was very interesting in the professional sales realm was Anthony Iannarino’s The Negativity Fast. This would be somebody who's one of the top ten thought leaders in B2B sales globally. After everything he's published and everything he is done, his second most recent book came back and said, “I'm going to talk about mindset and The Negativity Fast.”

One of the things that struck me so much was he's got research in there on the power of gratitude and the idea of actually being grateful for what you have, your family, your loved ones, your health, the wealth. Many of us look at ourselves and say, “I'm not as rich as the Joneses. My business is not as big as so and so's.” Anthony reminds us that 96% of the entire global population lives on less than $35,000 a year. I think in the past, we could take these things for granted. Now, I think you have to have an intentional plan, almost like a strategic plan, to keep yourself in the right mental and physical framework so that you can be successful.

I love that, Mark. I'm going to look up that book. I love negativity fast. I’ll tell you this failure that I had, which was a few years ago. It wasn't that long ago. It was in 2018. This is pre-COVID and pre-everything. Fifteen years of building this business, going all out. Long weeks, long years, you name it. To lose it all in a second, not a second, but a few months felt like a second. I remember sitting down after that feeling sorry for myself. The biggest thing that helped me was the power of gratitude. I looked at it a little bit differently at first. I wouldn't have called it the power of gratitude. What I called it was perspective.

I said, “I got a great wife, a great family. We're healthy. Two great boys. I have a home. I have a car. Yes, this sucks. Yes, this is going to hurt a lot of people. Yes, I could have done better, but in the grand scheme of things, there's a lot of people in life that don't have what I have right now, and I'm feeling sorry for myself. Slap yourself across the head, pick yourself back up. Figure out what you did wrong, figure out what you could have done better and get to work.” It's that perspective view of things that led me to this power of gratitude area which was, “This is really bad but not insurmountable.”

You get to the other side of it and you're like, “In the grand scheme of things, that was a blip on the radar.” I needed that to help me get to this area. You have a whole different positivity perspective on this big failure. I would've never celebrated failure before. Now I'm like, “Yeah, this is great.” I learned a lot from that opportunity experience. I don't want to fail again, don't get me wrong, but I know how to overcome that with the power of gratitude. I appreciate you sharing that. That's great.

Moving On After A Business Setback

John, how long did that take for you? I apologize. I'm sure you talked about it in the book, but how long did it take for you to let it sink in and maybe give a little bit of a mourning period to this business that you'd given your whole life to and all your energy and then say, “Okay, now I’ve got to pull up my socks here. Let's get going?”

I took a year's sabbatical from operating any business. I did have another business venture that I was partnered in and to focused a little bit on that. I took a year and said, “I'm not going to take any other role or operating job or do anything. I just really need this time to figure this out.” I was thankfully able to do that. I'd say it probably took me a good six months to be like, “Even though I'm still on this thing, I'm antsy. I'm ready to get going again.” I did take that time, like just a lot of self-reflection. What that self-reflection was like, I think it's relevant, and this applies again to salespeople and entrepreneurs, the same.

I was running so fast in building this business, and the business was growing so fast that at the end of it, when I lost it all, I asked myself, “What was I doing that for?” I’ve always been a very goal-oriented person. I had goals as an individual and goals as a business person, but they weren't aligned. My goals were short-term goals. One of the biggest things I came in that moment of perspective and gratitude is I said, “I'm going to design a 30-year life plan. What's the one thing I want to achieve in my life? What is the one thing? Thirty years from now, where do I want to be? How old am I going to be? What do I want my life to look like? That's a long time from now. Let me back backtrack. Where do I want to be in fifteen years? Where do I want to be in five years? Where do I want to be next year?” Got it. Now, I got a life plan. Now let me go do in business that will align to my life plan.

Why did I want to grow a company so fast and bring on equity and then lose my equity and then lose control of business? It was because I was chasing something. What was I chasing? It had nothing to do with my life plan. Now everything I do aligns to what I'm trying to achieve in my life, and I find a lot more symmetry. I find myself in the zone of doing things I'm passionate about, I know I can be the best in the world at, and it drives my economic engine. That is that hedgehog concept from Jim Collins, which is like, that's where you need to be. That intersection of the area. To me, if you're a salesperson, it's the same thing. Make sure you know what you're trying to achieve, and it's not just the commission check at the end of the month. What are ultimately trying to achieve in life, and then align your sales objectives to match that.

Tying back to the why, so helpful. Nice for you to bring out, by the way, the Venn diagrams I haven't seen since the finite math days at university, so it was nice to get scared by those again. Pulling those back out and saying, “Let's connect why we're doing this,” because now when I'm jumping outside my comfort zone on a regular basis, I actually understand why. By definition, it's never going to feel great jumping outside a comfort zone because you're outside your comfort zone. It's almost like the gang from Peloton are so good at coaching you on, you start to get slightly more comfortable being uncomfortable.

“I know this is not going to kill me. My heart rate's up, I'm breathing heavy, but I'm going to be okay.” I think it's such an important thing, and you talk about the true North concept in the book, but just aligning. The other thing I just love is that I forgot who you referenced in the quote in the book, but it said, “People overestimate what they can do in a year and underestimate what they can do in ten.” That quote stuck with me from your book, and I think it's just such a good thing to see sometimes that big picture is very helpful to get us through some of those challenges along the way, like having that big picture.

