The 4 numbers every CRO obsessively tracks (Ignore the Rest)

Ever walked onto a sales floor that sounded like a finals match and felt the win before seeing a number? That’s the spark Thomas Waites chases and teaches. From first-employee chaos to CRO and advisor in enterprise SaaS, Thomas shares the hard-earned plays that turn culture into a revenue engine and alignment into speed.

We explore how founder-led sales creates empathy and faster decisions, then show where it must evolve for enterprise motion. Thomas explains why enterprise deals still close on emotion backed by proof, and how technical founders can shift from feature dumps to buyer-led discovery. We get practical on alignment: scrap conflicting incentives and agree on shared definitions so sales, marketing, and customer success pull in sync. He narrows the noise to four steering metrics —so every meeting focuses on what actually moves the number.

Chapters

• 0:00 Kicking Off And Guest Background
• 1:15 Falling Into Sales And First Startup
• 4:13 Early Growth Levers And Culture Shock
• 8:28 Teaching Culture, Early Hires, And Safety
• 10:18 From Solar To SaaS And Leadership Roles
• 15:18 What Founders Get Wrong In Sales
• 19:20 Founder-Led Sales And Empathy
• 22:05 Cross-Team Alignment And Shared Metrics
• 25:20 Building A Winning Sales Culture Daily
• 28:05 Fewer Metrics, Clear Comp, High Care
• 32:25 Retention, Land-Expand, And Pricing Power
• 37:00 People Management, Red Flags, Coachability
• 42:00 Resources, Live Call-In, And Parting Advice

Transcript

SPEAKER_00: 0:00

Looking back to those startup days, what were the biggest as opposed to card factors that you saw? What were the building blocks that you now look back on today and said it's why the company scales?

SPEAKER_01: 0:11

You have a lot of protection, you pour yourself into it, and you're just willing to figure things out. I think you can, even if you don't fully know what you're doing, I think you can figure it out for sales. Like you have to be energized, and like resilience is so important. Um, and if you have that sort of camaraderie and that team energy and everyone's excited, I think resilience is much, much easier. No matter how great people are, we're inherently going to be misaligned, right? And so I I think that alignment is so so important.

SPEAKER_00: 0:38

What are some other uh factors that you think type into being a successful B2B enterprise sales team?

SPEAKER_01: 0:44

I try to only focus on a few metrics. A lot of sales leaders they have like 20 different metrics that they're like tracking, and then they often lead to confusion, and it's hard to tell like what's like most important.

SPEAKER_00: 0:57

Welcome everyone to another episode of SARS Stories, the first one actually of 2026. And I'm really excited to be joined by Thomas Waite, CRO and GTM advisor at TW Sales. Welcome, Thomas.

SPEAKER_01: 1:10

Thank you for having me join us.

SPEAKER_00: 1:12

Absolutely. Glad to have you on the show. Now, let's start where I love to start at the beginning of your journey. Um, you've led multiple high growth sales teams as well as being part of multiple acquisitions as well. Um, what drew you to sales in the first place?

SPEAKER_01: 1:31

Oh, that's a good question. Um I think I sort of fell into it, like a lot of people do. Um, so I I went to grad school for finance and economics, and wow, that's change. Yeah, yeah, yeah, yeah, yeah. It's very, very different. Like I'm I'm like the black sheep of my of my peers, I suppose. So um, so yeah, so I I wasn't really sure what I wanted to do. And then um what I decided was that I wanted to work at a startup and uh and that I would sort of figure it out along the way. And so I joined as the first employee at a solar energy startup. Um so we're based uh in Canada and then also the United States, and we're selling into the the US market um in solar energy. And uh it was sort of like through, I don't know, like a series of events that within like six months of graduating, I ended up leading our sales, which was not uh at all like what I had expected to do. And I was like actually a little bit resistant to it, to be honest. Like because I didn't, you know, there's like stigma about being in sales and that sort of thing. Um and then that company was acquired by a nine billion dollar company in Silicon Valley and then just sort of took off from there. So it was a bit of a like a wild series of events in my first year of working.

SPEAKER_00: 2:49

Yeah, it's interesting. I think it's because you you did decide to work at a startup that they just threw every single job at you being the first employee. Like I just feel like when you work for a big organization, you're kind of in your box. This is your lane, this is what you do. When you're at a startup, you're everything. So and sales make sense. That's one of you know, the most important ways to grow a startup. So um you must have had a natural flair for it. So they they gave you the opportunity in Baresti's history.

