Lessons in Scaling with Kyle Norton

What does it take to stay ahead in B2B SaaS? Winning in the margins. Welcome to the new Go to Market playbook. I'm your host, James Caicus, Chief Revenue and Experience Officer at testbox. In our interview series, I sit down with Go to market operators, leaders and industry experts who are defining the next era of Go to Market by winning in the margins. These leaders are focused on incremental innovations and non obvious advantages that drive big results. The goal of this interview series is for you to take action in your business. So sit back, grab a notepad and enjoy the episode. Kyle, thanks for joining me today, man. It's so great to see you.

Yeah, man, appreciate the invite.

Yeah, you know, I was thinking about today and I was thinking about how I know you. And what you don't know is that this interview is being recorded five years to almost the day when we actually interviewed when you were at Shopify for your solutions.

Wow, small world.

Isn't that crazy?

That is.

So this morning I was thinking, I was, I was prepping for our conversation today and I was like, oh, the first time I talked to Kyle, I was in Hawaii for my daughter's birthday. And I was like, wait, that's this week because I'm going to Hawaii after this, see my daughter for her birthday. And I was like, wait. And I looked through my emails and five years ago today we were emailing to schedule to meet two days from now. Wow. Isn't that crazy?

That is crazy. Small world. Five years.

Just goes just like that. Right, right, like that. And it's funny because I think officially met you in person was at the Go to Market fund event, but I thought that I had met you.

Yeah.

Previously in person. I think we've talked throughout the years.

Yeah, yeah.

You know how Covid is right now. You like never know who you actually meet because you build relationships over time.

I was just having this conversation last night with a bunch of people that I've known for years now and I've never, never met in person.

Yeah, no, it's. It's really interesting. And you know, I want to talk about you and your career and you know, I remember when I first met you and interviewed with you, I was like, wow, this guy is different. Right? This guy thinks about revenue the right way, you know, thinks about the role, the function and you know, the outcome is growth and you know, revenue for the business. But there's so many things that happen with intention that go into it ahead of time. And I really want to dig into that with you. I respect the hell out of you for the way you approach business.

Appreciate that. Thanks.

Why don't we start with like, tell us a little bit about yourself, your current role, your current responsibilities.

So I'm the CRO@owner.com so we're. You could think of us. Shopify+HubSpot for little tiny mom and pop restaurants. About that. The place you order pizza from on a Friday night. Your favorite Indian food spot. Take on delivery heavy concepts. And we do everything from website, online ordering, custom branded app, email and text message marketing. Like everything in this suite of tools you need to grow a restaurant and particularly compete online. Being with the company for a little over two years. GTM fund portfolio company. That's how I got introduced to them. We desperately wanted in the round and you know, Shopify restaurants. I was at Shopify. Yep. At the time. So spent some time with the founder to convince him to take our money and it's been a fun ride since then. It was very difficult to leave shop.

Yeah.

Did not really want to. And the timing was horrendous because I just had my second kid and so I was not looking for a change. But when those opportunities arise with, you know, a founder and a market and a product that, you know, has that special combination, you sort of have to take the leap and sounds like you.

Were also the perfect person for that job as well.

Well suited.

Yeah.

It's been going okay.

Yeah. So talk to me a little bit about. I want to talk about owner.com but.

Talk to me a little bit more.

About your Shopify experience. Right. You were pretty early there and saw massive growth.

Yeah, not that early. So I was 2019 to 2022 in terms of headcount, I think there were like 8,000 when I started and maybe 15,000 when I left. Something like that. But a very interesting point of time because I had nine months pre Covid. I ran the point of sale group, the go to market function for point of sale. So it was a go to market team. Completely hived off from the other existing sales and go to market function for the plus product. You know, we were all gas. Yeah. We went from five to almost 80 people in 18 months. But halfway through that was. Was Covid and point of sale in person. So that whole thing blew up and we thought the. We thought the. That growth would go to zero. We would be bleeding customers like crazy. We actually paused our commission plan. We just said we're going to pay everybody their full OT no matter what happens. Because Shopify is a great company like that. Yeah. But then we spent a couple weeks trying to figure out, okay, how do we take this massive crazy change and make it work for our customers, make it work for the business. And then eventually Covid sent Shopify on this crazy run, including the point of sale group, because even though it was in person, we could talk to businesses that needed to get online, had an in person retail experience. And we said, well, you know that thing's going to be closed for the next however many months. You might as well just move the whole business over. There's no change cost. And so that message really resonated. And, and so we even the point of sale product grew like crazy at that time.