I love the comment on that one. That was Bill Gates that made that quote. I found it to be so true. We live in this microcosm of, “What is my goal this year? How much am I trying to earn this year? What am I trying to do this year in my building?” Whatever it may be. Mark, I started thinking about it, and with the advances in AI and technology and everything else, you're either going to have a hardware or software problem in your body, and both of them are probably going to be able to be fixed.

You start looking out on the horizon and you're like, “In 30 years from now? That seems like forever from now.” When you have a long-term view horizon, you can actually start being a little more strategic on what you're doing, how you're doing it, and you can view some of these, “I didn't get the sale yesterday,” as not that big of a deal. You're still heading in the same direction.

That real long-term perspective and view on things meant a lot. I like to ask entrepreneurs all the time, “Do you have a life plan?” End of story. The answer is, 9 out of 10 times, no. Most people do not have a life plan, and when they start thinking about it, they start thinking about the next couple of years. I go, “No. Let's start with the end in mind. What are you ultimately trying to do long-term?” It's such a visionary thing for an individual to do to look long-term what they're trying to do, and then start marching towards there in their careers.

All of these things, by the way, team, this is why John's book is so valuable, The $100 Million Journey. I should have picked this book up years ago when we started In The Funnel. That would've been very helpful at that point in time. It's been a super helpful read now. We're at that stage of trying to get out of the lifestyle business, but frankly, John and team, we've got to do more thinking about that life plan and why because it is a pretty good lifestyle business and we enjoy this.

The $100M Journey: Your Guide to Growing the Business of Your Dreams without Going off the Cliff

You start to think about, “Am I trying to get to that next level just because I want a better answer when somebody says, ‘How many employees do you have and I want an impressive answer of 75 or am I trying to get to that next stage because it does something for me, Donna, our family, everybody we love and the sales community?’”

Maintaining Focus On Helping Clients And Achieving Success

One of the things that's a joy for us now is the contribution back into professional salespeople. That's why we run this show. We're actually trying to improve the lives of professional salespeople, and if they know what to do, things get a lot easier and their lives improve. John, I'm going to be very cautious of your time, but one more question before we wrap up here a little bit. Our topic, the customer, the client, we've talked a lot about what we do for us and our businesses, and whether it's salespeople or entrepreneurs, but everything starts with that focus on helping somebody else achieve this better outcome in the future, whatever that might be. Share with us a few thoughts about, whether we're entrepreneurs or salespeople, what we do to just maintain and clarify that intense focus on helping someone else and how that plays into our success model.

I think as an entrepreneur, and it plays as we've talking about this whole conversation as sales as well, is what does success look like for you? If you're hiring somebody, what does success look like for you in coming to work here for our business? If you're talking to a customer, what does success look like for you? If you're talking to a vendor, what does success look like for you, being a supplier, and working with us? To me, that one question never gets asked. For example, if a sales manager's talking to a sales representative, “What is the one thing I can do to be a better leader or mentor to you? They never ask that question. They just say, “Where are your numbers? What's going on?”

What does success look like? To me, it is not just something you ask and you never revisit. It's you ask, you document, and you celebrate the achievement of it. To me, that builds customers for life, that builds team members for life, that builds relationships for life because at the end of the day, the core to relationships are experiences over time. The more positive those relationships are over time, the delivery of what the success looks like over and over again. That's how you build long-term sustainable customers, employees, team members of the likes. To me, that one question isn't asked enough, it's not brought up enough, it's not celebrated enough, I think that is the key to long-term customer relationships.

It's so important. A friend of ours, Dan Sullivan from Strategic Coach, has something called R Factor question he Loves, which is, and I’ll paraphrase it, but if we're going to have this conversation a year from now on November 8th, 2025, what needs to happen, John, for you to be blissfully happy, personally and professionally with where you're at? It is just such a well-thought-out question. It's all about them. Back to Dale Carnegie. You can make more friends in 2 months by being interested in somebody else than you can in 2 years by trying to get them interested in you. People haven't changed in this period of time. By the way, it's more fun, the whole, “Who wants to pitch and talk about me?” I want to learn about you. That's why something like this show is so much fun.

John, this has been amazing. Team, by the way, the book we've been discussing is The $100 Million Journey: Your Guide to Growing the Business of Your Dreams Without Going Off A Cliff. By the way, it's a gorgeous book. One of the things that I picked up a couple of books, including The ONE Thing, there's many books in here you reference I haven't read. I’ve already ordered The ONE Thing on Amazon, so thank you for that. How do people learn more about you, John? After reading this, they're going to want to engage with you. What's the best way to do that?

Yeah, I think LinkedIn. John St. Pierre on LinkedIn. You connect me there. My website is 100mjourney.com. You connect me there as well. Certainly, I would love to talk to anybody and give free consultation calls to any business owner, entrepreneur, or sales rep for that matter to help them on their journey.

Thank you, John. Thank you so much for joining. What a pleasure meeting you. Team, thank you so much for joining the show. If you like this discussion, please like and subscribe to the show because that's actually how we get great guests like John, when you like and subscribe. One other favor, we know we're not perfect at running a show, and your feedback really matters to us. Please share your constructive criticism and great ideas for the show with me, MarkCox@InTheFunnel.com. That's my personal email, team, and I check and respond to every piece of feedback we get. Let us know what to do, and we love constructive criticism. Don't pull your punches, and thank you for doing so. John, thanks again. Team, we're going to see you next time.

Important Links

About John St. Pierre

John St. Pierre is an entrepreneurial strategist, business growth advisor, and co-host of the Entrepreneurs United Podcast with over 25 years of experience in co-founding and growing successful businesses across various industries.