SPEAKER_01: 3:19

Yeah, yeah. It was it's very interesting. It's like with startups, like when I when I mentor people, obviously startups aren't for everybody, but um, like nobody on the founding team really knew a whole lot about sales. And so sort of like in the land of the blind, the one-eyed man's the king kind of thing. And so I kind of knew I guess I knew a little bit more than everybody else, and and uh although looking back on it, uh still didn't know a ton, but I guess uh and had the interest in figuring it out, and then I ended up leading our sales. So yeah, it was it was a really cool opportunity that would only happen at a small startup like that.

SPEAKER_00: 3:52

Yeah. So in hindsight, looking back to the those startup days, um, what were the biggest, I suppose, growth factors that you saw? Like what did you have to do within sales? Who was the next hire after you? What were the building blocks that you now look back on today and said, this is why the company scaled?

SPEAKER_01: 4:13

Ooh, that's a good question. Um what it was sort of interesting at the time I was uh like in my first year or two, we were doing all third party sales. And so I was managing these like third-party sales all all across the United States. And so I had big call centers in Florida and Utah, and I had in-person teams, it was B2C. Um and so I had teams in like Massachusetts and California, and so I think the biggest thing for me was just like really, really heavily recruiting and having like a strong willingness to be kind of I want this to be taken the wrong way, but sort of like ruthless in terms of how I prioritize my my time, I guess. Right. And so, um, because I had hundreds, thousands of people, I suppose. And so um my teams that were performing well, I disproportionately poured my time into them and then also spent time with them to figure out because I was still learning, right? And and like how are they successful and and what are they doing to be successful? And then I would bring those to my other teams and and really just like empowering them and and and trying to recruit as quickly as possible and move as quickly as possible. And like it's it's sort of funny when I look back on it, because at the time I thought I knew what I was doing. Uh looking back on it, I probably didn't, but it went really well, you know, and and so I think just investing myself and putting that energy into it, I think uh especially with early days of a startup, if you have a lot of conviction and you pour yourself into it and you're just willing to figure things out, I think you can even if you don't fully know what you're doing, I think you can figure it out, sort of what happened.

SPEAKER_00: 5:52

Yeah, yeah, you absolutely need like a can-to attitude and you just need to be resilient, like mistakes are made, things aren't working, how do we bounce back and move on quite quickly? I think that's what startups have as an advantage um in the world of SaaS. But just coming back to to the the teams, especially those ones that you you invested your time in because they were doing well, what were they doing well? What from a sales point of view um did you find was effective?

SPEAKER_01: 6:21

Oh, uh really good question. Um so and and it really changed like I guess like my initial thoughts about sales and then how that evolved over time. Like, I think the biggest thing that I noticed with my with my teens that were because they were performing at like wildly different levels. Like it was like there was there was quite a bit of discrepancy between like my top performers and then my lower lowest performing teams. And the biggest thing that I noticed was was culture. And so like uh it was kind of cool. Like, for me, I'd never been in a call center at this time. Like, this is over over a decade ago. Um, and I'd never been in a call center. And I remember this one team uh that I had signed. I walked into their call center and it felt like I was like at like uh like the playoff finals uh of like a big game. Like I could just like as soon as I it felt like I was walking out into like a stadium, you know, like and it was like so much energy, and it was like it was like buzzing. And then I remember they were in sort of Central Florida, and then I remember I had a team uh that I visited, that was my first trip seeing my teams um in South Florida, and I walked in and it was like crickets and nobody was talking, and then there's like and it was just it was it was like night and day in terms of that like just that pure energy. Yeah, and I think uh for sales, like you have to be energized and like you're talking about resilience, like resilience is so important. Um, and if you have that sort of camaraderie and that team energy and everyone's excited, I think resilience is much, much easier. And I think you know, when you hear a no, you get picked up faster. Um, whereas uh the other team, it was like you like you could hear a pin drop basically, and so that was that was something I noticed, and I was and it sounds really maybe silly, but it was like me, like it was just a huge meaningful difference in terms of their performance, like it was just the culture and the energy.

SPEAKER_00: 8:15

Yeah, I think I think I can guess which team did the best um in that scenario.

SPEAKER_01: 8:20

Yeah, yeah.

SPEAKER_00: 8:21

Do you think that's like a teachable behavior and culture, or do you think that just comes with the type of people you hire and their personalities from the get-go?

SPEAKER_01: 8:32

Ooh, that's a good question. I think this some people might disagree with this. I think everybody wants to have fun at work, to be honest. Like I I think, but I think most people have like preconceived ideas about like what work is like, and they sort of have their like very like serious face when they go to work, and then there's you know, they're sort of a little bit different when they're at home or whatever. And so I think I think people, even people who are maybe more reserved or more introverted or something like that, or maybe a little bit more shy, like I think people do want to participate in that fun and that energy and being a part of something. I think everybody sort of has that. And if you have an established culture, I think when people join, I think they they naturally want to participate in that. With that said, like I do my early team members, because I I normally either have started the sales team where I am, or I've taken over like a very small team of let's say maybe five people or something like that. Um, I do think those early hires are really, really important. Um, because it's like it can't just be me that's promoting like a team culture, like it has to be everybody. And then after that, I think people just sort of naturally uh join in because you sort of have that energy and that inertia and it's fun and people want to.