And that's incredible. And so when the owner.com opportunity came up, you know, you obviously had aligned background, sound like a great company. What kind of growth has owner.com gone through in your tears?

So we have grown like revenue 10x in two years on a nice run. And we're growing at like just as fast a rate today as we were 18, 20 months ago. And with like really good efficiency. So we feel like we're in a good spot. I'm as bullish on the company today as I was probably more bullish today than I was a couple of years ago.

So considering how so many companies are struggling right now. Right. To be in the position that you're in is pretty incredible.

Yeah. Good product, great team. You know, it all starts with the founders. You know, do they have that, do they have that force of nature to attract great talent and move a market? So that's certainly there.

And as a CRO, like what departments, functions, what do you oversee?

So I have demand, gen, slash growth, sales. So BDR A enablement, rev ops, partnerships, which is a big area of investment for us. And then our customer onboarding function.

Yeah.

And then we hand off to CS and support from that.

Got it. Okay. And how has that function changed over the two years? Has it always been like this or no?

Well, most of that didn't exist. Yeah. Two years ago I inherited four reps, two of which were not a fit. Yeah. And. And a manager. And those three people are still with the business and doing awesome today. And then we had to scale it up from there. So the team was like, I inherited five, two we parted ways with and now we're like 100 people in our function. So sales is probably like 60, 70 folks.

Okay.

No, sales is call it 40 and change.

Okay.

And then you've got all the other stuff.

Yeah, that's a lot. So, you know, as A revenue leader and you know, owning sales and taking over demand gen in marketing. Right. How, how do you think about breaking away from some of the traditional norms of looking at marketing or growth or demand gen functions?

It's a hard question to answer. I think the biggest epiphany for me was you know, early in my career, especially as I transitioned into SaaS, I was just obsessed with best practice. You know like a lot of the, a lot of my success in my early sales and management career was I just read more than everybody and I just applied those things like really rapidly. And so I was like okay, like take a thing, apply it to my business. And then that had served me and then at some point that started to serve me a little bit less once I had had sort of broader ownership of things and it wasn't just like it wasn't just sales anymore. And I don't know who, who where I learned this but adapting my like blanket application of best practice and taking a, a more contextual approach. Yeah. And so I still read a ton and I think the reason that we do things, we do a bunch a little bit different is like I read a lot of different things and I try to learn about a lot of different crafts. Like I've spent a lot of the last few years learning about product and product management and how products getting gotten built and, and it's just incredibly applicable to go to market. And so there's a book called Range by David Epstein. Great book. Yeah, incredible. And he talks about why generalists rule the world, why people, you know, you bring, you're pulling from a broad set of mental models and ways to solve problems and, and I think that has been an advantage for me because you know I've, I've run sales for a long time but then I was a small business owner and I had to build my own website and stand up a CRM for this mixed martial arts academy that I own. Cool. And then I've had operations functions and CS and I just think like being open minded and trying to learn from everything from everywhere has been an advantage. And I now try to call best practices high probability practices.

I like that I haven't heard that before.

I like that I just made it up.

That's probably why I make sense.

And because it's not the best practice.

What is the best practice?

What I do in my SMB business is not the same that you'll do in a more mid market or enterprise oriented business. And so like forecasting, like I don't run a bottoms up Weighted commit. Oh, tell me what's coming in this. You can do that in smp, but that is a best practice in a high performance enterprise organization.

Yeah.

So some of these things don't work for your business or your leadership style or your market or your company stage. And so part of why I've done a lot different and like why, why we have fairly novel approaches is just a very broad approach to learning and applying that with an open mind and to the context of the business.

I love that response and Range is a great book. Big fan of that book and that concept generally. Right. No pun intended. Because I would say that even for my own career. Right. I've been a bit of a generalist.

Right.