He’s also the author of "The $100M Journey: Your Guide To Growing The Business Of Your Dreams Without Going Off The Cliff!", a book that shares his proven strategies and insights on how to scale a business while avoiding costly pitfalls.

John’s  passion is to help ambitious entrepreneurs achieve their dreams and create lasting value. By providing guidance on protecting and growing their equity, reinvesting strategically, fostering a culture of intrapreneurship, or moving from CEO to Chairperson.

John is currently the majority owner and chairperson of Rhombus Group, a private holding company formed in 2003 comprising several small businesses.

Winning Strategies For Selling Your Way In With Kristie K. Jones

Selling Your Way IN isn't just a book; it's a roadmap to sales success. Join Kristie K. Jones, the author, and Mark Cox for an insightful conversation about her journey and her passion for empowering others to succeed in sales. With a wealth of experience working with early-stage startups, Kristie delves into the complexities of the modern sales landscape. She explores the dual nature of sales challenges—business and personal—and offers strategies for professionals to identify their ideal customer profiles and maximize their potential. Discover how to identify your unique selling style, build lasting client relationships, harness the power of mentorship, and prepare for the future of sales.

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Watch the episode here

Listen to the podcast here

Winning Strategies For Selling Your Way In With Kristie K. Jones

Kristie’s Journey

Kristie, welcome to the show. It's great to meet you.

Thanks so much for having me on. I'm excited to chat with you.

I'm super excited to chat with you. We're talking about Selling Your Way IN: The Playbook for Setting Your Income and Owning Your Life by Kristie Jones. As everybody who tunes in to the show knows, we only publish episodes with folks whose books I really like. I like this book. I'll tell you from what perspective I think it's dynamite. It's such a helpful tool for somebody who's going into sales perhaps in the earlier part of their career.

When they go into a new organization, you and I both know that the onboarding plans are not magnificent with most companies. This book is such a wonderful guide for someone to drive their own onboarding plan and shorten that time to success. We're going to get into all of that but to start, maybe you could share the short story of your professional journey through university and starting as a buyer with The Jones Store Company. Tell us a little bit about how you got to where you are.

You're right. I went to the University of Kansas. I'm a proud Jayhawk, or maybe not during football season but I can't wait for basketball season to start. That's when we fly our flag with pride. I did start in retail. I spent my first eight years out of college in a retail environment. I was working initially for the Mercantile Group, which doesn't exist anymore, out of Cincinnati. The Jones Store Company was one of their stores in the Kansas City area. We had about 7 or 8 stores in the Kansas City area.

I cut my teeth working in the stores. Ironically, as a department manager, I started by working in the commission department. I ran the cosmetics department and the shoe department. Famous-Barr, which is part of the May Group, then hired me and moved me. I relocated to St. Louis so I could work there. Since they were rebuilding two stores, I got an opportunity there to close down the old physical building and move inventory and everything into the new building.

I then got a chance to go to the buying office. I spent my last about 5 years out of those 8 in the buying offices and the downtown store. A lot of my negotiation skills came from that as well as analytical skills people. I say to people, “It sounds glamorous, but no one invited me to Paris to set fashion trends.” My boss wanted to make sure I didn't run out of pink tees in the middle of summer in size medium. It was a lot of math and a lot of analytics.

I started my sales career in retail sales and then got disenchanted. That was a big Fortune 500 company with lots of red tape and lots of ivory tower-ish type things. I grew up in an entrepreneurial small business family. When I decided to make a leap out of the Fortune 500 world, I landed in a company with twelve employees in the SaaS space.

It’s a pure startup. That's a small SaaS company.

I'm so old that we didn't call it SaaS. We called it a subscription model back then. We had a subscription model. I spent ten years there cutting my teeth. I did everything but code. If the server needed rebooting,  I knew how to reboot the server. Initially, when I first got to the company, the server was down the hall in a closet on the third floor, which is horrifying to those in cybersecurity. It wasn't even locked. If you needed Post-its, that was me. If the copier was jammed, that was me. If you needed to help close a deal, that was also me. In a company that is that size, you wear a lot of hats.

It was an amazing opportunity. I worked directly for the owner for those ten years. About 2  or 2 and a half years in, I had full revenue responsibility, so net new sales and business development team. By 2003,  we had a BDR team. We were early adopters of that. We also had a customer success team, which when I first got there, we called account management. I've dabbled a little bit in everything.

From there, I loved the SaaS tech world. I fell in love with that, so I stayed in that swim lane, as I call it, and worked for some bigger companies. At some point, after leaving that company, after ten years, I landed at a VC-backed company, and then I got the VC-backed bug. I wanted to work with B2B SaaS companies that were VC-backed on top of everything else. I stayed in that world for a while until 2016 when I got restructured out of a SaaS company that was VC-backed to series E. I had gone from a lot of Series-A type companies or seed companies to the big dog.

In the midst of looking for my next VP of sales role, the universe conspired to take me in a different direction. One of my Kristieisms is when the universe speaks, you should listen. The universe was speaking very strongly to me. I had always wanted to dip my toe into the consulting role, but I still had a child in school and not off to college yet. I always had intended to do that after the fact, but it was very clear that that was not supposed to happen in my timeline. It was supposed to happen in the universe's timeline. The rest is history. I had been doing the right thing by people all along. I'm a giver. I say I've got 30 minutes for everyone.

Selling Your Way IN: When the universe speaks, you should listen.

I thought that was really interesting. I liked that idea in the book of saying whenever somebody reaches out, you make sure you offer them 30 minutes. Given the turnover and transition in professional B2B sales, I'm sure your calendar's packed with those kinds of meetings.

