How to scale sales at a startup

Benjamin Ard: [00:00:00] Hello and welcome to the Alignment Advantage Podcast, brought to you by Masset. This is the sales and marketing edition. In this edition, we interview some of the greatest sales and marketing minds in all of tech. We have a huge emphasis on internal alignment and believe that can be a superpower for your business.

We hope you enjoy the interview. All right, man. Well, I'm excited to have Jake Larson on the podcast. Jake and I go way back. I think we met when I was, what, 13 years old? Is that right?

Jake Larsen: Yeah. Like what? Fifth grade, something like that. Who knows? Yeah. Back

Benjamin Ard: in the day we started playing some basketball together and yeah, Jake had a big impact on my career.

He actually got me over to Weave and I had a lot of fun there, and we got to work together for quite a few years. But Jake's an excellent leader. One thing I really admire about Jake, besides the fact that he's just really good with sales is. This guy knows how to grind and loves the grind of early business in helping businesses be successful.

You've seen it firsthand in multiple circumstances. [00:01:00] So I just love your experience of understanding how do I build something from the very get-go? How do I experiment? How do I test? How do I try? How do I build, how do I grind? I think the perfect example of a sales leader, especially in an early stage startup.

So Jake, introduce yourself. Thank you. Walk us through your career so people know who you are.

Jake Larsen: Yeah, sure. Well, and so much so what Ben said about loving the early stage company, I went and did it again. So here we are. That's where we're at now, is the element. So yeah, career wise I got my start at Weave with Ben.

I was very early. On at Weave. I think I was like third employee or fourth. Depends on who you ask, right? But early, early at Weave when it was just all hands on deck. And some of the best, best days of my career so far where there's, there's just very stressful days. But really, really fun looking back at it.

Lessons that you, you can't, can't duplicate or can't replicate. There's just so many things that you learn when you [00:02:00] are just. Forced to, to grind and to figure out the solution that gets you from point A to point B. So, yeah, I was at Weave for 10 years. I, how, how detailed do you want me to go, Ben?

Benjamin Ard: As detailed as you want, lead us up.

What'd you do at Weave? And where are you at currently? What's your current role?

Jake Larsen: So yeah, at Weave really early on building all of the infrastructure and foundation to be able to scale the sale sales team. So our first vertical at Weave, we sold the dentist primarily at the beginning, and I did that for about five years.

Then we wanted to launch into another vertical. And so they asked me to go build out another vertical. So I built the optometry team there, and that scaled really fast because we had a lot of the foundational pieces already in place. So I think we, we went did 5 million in a r our first year. Another 10 million, almost 10 million in our second year.

And after that I kind of phased out and And left Weave. And today I am with a company [00:03:00]called Elements Technology Elements is a platform for financial advisors. For any people that use financial advisors, you're probably really wealthy because that's typically who financial advisors target so they can manage money for people.

I've learned a lot about that space over the last year since I started here. But Elements takes a little bit of a different approach to financial financial planning and advice. Making it more accessible to the to the majority of society rather than the, you know, most wealthy. So I've been at that for about a year.

Companies, about 20 people were probably shouldn't say too much, but just wrapping up a round of funding, which is a, a huge. Huge win. Especially in the markets that we are today. Most people are having to reduce headcount and their companies are making plans just to survive. And we're in a situation that we get to continue to grow and scale.

Cause we've had a lot of success this year. So yeah, that's where we're at. Build in our sales team here at Elements, putting all the pieces together so that we can be ready to grow. I love

Benjamin Ard: it. So I think you have a cool [00:04:00] story when it comes to your early career. When you started at Weave, you said employee three, employee four.

Weren't you technically an intern when you first started? Like that was your first thing, right? And you wore a million different hats. How does someone come into, like a brand new company, even at an intern level, and then start to take over major portions of the company when it comes to sales and all of that?

What, how do you scale yourself? What did you do to kind of put yourself in those positions to succeed in your career?

Jake Larsen: Man. Good question. So yeah. When I first started Weave, there was just me and the, the founders and it, it was all hands on deck, right? Just like you'd picture late nights. And I think that the first key thing is to get over yourself.

Just be humble and recognize like Doesn't matter what your position, your title, what your comp plan is, doesn't matter. The only way that you're gonna survive is by everyone just being all in and looking out for each other. So at the very beginning, [00:05:00] I think that was the, the main thing that, that got me some opportunities.