It's actually done well. It's worked out really well for me and I'm curious to dig in a little bit on the product aspect. So we're at SASTA right now and I was mentioning that I was at Jason Lemkin's presentation yesterday about like hiring a VP of sales and one of his slides was like hire a VP of sales and understands the product. And I would say coming from a solutions background, that has not been the norm in SaaS. So why do you think that that hasn't been the norm and why does it need to be the norm moving forward?

I don't think it's been the norm because it's really hard. It's hard to find a good VP sales. It's hard to find good sales reps. Yeah. And if you want to narrow down your search to. I want people with domain experience. I want people who understand. Yeah. The customer's problem, that becomes really hard. And finding a good revenue leader that you're, you know, you've got an alignment of leadership values and they have the craft and the skills and the track record and then now you want them to know that thing. That's probably why it doesn't happen. If you can find it, it's great. Somebody who, who gets the customer and maybe has that domain experience. I think people can learn it. Personally, I think you can fall in love with the problem if you have a, like a curious, learning oriented individual. But and depends on the market, you know, like it really depends. You could come into our business knowing very little about digital marketing and figure out pretty fast it's not, it's not super complex what we do. If you were in a business selling to DevOps and info like security folks. Right. You need an incredible depth and I would, I would certainly prioritize that. So like all things being Equal. Yeah. Hire the domain experience. And I think maybe one of the things that I've heard Jason talk about is related to this is they have to learn the product.

Right.

There's one thing to hire for it.

Yep. Yep.

I'm not as like, I'm, I think it's good. If possible. I'm not as like hung up on it. I certainly agree with the CRO or the revenue leader. They have to understand the customer first, then the problem you're solving and how the product works and solves that problem. It's. It's really important.

Yeah. And I'm really glad you bring this up and it's been a important topic of my general thesis and premise. Right. Is that I feel like in SaaS and software the last decade, we've lost sight of the customer. Yeah. Would you agree with that?

Yeah. I mean we've just gotten obsessed with growth. I mean 100%. Yeah.

And. And that has led to some things got easy. Things got easy.

And I think that issue of we lost sight of the customers just downstream of things were really easy. So all of these things got worse.

Yes. That's. That's a great call out. Right. And I, I think when I think about the modern go to market and how go to market's evolving, I think sales leaders, especially revenue leaders, heroes have to have a point of view and you have to understand the customer first. You no longer can just be a forecasting leader. Right. And forecasting culture, you have to understand the entire journey because role consolidation is happening. And so, you know, CROs are now being more and more responsible for solutions, for customer success, for things post sale. And I think that is a trend that's going to be happening more and more in SaaS. And I think that changes the profile of what happens with a CRO. Do you agree with that? Do you disagree with that?

I think fundamentally I agree that it should be the direction people go.

Yeah.

I don't know if there's enough leaders out there that can do it. Yeah.

I think that's a really interesting concept generally, is that if we think about some of the shifts in go to market that's happening even at test box. Right. Role consolidation, full cycle solution architect. You deliver what you sell. Right. And that there are not that many folks who have that type of expertise. Right. And I think that that's going to continue to happen across go to market. So I'm glad you bring this up because your concept and viewpoint of learning is something I've always admired. Right. Because I think too many People think that they know it all. Right. And I'm a big John Wooden fan. Yeah. And one of his best quotes is, it's what you learn after you know it all that counts.

Yeah. Yeah.

Right. And I think that general concept is what more leaders will need to lean into. And so I'm curious for you because let's talk about learning. Let's talk about enablement. That's as long as I've ever known you. Super core to what you do.

Yeah.

And for you to go through the growth that you have@owner.com, you've had to have a probably pretty sophisticated point of view and intention and how you approach learning and enablement. So can you generally talk about that.

Would even expand that opinion to be. I think that we underinvest in these functions in general.

Sure.

Like, I think we. Because you get into spreadsheet mode, like the thing that drives growth is number of reps times quota equals whatever. And we know that that's not what it is. It's. It's really pipeline generated times a conversion rate. And there's some function in that, in that equation that is, you know, the number of reps needed to drive that conversion rate to handle that volume of leads. So we just get into the spreadsheet mindset of scaling sales teams where we just obsess about like more reps. More reps or more reps. My opinion is that we should be investing in these other foundations much earlier than we, we are. And so like Rev Ops is the big one. I'm always pushing people to hire Rev Ops. Love that earlier than they do. Yeah. Because it makes everything downstream better if you have a good Rev Ops leader. So coming back to your question about enablement. Yeah. We, I have consistently made like early investments in enablement because if you're playing the traditional venture game where you're trying to be fairly aggressive, then what you find is you run out of time. Like by the time you have 15 AES in seat and the conversion rates are mediocre, you're like, oh, because our onboarding plan isn't very good and nobody knows the product and, and we don't have like, you know, a structured way to teach the sales system that we want. Now you're like nine months behind because you can't, you can't find a great enablement leader and then have them come in and learn. It's a very high context role, learn all of this stuff and actually build and deploy and then change behavior.