SPEAKER_00: 9:54

Absolutely, I agree with that. I think the first hires are definitely very important at setting the scene, and then anyone else that joins, I I think if they find it like a safe environment, they can be a bit more authentic and themselves rather than having to come in with a serious space to work. So um, yeah, we'll definitely touch a little bit more on culture, but um curious after that first startup experience and kind of accidentally falling into sales, where did the rest of the journey lead you? How did you eventually get to TW sales?

SPEAKER_01: 10:26

Oh, good question. So um so I I was in the solar energy space for I think it was about five or six years. Um uh and then I ended up having like uh direct sales teams, uh, so they were employees, and then I also had um our third-party sales team, so I had a mix of both. Um ended up leading our customer success team uh for a while. Um I wasn't like overly keen on it at the time, but it was it was a bit of a fire for us, and so it was just something that I was gonna sort out, and I did that. Um and then after that, I actually tried to leave sales, which was really interesting. Um, because I was feeling like really, really burnt out. And um I kind of like there were some like negative things that were going on with like the teams that I was working with or the teams that I had. And I don't think I had like the wherewithal to like realize that like I could correct and change these things. Like they kind of put to me, it felt like um like where you'd have like toxic competition or something like that, or and and it really like burnt me out because I'm not I'm not really like that. And and I was working like 24-7, and and so I was just I just really burnt out. And so um I went to a company that was um oh, I was gonna say Canada Zillow. Maybe your Australian audience might not know that. Um, but it was it was like a really large like uh prop tech company in Canada, and so I joined just after the series A and I was trying to get out of sales, and then like six months later, our co-founders were like, We need to have a sales team. Would you start? And I said, sure. And then it was a really cool opportunity for me because I was like, okay, the things that I didn't like, it's like I can actually like control for those things, and I can actually build the sort of culture that I want. And like the cultures that I had before were like very energized, but there's still some of that like sort of more typical negative stuff that you might think of with sales that that was really draining to me. And then so then I built that team and I scaled that up and we raised about I think about a quarter of a billion dollars. Uh and so yeah, yeah. Um, especially in the Canadian market, it's like fairly large. And then after that, I was recruited to lead sales at a global SaaS company. We were selling uh mentorship and peer-to-peer uh software to like large companies like uh Netflix, Coca-Cola, Disney, stuff like that, and uh was VT of sales uh and strategic accounts there. And then we sold that company. I joined just after the series A. And then we sold that company when we were going to do our series B. We just got like an offer we couldn't refuse. Uh so that was last December, just over a year ago. Um, and it was really nice. Like they they paid us out on all the equity up front. So then I was like, that's great. And I'd already been a part of uh a few successful acquisitions. I didn't want to go to the acquirer, and they gave us the money, so I said, cool. And then so I quit later that month. Um, and then I went and joined a CRO at a company that I'd been an advisor at for two years. Um, and so I was CRO there for eight months, um, just trying to sort of transition them. Um, like we made a ton of changes in the eight months, um, and then scaled them up and then uh started pursuing uh just working at TW sales, like my own company. Um so I'm still an advisor to that company, and then I advise other companies and a fractional CRO uh with them.

SPEAKER_00: 13:53

Wow, amazing journey there. And um uh you you've also fallen into the world of SaaS as well. So um did did that accidentally happen, or did you kind of get drawn to that world?

SPEAKER_01: 14:05

Yeah, it was sort of interesting. Like I most people don't do like B2C and then switch to like enterprise SaaS, which is what I did. So uh yeah, I like to be honest, like I've like candidly, I thought that B2B SAS was kind of boring. Like, um, and so like I'd think about like I was like, I don't wanna like if I worked at DocuSign or something, I was like, that would really make me sad. Like I would just like because I just uh wouldn't be excited about that every day, right? And so and so when my uh when the CEO of this company called Together reached out to me and it was mentorship and peer-to-peer learning software, I was like, oh, that's super cool. I didn't even know that existed. And I'm really, really big on mentorship and um something that I'm very passionate about and I care a lot about. And so I was like, oh, that's like the perfect opportunity to do B2B SaaS. Um, and so that's how I started doing that. Yeah.

SPEAKER_00: 14:57

Yeah. And so a lot of our audience is in the world of B2B SaaS, and actually a lot of them are based in North America, so um, not just Australia. Yeah, it's interesting. Um now you've seen sales from inside startups, scale-ups, and also B2B enterprise organizations. I suppose my question really is when you work with SaaS founders, um what do they usually get wrong when they're trying to scale? And like what what are they doing wrong when they're trying to do sales as well?