Was just showing a willingness and a hunger to, to help wherever I can. I mean, I, I remember there was one time that we were moving to a new building and my dad has a construction company and I literally went and got this big trailer from his office, like an enclosed trailer and like moving the refrigerator and like all the stuff from that office to the next office.

You know, there, there was nothing that I ever acted like I was above it. It was just, hey, whatever we gotta do to, to grind. And then as you prove yourself, you get chances, you get opportunities, right? If you're successful with one thing there, you know, if you know how to solve problems, especially at an early stage company, like problem solving is probably one of the greatest skills to have.

And I proved that I had an ability to solve problems and as you. Show success and an ability to, to find solutions, and then you're willing to take [00:06:00] on new responsibilities and continue to show those oppor the, the, the success that you can have. I think that's, that's the key at an early stage company is to be, be humble, be willing to, to do whatever it takes, and then when you do get the opportunity, make sure that you capitalize on it and that you always stay grateful.

I think great gratitude is a. Is an underrated superpower that that really hurts people if they if they don't have it. So always stay grateful for what the opportunities you get. It'll, it'll help you capitalize on the next one.

Benjamin Ard: I love that there's no real entitlement at a startup. No one's entitled to anything cuz there is nothing to have yet.

There's nothing. So I think it's a, a great lesson. So you mentioned you opened up a brand new vertical. You went out there and, and you started to build out the sales motion for optometry. Walk us through that process. You know, a brand new industry that the company I never really worked with. How did you start to tackle that problem?

How did you build the team? What did you do and how did you approach that [00:07:00] challenge? You know, a few years into Weave? Yeah.

Jake Larsen: That one was unique, right? Because. Imagine starting a business inside of a business that you already know all of the problems that you're gonna run into, right? Like, if you already know what's gonna happen, you can kind of see the future.

You can go so fast. So that was, that was interesting because during the first five years of growth that we've, we focusing primarily on dentists, like we made a lot of mistakes that we learned from, and we grew from, and, and it still went really well. But then when the opportunity came to launch a new vertical the product was very similar.

Opt, optometrists and dentists had a lot of similarities, so we knew the type of partnerships, the, the language, the value propositions, the, the training, the hiring, like we had all of those things already dialed in. So we started that team and we br I broke off with three AEs from the, from our my original sales team.

And then by the time I left, we were at I think we almost had 20. I think 15 or 20 AEs scaled it within two years. And, and we were doing probably average [00:08:00] about 750 K in new a r r every, every month. And the other part of that motion was my counterpart on the marketing and business development side.

His name's Monroe. Shout out to Mon to Mony. If he's listening to this, we'll get him one here one day. Yeah, we'll get Monroe. But Monroe he was a huge contributor, contributor to that because we had the machine to move the revenue right. To get, to get the deals coming through. But between partnerships and opportunities and marketing initiatives and all these things like the collaboration that Monroe and I had, With with the different people on our teams was just phenomenal, right?

We were super in sync. Everybody was grateful for what the other person was doing, and they were working hard for each other. And it, it was just beautiful kind of the harmony that came from that. And it, it really just allowed all cylinders to fire because we were so in sync between the efforts of all these different people that were making that machine go.

So[00:09:00] Yeah, the, that's, that was kind of the key to that o optometry initiative. And it probably like the highlight and I don't know if there will ever be anything better than what, than what happened on that team. It was, it was like magic, like all the things came together perfectly.

Benjamin Ard: That's awesome.

So is your scaling for just a handful of AEs and you're, you're kind of building that team, how do you train and pass along information as you're scaling from two to 20 to make sure. Everyone's doing things the right way and you're passing down, you know, that tribal knowledge. Mm-hmm. How do you make sure that takes place on a team like that?

Jake Larsen: So one of the things I think is important when you're leading a team is understand that you need to build other leaders. And sometimes we get so caught up in ourselves that we think, well, I have to be the one to do the training, or I have to be the one to do this. And it really limits what you're able to do at scale and it slows everything down.

