In this episode James Kaikis, Chief Revenue and Experience Officer at TestBox, sits down with Kyle Norton, CRO at Owner.com, to uncover how modern revenue leaders are driving transformative growth. Drawing from his experiences at Shopify and Owner.com, Kyle shares tactical insights on scaling SaaS businesses, fostering customer-centric growth, and building efficient, innovative teams.
Kyle opens up about leading Owner.com to a 10x revenue growth in just two years, leveraging unconventional strategies like centralizing lead research for BDRs and designing compensation plans tied to customer outcomes. He reflects on the critical importance of enablement, rev ops, and continuous learning in creating a high-performing revenue organization.
James and Kyle dive into the evolving role of CROs, why transitioning trust post-sale is essential for long-term success, and how businesses can avoid the pitfalls of “spreadsheet scaling.”
Key Takeaways:
Tune in for lessons on how to scale smartly, win in the margins, and create a playbook for SaaS success.
Kyle Norton is the CRO at Owner.com, where he champions growth for independent restaurants through direct online sales channels. With extensive experience in B2B SaaS and a track record of driving startup success, Kyle has held key roles at companies like Shopify and League Inc., focusing on go-to-market strategy and revenue growth. As a Limited Partner at GTMfund and Stage 2 Capital, Kyle brings his expertise in scaling SaaS companies and building customer-centric sales strategies, making him a sought-after leader in today’s competitive SaaS landscape.
Follow Kyle on LinkedIn: https://www.linkedin.com/in/kylecnorton/
Most companies get stuck in ‘spreadsheet mode’ when scaling sales, focusing on headcount and quotas instead of what drives conversion and customer value.
I believe in calling best practices ‘high probability practices’—what works in one context may not in another. Adaptation to the specific needs of your business is key.
I think we should be investing in these foundational functions much earlier than we are—RevOps, enablement. These investments make everything downstream better and ultimately drive sustainable growth.
Voiceover: What does it take to stay ahead in B2B SaaS? Welcome to The New Go-To-Market Playbook. I'm your host, James Kaikis, 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.
James Kaikis: Kyle, thanks for joining me today, man. It's so great to see you. 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 solution.
Kyle Norton: Wow, small world.
James Kaikis: 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 previously in person. I think we've talked throughout the years. You never know who you actually meet because you build relationships over time.
Kyle Norton: 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.
James Kaikis: I want to talk about you and your career. 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, thinks about the role, the function and you know the outcome is growth and and 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've approached business.
Kyle Norton: Appreciate that. Thanks.
James Kaikis: Why don't we start with you telling us a little bit about yourself your current role your current responsibilities?
Kyle Norton: So I'm the CRO at Owner.com. So we're you could think of us Shopify plus HubSpot for little tiny mom-and-pop restaurants like that the place you order pizza from on a Friday night, your favorite Indian food spot. 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 compete online. Been with the company for a little over two years, GTM Fund portfolio company, that's how I got introduced to them. Desperately wanted wanted in the roun, it was billed as the Shopify of Restaurants. I was at Shopify 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 Shopify. 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 a founder and a market and a product that has that special combination — you sort of have to take the leap
James Kaikis: Sounds like you were also the perfect person for that job as well.
Kyle Norton: Well suited.
James: So I want to talk about Owner.com, but talk to me a little bit more about your Shopify experience. You were pretty early there and saw massive growth.
Kyle Norton: So I was 2019 to 2022. In terms of headcount, I think they 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. We were all gas. Yeah, we went from five to almost 80 people in 18 months. But halfway through that was COVID aSo that whole thing blew up. And we thought that growth would go to zero. We would be bleeding customers like crazy. We actually paused our commission plan. We just said, we're gonna pay everybody their full OTE, no matter what happens because Shopify is a great company like that. But then we spent a couple weeks trying to figure out how do we take this massive crazy change and make it work for our customers and work for the business? And then eventually COVID sent Shopify on in this crazy run including the point of sale group because even though it was in person we could talk to those that needed to get online, had an in-person retail experience and we said that thing's gonna be closed for the next however many months. You might as well just move the whole business over. There's no change cost. That message really resonated. And so we, even the point of sale product, grew like crazy at that time
James Kaikis: And so when the Owner.com opportunity came up, you obviously had an aligned background, it sounded like a great company. What kind of growth has Owner.com gone through in your 2 years?