I'm getting a lot of those types of calls. Not long ago, an SVP at the organization that I was reorg-ed out of reached out and is looking for a new opportunity. An SDR leader that I placed a few months ago also reached out. In that case, that was a different situation, which is something that we are dealing with. The organization decided everybody was going to be back in the office five days a week and he was hybrid. Since they were hybrid, he had moved 2 hours outside of the city and was making that commute 2 days a week but wasn't willing to make it 5. I got two of those calls.

I spent a lot of my time helping those companies that are in that early series A B2B SaaS world, even transitioning from founder-led selling into hiring their first sales rep and putting all the sales processes together. I spend my days mostly working with companies that are $0 to $5 million in revenue and need to proselytize and document those types of things.\

Role As A Buyer

That’s fantastic. Thanks for the share. Tell me a little bit about your role as a buyer. Outside of the negotiations, how did that help you have a little bit more empathy for what buyers are going through? Also, tell us about what they see when salespeople are coming in to visit them.

I spent one week almost every month in New York negotiating, trying to negotiate my best deal and trying to make sure I've got the assortment that I need. I don't ever believe that negotiation has to be 50/50 but it does have to be win-win. There has to be something in it for everyone. I was bonused on margin, so gross margin was really important to me. Now, I live in a world where people are like, “What’s profit?” That was important. Each $0.5 mattered. It could be because the quantities of material or clothing that you were buying, all of that made a difference.

There's a great example of something where if you really understood that buyer and how they were compensated what's important to them personally and then professionally for the organization, you start to align to figure out how you can best help them. It may not be top line fee for the actual service, but if they understood you, your business, your world, and what was most important to you, they might be able to, at the negotiation table rather than trying to split a pie, make the pie a bit bigger for everybody.

When I'm talking to clients and taking them through as I'm building out sales processes, I make it very clear that there are two types of problems. There's the business problem and the financial impact that's having on the business, and then from the economic buyer or the influencer standpoint, there's a personal problem and the impact that that's having on them personally, their career, and their day-to-day life. I'm always telling my teams to look at both problems. You said that based on my background, I was trying to do the best thing for the company, but I also had a personal stake in that game very much.

That's the one that we get tied to emotionally so much. We had Alice Heiman on the show. Thank you, Miller Heiman, for one of those core models that has really stood the test of time. I know you've got a lot of respect for a lot of other sales process books out there. Miller Heiman, to me, is something that's so universal because there are still multiple people who influence a sale. You have to get a consensus. They have personal and professional needs and wants. It's universal.

You dropped Alice's name. Alice and Liz Heiman are part of a networking group that I belong to that's a fairly exclusive group of female sales consultants called Women Sales Experts. Trish was a member, but Jill Konrath started it. Trish was an early member. Lori Richardson was running it. I've been spending a lot of time over the last few years with Alice and Liz. They are products of the Miller Heiman School of Business.

It's a great gang. 6 or 7 of that group have been on the show. Lori has been on the show. Lisa Manuson has been on the show. Without looking at the list, we're at 100 episodes. They were magnificent conversations. They’re all thought leaders. One of the things I love, and you speak a lot about this in the book, and what I'm jealous of is it's such a great peer group and support group it is for all of you. In the early days a couple of years ago, when I used to do an episode with one of them, they would then send me an email saying, “You should put these three people on your show.” That's how I ended up getting all these great people. It's such a good peer group because they look out for each other.

You know from reading the book that one of my other mottos is, “Your circle matters.” Without having this circle, I don't think my business would be where it is. I've never been a part of any kind of group, female or not, that has been so transparent about what they charge, how they decide to charge, sharing contracts, and sharing pitfalls.

Your circle matters.

One of the first conferences I attended of the Women Sales Pros was in Minneapolis where two of the presenters were talking about how their business was on the brink of failure. It was very vulnerable. People were passing tissues around. I'm like, “I did not think I was coming to a conference where I was going to need a tissue.”

The fact of the matter is that a lot of times, men don't talk about failures in a very open and transparent way. The people who were brave enough to share that year about the things that had gone on in their personal and professional lives that caused them to be on the brink of failure were doing it so that we wouldn't end up in the same place. It was so the rest of us in the room wouldn't end up in the same place. It was from a place of giving.

Developing A Personal Plan

Your book's very giving. Let's talk about some of the positivity you're putting into the universe with the book. The book is structured into three great sections. The first one is so unique that we don't see a lot of it. We're going to talk a lot about it. Section one is developing your personal plan for becoming a rockstar professional. I love the term rockstar for a couple of reasons we'll get to in a second. According to Harvard, if you graduate college or university, you've got a 50% chance of being in a professional sales job at some point in time in your career.

That doesn't surprise me.

Everybody's going to be in a professional sales job from this point forward. You talk a lot about, “Take a look inside first. Who were you? let's understand who you are.” What drove that for you, and what guidance can you give to folks when they're trying to do that assessment of who they really are?

I see so many sales professionals who are not in the right sales role. They're not in the right sales role selling the right product or service into the right industry at a mid-market versus SMB versus enterprise and working for the right company or even the right sales leader. The better you know yourself, things like, “What comes naturally to me? Where are my superpowers?” as well as things like, “How do I like to be rewarded?” come to you. What I think people don't understand is the breadth of sales roles that are out there. As you know because you read the book, I grew up in a family where we owned a real estate company.

You were kitchen table entrepreneurs.