I think one of the things that we did great on that team was empowering even people that [00:10:00]didn't have a leadership title, to have opportunities to demonstrate and to be a part of that tribe. And to bring more and more people in. So whether that's team leads, I remember, you know, when we did when we, when we would onboard a new ae, I would actually attach a little bonus to the, whoever trained that person for the success of the other person.

So they had some incentive. And so that was, it was also an opportunity for those people that would bring in, as, would bring in new people. They could demonstrate their ability to lead and train if they just started with one person. And so I wasn't, I wasn't always training someone one-on-one, me with a specific individual.

It was me with a group of people that are training another group of people. So really just focusing and incentivizing people to. Build that team camaraderie to build a, a team of helping and uplifting others to, to make sure that everybody felt like they could [00:11:00] play a role in that, that they weren't just a chess piece.

Right. That they were actually a part of what we were doing. And it really helped with, with people being feeling a part of it and buying into the vision that we had created and, and helping us grow quickly.

Benjamin Ard: I love that. And to your earlier point about humility, I think some of the best leaders have to be humble and be comfortable, like training up new leaders that can take on responsibility and they're not afraid of their own position being replaced by having these amazing, amazing leaders, but like really lifting everyone up with them.

And I think that makes a lot a lot of sense there.

Jake Larsen: So technology's powerful on that, right? Yeah. Like. Recording calls, those types of things, and encouraging people to go back and watch game film following the best the, the most successful reps, those types of things. Technology's a big piece in that too.

Benjamin Ard: I love it. So you said that there was like this really good harmony on that team and you had a really good counterpart in business development with Monroe. How were your goals aligned when you look at [00:12:00] marketing and sales and business development people in the go to motion or go to market motion? How do you prefer goals for those teams be aligned so everyone's really fighting for the same objective.

Jake Larsen: Yeah. This is a lesson I learned early on at Weave, just when it came to sales reps, comp plans. I know this is a little bit of a tangent here. Yeah. But I remember there was, I was watching Monday Night Football or something, and there was a, a defensive end. It was, his name was Dwight Freeney. For those that are football people out there, you might know who Dwight Freeney was.

And he was older. And I remember there was a game, it was like Arizona Cardinals and the, and the Minnesota Vikings and Dwight Freeney got a sack, and the commenters talked about the way that his comp plan was structured, that he had an incentive that at a certain number of sacs, He would start to get bonused and like as they got closer to playoffs and like big games.

Dwight Freeney you know, he, it was timed perfectly, so like by the time they got to those games, he would hit [00:13:00] his tier and like every, so that one sack, it was worth like a quarter million dollars to Dwight Freeney and everyone after that. And so they, and he wasn't like a full-time starter, he was just put in the game at the end, like to make big plays.

But he had as, as much motivation as anybody to get to that quarterback. And he like came up with two big plays and the commentators were talk, talking about this guy and how he was like, How much money he was making every time he got a sack. So I just remember thinking about that. And at the time I was building comp plans for like SDRs and, you know, some people would comp on demos that they set, or demos that were held and there were demos that were, or, or on revenue.

And I think at the time we were co, we were comping on demos being held or something like that. And I was like, there was just misalignment, right? The. The sales, the SDR just wanted the demo to hold regardless of the quality. And the AE was mad at the SDR cause they were set in really crappy demos. And so I learned at that point, like how, how important it is as an organization to be a.

[00:14:00] Motivated by the same number. Right? So Monroe and I were very focused on a revenue number and there was a lot of work put into the planning initiatives and what the, what the KPIs were that would lead to that and the ownership that we had underneath it. But both Monroe and I, we were both comped on on our success to that.

Primary kpi, which was revenue. And we were both collaborating on all of the KPIs underneath that with our own responsibilities. So with, with Monroe, it might be certain, a number of partnerships that he would land that would open up TAM for us. There would be certain products, initiatives of what we could use to increase our A C V.

So there was a lot of different pieces and parts to that revenue number, but the. The goal that he and I talked about all the time was the revenue number and everything. That was what was most important across the board. And yeah, there's a lot of collaborate, collaboration that came to make that a reality.

But I think it's really important for people [00:15:00] to all be. Chasing the same goal. Cuz as soon as there's something different, they're incentivized for demos held or for this or that, now it's now you're opening the door to finger pointing, finger pointing and whatever it might be that's gonna disrupt that culture and slow you down.

Yeah, I love that.