Sure.

You just, you're, you're you're out of time. And so you end up in, you end up where a lot of companies see like a ton of growth. Do they hit some rep number where the, the leader can no longer influence every deal or every person individually and everything starts falling apart. So, so like that early in investment and enablement is important and just in general as a, as a principle, you know, like, I believe that growth is the thing that differentiates. Growth and learning are the things that differentiate the individual and their success, the team and their success. So if you want to have an awesome learning and growth culture, you, you need somebody dedicated to that function.

Okay. There are so many things that I want to take in on that. I love that. Right. One of the things that has always irked me a bit about enablement is sometimes that the function has been more of a communication function than an actual empowering function. And I worked at Showpad, right in the sales space. Right. So like we always had a point of view. And so for you and you said, like hiring the right enablement leader, what are some of the things that you do to make sure that that enablement function is delivering value and is not just communication per se.

So there's a lot I'm trying to figure out where I want to go.

Let's tell one thing, one thing that's really made an impact.

Yeah, your preamble there is worth double clicking on. Like, enablement is often this communicator certification. It is, it becomes a bureaucracy. A lot of enablement is bureaucratic and I believe the function of enablement is incredibly important. And I, but I, I think as a, as a group, as an industry, it's not a very well, it's not a very well done.

I could agree with you craft. I could agree.

And so what I've traditionally done with enablement leaders is just find people that like, do understand the craft. They've carried a bag, they know how to sell, they care about sales. They're not like an extension of hr learning and development. These are people that really understand the day to day think from a servant mentality, from a servant leadership mentality. First, I would say this is the number one thing for both rev ops and enablement is like, do they solve problems from the top down and think about, you know, what data do, what data do I need to serve my desires? Okay, I'm going to make a required field, required field, required field. And now closing a deal is like an hour and a half process. Right? Same thing with enablement. Uh, we want demos to be run In a more consistent manner. Have them do a certification and do this big song and dance and it's about problem solving from the, the perspective of the business versus okay, like what does this rep need? How can I make this reps day to day better? How do I equip them to do things? And I actually don't need to do it much. Today I have an awesome enablement leader but fantastic. Traditionally I'm all especially shopify. I was like we're where we were pulling where there was a larger apparatus. You're constantly pulling and pushing. Be like okay, this, this doesn't serve the rep. Yeah. Or like this needs to be re architected in a way that they're going to be excited about. Like if they're.

It's great clout.

If they're doing things because they're checking a box, then enablement has gone wrong. If they're walking out of this training and you're getting slacks that are, that people are excited. Oh man, I wish we had done this earlier. I'm going to go back to these deals like that then that's a high bar. But it is very much possible.

Yeah.

A manager was sharing screenshots from their newbie reps four days in and they're talking about my enablement leader was running a thing like Rob's a legend. This was great. I'm like, like they're stoked. Love that that needs to be the bar has to be and it's almost never.

And I'm really glad that you bring that up because I tend to think that enablement is. This has historically been this like one time function. Right. It's like all right, we train people one time, we've checked the box, move on. But enablement and success is ongoing. Right. It has to be continuous learning. And I want to shift our focus a little bit around sales and the sales rep and kind of the future of sales. Right. Because you talked about growth and growth mindset a little bit earlier. And so how do you go and hire for reps to make sure that they have that growth mindset?