SPEAKER_01: 15:34

Uh do you mean like sort of early stage like seed or sort of like later stage?

SPEAKER_00: 15:40

Let's do both. Let's do both scenarios because I think we have two audiences here. You know, everyone's probably in this category or that category. So let's have an answer for both of them.

SPEAKER_01: 15:49

Okay, okay. Yeah, because I do uh I'm uh I think it's called an expert or entrepreneur in residence at a couple of uh incubators. So I I do work with a lot of early stage founders, uh, and I really like that. So I think with founder-led sales, so actually, sorry, I'll step back a sec. I I think the biggest challenge that a lot of founders have both with selling and then also with hiring, managing, um uh anything like that, either sales like their first salespeople or you know, their first sales leader, um, is that most founders, not all of them, but most founders uh come from a technical background. And um a lot of them have like STEM background, engineering, that sort of thing. Uh and they tend to be really, really great problem solvers. They tend to really love ambiguity um and these sorts of things. And and uh or they might come from a business background where they they really like where there's like a case made for things and the sort of the formalities of business or or consulting or something like that. And the thing is, is like it doesn't translate very well to um selling and it doesn't translate very well to managing sellers either. Um and so like as an example, um a lot of people and a lot of founders when they're doing founder-led sales, they think about connecting with people and just giving them as much information as possible. And they're like, the facts will sort of win the day and I'll send them this info and and and that sort of thing. Whereas uh I would argue that sales is done on an emotional level. Even when you're selling B2B uh SaaS to large enterprise, um like one of the last deals that I closed up together was with Microsoft, and it's like I was working with their executive team, it was still very much like connecting with them at a human level, um, even though you know they might have mentioned oh, the ROI, that sort of thing. And it's like, yeah, you have to bring that, but it's like you really, really need to connect with people. And I think that most founders, especially if they come from a technical background, I think that they tend to not understand that. Um, or like a lot of founders, they think that they have to have like their pitch down and they think about selling, although I've been dominating this conversation, I was gonna, but um, they think about like a salesperson as somebody who does a lot of talking, or they're like that Don Draper person, they've got this like eloquent pitch and that sort of thing. Whereas like my sales style, um, like my talk ratio is normally like 20 or 30 percent. Like it's very, very low and it's very listen first, and it's very discovery heavy. Um, and people just don't sort of think about that, I think. Like for founders. And so when I coach them on founder-led sales, there's a lot of like aha moments with that. Um, or even when they're doing like cold emails as an example, like most founders, if they show me the cold emails they're sending, it starts out with like an introduction about them and like who they are and what their company does, and that and it's like normally like very lengthy. Yeah, yeah, yeah, yeah, yeah. And it's like it's like no, no, no, it's like you have to start with the with the prospect, and you have to start with with what's important to them. And you know, they sort of think about it almost like when you meet somebody. It's like, well, I meet somebody, I introduce myself. Like it's it's a normal thing to think, right? But and so there's a lot of gaps on that. And then I think when they transition to managing salespeople, um, like let's say uh IC sellers, um I think that they expect that those sellers will have the same sort of like um problem-solving mindset that they do, and that they're gonna be really great with ambiguity. And like the analogy I always use with founders is that like sellers are sort of like they're at their best when they're like horses with like their blinders on, you know, and it's and it's like they have a process to follow, like they know they know what the sales process is, they know what the pricing is. Like oftentimes there's no like no pricing model, it's just sort of made up on the fly, and it's like that that can be a real problem. And so I think there's a real disconnect because they expect the salespeople to have the same sort of mind that they do, um, and they just simply don't. Like most salespeople are really, really bad when when you introduce ambiguity and they have to do all this problem solving, or you know, uh, especially early stage startups when there's relatively few sellers where you know the products are the like the product features are changing like week to week or day to day sometimes. And um, it just like it really, really um subverts the success of the salespeople. And then when they bring on sales leaders, oftentimes like they want the sales leader to probably be more numbers heavy, more quantitative, um, that sort of thing. And and they end up sort of talking like two different languages with the sales leader, and and there's normally like a huge disconnect. So, like a lot of the advisory work I do at the companies that uh that I work with is I end up uh working with the CEO or or the co-founder who is leading the sales team or is in charge of the sales team. And then I work with the sales leader, and then I normally work with them individually, and then I normally work with them together to to bridge that gap. Um and it's it's not that you can't bridge the gap. And and you know, they they both want to understand each other and they both want to be successful, but but they normally are just they're talking very, very different language, I would say.