Benjamin Ard: So let's transition you you eventually left Weave. Moved on again. You're like right back at the thick of it with elements right at the beginning. What what have you done to scale the sales team this time around that you maybe learned some lessons from Weave so you could kind of be more effective this time around?

Jake Larsen: Yeah, it's interesting doing it a second time because when I did it the first time, I didn't know what I didn't know, so there's nothing to be afraid of cuz you're like, just going a million miles an hour now. Now I know what I know. Some of the main, some of the first things that I did was I changed the, the way that clients customers pay for [00:16:00] elements.

It used to be a very complicated model that made the decision very hard to say Yes. It, it, it made for a bigger tam. But. Just making it simple so that the buyers have, it's an easier decision for them to make with upside at the end. So that was the first thing. One of. At Elements, there was not a lot of sales that had happened before I got here.

So we didn't know a lot of like what was possible, what was a good sales price, what was the right quotas to set for the sales team. So for the first half of this year, there's been a lot of discovery. Around that. I think a lot of times people get really excited. You raise some money or you've got this new business, so you just wanna like go.

And you wanna hire and you wanna set quotas and you wanna do these things. I think it's important that you have some clarity and that you communicate really well to your team, to your reps, to, to, to whoever, like what stage you're in. Poor fire fuel on the fire. Once you have [00:17:00] clarity. Around what scaling actually looks like.

What does success actually actually look like? And you can replicate that. Don't just scale for the sake of scaling. You'll burn through cash. You'll you'll create a lot of problems for yourself. So make sure that you see scalability. So once it was about six months into it that I was like, okay, I'm seeing consistent behaviors from my reps, like what I can expect.

And, and then we started to put some quotas in place, like some specific metrics and KPIs that were proper expectations to push them. And now we are, we'll be probably eight to 10 AEs by the end of next year. Right now we're at four.

Benjamin Ard: Very cool. How long were you actually taking those sales calls when you joined Elements?

Jake Larsen: Well, how I basically January until. It kind of tapered off, like at the beginning, I wanted to get as much information as I possibly could. And then once I feel like I had, I felt like [00:18:00] I had some direction, I started to taper off. So doing demos and stuff on my own, probably like SEP October-ish.

So it hasn't been that long since I've completely stepped away. Now that I know that I, I feel like at least I have an idea of the pieces that need to be there to start to scale this. So, yeah.

Benjamin Ard: That's awesome. And how how do you work with marketing now? Do you have, what are your goals? What are the structures?

What are the handoffs? How does that whole relationship work right now at Elements?

Jake Larsen: Yeah. I've tried to take a lot of the lessons learned, especially with my experience at Weave, the latter half mainly and we have. Tried to stay really, really tight. I have, I had one sales leader I remember sitting in my room with, with him and the, it felt like it was you know, like sales is doing everything.

And inside I'm like, no. As soon as we have that, then it, it's gonna break. Right. And I want to avoid that like the plague. I asked my team [00:19:00] now to, I mean, Proactively as much as possible, we're trying to celebrate victories for every other department because we recognize that like without marketing, without product, without cs, like all those different things, we can't do what we're gonna do.

And so, Definitely trying to make sure that we have a culture within our organization that every goal that we hit as a sales team is a result of everybody at the company doing their part. So that's more from like a culture standpoint, is embedding that sense of team and gratitude and, and everything from the, the.

The very beginning. And then functionally we have a great leader on our marketing, on our marketing team. He is his name's Jeff Morgan. He's absolutely phenomenal. And similar to what I did with Monroe, we, we have specific. Targets that are revenue targets that we're working towards, and then we know that there's KPIs underneath those.

But those are all decisions that he and I make together. And as much as we are [00:20:00] expecting a lead or a quantity of leads or some initiative from marketing, I'm making a conscious effort to make sure that there's a sales initiative associated to that. So, hey, you're gonna do this. This is what I'm gonna commit to.

You're gonna generate this list for us to go after. Here's what we are gonna do. And it's holding each other accountable to that. So there's we, we try to keep any window for finger pointing or blame to, it's cuz at the end of the day, if we don't succeed, who's fault is it? It's not one person's right.