It's a part of our framework. So the first thing you have to do with any hiring at scale is get really specific about what you're looking for. And so we have a interview scorecard and 50 to 6 depending on the role, like 50 to 65% of that scorecard is just like traits and, and they're things that are fairly difficult to, to teach. Do you have drive? Do you have. Are you a curious person? Are you interested in learning Are you a lifelong learner? And then you just architect. Okay, if this is one of the top five most important things to, to hire against, what are the questions that go into the, into the interview process? And, and then as a leader, we're like very intentional about how we teach people to run these interviews. Yeah. So it's the same questions in the same order. They've got prompts. And I explain why these questions are asked in this way. And they'll, there could be little things. So like in the case study, for example, they'll do a mock call and then the manager, the interviewer will give them feedback and then they'll do it again. And then after, at the end you say, okay, cool, awesome, good job. Here's some good things. So let me ask you if you could do it all again, like, what would you change about this mock?

Love that question.

And some people are like, oh, I would like prepare more. Not a good answer. Like, I just gave you the things.

That you should do different.

And it's, it seems silly, but that tells you so much about somebody's interest in other people's feedback and ideas. If they don't instantly go like, oh, like all the things you said. Like, I just, you know, as soon as you said it, I was kicking myself. So you, I really specifically architect in those opportunities to learn about the candidate.

Yeah.

Like what made you successful and why and how did you learn that and what was the process of getting better? And so we like really pick away at that stuff. Even when I interview VPs of sales, like I hired a VP of sales six months ago and same sort of thing. I want to understand learning mindset. He did a role, we did a role play where I was the sales rep, he was the manager. He was coaching me on this. Like we sent, I sent calls.

Right.

So he reviewed all the calls and then ran this coaching meeting. So where I was the rep and this was the call and he was trying to get me to do the thing. And even in that run it the first time I gave him feedback. Run it again. How well can that. There's a VP sales campaign.

Totally.

How can they, how well can they incorporate that feedback? Are they interested in that feedback? Do they have follow up questions on that feedback? And, and sure enough, you know, like when I give Brett feedback in the role now, like, I see it within days. Yes. You know, that's, that's, that's huge. It has to go like that coachable mindset. And that learner's mindset has to be top to Bottom.

Yeah, I love that. And as a solutions leader for most of my career, I would always ask the same three questions after every customer meeting. What did you do well? What didn't go well? And if you could redo that meeting, how would, how would you re. Approach the situation? And you're right. You learn so much about how people take feedback and how they think about how they should improve the approach because they always have to get better. They always have to improve. So I love that you've done that. Was that inspired by Marco Barish and some of his.

So I. Yeah, my original hiring framework was all sales acceleration rip off.

Yeah, it works.

2015 and I had just moved into SaaS and. And so I stole the whole thing and now I've added a couple things. And you made it your own. Made it my own. But it's still like that. I took the importance of scorecarding from him and then Danny Kahneman from thinking fast and slow when he talks about hiring for the IDF and like scorecarding and the importance of like halo and horns effect. So being really rigorous in how scorecard is architected and being like diligent about assessing like the exact trait that you're hiring against. Like again, it's just, it's attention to detail. It's systems engineering. And I think this is the thing that leaders just generally get wrong. It's hard. It takes a long, long time to sit down. It's hard. Write all this stuff out and make sure it's great and review it every couple months and. And people just don't want to do that hard work.

It takes intention. And you know, in sales and revenue generally we're always moving so fast. We're trying to do so many things. So take a step back and slow down. I really respect that. And I would say I've gotten to know some of the stripe leadership team through Signal Fire as well. And that was really the feedback they gave me is like when they scaled and how they were able to keep such a high profile was like being very, very rigorous about their hiring standards. Because I think like you just said, I would say a majority of companies from my experience are not keeping that level of consistency amongst interviews. So like you're never comparing on an even, even line. You know, it's.

It's really challenging and you have new managers and you know, in the really early days I ran every single interview y. You can assume and nobody's going to be perfect but like you're assuming your standard is going to be the best and then you bring in now a VP now managers. We're hiring directors right now. It's really difficult to make sure that at the manager level that consistency is there. And that's why we buddy up and that's why we record interviews and yeah, the VP will review those recordings and make sure. And we're trying to find a way to do this with AI now to. To figure out like did. We're all those questions asked like in the same language that they're written in the. The lever template. So we're trying. I'm trying to like learn. Figure out how to do this at scale now.

Yeah. That's really interesting. And I think that dovetail well into a question I want to talk to you about. It's like AI's impact, right. Like, how do you think AI is going to impact, you know, you as an executive, but also your sellers and your frontline leaders out there in the field.