My mother was 100% commissioned. My dad only took a salary when he didn't have to give it up to make payroll for the rest of his employees. It was everything from a 100% commission sales rep to a 100% base salary person and everything in between. What's your risk profile? How do you like to be rewarded? How do you like to be managed?

If you've been in sales, this book is not only for newbies but people who are maybe not in the top 10% yet and can't figure out why. Do you need a quicker sales cycle? Are you struggling to keep the sales cycle alive, if you will, over 6 to 9 months? Are you an instant gratification person? Do you have patience for, “I like the game. I like playing the game and all the things it would take to play the game over six months,” let's say?

You mentioned you downloaded the workbook. There's a lot of opportunity in the workbook to answer those questions and put them in writing. You won't figure it all out, but there's a lot of it you already know but you haven't gone to a quiet spot to think these things over. When you do, then you'll be able to say, okay, “I'm an instant gratification person. I need a sales cycle that's no more than 60 days. My risk profile is at about 70/30. I need a little bit more base salary and a little less variable,” or vice versa. Maybe you’re like, “I want unlimited potential. I would take a 30% base salary and a 70% variable commission plan.”

Once you start to figure those things out about yourself, then all of a sudden, your sales world narrows. I've got a passion for whatever reason. I have a passion for healthcare. For personal reasons or other reasons, I really do well with healthcare professionals, or I do well with HR professionals, or I don't mind dealing with those finance folks. That CFO doesn't scare me. When you start to figure that out, then the sales world isn't this big. I want you to find your swim lane because that's where you have the best chance of getting to the top 10%.

Once you start to figure those things out about yourself, then all of a sudden, your sales world narrows.

It's such great advice. This is where the book really resonates. It's right at the beginning but it stuck with me. Far too often we're, we're all driven by this outcome. You’re like, “I want the job. I want to say that I worked for Salesforce. I want to say I did this. I want to say this,” and then you take a step back and go, “Let me think about me. What do I like doing?”

The other thing I think is a really good thought for folks is you may jump into an organization and realize you are in the wrong spot. That's okay. It's not failure. It's saying, “What's right for me?” Sometimes, you have to try a few things, get out there, and figure out what's right for you and what's wrong for you. People always say, “Do what you love.” What I love doing is playing drums and hockey. I wasn't good enough at either of them to be paid a lot for either. I happen to really love doing this, but this is something I love that people will pay for. It's okay to try some different things.

You snuck in, in my view, what’s almost the most important part there. You said, “What kind of leader do I work well with?” No matter who you are in sales, the X factor of professional sales is your leader. There is a lack of great sales management out there in the world. For lots of good and logical reasons, venture capital is the cause of some of them.

I don't disagree with you.

Principles And Practice

I like that takeaway, thinking about yourself and playing to your strengths. Get into your swim lane and know what's right for you. We then get into two principles and practices of a rockstar sales process. One of the things that is an indisputable truth in B2B sales is to start with the ICP. Know who you're selling to. You spent a lot of time talking about this. Why was that the first thing you jumped into in terms of the sales process? Why is that so important for anybody out there tuning in to this show? 

It's probably a product of my working with startups who, a lot of times when I get there, don't have a defined ICP. I talked to a client who said, “We want to talk to companies who are in growth mode.” I said, “You only have two AEs. I hate to be the bearer of bad news, but you have a human resource issue. You don't have enough humans to decide that that's your ICP.”

They have a very specific industry, so that helps. I said, “First off, ZoomInfo doesn't tell you that. Apollo doesn't tell you that. Databases don't tell you that. They don't have a checkbox for, “Are they in growth mode or are they not in growth mode?” We can't even go in and filter on that, so that makes that a bad ICP characteristic, if you will.” It's not even a firmographic. It's a subjective item.

A part of it is the product that I work in that $0 to $5 million world where we're still trying to identify that. I told them, “You can't boil the ocean with 2 humans and even 20 humans. Even if you had twenty account executives on your sales team, you wouldn't be able to boil the ocean. What do you really want to be known for? What do you  want to own?” I use my personal example all the time. You may have had Brynne Tillman on the show.

We have.

Good because I was like, “If not, add her to the list.”

We talked to Brynne.

I had Brynne help me revitalize my LinkedIn profile. At the time, there were X number of characters that I could use to describe what I do. I gave her my punchline and she said, “Too broad.” I said, “Okay.” I did it again and she was like, “Too broad.” We did that a lot of times, so I got irritated and was like, “What do you think I should say?” She goes, “You work with companies and startup founders at $0 to $5 million who don't have any formal or documented processes or maybe don't have more than one or two salespeople. What you do is very specific.” It sounded terrifying.

You feel like you're cutting off the rest of the market.

That's right. I'm like, “I'm a sales trainer, a sales coach, and a process expert.” She goes, “So what? Do you know how many sales trainers are out there? Do you really want to compete with all those people?” I'm like, “No, I don't think so.” She said, “You don't have to because most of us don't want to deal with VC-backed early-stage startups between $0 and $5 million. If you say that, it will narrow your world.” It was the scariest thing I did and the best thing I did. I credit her for pushing me in that direction because my elevator pitch is very short. People go, “That's really specific.” I'm the first person people think of when they need something that fits that specific swim lane that I live in.

We love Brynne. For folks reading, you can go back to an episode of the show. Brynne Tillman is an expert on leveraging LinkedIn for sales. She's got really practical advice for doing so, like this. Frankly, the advice she gave you is business strategy. It's not a LinkedIn suggestion. It's a core business strategy. Although our ideal client profile is larger than yours, they still have these issues where you have folks selling into a market, and they may have lots of clients but they haven't been quite specific about their ideal client profile and the one they want to replicate. You get into the Pareto principle with them.