Kyle Norton: So we have grown revenue 10x in two years. On a nice run and we're growing at just as fast a rate today as we were 18, 20 months ago and with really good efficiency. So we feel like we're in a good spot. I'm as bullish on the company today as I was … well probably more bullish today than I was a couple of years ago.
James Kaikis: Considering how so many companies are struggling right now, right? To be in the position that you're in is pretty incredible.
Kyle Norton: Yeah. Good product, great team. It all starts with the founders. Do they have that force of nature to attract great talent and move a market? So that's certainly there.
James Kaikis: And as a CRO, what departments, functions. What do you oversee?
Kyle Norton: So I have demand gen/growth sales, so BDR a enablement rev ops partnerships, which is a big area of investment for us. And then our customer onboarding function. And then we hand off to CS and support from that.
James Kaikis: Got it. Okay. And how has that function changed over the two years? Has it always been like this or has it?
Kyle Norton: No, well most of that didn't exist two years ago. I inherited four reps, two of which were not a fit 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 40 and change. And then you've got all the other stuff.
James Kaikis: Yeah, that's a lot. So as a revenue leader and owning sales and taking over demand gen and marketing, right? How do you think about breaking away from some of the traditional norms of looking at marketing or growth or demand gen functions?
Kyle Norton: It's a hard question to answer. I think the biggest epiphany for me was, early in my career especially as I transitioned into SaaS, I was obsessed with best practice. A lot of my success in my early sales and management career was that I just read more than everybody and I applied those things really rapidly. Take a thing and apply it to my business, and then that started to served me a little bit less. And once I had had sort of broader ownership of things and it wasn't just sales anymore, but adapting I started adapting my blanket application of best practice and taking a more contextual approach. 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 get built. And it's just incredibly applicable to go-to-market. And so there's a book called Range by David Epstein. And he talks about why generalists rule the world. You're pulling from a broad set of mental models and ways to solve problems. And I think that has been an advantage for me because, you know, 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 arts academy that I owned and then I've had operations functions and CS. I 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 just made it up. That's probably why it's cool though. It makes sense. 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 mid-market or enterprise oriented business. And so like forecasting, I don't run a bottoms up weighted commit, tell me what's coming in. You can’t do that in SMB. But that is a best practice in a high-performance enterprise organization. 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 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.
James Kaikis: I love that response and Range is a great book. Big fan of that book and that concept generally. 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 SaaStr right now and I went to I work at SaaS right now and I went to Jason Lemkin's presentation yesterday about hiring a VP of sales. And one of his slides was like, hire a VP of sales that 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 hasn't been the norm and why does it need to be the norm moving forward?
Kyle Norton: 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. And if you want to narrow down your search to I want people with domain experience, I want people who understand the customer's problem, that becomes really hard in finding a good revenue leader that 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 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 curious, learning -oriented individual, but it depends on the market. It really depends. You could come into our business knowing very little about digital marketing and figure out pretty fast. It's not super complex what we do. If you were in a business selling to DevOps and security folks, I would certainly prioritize that. So like all things being equal, yeah, higher 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. It’s one thing to hire for it. I'm not as like bullish as Jason is, I think it's good if possible. I'm not as hung up on it. I certainly agree with the CRO or the revenue leader they have to understand the customer first the then the problem you're solving and how the product works and it solves that problem. It's really important.
James Kaikis: I'm really glad you bring this up. It's been an important topic of my general thesis and premise. I feel that in SaaS and software the last decade we've lost sight of the customer. Yeah, would you agree with that?
Kyle Norton: Yeah, I mean, we've just gotten obsessed with growth. 100%. Yeah. And that has led to some bad behaviors. And 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.
James Kaikis: Yes. That's a great call out. And when I think about the modern go-to-market and how it is evolving, I think sales leaders, especially revenue leaders and CROs have to have a point of view, and you have to understand the customer first. No longer can just be a forecasting leader, right, in 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 going to be happening more and more in SaaS. And I think that changes the profile of what happens with the CRO. Do you agree with that? Do you disagree with that?
Kyle Norton: I think fundamentally I agree that it should be the direction people go. I don't know if there's enough leaders out there that can do it.