SPEAKER_00: 21:21

Yeah, no, that makes a lot of sense actually, because I mean if the founders do have that engineering background, um, technical background, they're not really thinking, you know, relationships, especially in the world of you say you're targeting B2B enterprise, that you know, that can have like 12 to 18 month sales cycles sometimes. And so it really is all about relationships. I think a lot of the founders that are technical that I meet, they're hoping the product sells itself, like products let grow. So, oh, we built it, it has the most amazing features, so it should just sell itself, like they will come. Um, which doesn't necessarily I want to touch on founder-led growth just for a second because I have met a lot of companies that that's how they start off. Um, and I think that's great. It's very effective, but it's not always scalable when you get to mid-market enterprise level. So, do you think that all startups should start as founder-led growth and then move on from there? Or do you have other ideas about that?

SPEAKER_01: 22:27

Like the founder doing sales initially.

SPEAKER_00: 22:30

Yes.

SPEAKER_01: 22:31

Yeah. Um, that's a good question. Like, I think I think it's really, really good for one at least one of the founders to sell and get an understanding of sales. Like, um, when I was at Together, um, company that we scaled up and then sold just over a year ago, um my CEO, he he he had a business background, but he was still very like very quantitative. Um, he'd he'd worked um uh he'd worked at Boston Consulting Group. So it was like you know, sort of typical like consulting and that sort of thing. And and I suspect his name's Matt. I I think the world of Matt, like I suspect he never thought that he was ever gonna be in sales. Um and I actually asked him that sometimes, and he'd be like, Yeah, I never thought that I'd do sales, but he did our first million in ARR. Um, and yeah, even though he's like fairly uh introverted and all these sorts of things, but he was like very, very successful um in doing the first uh million in ARR. And then what was really helpful about that is that he was very like when I needed things, um, either for myself to be successful um or uh for my team to be successful or I wanted to make changes, Matt had a lot of empathy, I think, and and a lot of understanding. Because some of the things around sales, like and sales success can sort of seem like voodoo or black magic or like it they could sometimes be hard to give like a really objective or quantifiable reason. Like I certainly try, but uh it can be challenging, right? And so, you know, oftentimes in our senior leadership meetings, like I would propose something and there might be some folks in disagreement, but oftentimes Matt uh would agree with me and and sort of understood the perspective of sales because he had done it himself. Um and I was always so appreciative of that, like it was very sincere and and um uh and he really, really, I think because sometimes at sales or at SaaS companies, like the sales team is not well regarded and um they're not like they're sort of thought of as like a necessary evil or that sort of thing that sometimes happens. Whereas I think Matt uh knew like how challenging sales could be and and how difficult that job could be. And so he he really seemed to deeply understand that. And so I think in terms of um empowering me and supporting me, it was it was excellent that he had that experience. So that was really wonderful. And then also, too, I think it's important for founders to be talking to the early prospects and customers so that you know they understand it's like what are their pain points, like what do they think about things, like what features are really important, like um all those sorts of things like I think are really, really important uh for the founder to understand in the in the early days. Like eventually, I you know it's not necessary for them to keep selling, but I think early days, I think it's it's pretty crucial, both for the early success, but then also for future success as well.

SPEAKER_00: 25:31

Yeah, I agree. I agree with that completely. Switching gears a little bit, and um, I suppose more for our mid-market and enterprise audience, um, you know, this is where obviously they have sales teams, they have marketing teams. I think the biggest issue I see in those organizations is misalignment because the teams get really big, marketing's doing their own thing, sales is doing their own thing, maybe there's no and customer success is over here, product teams are over there, in the world of SaaS, it's just it's really easy to get disconnected from the common mission or the common goal. And you talk a lot about building winning sales cultures. So, from a practical sense, what does the day-to-day of that look day-to-day look like? Building the winning sales culture?

SPEAKER_01: 26:18

Good question. Um, and do you mean just within sales or sort of aligning with other uh teams as well?

SPEAKER_00: 26:23

I think both, because I do think alignment is really important. Um, I do think sales does need the backup of customer success and marketing, just to, I suppose, get that data and knowledge and get supported as well. So yeah.