You’re like, “Who are our best clients? Why do we want to replicate them?” The more specific you get about your ICP, the more the ICP values what you bring to the table. The unique value to your market, they'll realize it because they're your ideal client profile and they'll pay for it. You get away from negotiation, price-getting, and all those kinds of things.

I really like you sharing your focus with the business. A lot of us can refine that. When we start to think about our sales plans for Q1 of 2025 based on when you're tuning in to this episode, sometimes, we need to recalibrate those things and take a look at what's working and what isn't. It’s like, “Which clients are trying to negotiate us into the ground or think we're a commodity?” If somebody views you as a commodity, they're the wrong ICP. They're not seeing the unique competitive differentiation or value you bring to the table. One of Kristie’s is the fact that all she does is work with VC-backed startups, so she understands that world so well.

Even to take it a step further, your company that you work for may have an ICP, but you probably have a personal ICP. A lot of the clients I work for are like, “We're industry agnostic. We have software that can help accounting teams.” That's industry agnostic. You personally might not be industry agnostic. You may do better with manufacturing. You may do better with software companies. You may do better with how healthcare. You may do better with a logistics company.

That's what that whole second section of the book is. It is customizing and tailoring what the company ought to be providing you. If you came out of section one, which is understanding what your superpowers are, how you like to be rewarded, and what you do better than other people, then you may say to your sales leader, “Instead of going after these 70 industries, I'd like to go after these 7 because I understand those.”

Even within personas, in most companies, there are 3 to 5 personas that you can sell into everything from the economic buyer to the champion or influencer. It’s the same thing. You’re like, “The IT team may need to be involved from a security standpoint or this and that. I don't do so well with them so I'm going to start with a different department. I may get a partner and bring in a solution consultant or a sales engineer to help me with that other side.”

You and I know that not always do we walk into a situation in a company where everything is baked out, if you will. Some things are half-baked or some things are frozen. If there is any baking going on at all, even if it's half-baked, you should really be thinking to yourself, “Even if I'm being put into a territory, within that territory, what industry, what personas, or what size companies?” If you understand that, you're going to be able to play to your strengths.

The guy next to you or the girl next to you, let them go after the industries you don't care about or the personas that aren't doing so well. Let them go hunt big game. I always say to people, “Enterprise sounds sexy but it's hard. There aren't that many of them. The majority of the world lives in the SMB and mid-market space. Go get mid-market. It’s a faster sales cycle. It’s easier to make decisions. There are fewer pieces of red tape. Legal doesn't get involved all the time.” You have to think through all of those things. Even when you've chosen a company that says, “This is our ICP and these are our personas,” you have to be saying to yourself, “Where within that can I really  shine and win?”

That’s great advice. One of the things that's nice about that is if you go after consistent ICP, they value the competitive differentiation you bring to the table. You learn. In every sell cycle you're involved in, you're not learning everything in the universe. Let's pick an example. You sell into industrial manufacturing. You're understanding the trends, the issues, the challenges, the obstacles, what they face, and all those kinds of things.

What I found really interesting when you were sharing your thoughts on knowing your industry is you had a great stat. The Training Industry Inc. and ValueSelling Associates conducted a study to determine how B2B sales interactions are perceived by buyers. They found that 75% of buyers say that sales reps don't demonstrate knowledge of their industry structure and only 37% of sales reps provide unique industry insights. 

In onboarding new clients, I'm part of that. A lot of times, I do what I call hiring help. I'm helping companies hire their first few sales reps, and then I stick around as part of that package to help do some onboarding. I train them on four things, which are industry, product, sales process, and sales tools. The very first thing I do, and I can spend up to a week doing this, is industry. Not only do you understand the industry, but where your place in the ecosystem is as a company. The company that you're working for, where do you land in the ecosystem of that? Manufacturing is a big industry. Where within that specifically does your company play best?

I couldn't agree more. When you think of the life of a salesperson, one of the things you want to be doing in any sales interaction is adding value to that conversation in some capacity. You want to be making some form of deposit before you ask for a withdrawal. Frequently, the folks who win sell cycles are the ones where the buyer felt like they understood the buyer's world better than somebody else. If you do understand that buyer's world better than somebody else, then you can figure out how to take them to a better place in the future, but you have to understand it.

One of the opportunities for everybody tuning in is in that next call, whether it is an existing client, an SDR reach-out call, or a mid-cycle call to continue a discovery, do we have value, insight, and knowledge that is of some value to the recipient on the other end? A lot of times, we underestimate how much our organization knows about our client base. We're not leveraging everything in our four walls to pull the information from client success, the product team, the CEO, the executive team, or even our VP of finance to say, “What do we all know about the people we're selling into so that we can better arm our sales organizations to have intelligent conversations that provide value and insight?”

Agreed. There's a wealth of information out there. I'm always surprised when I ask candidates as I'm interviewing them, “Did you join your local association?” The answer is no most of the time. I'm like, “If you want to really understand your industry and become an industry expert, it probably costs you a minimal amount of money to join your fill-in-the-blank. There are associations for everything. If you're selling to morticians, The National Mortician Association exists as well. There are associations out there. You should be attending your local association. Meaning, the regional or national if your company will let you go. Those things are invaluable. They’re not that expensive. It’s probably an hour or two a month.