Yeah. So I use chatbots every day just for my like general stuff. Yeah. It's funny, you know, it's hard to. It's hard now to describe like where I use. Where I use ChatGPT. Sure. Just like just sort of always, you know, I'm speaking at Saster tomorrow and to prepare my speaking notes, I just pitched the deck out loud with GPT voice going and. And I said I'm going to pitch you my slides, you know, take notes. And then it. It created all of my speaking notes so now I don't have to, you know, it took me 30 minutes.

Yeah.

And as opposed to going slide by slide and what am I going to say? And then writing it out and it was. It was great.

That's such an unlock.

Yeah. And so books, like if there's an old book that I want to go back to and I can't really remember, I like upload the PDF into Chat GPT and now you can rag. Search. Yep. And I can find. It's like give me the chapter by chapter breakdown. Oh, so it was in chapter seven.

So.

And then I can ask it questions about the idea. I'm trying to like re. Remember.

Love that.

And so it just all the time.

Always be more efficient generally. Right.

Yeah. And once you get in the habit. I don't know who I stole this from. I wish I could give them credit but. Oh, it was Ryan Staley.

Okay.

Yeah. He was like the easiest way to get people to start using AI is just have them replace Chat GPT, have them replace Google searches with ChatGPT.

I've heard that. Yep.

It. You just Build a new rhythm. And now, you know, I wanted to, I was trying to figure out a form, like I didn't know how to make a formula in Excel Chat. GBG told me in like two seconds.

So that's amazing.

Individually, it's sort of always on all the time. And then as a business we've done a bunch. So my opinion here is we don't really use AI to carpet bomb our industry with like crap messaging. I think that's like short term oriented and not all that durable of an advantage. So we've actually just used, we used AI predominantly internally. Okay. And this is because I, I believe that you know, the quality of data that you have access to that you're going to layer AI tools on, that's going to determine how successful you are with, with those tools. Garbage in, garbage out. And so we use Momentum, for example, to capture information from sales calls and, and add all of those things to custom Salesforce fields. We write custom prompts so that I'm continuously capturing way more data from unstructured sources like calls and putting it in. We use, we have a machine learning model that does lead scoring and enrichment. We use AI in our onboarding function to like write website copy and do a bunch of stuff. So we have, we have predominantly used AI internally. I continue to think that that's the most high leverage use case. Like you just saw Klarna saying that they're going to rip out Salesforce because they built their own CRM with AI and then workday. Yeah, well, because Klarna, they replaced what, 40% of their support staff with AI chatbot and now they're like rebuilding their SaaS tools. And so again, but again, that's mostly internal, internally oriented. We were also using AI for support.

Sure.

Chat support. It's like it's arguably higher quality than human.

I agree.

Support.

Absolutely agree.

It's everywhere. And we continue to look hard for opportunities while all collectively trying to avoid chasing shiny objects.

Sure.

Because it's really easy. I'm excitable, I like new technology. I've had, I've been early on a bunch of these big trends, which has been a competitive advantage for me.

Right.

But the other side of that is, yeah, I can, I can get overly interested in the new stuff, but at.

Least you get in and you test it before you're rolling it out. Broadly.

Yeah, yeah. I still take all these demos myself. I take two, four demos a week with companies.

Because it's a lot.

Yeah, 30 minutes.

Yep. You know, it's worthwhile.

Yeah. I Just want to see, I like, I want to see what's going on, I want to see what's happening and most of them, you know, it's, it's pretty thin.

Yeah, I can understand that one.

But there's some really, there's some really interesting ones.

Yeah. I want to ask you a little bit of question about future of sales rep. Right. I feel like if you're on LinkedIn nowadays you like take some big swing at a con, you know, a topic and it goes viral. But how do you see the role of the sales rep changing over the next couple years? And the reason I asked this question is one, we're talking about technology, we're talking about consolidated role function, we're talking about points of view. You're in vertical SaaS. Like what do you think the next couple years look like?

Not to be a contrarian, but please be a contrarian. I don't actually think the role of a rep is going to change that much. Like if you zoom out, it's not going to change much more than it has already changed over the last 20 years.

Sure.