SPEAKER_01: 26:38

Yeah, definitely. I I think in terms of working with the other teams, I think it's so, so crucial because you're right, like sometimes sales, marketing, and customer success can end up working at cross purposes with each other, and and it's it's a real shame because you end up like one, it's not nearly as enjoyable for everybody, and there can be like hostility and that sort of thing. Um, but then the other thing too is like you won't be nearly as successful as a company um if if you don't have that alignment. So like one of the things that I try to do um is make sure that we're all tracking to the same metrics. So for example, um, like I for top of funnel, like I like to measure um like like I'll give the example of when I was at together, like I like measuring demo calls sat. So it's like demo calls that we booked, and then that person showed up. Um and top of funnel. Top of funnel, yeah, yeah, yeah. Uh there's stuff earlier than that, but like that's one of the one of the main ones I would track. And so, but then our marketing team was tracking like MQLs, and right. And so, and so it's like those are like uh it some it could be aligned, but it won't necessarily be aligned, right? And then um, or there was a time where they shifted and then they were doing demo calls booked, but demo calls booked is different than demo calls sad and qualified, right? And so, um, and I remember having a uh conversation with um with uh my peer who was who was running marketing and she was really great. Um, we had a lot of inbound leads that she was generating. And uh as it turned out, like it was just that her uh we had our marketing team have fairly heavy variable comp as well, which I thought was pretty cool actually. Um, but their variable comp was set up differently than the sales variable comp in terms of like what we were measuring. And it's like, okay, well, it's like, well, let's go change that, right? And then so I said to her, is this like let's go have a chat with our CEO. Like we both reported to him, and then we did, and then we just aligned our our comp so that we're all on the same page because it was like it wasn't fair for her to be tracking the metrics I wanted if she was getting paid on something else, right? Like it did so like I that was like a pretty crucial discovery. And then similarly with our CS team, uh, which I I ended up um uh some of that ended up moving over to me, but it was very similar, is that we were just measuring different things and we were comped on different things. And so it's like, well, it's like of course we're gonna like no matter how great people are, we're inherently gonna be misaligned, right? And so I I think that alignment is so, so important to working harmoniously and and just making sure that that everybody is is sort of rowing their boat in the same direction, if that makes sense.

SPEAKER_00: 29:23

No, absolutely. Are you familiar with account-based marketing?

SPEAKER_01: 29:27

Mm-hmm. Yeah.

SPEAKER_00: 29:28

I I love account-based marketing for exactly that reason. It it aligns the teams together and they they actually work on common metrics and and common goals. Unfortunately, with larger organizations, it is a little bit of a change management uh experiment as well. So it does take a while to get them on the same page. Um, but coming back to to the earlier question just around building a winning sales culture, so uh a stepping away from the other teams, um what's your day-to-day on that one?

SPEAKER_01: 29:59

Well, good question. So I think uh so I wrote a fairly long form article on this. Um uh so I think there's like a few sort of main pillars. Like I think the one of the biggest things is I try to shift from being like individual focused to being very team focused. And so um like a lot of I think a lot of SaaS sales teams are really like they're thinking about like the individual, the individuals are thinking about themselves. Um, there's like a lot of around like leaderboards and like those sorts of things. And um, and people aren't thinking about like a common goal. And so like the like the first thing that I try to do is make sure that we understand like what our goals are. So it's like what's our target for the quarter? And then um I have like weekly or sorry, daily theme meetings. Um, and at my sales kickoff, which I do on Tuesdays, um we always show like the stats for like how we're tracking in the quarter. But like when I show those, it's it's typically very team focused. Like I do show some individual stuff, but it's more about how we're progressing as a team. So that's like the the first thing. Um, and then the next thing would be I I normally try to set like some like outrageous like team target or goal or something like that. Um, and so like a lot of companies, they do like Presidents Club, and so it's like the top performers, like uh they get to go to whatever, they get to go on a vacation or something like that, or they get their medals or whatever it might be, or a dinner. Um, whereas what I do is is we set a stretch goal as a team, and then um we uh either all get to like reap the the benefits or or none of us do, is is is how I try to do things. And so um, like the first time that I did that uh together as an example, like I took the team down to South Florida in the winter, which for Canadians is a really big deal. Rented like a really cool house on the beach, and we had this like great time. The next time we did it, um I took them all skiing out in uh British Columbia on our west coast, so that was a lot of fun. Um, with uh when I was CRO at Median, uh they'd never done this before, so I took them all out. We have this big thing, it's called the Stampede, the Calgary Stampede. So it's like the largest rodeo in the world. It happens uh in in Canada and in uh Calgary. And so we all went to that and they all voted on that. That's what they wanted to do. And so, and so like what ends up happening when you're focused on that and you're all like focused on winning as a team, then it just sort of like naturally happens that way. And and people are competitive with themselves and they want to get better themselves, but they're not competitive with each other. Like they actually like people will ask me, they'll be like, like, how far are we away from our target? Like that's and they're thinking more about like the team goal as opposed to the individual goal that they have. So that's like one of the biggest things I try to do because I think you can't have a strong positive culture if people are are uh sort of toxically competing against each other or they see it as like a zero-sum game.

