From Startup to Exit: Lessons Learned on the Journey to Success (Best of Series)

Dr. Jim: [: 00:00:00

So now you have your stunt double host on the show. And we're going to hear a little bit more of the story. So welcome to the show. Welcome to your show.

Lucas Price: Let's have it. I'm ready for it. Thank you for having me.

Jim: It's your show. So it's [: 00:01:00

Lucas Price: So Zipwhip is a company that it was that handled business text messages. So we would take business phone numbers, non mobile phone numbers, and turn them on to the mobile text messaging system, and then give them software to manage their customer conversations. And I joined Zipwhip when it was on the B2B side.

Was less [: 00:02:00

It was a journey of about five, five and a half years. I had incredible learning experiences because I went through so much change there and so much fast growth, it's, if you're really keyed into, to that type of experience, it's you get so much growth very quickly,

Dr. Jim: one of the things that I'm particularly interested in is you join zip whip as the leader of the sales organization, but I want you to wind the clock back a little bit. And tell us a little bit about the experiences that you had prior to that, that got you prepared to succeed in your role at Zipwhip.

or a very long time before I [: 00:03:00

I think gave me an understanding of what success looked like in sales because I was working with salespeople every day when I moved into a sales role, I struggled to get consistently productive in sales. It wasn't something that was easy for me. But one of the things I did notice that I was good at very early on was working with other salespeople and helping them strategize on what their deals were.

So I'd never put myself as one of the top salespeople, but I think I've always been really good at helping salespeople. And so later transitioning into becoming a founder and then a VP of sales and now a founder, again, I think that ability. To help salespeople succeed has helped me in all of those roles.

llence through struggle is a [: 00:04:00

Lucas Price: I think there's always a bit of naivete involved in any sort of decision like that. But the thing from I met the people. I liked the people involved who were running the company. It was about 15 people more or less at that point in time. And I and I just felt like I had a vision for Hey, they need someone to help with sales and help with kind of the go to market model.

something big. I thought the [: 00:05:00

The company sold to Twilio a little over two years ago for 850 million. I think that part of being right about that was lucky, a big part of being right about that was lucky. And so when I look back at the journey, I think there was a lot of luck involved, but for me, it was just the conviction at that point in time that this company can succeed and I can play an important role in their success.

ey end up getting stuck in a [: 00:06:00

Lucas Price: For me, it was sharing stories from when I'd been a founder before. About the challenges that we faced and how we overcame those challenges that I anticipated ZipWhip was going to have very similar challenges and that in some cases, they already had those challenges. And so it was sharing those stories about the challenges we I'd faced as a founder.

And how we had overcome them. I think that was the biggest thing that probably brought the existing leadership team from Zipwhip into believing that I had the ability to help them succeed in that role there.

d you have to give them that [: 00:07:00

Lucas Price: Yeah. I think it's, there's a couple of things, like one of the things is and I think a lot of people realize this, but it's always good to have the reminder is that, people connect to stories. And so when you're trying to build that alignment around stories that the founders are going to be able to relate to.

And the other thing is ask the founders what's important to them, try to understand their point of view. And I remember once I was in the seat in my very, some of my very first days at Zipwhip, we were in a situation where it was like, okay. We're waiting for a few things to happen. So Lucas, in a few months, you're going to go out and start hiring salespeople.

the small team, like what's [: 00:08:00

His answer was like. Lucas, get to the truth. I want to know the truth about what's going on with our sales right now. And there's a sense that, of course, john knew the truth, but he he didn't have perfect clarity or perfect or high fidelity in the truth. He's looking at product and marketing and sales and business development and all of these things that he's, that he has to keep on top of.

And his fidelity into what was happening with the existing sales team was not as high as my mind could be if I go and, really make sure that we're collecting the data the right way. We're reporting on the data the right way. We have the right systems in place to get the data. And so he, his first piece of advice for me was like, go find the truth, Lucas.

nk it's the first thing that [: 00:09:00

What customers are renewing? What customers are upgrading and spending more? What customers are churning out? How long does it take to sell? Are there certain segments that are buying for higher dollar values or for or the sales are going faster? Which salespeople are most successful? What are they doing different than the less successful salespeople like get, like getting a full understanding of all of these questions was like incredibly helpful for me in terms of being able to figure out.

This is what we should do next. And this is what we should align around.

different [: 00:10:00

Lucas Price: It depends on what the biggest problem is I remember a conversation with a friend at one point in time where he had gone into a sales leadership job and he said that look, my team is signing up customers, but we're losing the customers. And so I could hit my goal, but the company wouldn't succeed.

If, you're trying to drive up[: 00:11:00

And so I think that it depends on, what problems you're trying to solve, like where you think you can have the first impact. But that having been said, I do think that there's a bunch of these doors that you have to look at and like gathering this type of information. Even starting from zero, it's not going to take you a year.

It's something that you can with the right team, the right people, the right tools, you can start to look in a lot of these doors like pretty quickly and start to, use that information to go back to the rest of the team and align around the rest of the leadership team and align around a plan of Hey, as a product organization and a marketing organization and a sales organization, these are the customers that are most important to us. And these are customers that, historically we've signed up, but actually should not be as important to us. And so we should change our strategy in these ways.

sales leader can gather that [: 00:12:00

Dr. Jim: Yeah. And that makes a lot of sense. There's another aspect of your answer that I'm curious about. And that's this, you, during your time at zip whip, you joined at a million dollar organization with 15 people and then you eventually scaled it both on a revenue side and hiring side.