Hiring For Professional Sales Jobs

That’s great advice. You snuck in there when you're helping organizations hire and then you help them onboard. Onboarding is a pet peeve of ours. I experienced a wonderful onboarding plan a long time ago. I had a beautiful head of hair like yours in those days. Those days are gone when organizations would onboard you for 90 days in a different country in a sales education center that was built for onboarding. Those days are over. I really like everything in the book that's talking about how we do that. Let's talk about hiring for a second. What are the attributes that you look for when you're interviewing somebody for a professional sales job? 

Success begets success. First and foremost, I want somebody who has been successful in a prior role, or even coming out of college who's been an athlete,  or who's been a leader at some sort of club or something at school. There's a physiological reaction to winning. If you felt it before, you know what it feels like and you want to feel it again. I want people who are ambitious. I want people who are independent. I'm going to provide them some structure, but I always say, “Please don't check your brain at the door when you walk through it every day.”

There's a physiological reaction to winning. If you felt it before, you know what it feels like, and you want to feel it again.

This is a high-rejection sport, so I need people who are gritty and resilient. I need people who are going to be able to get up every day and hear the noes and then keep on going. I also want people who are enterprising but also innovative. In the world I live in, the founder is probably a tech founder and he probably has sold very little. It is what he needed to do to get past the founder-led selling stage. I want to make sure that people are coming with some sort of personal process.

I do spend a lot of time talking to people about, “Tell me about the current process,” and then I ask them, “How have you customized that? What's your personal sales process? Which part of that sales cycle is your strength and that you're playing to? How has that made a difference in your close rate?” and those types of things.

I also spend a lot of time looking for the intangibles, so to speak. The top ten percenters are doing things outside of work to better themselves personally and professionally that the other 90% are confused by and aren't doing. When I ask a specific question, like, “What three things do you do consistently regardless of the company you're in or the sales role that you're currently in that you truly believe, “If I do these things, I can be successful?” the top ten percenters and people who know themselves will say, “I'm at the gym every morning by 6:00. I have a tight circle of friends and we get together quarterly to support each other.

I listen to a business podcast instead of watching The Bachelor. I read a business book. I'm putting the right things in my body. I gave up drinking a few years ago because it wasn't serving me. I have a spiritual or religious practice.” Those are the tipping points. When I hear that right away, I know I'm dealing with a different type of candidate. There’s their prior success, skill, and whether they can sell what we want them to sell, but in general, those people will figure it out. They have the discipline. 

That's the other thing that we haven't talked about yet. In order to stay within your ICP, in order to be a top ten percenter, or in order to do all those things and be top talent, it requires an extreme amount of discipline because there's always a Happy Hour to go to instead of going home to family or going to the gym. There's always something that can keep you from doing the right things. People with discipline know, “I need to do these things.”

I'm an eight-hour sleep girl. My friends, if we go out, I say to them, “At some point, I'm going to turn into a pumpkin.” I'm going to disappear on them. I'm going to Uber myself home because I don't need to be out until 1:00 or 2:00. That's not how I live my life anymore. I love going to happy hour, I love going out with my friends, and I love a good cocktail, but I also know that if I don't get eight hours of sleep, I'm going to be not the best version of myself the next day. 

Going back to the core question, I love this idea of trying to smoke out discipline and growth orientation. Many of those things that you called out, like, “What are you reading? Do you go to the gym? What's your system? What podcast do you listen to?” and all those types of things are a combination of discipline and this growth orientation. It’s like, “I know enough to become a learn-it-all instead of a know-it-all.”

It’s lifelong learning. You can't teach that. That’s an innate desire.

Carol Dweck has a great book called Mindset. She talks about the difference between a growth mindset and a fixed mindset and the impact on your own mental health, frankly. You have this fixed mindset and you don't think you can get better than any time you fail. It's like a Scarlet Letter. It crushes you. If you have this growth mindset, you go, “I lost that hockey game. I let in a couple of bad goals. Let's watch the film. Let's try and get a little bit better. I'm going to be a bit careful. I'm going to make sure I don't move before the shot next time. I'll respond instead of anticipating.”

I call it victim syndrome. We don't want to hire people who have victim syndrome. They’re like, “My territory sucks. My manager sucks. My SDR sucks. Marketing sucks.” You can identify those people right away. We can eliminate those pretty quickly.

It’s accountability. When we hire, we like intelligence, drive, and humility, and then we like passion and optimism.

I like all of those.

I'm certainly no rocket scientist. You don't have to be on the top end of the spectrum in terms of intelligence to be good at sales, but you do have to be clever, quick, intellectually curious, and all of those kinds of things.

I'm hiring for a company. The sales manager taught me a new term, which I love and wish I had known before the book came out. I would give him full credit. He calls it situational fluency. That is one of the traits he's looking for. I'll call him out. His name is Guy Caldwell, a Sales Manager at BizLibrary. I'm helping them do a bunch of hiring. He says, “I'm looking for situational fluency.” I'm like, “Wow.”

It almost feels like that's this combination of curiosity and emotional intelligence to be able to read the room and read the situation. I like that term. That one will take off.

I know. That's a good one.

The Concept Of Mindset

One thing I really like is section three of your book, Selling Your Way IN. We're talking about bringing it all together and creating abundance. There was this theme about a mindset throughout the course of the book. You shared putting positivity in the world by taking a 30-minute meeting with people. Most of the time in professional sales, those 30-minute meetings come when somebody's in between jobs.