SPEAKER_00: 33:04

Yeah, I love that. I absolutely love that because you're right. I think when you've got the top performers, it can get quite toxic. Like you'll go to work and I don't know, it's almost like bullying in the workplace is just like a bred in such an environment and it can be quite toxic. And I think you probably get some people in there that just don't want to be in there. So that energy you were talking about is probably quite negative to start with. Whereas if everyone's kind of working as a team towards a common goal, they're probably helping each other out, like you know, oh, I've met my targets, I'm gonna help this person meet this so that we can achieve this together and go on that amazing ski holiday that we were promised.

SPEAKER_01: 33:44

Yeah, yeah. And and the other thing too is that it keeps people trying to win the entire quarter, the entire year. Because, like, let's say, for example, let's say you're like the lower performing account executive and it's like midway through the quarter, and you're like, there's absolutely no way I'm gonna make presidents club, then you just sort of like give up, right? Yeah. Whereas like the way that I do things is like people are always like even the people who are sort of behind or lower performers or they're still ramping or whatever, like they still can contribute to that. So they're never like sort of like out of the game, if that makes sense.

SPEAKER_00: 34:20

No, that makes sense, yeah. Um sticking to the point of B2B enterprise SaaS sales, um, we touched on relationships, we touched on long sales cycles in that world as well, a winning culture. What are some other uh factors that you think tie into being a successful B2B enterprise sales team?

SPEAKER_01: 34:43

Question. I think um so I have like a few pillars in the article that I wrote. So um one of them in this, I remember I presented on this in August uh to a big SaaS group, and I I don't know if this is controversial or not, but um I try to only focus on a few metrics. Um and so it's really interesting to me is like a lot of sales leaders, they have like 20 different metrics that they're like tracking, or even maybe even more. And um salespeople generally aren't great with math and numbers. And so I think what ends up happening is their team has like no idea what these things mean. And then when all when you're tracking all these metrics, like sometimes they're at odds with each other. Um, and then they often lead to confusion, and it's hard to tell like what's like most important. And so, like one of the things I try to do is I I have like dashboards and we present it every week um in terms of our numbers. I think that's really important, but I try to stick to just four. Um, so I do like a top-of-funnel metric, which would be uh disco calls or demo calls sat, like depending on how things start. Uh ARR close, so closed one. Uh, what's our forecast? Discounted forecast. And then um I normally think of sales like normally I have the account management team under me. Um and so a retention metric like GDR, NRR, you could do logo retention, but but I really just focus on those like four. And so it's like everybody's like very, very laser focused on those things. Whereas like I remember I had uh I have a really good friend, he's a very successful account executive, and he asked me a few years ago, he's like, What he's like, what do you target for your AEs in terms of like sales activities, like number of cold calls, emails, that's right. I was like, I don't, and he's like, really? I was like, no, I was like, I don't do that at all. And and because he had just had a new VP come on, and even though he was really successful, he was like every meeting he had with the VP, the VP was like, you're not making enough calls, and that even though he was already well past his target, you know, and so so stuff like that happens, and I I think it it's it's confusing to people and and it it sort of breeds resentment and that sort of thing. Whereas like for me, like I I might look at those metrics with somebody like let's say they're really behind, like, yeah, we can like dive into stuff, but I I certainly don't target them. Like, there's um and so I think that's very clarifying and and helpful for people. Um, in terms of comp, like um, in terms of individual comp, it was really interesting. Like, I learned this early on when I was managing all these like third-party sales teams, uh, they all had like different comp structures. And like when I would ask the sellers, like, how are you comped? Like, sometimes they couldn't explain it to me. It was like, you know, it was like a John Nash, like beautiful mind equation that they had to do to figure out their variable comp. And it's like if people don't know how they're getting comps, uh, it's like, well, then they're not gonna be motivated by that, right? Or or if it's like, let's say you're a BDR and you only get comped if like the deal closes. I've seen that before. It's like, well, that's not really in your control. Like you could have done a great job as a BDR, and maybe your counterpart who is an AE like did a terrible job on the demo, and then you you don't end up getting comped, right? And so um I try to make it within so I try to make it simple, known. Um, it's like you do X, you get Y, um, those sorts of things. So I think comp's really important. Um something that's I think like a cornerstone of my teams is um what I would say is like high care, high expectations. So I have like really, really high expectations for my team. Um, but at the same time, I'm like very, very high care. So it's like um like sink or swim would be like high expectations, low care, right? Like uh like the classic. Whereas for me, it's like I have high expectations, but like I have all the time in the world to to do coaching or or to help people, like those sorts of things. And so um I really, really try to do as much development with people and mentorship and set them up for success as as possible. So it's like so that we're in this together. Um, another big thing that I do is employee-driven development. So something that like I I noticed is that um this is that together. So it was sort of like a aha moment for me. It was was that I was like noticing that my like the people reporting to me, they were sort of like waiting on me to like tell them who I thought they could be, or when I thought they could be promoted. Or it's like, you know, if it was like uh early on, if it was like a BDR, like they're like, can I be an AE or can I be an AM? Or if it was like a more senior AE, like later on, like they're like, can I be an AE lead? Or like and and it's like well it's it's really up to you, right? Like it's it's it's like it's like you tell me like what what you want to do, and then we'll get you there. And so um I think or or people would want me to tell them like what their gaps are and that sort of thing. And it's just like, no, no, it's like it's like you like you really need to like own these things and sort of like drive your development, and and that's been like a really, really powerful thing. Like it's not me abdicating responsibility, it's it's me sort of giving people I think more autonomy and more empowering them. Because for me in my career, like I've like sort of always been the sales leader. I've never had anyone say, like, yeah, Thomas, you can do this, or you can do like it's like no, as for me, it's just like the world's always been open. And so I try to instill that with my teams as well.

