Building Your Sales Organization for Scale | Podium EVP of Sales + Head of West Coast Sales

The goal of this is to give you again, the 5 lessons that we've learned as we've gone from— I joined Podium at roughly about $1 million of ARR. Carly joined shortly thereafter around, I think, $5 to $6 million of ARR. And so we've built this thing to now over $100 million plus, and obviously hoping to continue and go onward and upward. And so the goal of this is to really give you guys some of the lessons we've learned along the way. Obviously, there's hundreds of things we could teach, hundreds of mistakes that we've made. Things that we've learned, good things that we've done, but we tried to boil it down into kind of 5 core lessons and largely focus on a couple of things that are both very tactical and what we thought are like strategic logistical, as well as like cultural. And I do think there is a fine balance between those 2 elements as you're trying to build. And interesting, you know, as we thought about it, if nothing else, some of the core messages we hope that you learn from here and what we believe are the building blocks is Really, like, at this stage, and particularly early on from $1 to $50 million, it's really more science than it is art. I know in sales, we like to believe it's a perfect blend of those two. But we're believers here at Podium, it's a little more science than art. Obviously, it's all about the team that you build and put together, and who you bring along with you on that journey and working to win together. And then ultimately, none of this matters if you're not bringing incredible value to the customer and focused on the customer. So those are sort of the core building blocks. The way that Carly and I built this is to provide you with those principles, and then try to share lessons at each of the various stages. Obviously, some of these principles played a bigger role and impact early on. And then we had to evolve and change as we hit different stages. As anyone knows who, who's been through this, you are kind of reinventing yourself at each one of these stages. And, you know, Podium, now that we're well over $100 million plus in ARR, we're even reinventing ourselves today. And so we'll talk through just some of the things we had to do, the reinvention the new playbooks we had to write, and hopefully give you some, again, things to really take away at each of these different stages. Brief history on Podium, just so you know a little bit about us. We are software built to help local businesses win. We really focus on businesses that serve their local communities, brick and mortar for the most part. We were born out of a tire shop. This is actually our founder's dad. He, our founder, worked at a tire shop up in Canada for most of his high school career, realized very quickly that The software that his dad ran, used to run their business, was very inefficient, and there was so much we could do to support local business owners who work tirelessly to build their communities and bring value to both their families and the communities that they serve. And that's our mission, and that's our goal. We've been on a really great growth trajectory over the last 5 to 7 years. I've had the chance to be there from the very beginning, and you can see just our growth charts. And again, a lot of lessons, a lot of fun, and a lot of Unfortunately, failures and lessons learned along the way, but we continue to grow. So let's go ahead and dive into it. So the first thing that we want to touch on that we believe is core to Podium success is really ownership is key. And what we mean by that is the more that you can specialize and focus your team, your organization, and even the individual sales reps, the greater the chance that they have to succeed. I see a lot of young startups when they're getting into that million to $10 million phase, they tend to allow people in this kind of Wild West scenario where everything goes, let's just get to the customers as quickly as possible. So for example, at Podium, when I came in, you know, we sell to local businesses, and we were selling to anyone and everyone all over the country, every type of business. In fact, I remember my first couple days there, we sold a limo business out of New York and I was kind of shocked to see just generally how maybe little direction there was in terms of what our core opportunity was and who we were going after. And so one of the things that, that I did, and we did as a— as with working with our founders early on, was to get very specific in terms of what was our core focus, who we were going after. So for example, we said to one of our reps, hey, you are going to call just you know, car dealerships in Florida. Another one, it was you're going to call just, you know, dentists in, in California. And we got that specific because we knew that without that type of specificity and that specialization, it created a lot of challenges for reps because they're just going to go anywhere and everywhere. And there's a lot of wasted time and inefficiency. And so a lot of what I believe in is make people CEOs, give them ownership. Good fences build good neighbors. The more you can create a world in which they are focused and specialized in terms of what their goal is, the more success they're likely to have. And of course, that's going to be really scary for a lot of sales reps and sales orgs initially, because you want to go after the big market. Anytime you consolidate a rep's focus, they get nervous. But you have to obviously get them to believe that this is going to be the best for them. And so at $1 million of revenue, we started to really dive in and focus and even establish what we wouldn't do and who we wouldn't sell to. And that really helps us to start to scale and grow quickly. And then at $10 million, Carly, if you want to jump in and share some of our successes there.