James Kaikis: Yeah, I think that's a really interesting concept generally is that if we think about some of the shifts and go to market that's happening, even at TestBox we did role consolidation. We have full cycle solution architects and you deliver what you sell. And there are not that many folks who have that type of expertise, right? And I think that that's gonna continue to happen across good markets. So I'm glad you're bringing 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. And I love one his best quotes:it's what you learn after you know it all that counts. 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. As long as I've known you, enablement has been super core to what you do. And for you to go through the growth that you have at Owner.com, you've had to have a pretty sophisticated point of view and intention in how you approach learning and enablement. So can you generally talk about that?
Kyle Norton: I think that we under invest in these functions in general. Like I think that 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 really pipeline generated times a conversion rates and there's some function 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, more reps. My opinion is that we should be investing in these other foundations much earlier than we are. And so like RevOps is the big one. I'm always pushing people to hire Revops earlier than they do, because it makes everything downstream better if you have a good Revops leader. So coming back to your question about the need one, yeah, I have consistently made 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 we don't have a structured way to teach the sales system that we want. Now you're like nine months behind because 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. By that point you're out of time. And everything starts falling apart. So like, that early investment in enablement is important, and just in general, as a principle, you know, like, I believe that growth is the thing that differentiates the growth and learning of 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 need somebody dedicated to that function.
James Kaikis: There are so many things that I want to take in on that. One of the things that has always irked me a bit about enablement is that sometimes that the function has been more of a communication function than an actual empowering function. And I worked at Showpad in the sales enablement space. So we always had a point of view. And so for you, and you said 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.
Kyle Norton: So there's a lot. I'm trying to figure out where I want to go with this.
James Kaikis: Give me one thing that’s really made an impact.
Kyle Norton: Yeah, your preamble there is worth double clicking on. Enablement is often this communicator, certification. It becomes a bureaucracy. A lot of enablement is bureaucratic. And I believe the function of enablement is incredibly important, but I think as a group, as an industry, it's not a very well done craft. And so what I've traditionally done with enablement leaders is just find people that 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 leadership mentality first. I would say this is the number one thing for both revops and enablement. And do they solve problems from the top down and think about what data do I need to serve my desires? Okay, I'm gonna make a required field, required field, required field. And now closing a deal is like a hour and a half process. Same thing with enablement. 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 perspective of the business versus, okay, 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 traditionally, especially Shopify. I was constantly pushing and pulling, where there was a larger apparatus, to say this doesn't serve the rep. Or like, this needs to be re architected in a way that they're going to be excited about. If they're doing things because they're checking a box, then enablement has gone wrong. But if they're walking out of this training and you're getting slacks that are that people and are excited - that’s it. A manager was sharing screenshots from their newbie rep four days in and they're talking about my enablement leader and saying things like, “Rob's a legend,” “this was great.”
James Kaikis: And I'm really glad that you bring that up because I tend to think that enablement is is has historically been this like one-time function. We train people one time. We've checked the box. 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, because you talked about growth and growth mindset a little bit earlier, and so how do you go and hire your reps to make sure that they have that growth mindset?
Kyle Norton: 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. So we have an interview scorecard and depending on the role, like 50 to 65% of that scorecard is just like traits and they're things that are fairly difficult to teach. Do you have drive, 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 hire against, what are the questions that go into the interview process and then as a leader, we're very intentional about how we teach people to run these interviews. 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 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 that at the end and 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 call? And somebody would be like, oh, I would prepare more. Not a good answer. I just gave you the things that you should do different and it seems silly, but that tells you so much about somebody's interest in other people's feedback and and ideas if they don't instantly say all the things you said or as soon as you said it I was kicking myself, you know they aren’t interested. I really specifically architected those opportunities to learn about the candidate. Like what made you successful and why and how did you learn that and what was the process of getting better and so we really pick away at that stuff. Even when I interview VPs of sales. I hired a VP of sales six months ago and same sort of thing. I want to understand the learning mindset. We did a role play where I was the sales rep, he was the manager, he was coaching me on this, like I sent calls, so he reviewed all the calls and then ran this coaching meeting 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, I gave them feedback, run it again. How well can they as a VP sales candidate, how well can they incorporate that feedback? Are they interested in that feedback? Do they have follow-up questions on that feedback? And sure enough, when I give Brett feedback in the role now, like I see it within days. You know, that coachable mindset and that learner's mindset has to be talked about.
James Kaikis: 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 you approach this 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. I love that. Was that inspired by Mark Roberge and some of this thinking?