If you think about the day to day of a rep, 20 years ago you were just calling out of a phone book or like you purchased a database, it was like pretty manual and then you got a CRM. Then data providers that made things a lot more efficient. Then sales engagement and acceleration tools came up. Now you're sending out hundreds of automated messages with sequences and follow up like every week. So you know the role of the rep has, the experience of the rep has changed a lot but the role of the rep hasn't really. What's the role of the rep? To spend time talking to high fit prospects, understand their business and talk about why you might be able to solve those problems in a unique and valuable way. And like why now? And the rep's still going to do that. You know you can layer on all these cool AI tools and yeah, the, the reps will get a lot more efficient and you should have a lot happening in an automated fashion for them. But does the role like, does the core role that if you think jobs to be done, is the jobs to be done of the rep all that different? Sort of. No. And if anything we actually just want to. A lot of my approach today is how can we take away the things that aren't in that jobs to be done, the non revenue generating activities. Like how do you get rid of that lead? Lead research. Like none of the BDR. None of our BDRs do lead research.

Great.

All Done centrally controlled by our data team. It's like scraped and scored lists with a cool down. And we go so far as our head of biz ops built an internal tool that looks at through the salesloft APIs, looks at the number of call do call tasks that the rep has. The next day we want them to make like 80 to 100 calls. So if they have 60 calls, then it's called I routing. Iroute will put in 20 or 30 leads into the right cadences for the rep. Wow. So the next day it's not even like they have to import to cadence or find the leads. No, it's just. Just sit down and you've got your cadence. I love that in front of them. And, and so that's a good example of did the experience of the rep change? Yeah, for sure. That's. That's sure. You know, like we've car if in SMB we've probably saved them two hours of, of like data entry and crappy work every single day. So their experience has changed a lot. But the role of the rep hasn't changed. We've actually just gotten them to spend more time on what, what the role really is.

I, I really appreciate that perspective because I think everyone wants to lean into like, oh, we're replacing humans, we're replacing this, replacing that. If you look at history, things always take a lot longer and it's always augmentation and it's always making us more efficient. So yeah. I've really enjoyed hearing your perspective and talking about this with you. I have one question that I'm really curious. Right. Is we talk about modern go to market evolving go to market. Is there one unconventional strategy that you're using today that you think will be more common in one or two years from now?

There's a few things that are unconventional, but I don't want to give away.

That's always the toughest thing, right? Yeah. Maybe more generally then like not letting.

BDRs do lead research. Not not letting, but like I was thinking, having BDRs not do any of their own lead research is surprisingly unconventional. But I would agree is definitely a thing like we're going to continue to lean into. We have a fairly unconventional comp plan now that we feel really excited about and is like driving rep customer company alignment.

Can you share any more details on that?

It's very much tied to customer outcomes.

Yeah, that's great.

Yeah. Even, even like sales leadership comp. I think a little bit differently about and I think strapping a revenue executive with a 5050 plan is pretty silly. And I learned this lesson in Shopify even though I like sort of kicked and screamed about it when I originally got my offer.

Yeah.

Revenue leaders on 5050 plans, like you can't help but think about what's right in front of you.

Yes.

Like as a first time VP of sales.

Yeah.

When it was, you know, close these deals and get to my number and be able to like not be in a financial pinch versus hey, like the deal quality is not that good. We're going really fast and loose.

Yes.

You know, we're agreeing to things that like maybe we don't want to agree to. I think over time moving revenue leaders to a less highly leveraged plan would be smart.

I agree.

And like technically that has not worked for me because like we've hit our number every month but one for the last like 20 months. So I have sacrificed income technically but like I'm making way better, more holistic decisions about the business that are long term oriented and I don't have to sweat that stuff. Agreed.

I'm on the similar comp plan and it makes sense.

Yeah. Even again we made a fairly drastic change to the quality threshold that we wanted to close. And so we was almost 40% of deals that we closed. We're like, yeah, we don't love the churn. We don't love the churn of those customers. Like they're fine. But you know, we want, we want Churn to be world class. And like these customers aren't going to get us to world class. And so we just said we're not going to do that anymore. And that was my suggestion. I love that. And to, for a revenue leader say to say I want to sacrifice 40% of my number, maybe I would have done it if I was on a 50 50, but probably not. I get it. It would have just been so much more challenging. And so the, the comp alignment like Robert just talked about this on the science of scaling a bunch, you know, having more company aligned plans or he talks about it with reps as well. I think leaders especially important. But that would be something else that's probably.