For sure. Around the $10 million mark, just to add on to what Than was saying, I think a lot of times as leaders, especially sales leaders, we feel we hire adults, they should be able to figure it out. But that is, in my experience, the dead opposite. Sales reps and individuals, especially at startups, they need to have direct direction. They need to have clarity. And so with a lot of trial and error that Than talked about, as a company, we were able through data and trial and error, able to understand what are the true strike zone, strike zone businesses that we want to target and we want our reps to go after to bring onto Podium. So looking at which businesses are performing well, they are our ideal customer profile. They're not churning. They're staying with Podium. They're a great fit and a long-term customer for Podium. And we're able to support them with our out-of-the-box solutions. And it's a great product-market fit in those industries. So building a team structure around vertical organization and having a very, very focused set. To Than's point, we had people focusing on specifically healthcare in their territory, specifically home services. So we were able to provide each individual rep with clarity, direction, and then they were also specialized, which helped scale the business immensely. And that is something that we found be very, very successful. And you'll see as a theme throughout what we talk about today is being able to provide direction, focus, and clarity for reps is huge to make sure that they are successful and comfortable going after the goals and achieving their goals.

Yep. And in fact, Carly, I'd add that we even did pretty specific things around compensation to incentivize going after the right businesses, not going after the wrong businesses, and making it something that, like, we were pretty intentional about how we thought about that specialization and even building comp models around that. One kind of just final statement we'll touch on is we really believe, again, good fences build good neighbors here at Podium. You, you, everyone wants this ideal of like an open neighborhood, no fences, but the reality is fences help us establish boundaries and relationships. And so early on, we established again, territories, verticals, the type of deals or sales cycles you would be a part of whether you were a transactional rep or a more long-term strategic rep, and even like clarity around rules of engagement between sales and marketing and others. And we thought The more structure we built around there, the faster we can move, the better the culture. And overall, that focus added to a lot of our early growth and success. And, and that kind of blends us into— go ahead, Carly, jump in.

I was gonna say one last thing too. As you grow and scale, especially with sales reps, how we are sometimes more emotional. And we need to be reminded of having an abundance mentality. Because every time you grow and scale as a sales rep, your territory potentially shrinks a little bit, or there's changes that come. And so helping instill that sense of an abundance mentality rather than a scarcity mentality is huge as you scale an organization to make sure the mindset of your reps are in a great spot, and then also long-term being able to retain reps that you want to grow the business with.

Thanks, Carly. Which then leads to our second principle, which is this idea of science over art. You know, we believe at Podium that Generally speaking, we talk about the math all the time, that if we do the math, the results will come. And, and obviously every startup is a little bit different, and it depends on your scale when you're growing of how successful or how predictable that math is. But the more predictable you can make it, the more you can focus on the science over the art, really the more control you have over the outcome. And so our goal was to always make it more about science than it was about art. And early on in my career, I had a great mentor, Dan Rosenzweig, CEO of Chegg. And I asked him one time, like, how do I become like a great sales leader? And one of the things he told me is, you have to make it like crystal clear every day what good looks like and give your people a vision of success. And so taking that feedback, walking into Podium early stages, I decided, I want every rep to know what is, what does a good day look like. And so we established a mantra here at Podium that we call 3-2-1. And the idea there is every day we want every rep to have 3 appointments, 2 demos, and 1 opportunity that they can close on their calendar. And we started to repeat this mantra, we started to coach towards this mantra, we made it a principle that for us was, this is what good or great looks like. And if you, if you leave today without having accomplished 3-2-1, your goal would be to come back the next day and be successful. And so I would really challenge all of you as you're starting at this early stage, a million to $10 million, what is that mantra? What does good look like? When reps know what good looks like, and when your sales teams know what good looks like, they're much more empowered to go and achieve that. And so that would be one element of science over art, is establishing that vision of success.