We all, we all miss. So that connectivity is, is really important to me, not just from the functional side. I feel like that functional side is talked about so much, but. The key, in my opinion, is on the culture and everybody knowing, like we joke around, I have four girls. Ben knows this at my house, a eight year old, six year old, four year old, two-year old, they're all girls.

So there's a lot of high school musical and stuff in my house. It just is what it is. And there's it, there's a high school musical thing. The song, it's like we're all in this [00:21:00] together, like that's like our theme song on our team. It was just like, we're all in this together and we make sure that that is embedded in everything that we do.

Benjamin Ard: I love it. Yep. I know that feeling. We've got four boys just about, so we are complete opposite of you guys, but, so no high school musical in your house, I'm sure. No, not quite yet. But we'll see where it goes. So how do you guys look at data? In the last podcast we talked a lot about data alignment, definitions, scenes of that nature.

Throughout your whole career, when have you seen. Data helping the alignment. And when have you seen data hurt the alignment between the two teams of, of marketing and sales?

Jake Larsen: That's a great question. When have I seen it hurt and help? The, the hurt? So I'll start with the hurt side of things, cuz I feel like there's more of that.

Like once you find the good, then you stick with the good, right? So you go through more bad stuff to find the good So the first thing is making sure that the sources of truth, like everybody's pointed [00:22:00] at the same place. I think a lot of the friction that can occur is typically misunderstanding.

I think most of the time everybody has good intentions. There's been very few people that I've worked with that are just. Bad people like there? I don't, I, there's probably only a few of those. So most of the time everybody wants to help at each other. But I have seen often where one person looks at one report or one piece of data.

And another looks at another, and they both think that they're true. And so they're, and then as soon as something comes together where they find where the error is or what their perception was versus what your perception was like, that is the key thing. The, probably the biggest hurt that I've seen is just misalignment and misunderstanding.

And maybe people with a lack of willingness to like be, be wrong. Like, oh my, I was looking at the wrong thing, or there was something wrong with the way that I was thinking about this. So I'd say that was, that was the first thing, [00:23:00] obviously with the alignment of what your goal is, what, what number is your key number.

I mean, early on in weaves right there, there was a lot of focus on number of leads and those types of things. And and. Then it wasn't about quality. And then, you know, there all that stuff, I'm sure every leader out there has probably seen those same pro problems occur. So that would be the, the first thing that I would say is just making sure that you are aligned and actually understand where each other are coming from.

What did I see that was, was really healthy? Man, and Ben, you and I went back and forth on these things a lot, right? Like figuring out the, the best, the best way to track. The, I think the magic really happened at we've and even at Elements today, I think about some of the initiatives and things that Jeff and I are working on and I, I, I know I just keep coming back to the same thing, but we, we focus on the initiatives that are gonna actually move the [00:24:00] needle.

Like, we're not, it's not fluff, it's, it's what is, so if there's a, a campaign, we have specific metrics that we're, that we're both aligned that, hey, we think that it should be this. And then we're coming back and talking about, okay, what did we do? What did we not do? So I think it. As I think about like, what was successful, and I try to just kind of narrow it down to one or two things.

That, that just is what comes to my mind is being aligned towards the same, same goal and just taking ownership of the parts of that that, that you are responsible for. And Being humble to like admit when you're wrong and to collaborate and work together to fix things that are broken. So, I don't know.

I love it. Maybe not the best answer on the things that are right, but

Benjamin Ard: no, I think that's great. I think that's a great definition of exactly how to use data the right way.

Jake Larsen: Just sound like a broken record. I just keep saying the same thing. Well,

Benjamin Ard: I think it's important, obviously your relationship and your alignment of goals.

Your goals [00:25:00] are what drive your data. Right. And so if you're aligned with the goals you're collecting, hopefully the right data, and everyone's looking at the same metrics and they're aligned, and you can say, okay, what doesn't work? What does, and how do we replicate the successes? And how do we eliminate some of the failures and how do we try new things together?

And it takes a lot of trust. I mean, as a marketing and a sales leader to get in the same room. And you know, potentially, I'm guessing you're having conversations where the marketing leader says, I want to try this, and you're able to raise the red flag and say, you know what? I'm not sure that's gonna move the needle.

What if we try this or that? And having the trust and the alignment to say, okay, yeah, let's go and do that. You, you bring up a great point and no one's getting their feelings hurt, but they're feeling really collaborative and, and able to work together

Jake Larsen: on that note of trust. I ha the other thing, you gotta be able to, you have to put your own it.