I love that you brought that up. And I'll say a test box. I have a, a similar comp plan where I'm not just incentivized on that new revenue and I didn't want to be. And because I'm responsible for solutions and, and value realization. Everything post sale.

Yeah.

My team's responsible for implementing everything that we sell. So I sell a bad deal. It's going to create downstream problems for me and I don't want to deal with those problems. Right. So we've gotten really great about the icp. So I love that you've done that if you can.

You want your revenue leader to own onboarding.

Yeah, I love it.

Just you just now that problem is this person's problem. And as much as we're. As much as you can try, it's like, no, no, no. I'm still going to close the right deals. When that team is like not your problem. When deals start blowing up and it's some other leaders that you don't have to look at the in the eyes as your direct report every single day, every single week, it just, it's just harder to feel that same sense of accountability. And so I started, I started owning onboarding early in my Shopify days and sure enough, sales alignment got better really fast.

Changes everything. Yeah, no, I love that and I appreciate that. I feel like I can have a whole, you know, interview with you on that topic. Right. Because even for us, when we made the full cycle move on essays, it just changed the viewpoint of like, oh, wow, I need to ask different questions in the sales process because I'm responsible for delivering this. Yeah, yeah, I Love that.

Yeah. Ses stopping it, stopping at the closed one is also. Doesn't make any sense.

I don't think it makes any sense.

That's another, that's another, I think really critical. And this is what we did again at Shopify. So we had, we had the solutions engineer stay all the way through implementation.

I think it's the right move. And I've had a lot of people in my own profession, you know, disagree with me.

And how unconventional is that?

It's pretty unconventional. Right? It's when you first start within a company, like when I was one of the first ses of Showpad, I, I was responsible for that. But then when the functions start to grow, you typically put a dedicated PS person, SC person. But then there's no accountability after the sale. Right. And there's just like this handoff that you lob over the fence and the relationship is.

Yeah, yeah, yeah. Okay.

This is like one of my biggest things about tech generally is like, how can you not leave? How can you not have responsibility? Post signature. You build all this trust. You spend all this time building trust, building relationship, and then all of a sudden you just say, I'm gone, here's somebody else.

Right.

And so I like to call it transitioning trust. Right. You like build the trust you know, you close a deal but you're still involved. Like our account executives are full life cycle. Right. They still own the account and they work with our, our post signature teams because we don't call post sale because there's always upsell, there's always expansion to continue to transition trust.

So transition trust.

Transition trust, yeah. That's a concept I think I'm pushing more and more. But yeah, that's why I like to call because think about it like a traditional mode. You close a deal and because they have trust with you, you think that they have trust with your company and you going to rebuild everything. So why not just kind of transition the trust through the rest of the org and get more and more people involved? Because I think personally it's like one of the most like clown moves of like sales rep sells a deal, they disappear and all of a sudden like 30 days left to renewal, they pop up. Okay, here I am. It's like where were you?

Yeah.

During this whole time? Right.

And so I have seven escalated support tickets that I need.

Yeah, yeah. So I think that's like this trend that I'm staying, trying to stay super on top of, which is super interesting to me.

Yeah, it's the right thing. Will people do it?

I agree with you and I think this is like the crux of you in these conversations is I don't know that we will always have a choice in what we want to do here. I think that the, the market and forces are going to make this happen and we're going to adapt. Right. Which is why digging into your thoughts on learning and growth, all that is super important because I think we're just going to see this new wave of go to market professionals all the way across, individual contributors, leaders. Because the customer is now back at the center of everything that you do.

Yeah.

And that's going to mean that you have to change. Not every company is going to be able to run the same playbook that they've been running and be successful.

When you don't get 115% freebie NRR, the customer starts to matter a lot more. So we're, we're in a very new world in that way and I think it's, you know, it's producing positive outcomes and hopefully we won't forget those lessons.

I hope so. Kyle, it's been awesome talking to you. I really appreciate you joining me and it's been great getting to know you over the last couple years. I really respect your leadership style and excited to see, you know, you continue on your journey. Thanks, man.

Appreciate it. Thanks for having me.