Moving into the $50 million mark, you definitely are bringing in more and more new reps that are newer, and they're not just here for that initial mission of the startup and the new phase of, of Podium. So what we found, just to add to what Than was saying, was providing that clarity on what a good day looks like. And one big thing that I found really helpful and successful, every single morning we do morning team meetings at Podium to kick off the day. It's a 30-minute meeting. We're having each rep tell us what their goals are, what their day is going to look like. And when I started doing this, I realized some people's goals and what we expect, they were coming in lower or not where I would expect them to be, especially if they were pacing behind in the month or they had more potential. So one thing we started doing in our morning standup meetings was on the screen share, with everybody pulling up each rep's calendar to help reiterate and understand and see what their day-to-day is looking like. What does their calendar look like today and where should they be focusing their time to achieve that 3-2-1? So that's been a big way to move the needle and have a visual there. So people, if your peers are seeing your calendar is just white space, that's embarrassing. So what are you doing each day to be accountable to those commitments that you're making to set your calendar up to have that 3-2-1? And then also, what are you doing all day if your calendar has white space? We talk a lot about— and one thing Than said when I first started at Podium that's always stuck with me, he says, we can be busy all day long as sales professionals doing things that make us zero money. They don't move the needle, but we're busy all day. So making sure we're really, really efficient with our time. And that really boils down to what can you do as a sales leader to take any sort of barriers or things off your rep's plate that slow them down from achieving that 3-2-1, that slow them down from pacing the quota on the month or the quarter. And so making sure that they understand what a successful day looks like, how they can be most productive, when and how they should schedule their calendar is a huge thing that a lot of reps, especially junior reps and even senior reps, sometimes need a lot of training on. Owning your own calendar and understanding when and where to time your day and set your day up every single day with a plan has been huge in making sure that our reps can become consistent day-in, day-out performers and feel successful at Podium.

Yeah, and with that, so we're big believers here at Podium that we can empower our people with metrics. And what we've learned is, you know, obviously as an executive team, we probably monitor 50 to 100 metrics across product, customer success, and other organizations to help us run the business. But when it comes to sales teams and organizations, particularly in go-to-market, I believe it's 3 or 4 metrics, like find the 3 or 4 metrics that really matter. One of the examples I always like to share is this idea of like, you have to have the recipe for Coca-Cola, right? And, and Coca-Cola didn't change the recipe for 90-something years. Before they introduced Diet Coke. But even then, like, Diet Coke is still Coke, right? The recipe is similar, it's vaulted. And, and I think most sales organizations, the more you can create that recipe and focus on those 4 core principles, the better chance you have success. And, you know, a lot of times we want to allow people to be creative and have personality, and I, and I'm all for that. But my thing is, hey, you get personality, when you have the recipe of Coke. You can be Diet Coke, you can be Coke Zero, you can be Cherry Coke, but at the end of the day, this is how we do it here at Podium. This is what we know works. And the more you can hone in those 4 core metrics and be ruthlessly repetitive and only tolerate those 4 things, the better your chances of success and being able to build a motion that really starts to pick up. And so, for example, you know, here at Podium, We have our math and we know exactly what it takes, the inputs needed to be successful, and we hammer and preach and talk about this math all the time. And this is really a core focus for us, which then leads us obviously to the next thing, which is now that you've established what success looks like, you've built the math, then you have to build a team around that that can obviously help you actually get there and be successful. And so, a couple of things for us is we obviously early on at the million-dollar stage, you're really selling the vision of what Podium's going to be or what the opportunity is and trying to bring absolute A players in every seat and give them and show them that clear career progression and what the opportunity looks like for them. And I think one thing one of my mentors, Adam Edmonds, said to me once is the great VPs are able to not just get the good hires, but the great hires, and convince people better than them to come and work for them. And that's been, of course, totally true here at Podium is The ability for us to bring better people in to help us grow is critical. And so I would say a lot of your job early on is to sell the vision and bring better people than you into the organization to help you scale and grow.

One of the biggest things with that too, when we were transitioning into that $10 million mark, was making sure we were bringing in people that were scrappy. So they were— we needed self-starters. We needed people that would only— that wouldn't only perform with a turnkey operation. We needed people that wanted to come in and they wanted to build, and they wanted to build that and create that playbook with us. And they didn't need a playbook, which is huge. I honestly like to bring that up in interviews. I like to almost talk people out of wanting to work for us sometimes, because if they are used to being in a place where they show up and everything is weren't locked and loaded, especially in the early days of Podium, it was not going to be a good fit for them. They needed to be able to follow the math, but then also be really solution-oriented and proactive in order to help us build here at Podium.

Yeah. Oh, go ahead, Carly. Yeah, we'll touch on diversity and inclusion as well.