Kyle Norton: Yeah, my original hiring framework was all Sales Acceleration ripoff. I had just moved into SaaS and so I stole the whole thing and now I've added a couple things and made it your own made it my own but 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 the importance of scorecarding and the halo and horns effect. So being really rigorous in how a scorecard is architected and being like diligent about assessing like the exact trait that you're hiring against, like again, it's just attention to the 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 and write all this stuff out and make sure it's great and review it every couple months and people just don't want to do that hard work.
James Kaikis: It takes intention and 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 gone to know some of the Stripe leadership team through SignalFire as well. And that was really the feedback they gave me. It's like when they scaled and how they were able to keep such a high profile was like being very very rigorous about 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. So like you're never comparing on an even line, you know?
Kyle Norton: It's really challenging and you have new managers and you know, in the really early days, I ran every single interview. You can assume, and nobody's gonna be perfect, but like, you're assuming your standard is gonna be the best. And then you bring in now 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 the VP will review those recordings and make sure and we're trying to find a way to do this with AI now to figure out if all those questions were asked in the same language that they're written in the template. So we're trying I'm trying to like learn figure out how to do this at scale now.
James Kaikis: Yeah, that's really interesting and I think that dovetails well into a question I want to ask you about AI's impact. How do you think AI is going to impact you as an executive, but also your sellers and your frontline leaders out there in the field?
Kyle Norton: Yeah, so I use ChatGPT every day. Just for my like general stuff. It's hard to describe like where I use where I use chatGPT just like just sort of always, you know, I'm speaking at SaaStr tomorrow and to prepare my speaking notes, I just pitched the deck out loud with a GPT voice going and I said, I'm gonna 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 as opposed to going slide by slide and what am I gonna say and then writing it out and it was great. And like books, if there's an old book that I want to go back to and I can't really remember I upload the PDF into ChatGPT and now you can RAG search. 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 remember. I stole this from Ryan Staley, but he was like the easiest way to get people to start using AI is just have them replace Google searches with ChatGPT. I was trying to figure out a formula in Excel. ChadGPT 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 we don't really use AI to carpet bomb our industry with crap messaging. I think that's short term-oriented and not all that durable of an advantage. So we've actually just used AI predominantly internally. And this is because I believe that the quality of data that you have access to that you're gonna layer AI tools on, that's gonna determine how successful you are with those tools, garbage in, garbage out. And so we use Momentum, for example, to capture information from sales calls 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 have a machine learning model that does lead scoring and enrichment. We use AI in our onboarding function to write, website copy, and do a bunch of stuff. So we have predominantly used AI internally. I continue to think that that's the most high leverage use case. You just saw Klarna saying that they're going to rip out Salesforce, because they built their own CRM with AI and then Workday. Well, because Klarna, they replaced, what, 40% of their support staff with AI Chatbot. And now they're rebuilding their SaaS tools. But again, that's mostly internal, internally oriented. We were also using AI for support, chat support. It's arguably higher quality than human support. It's everywhere. And we continue to look hard for opportunities while all collectively trying to avoid chasing shiny objects. Because it's really easy. I'm excitable. I like new technology. I've been early on a bunch of these big trends which has been a competitive advantage for me. But the other side of that is I can get overly interested in the new stuff. I still take all these demos myself. I take two, four demos a week with companies. It's worthwhile. I want to see what's going on, I want to see what's happening. And most of them, it’s pretty thin. But there's some really interesting ones.
James Kaikis: I want to ask you about the future of sales rep. I feel like if you're on LinkedIn nowadays, you take some big swing at a topic and it goes viral. But how do you see the role of the sales rep changing over the next couple of years? And the reason I asked this question is when 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 of years look like?
Kyle Norton: Not to be a contrarian, but I don't actually think the role of a rep is gonna change that much. Like if you zoom out, it's not gonna 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 like 20 years ago, you were just calling out of a phone book or you purchased a database. It was 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 and now you're sending out hundreds of automated messages with sequences and follow-up every week. So 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 why now. And the rep's still going to do that. You can layer on all these cool AI tools and the reps will get a lot more efficient and you should have a lot happening in an automated fashion for them. But if you think of jobs to be done, is the job to be done by the rep, all that different? Sort of no. 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, how do you get rid of that? Lead research, none of our BDRs do lead research. It's 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 BizOps built an internal tool that looks at, through the Salesloft APIs, looks at the number of due 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, iRouting will put in 20 or 30 leads into the right cadences for the rep. So the next day, it's not even like they have to import to cadence or find the leads. No, it's just sit down and you've got your cadence. And so that's a good example of, did the experience of the rep change? Yeah, for sure, we've probably saved them two hours of 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 the role really is.