And it eventually led to a to an exit. So when you look at that arc, how did the things that you learned? That were components of the truth influence, how you hired and who you hired. Is there a connection there that that you can share with us?

in a very like transactional [: 00:13:00

A different kind of product. It sold our connectivity to the carriers and our API, and it was a different buyer. And we sold it through a different team because it was a very different ICP, different buyer, different conversation. And so each of those teams, what we're looking for in a seller was a little bit different.

And all, and those channels developed over time. And so the way we hired into those. Developed over time as well. And There's not just one answer to that, but we definitely it, it is very specific to your business. And we looked very carefully at the specifics for trying to decide what we were looking for in sellers.

people. That we were hiring [: 00:14:00

We, we thought that this was like a great opportunity for people to get into sales. And and so sometimes they were coming from retail, sometimes they were coming from, they were, fresh college grads, sometimes they were like, we had a great great seller who was, had previously been a teacher and wanted to do a career transition.

A lot of times what we were competing for, who we were competing with in that situation. Was larger companies who would hire these same people into SDR roles, but we would say, hear it, it zip whip. You're going to be in us in a role where you can close business, you can make, full commissions on your sales.

And so that was part of our pitch to them was come into this full cycle role that included closing. Instead of just being in a, in an SDR prospecting only role.

sting that you're describing [: 00:15:00

Lucas Price: That was definitely one of our selling points. We had we had a big sales floor that had a lot of energy on it that we, we played music, which some people didn't like, but other people liked, and I'll have to say I'm not the best at this, but some of the people who worked very closely with me were like very positive, very high energy people.

best person at creating that [: 00:16:00

And so that certainly appealed to candidates.

Dr. Jim: Really great stuff, Lucas. And I think we covered a lot of ground, but when I look at the arc of the story of zip with. You joined at a million, you eventually led it to an exit. There's a lot of stuff that happened in between what caught you by surprise that you didn't expect, that you feel is important for other sales leaders to pay attention to, especially when they're in this growth trajectory and hiring trajectory where they're in rapid growth.

Lucas Price: Yeah. I think some of the things that caught me by surprise were the inspirations for me to start yardstick. I think like one of the things that I think I was slower to realize than I should have was that the most important thing for my career trajectory and the career trajectory of everyone else in the sales organization, and to a lesser extent, everyone else in the company.

ed. And so the importance of [: 00:17:00

And and the success of yardstick had a tremendous impact on my career trajectory and my career opportunities. And that's true for, lots of other people at Zipwhip. And if we had been more successful, it would have had a bigger impact on us. And if we'd had less been less successful, it would have had a lesser impact on us.

So I think the importance of that is something that really caught me by surprise. And at the same time. Like the, when you're part of the reason it catches you by surprise or caught me by surprise is that when you're in the role of the VP of sales or the head of sales or the chief revenue officer, there's all these other things that feel like higher priorities.

your, weekly one on ones, et [: 00:18:00

Dr. Jim: It's interesting that you mentioned that and I'm wondering if we can make a broad lesson out of that. It sounds to me that one of the things that you realized was that a more detailed focus on the hiring process would, could have potentially gotten you further ahead faster. And I might be paraphrasing it, the thing that I'm wondering if there's a relationship with. Is this as a sales leader, would you agree or disagree that you need to take inventory of all the things that you're responsible for and maybe pick the ones that you're putting off and procrastinating on and reprioritize that as high on the list. Because that's probably an indicator of a problem that you're not willing to confront.

What do you think of that theory that I'm cobbling together?

It reminds me of. The seven [: 00:19:00

And a lot of times we work on the urgent tasks, the most urgent tasks instead of the most important tasks. I think we should always be looking at what's most important, but we have it done because it's not most urgent.

And how do we make that urgent? How do we prioritize it and get it done? Because that the things that are going to have the biggest longterm impact should be prioritized over the things that people are just trying to push on you to get done today or tomorrow or this week.

erm desired outcomes for the [: 00:20:00

So that's really great stuff. We covered a lot of ground Lucas in this conversation. What I'd like you to do is highlight for the list. There's Maybe the top two or three things that they should have in mind when they're trying to go on this scaling journey when they're that new sales leader. What are the things that you feel is important based on your experience at ZipWhip that sales leaders need to be focused on?

Lucas Price: I get asked about this quite a bit because I think it's relatively unique to go as the sales leader from less than a million and building the team that goes over a hundred million. And I think that my, the reason that I was able to do that and succeed in it. Is that I was, I tried to look very closely at what I was not doing well all the time and tried to be really software.

ly trying to pay attention to[: 00:21:00

That's changing really fast. And for me, I was there for after 18 months. The job was totally different the next 18 months, and then it was totally different again after that. And at each of those stages, I really had to say like, how do I change as a leader to keep up with the way my job has changed? And and so self awareness being willing to change putting people, being willing to put people around you who are good at the things that you're not good at, those were all things that helped me succeed, I believe.

Dr. Jim: Great stuff, Lucas. Really great conversation. Obviously, for those of you who are listening and want to find out more, you can certainly reach out to Lucas directly at lucas at yardstick. team, or you can go to Yardstick's website. That's, Yardstick that team as well. When I think about this conversation There's three things that stand out to me that I think is important to highlight One is your point about finding the truth.

're a new sales leader in an [: 00:22:00

If you're misaligned, you're going to have a lot of trouble getting traction, especially if you're trying to scale and grow an organization. So that's the second thing that stands out. And the third thing that I think is important to highlight in this conversation, at least for me, is That as a startup and as an organization that is looking to hire and grow, you have to be really disciplined about finding the competitive advantage that your opportunity has over the other opportunities that exist within your landscape and play to that.

other similar. Positions are [: 00:23:00

Thanks again for indulging me and doing a little bit of role reversal for those listeners who have checked out the episode. Leave us a review and then tune in next time where we'll have another great leader on the show to talk about how they've built elite sales teams,