Yeah, I'll go ahead and touch on that. One of the biggest things too when we were bringing on people that we fell short at at Podium was we were sprinting the first few years. We were sprinting, we were hiring, we were bringing in top talent people, but there wasn't a huge focus on diversity inclusion. And fast forward, we have paid for that as an organization. And it's actually been a deterrent for some hires, some diverse hires that we want to bring on because we all know that that helps an entire organization level up. For a use case, for example, pulling data, teams at Podium that have women sales reps on that team, they perform better, much higher than teams without. And so That's just one data point to look at. And there's so many more, we could do an entire presentation on that, but making sure we're really intentional now with who we're hiring and why we're hiring them. We're getting still A+ players in the seat, but also being mindful of making sure we have diverse hires and resources for those diverse hires. One thing that I saw a need for early on at Podium, and Than really helped and encouraged and enabled me to do and provided budget from the sales organization, was we have a monthly professional development opportunity for the women in sales where we do a luncheon and we have a guest speaker. We have senior leadership come in, or we do some sort of tangible skill workshop type of training. And it's been a huge asset for all the women to help improve retention. And in addition, bring in talented women because that's something that helps them feel more comfortable coming into Podium and being successful long-term.

In the interest of time, I'm going to, I'm going to jump a little bit here just to show one of the things that we've always had to focus on at Podium is making sure, really at any stage, right, bringing people on who are mission first versus individually focused. And so we use a quadrant here at Podium. I won't spend a lot of time on it. I'm sure you've seen this before, but just this idea of how do you find people who are not only high performers but are incredibly team-oriented? And making sure that you keep people up in this upper right-hand quadrant and not ever allowing people to become too individually oriented, no matter how high-performing they were. And that was something we've been really intentional about here at Podium because it really is all about that team. And so that's something to think about. But the next thing I wanted to— we want to touch on is how important focus becomes and really focus at every stage. And just to quote quickly talk about some things. So like at $1 million, one of the things we had to do is focus on what we— who we wouldn't sell, right, which verticals we wouldn't go after. And we had to basically put those guardrails around reps and even myself and our founder, Eric Ray and Dennis Steele. They were my guardrails because obviously, as a revenue leader, I wanted to chase things at times. And so that partnership with them was really powerful because they were really good at helping me grow as a leader to say no, like these are the guardrails you have. So we put guardrails at every stage to make sure we stayed focused. At $10 million, it became more about what products we would or wouldn't sell. I mean, there's a lot of things that we could do to support local businesses, and we had to be very thoughtful about the timing of when those products mattered and, and what we're going to go after. Of course, at $50 million, we started to see things like enterprise versus SMB, and, and how do you think about that? And when was the right time to go upmarket or go downmarket? And and some of those trade-offs. And, and the key for us is every time we focus and we've made a hard trade-off, we've succeeded. And, and I would— it's always so hard, but it makes a huge impact. And of course, if you look at things from the lens of an opportunity versus a threat of what you're not going after, it allows you to really thrive in that abundance mentality. I think it's important we touch on inputs. Carly, if you want to share some thoughts there, you can go to the last principle real briefly here.

Inputs are absolutely the only thing as a sales rep you can control. And it's something that you can deliver on every single day. So making sure you provide that clarity and people understand what they need to do every single day from an endpoint, input structure, and focusing and making sure you have a mindset within your organization of focusing on what you can control, because there's— everything will always be changing at every stage of your business. And so making sure your reps can only focus on what they can control, and make sure that they're getting those inputs because everything else is a distraction. And making sure as leaders you help them understand that and focus on themselves and what they can control is huge. And then making sure along the, the different growth stages, you have the right resources to make sure that you are able to support those inputs and make sure everything is really, really streamlined.

The final, the final element here for us is like, this is something across every stage. This is a real cultural thing that we've had to be very intentional about through every stage. Even early on when, you know, the product-market fit was coming together, I felt very strongly, and we preach this at Podium, that we want to be a sales-driven company, never a sales-dominated company. And you can get those two things mixed up really quickly, especially in high-growth companies. I constantly remind our sales org and our sales team of how, how lucky we are to have a great product team behind us, an amazing marketing machine that drives, you know, great quality leads and opportunities for us, you know, how lucky we are to have a customer success team that, that takes care of our clients in a, in a really high caliber. And so one of the things that for us I've tried to teach is this idea of how important it is to like stay really aligned to those different organizations so that we break down silos, we remove sand in the gears, because ultimately, if you don't do that early on, as you scale, that, that inefficiency just only continues to pick up. And it can, it can create a cultural disaster if you've allowed your sales team to be too dominant inside your organization. And so I always make sure I check their ego a little bit, understand that like, we are only successful because of the people around us. And of course, that leads to our customer, which this is what it's all about. And I'll let Carly touch on that and then we'll take some questions from everybody.