1 in 3 people churn jobs every year. Most people in sales last about eighteen months in their current roles, even CROs. That 30-minute meeting with someone like you who's got a network is a lifeline to someone. Even if it doesn't turn into anything, the fact you took the meeting is such a great thing. Tell us a little bit more about section three and this idea of abundance versus scarcity and this concept of mindset. 

That mental side of sales has played into my career and my success. That's what separates the 10% from the other 90%. This is what I call once you've gotten there, this is the get-back. This is a 30-minutes-for-everyone type of situation. I do it in a lot of different ways. I'm also a Junior Achievement instructor. I like to go to schools. I want young girls to see me as a role model. I want them to know that they can own their own business as a woman.  One of the things I love about Junior Achievement is it has a financial component to every single grade lesson. Most people in the country and other countries don't have financial literacy, financial acumen, or business acumen. I really like that part about it.

I've had plenty of these people in my life. Mike Weinberg wrote the foreword to my book. He has always been one of those generous people who makes sure that he takes 30 minutes for everybody. When we got ready to do the book launch, he was in constant contact with me. He was calling me all the time and was like, “What are we doing? When are we dropping this? Here's what I'm going to send out to my people.”

The universe takes care of you. I'm not just doing it because of what I’m going to get back. I say this in the book. Since I was raised in an entrepreneurial family in the way that I was, and I call it getting my MBA at the kitchen table, I feel like I have a responsibility to help share things that I learned along the way that other people's parents couldn't, wouldn't, or didn't know how to teach them and environments that they grew up in. A lot of my friends get frustrated sometimes with things. They're like, “We didn't grow up like you.” I'm like, “You're right.”

My dad had very strong financial foundations. When I got my first job with The Jones Store Company, he said, “How soon before you can contribute to 401(k)?” I was like, “I don't know.” It turned out to be three months. He said, “From the very second that you can contribute, contribute the max that they match. The goal is 10%. If you do that right away, you'll never miss it. It's gone. Every time you get a raise, add another percentage until you get to the maximum.” I'm at the age where I can do some catch-up because there were a couple of years where I didn't always max out. Since I've owned my business, I have a personal 401(k) and I max it out every year at the government's maximum.

People aren't taught even those basic things. When I get into companies where stock options have been presented, I sit new employees down and say, “Do you even know what this means?” People go, “Does it come with stock options?” I'm like, “It sure does.” I then sit down in my office, close the door so we're private, and go, “Do you even know what a stock option is?” They're like, “Yeah. You gave me a piece of the company.” I'm like, “It could also be that you have to buy it.”

You mentioned the eighteen-month abortion. It’s where people like, “We're out of here. Abort. In eighteen months, we're gone.” People don't understand that they have to purchase those. In a lot of companies you're at, you don't want to leave without having done so. I always say to reps, “When you get a really good commission check, you should put some of that toward your stock options.”

I truly believe that I have a responsibility because I was raised in a way that other people weren't raised. If I can help people better themselves financially, whether that's because I've got some sales advice for them or I have good kitchen table advice that I learned while listening to my parents talk business every night, that's part of my give-back as well.

That’s great and indisputable. I'd be one of those people that did not have good financial. I had good book smarts financial acumen up until my mid-twenties. I had some good things happen very early in my career but that money went up in flames. That money went to bars and good times. It's all gone.

Your entertainment budget was high.

It was pretty high back in those days. I can't believe it, but it looks like we're running down on time. First of all, I want to say thank you so much for joining the show. One of the real pleasures of running this podcast is I get to read a whole bunch of amazing books by sales leaders, thought leaders, and all that good stuff and then meet the people. It has been a real pleasure meeting you. I enjoyed very much reading Selling Your Way IN: The Playbook for Setting Your Income and Owning Your Life. How do the folks who are tuning in learn more about you or engage you?

If you want to know more about the book, you can go to SellingYourWayIn.com. It will take you to a section of my website, so then you'll also be on the website if you'd like to learn more about the services I offer. What I'd really love for your audience to do is connect with me on LinkedIn, drop me a note, and let me know about their one takeaway from our conversation.

That’s an amazing ask. Thank you. We have to do that moving forward. That's a great idea. Thank you again for joining the show. Team, thank you for tuning in to the show. We do this show because we're trying to improve the performance and professionalism of B2B sales teams. Since we believe in doing that, we improve the lives of anybody associated with professional sales. Thanks for tuning in.

If you enjoyed this episode, please like and subscribe to the show and tell your friends because that's how we get great guests like Kristie. Also, we're growth-oriented. We know we're not perfect at doing this and we know your feedback is awesome for improving the show, so please keep the feedback coming. We're growth-oriented. We love constructive criticism. Send your suggestions to us on running the show or ideas for guests to MarkCox@InTheFunnel.com. That's my personal email. I personally respond to everybody who gives us a suggestion. Thanks for doing so. We'll see everybody next time on the show.

Thank you.

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About Kristie K. Jones

Kristie, author of “Selling Your Way IN”, is a speaker, coach, and sales process consultant. Companies hire Kristie to elevate their sales organization because most sales leaders and professionals are discouraged and frustrated about anemic pipelines, low close rates, and missed targets.

Kristie’s willingness to get her hands dirty and her “take no prisoners” approach when helping companies drive more revenue from their Sales and Customer Success teams is what makes her so valuable to her clients. Her mission is helping companies find top talent as well as creating a sales accountability culture to ensure revenue growth.

Kristie is passionate about coaching sales teams to leverage their superpowers to reach their full potential, and she wants representatives and sales leaders to identify and embody the practices and characteristics of Top Ten Percent achievers.