You go aside and make the other person feel like a million bucks, right? Like, Make sure you give credit where credit is due. If [00:26:00] marketing was the reason that sales hit their number, the first person in the better stand up and thank marketing is the sales leader. Right? You've gotta, I've seen sales leaders that stand up and say, yeah, our team crushed it.

And the marketing person sit in the back, dude, what? Because we did X, Y, and Z. Like that fed you guys so much opportunity. Yeah, you closed it. But these were our, our campaign was so good. It did so much. So you gotta make sure that you recognize people for what they did, otherwise they're not gonna wanna continue to collaborate.

So I love it. I saw that happen a few times.

Benjamin Ard: Yeah. That's amazing. That's a great point. All right. The next question's kind of out of the blue. What what's your favorite book on either business or marketing or sales or anything of the sort, if you had to recommend. One book that people read, it could be something you read recently.

It doesn't have to be a favorite for anything like that, or even one resource, like one blog post [00:27:00] or podcast or whatever. What would you recommend people read, you know, just out of, of your experience, what's

Jake Larsen: really helpful? So I'll go first is favorite atomic Habits? Great James Clear so many good things, not just on an individual basis, but there's a lot that you can pull out for a team as well.

That's definitely a favorite. I would say, and we, and I know Ben's read this one too, it was actually something that we did at Weave. It was extreme ownership. I really thought that the principles there were very true about and I think it's just critical for people to, to own, to, to, to own their, their, their successes, own their failures, and be true leaders.

Benjamin Ard: So, so I guess one last question for you, cuz I think you have a unique, you know, experience and career. For someone going into a brand new startup, you know, even in today's economy where things are always [00:28:00] uncertain, and you know what? If you're in a brand new startup, it's always uncertain, and that's just kind of what you gotta deal with.

What did you tell yourself day in and day out to keep yourself motivated, even when it was tough because you've got no resources. You've got very few people there, you've got very little momentum. How in the world can you stay motivated to grind it out for the first two, three years or so that it takes before you get enough momentum that you feel like you're even at a legit business?

What did you, what did you do? What did you tell yourself to get through those tough times?

Jake Larsen: So I think that there's a handful of, of parts to this. I don't think that it can just be one thing. I think a really important part of this is making sure that you're aligned with the vision of the organization.

If there, if it's a mission that you believe in, if it's a product that you really believe in then I think that you can always turn to. What the value propositions are and really, and be excited about that. At We, I, I always [00:29:00] believed that the, the value that the actual software brought was, was critical.

At at Elements. Same thing. Products really good, but there's internal wise behind it. And for me it's always keeping in mind the, the why. I am, I'm, I'm blessed with a short memory. Like, I can move on real fast, and I think that that's necessary in any startup. But I think the key to that is understanding, like why, why are you in that to begin with?

If you're in there, just because you're hoping for an I P O or some exit someday, that's not gonna be enough to get you through. It's gotta be something deeper than that. And the last thing I would say is the people that you work with, the culture that's created. If you're a leader of a startup, You, you really gotta work hard on that culture and making sure people feel like they're a part of something, that they, that they have a role to play that they because that there's gonna be rough times.

And if there's someone that's that doesn't feel that way and things get [00:30:00] hard, it's gonna be a lot easier for them to bow out. But if they feel like you've got their back, if they feel like you're a team, if they feel like you're. That you're, that you care about them, then, then that can help the team as a whole get through.

So yeah,

Benjamin Ard: I love it. All right, Jake, thank you so much for being on the podcast. If someone wants to learn about Elements, how can they find your website or get in contact with you?

Jake Larsen: Go to getelements.com. Would probably be the best place. Our founder is really active on LinkedIn and on Twitter. His name's Reese Harper.

You follow his content. There's a ton of good stuff that's shared on there, but yeah, probably the best place if you just casually wanna learn about it. Go to get elements.com, take a peek, see what we're doing.

Benjamin Ard: Love it. Awesome. Well thanks for being on today.

Jake Larsen: Yep. Thanks Ben. See you man.

Benjamin Ard: hope you enjoyed the interview.

If you'd like to see the video recording of this podcast, go to getmasset.com Have a great day.