Yeah, Podium has always put the customer first and in high growth, it's really easy to let revenue become the main focus and objection. One of the biggest hurdles and downfalls I've seen, especially at different companies I've been at or hearing from different friends, there's nothing worse than making sure your sales are up and up and up to the right, but then making sure growth and support for customers and taking care of customers isn't there. That will diminish the confidence sales reps have in the product and the support that they're going to have for people that they bring on to the company. It is one of the quickest ways to lower their confidence and make them less confident in selling and pitching a product to people every single day. They want to make— you want them to feel empowered to tell people, we're going to take care of you, this is a great product, it works, and we have the support to back it up. So that's huge. And making sure, as we've grown through Podium, realigning our values and making sure that on the back end, the customer success team and the sales team at Podium, our destinies really are intertwined. And we do depend heavily on each other to be successful at the end of the day and become and grow as a company that we want to be. To wrap up here, essentially the key takeaways that we had— there's hundreds and hundreds of lessons that we really can cover. And overall, the 3 main things that we found to be very, very successful and help with the hypergrowth, and then also making sure you have successful, consistent sales reps, which are really rare and hard to find, right, is making sure you have the clarity, metrics, and inputs, the 80% science, 20% art. It's all about the team. We win together, and that's what creates a winning culture. And then always making sure you're putting the customer first. It's always about the customer and taking care of them. That will, at the end of the day, always serve you well as an individual, as a leader, and also if you want to grow and scale your company the way that you want to at the end of the day.

Yeah, I'm going to try to tackle a few questions here, Brian, while we've got 3 or 4 minutes still. I think I can, I can put some of these in groups. Really good questions. So first off, one of the questions, like sales reps to manager ratios. I will say that early on when you hire people who are really bought into the mission and you have a little bit tighter span of control, we were a little heavier of like almost 12 to 14 to 1 leader to manager ratios. We hired a lot of people who we said, hey, here's the role, we need people who can figure this out together. As we've scaled, we've seen that tick down to where now we run closer to an 8 to 1 leader to rep ratio, a more standard that you'd see. But early on, we definitely stretched those limits, A, from a cost and budget standpoint, B, because we could hire people who just wanted to come and help us figure it out. And so that was something that we focused on. As far as like sales to revenue ops, we really started to invest pretty heavily in revenue operations around that $20 million-ish revenue mark. Early on, it was a lot of me and my sales leaders of just spreadsheets and Google Docs and things like that. As we scaled, we started to see those were those investments started to tick up. And, you know, sales ops is a big category, but we probably see about 20% of our headcount across the board, probably closer to 10% of our total headcount dedicated to sales ops, enablement, solutions consultant, you know, versus the, the account executive and IC, or IC quota-carrying headcount. As far as like SDRs to AEs, big, big believer in that. We've seen incredible success, mostly because they know our culture. They know what we expect, they understand the metrics that matter. So we are big fans and big believers of SDRs to AEs. And it doesn't have to be a promotion path. We have a lot of SDRs who fill a lot of roles here at Podium. But we definitely believe that SDRs are some of the best people you can grow in your organization because they internalize the mission and the culture. Carly, there's one here about like an abundance mentality versus scarcity. I don't know if you want to take that while we have some time.

Yeah, for sure. I think the abundance mentality compared to a scarcity mentality is— to boil it down, it's just people that feel like they're panicked and they're afraid of the quota monster and they don't know how to set up their day and focus on what they can control to be successful. And so making sure that they understand and take ownership of how to be successful and back into their number, which ties into the other question about which metrics really matter, and we did touch on that, but make it— it's a game changer as a sales rep to say— for someone to help you understand and back into math of here is what your, your quarterly or monthly quota is, this is what you need to do each week, and this is what you need to do each day. And at Podium, we have 7 years of math to back that up. So making sure you're in the details of the data and utilizing that to say here's what an average rep needs to do to be successful, and this is what it would look like, that also helps with that abundance mentality of them understanding that they have a ton of opportunity and they know exactly how to accomplish what they're looking to do. People say, oh, my reps aren't bought in. It's like, okay, well, can they do math? That's really what it is. It's not if you're bought in or not, it's if you can do math and understand how to be successful with metrics and having leadership to help you understand the opportunity and the growth and abundance of what the, the large-scale picture is for the company and how much opportunity is out there and what your target market is and the TAM that you have out there to be successful. That is— I felt a little rushed, but that's what I would think an abundance mentality really boils down to.

Brian, I know we're out of time. You want to take any more questions or— I was just about to say, this was unbelievable. This was a really great session. Carly, Than, you did a wonderful job. If you have more questions, by all means, please reach out and connect with Than and Carly. But that said, this was a great session. We have a lot more great content coming today, so see you all in the next sessions. Thanks, everyone.