James Kaikis: I really appreciate that perspective because I think everyone wants to lean into like, "Oh, we're replacing humans, we're replacing this, we're 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 about. 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?
Kyle Norton: There's a few things that are unconventional that I don't want to give away. Not letting BDRs do lead research. Well not not letting them, but having BDRs not do any of their own lead research is surprisingly unconventional, but is definitely a thing we're gonna continue to lean into. We have a fairly unconventional comp plan now that we feel really excited about and is driving rep-customer-company alignment.
James Kaikis: Can you share any more details on that?
Kyle Norton: It's very much tied to customer outcomes. Even like sales leadership comp, I think a little bit differently about, and I think strapping a revenue executive with a 50 /50 plan is pretty silly, and I learned this lesson at Shopify, even though I sort of kicked and screamed about it when I originally got my offer. At revenue leaders on 50 /50 plans, like you can't help but think about what's right in front of you. Like as a first time VP of sales, when it was like 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's not that good. We're going really fast and loose. You know, we're agreeing to things that maybe we don't want to agree to. I think over time moving revenue leaders to a less highly leveraged plan would be smart. And 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 compromised 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. Even again, we made a fairly drastic change to the quality threshold that we wanted to close and so it was almost 40% of deals that we closed. We don't love the churn, we don't love the churn of those customers. Like they're fine, but we want churn to be world class and like these customers aren't gonna get us to world class. And so we said, we're not gonna do that anymore. And that was my suggestion. And for a revenue leader to say, I wanna sacrifice 40% of my number, maybe I would have done it if I was on a 50/50 plan, but probably not. Like it would have been so much more challenging. Having more company aligned plans. I think leaders especially are important, but that would be something else that's probably coming up for GTM orgs.
James Kaikis: I love that you brought that up and I'll say at TestBox, I have 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 value realization, everything post sale. My team is responsible for implementing everything that we sell, so if I sell a bad deal it's gonna create downstream problems for me. So we've gotten really great about the ICP. So yeah, I love that you've done that.
Kyle Norton: If you can you want your revenue leader to own onboarding. Because now that problem is this person's problem and 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 not your problem, when deals start blowing up and it's some other leaders problem that you don't have to look in the eyes as your direct report every single day, every single week, it's just harder to feel that same sense of accountability. And so I started owning onboarding early in my Shopify days. That's another, I think, really critical one. This is what we did, again, at Shopify. We had the Solutions Engineer stay all the way through implementation.
James Kaikis: I think it's the right move, and I've had a lot of people in my own profession disagree with me.
Kyle Norton: How unconventional is that?
James Kaikis: It's pretty unconventional. When you first start within a company, like when I was one of the first SE at Showpad, I was responsible for that. But then when the functions start to grow, you typically put a dedicated PS person and CS person. But then there's no accountability after the sale, right? And there's just like this handoff that you lob over the fence. This is one of my biggest things about tech generally, how can you leave and not have responsibility post-signature? You build all this trust. You spend all this time building trust, building a relationship, and then all of a sudden you just say, here you go, you're somebody else’s. And so I like to call it transitioning trust. You build the trust, you close a deal, but you're still involved. Like our account executives are full life cycle. They still own the account, and they work with our post-signature teams, because we don't call it post-sale, because there's always upsell, there's always expansion. That's a concept I keep pushing more and more. In at traditional mode, you close a deal and because they have trust with you, you think they have trust with your company and you know 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 and say here I am. Like where were you yeah during this whole time? It’s a trend that I'm staying trying to stay super on top of which is super interesting to me.
Kyle Norton: Yeah it's the right thing. Will people do it though? I don’t know.
James Kaikis: I think this is the crux of these conversations - I don't know that we will always have a choice in what we want to do here. I think that the market and forces are going to make this happen and we're going to adapt. Which is why digging into your thoughts on learning and growth, all of 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. Because the customer is now back at the center of everything that you do and that's gonna mean that you have to change. Not every company's gonna be able to run the same playbook that they've been running and be successful.
Kyle Norton: When you don't get 115% freebie NRR, the customer starts to matter a lot more. So we're in a very new world in that way and I think it's producing positive outcomes and hopefully we won't forget those lessons.
James Kaikis: I hope so. Kyle, it's been awesome talking to you. I really appreciate you. You've joined 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 continue on your journey.