SPEAKER_00: 40:10

Yeah, I love that empowerment. I think it's important. I love that you mentioned retention as one of your metrics, by the way, because typically when you go into a B2B SaaS and enterprise environment, um, the sales team's all about net new, net new, new logos, pass it on to customer success, fingers crossed. You know, sometimes the communication between the two isn't there. Um, but I've come to realize um customer success is actually really important. And I've had a few customer success experts on the show, and I'm a big fan of Jason Lemkin, who writes all about SaaS. Um, and he actually says 90% of the revenue is with customer success because retention, growth, upsell, cross-sell, but then also that those customers um advocate and get you new customers, it's quite important. Um, so I'd love to get your opinion on that on retention. It's one of the metrics you mentioned in in your top four. And um, what's your what's your experience been with it?

SPEAKER_01: 41:14

Yeah, good question. So I think I think like the right model around like customer success versus like more of a revenue focused, sort of like what I would call like a like account management and C uh CS sort of mean different things at different places. So it's not always clear like what when I say this, like, but I think that like at the last two companies I've been at, like Median when I was CRO, and then together when I was uh VP there, um, I had very, very strong account management teams because we had uh sort of a land and expand model. And so if you have a land and expand model, you really need somebody like quarterbacking those customers that's very, very revenue focused, right? Um whereas like if you like if the deal when it's sold is roughly what it's gonna be in like three years, it's like you probably don't need somebody who's revenue focused, right? Like it probably is okay for it to be CS. Um but like at Together, and then also Median, we just closed the year. Um I started the AM function early on when I joined as C uh CRO. Um in my last year at Together, more than half of our revenue came from um uh sales from existing customers. And then Median, we just spun up the account management function when I joined uh just over like just a year ago. Um, and I think uh revenue from existing customers, like net new revenue from existing customers um was like 59% of revenue. Uh like like of like the incremental revenue on the year. Yeah. Yeah, yeah, yeah. Because like at Median, um, the companies existed for 11 years, but no one had ever um really done uh upsells properly. We did a massive write-sizing campaign because a lot of folks were paying like way, way too little. Um, and so there's just like so much opportunity there. So I think it depends on like what the nature of your sale is and and how much um potential there is with your customers. But if you have a land and expand or a lot of SaaS companies, they tend to underprice their early customers, like um and then they forget to put the prices up later. Yeah, yeah, yeah, yeah, yeah. Like we did a campaign um uh uh this past year where we increased price uh for some customers like a thousand percent, um, which seems crazy, but it's like that's just how much and we didn't lose a bunch of people, it's just we were just underpricing them significantly. So I think it's a good idea.

SPEAKER_00: 43:42

I think Campbell was in the news recently for doing something ridiculous like that specifically. But I I've had a few pricing guests on the show, and and they have actually confirmed when you increase your price, everyone's scared they're gonna lose customers. You might lose a few. Well you actually end up keeping the ones that are the right customer.

SPEAKER_01: 44:04

Yes.

SPEAKER_00: 44:05

And it's easier to scale from there, I think, because you've got less um account management that's involved. You've got the right customers and you're charging the right prices.

SPEAKER_01: 44:15

Yes, definitely. Um like two companies ago, we were only working with really big logos because our mentorship software was only appropriate for really large orgs. And it was really interesting. I looked at the agreements that we had when the renewals were coming due. And I think people had priced them low because they're like, oh, this is a really big logo. And so they they're like, we we should give them a lower price. Whereas like my mindset was like, oh, this is a really big logo, like they can afford to pay significantly more, right? Like it was like a completely different mindset. Uh and so we got a lot of wins from that. So I think I think a lot of SaaS companies, um, especially early days, like there's a lot of easy wins they can have, like as long as they can sort of stomach some of the complaints and stuff they might get. Which can be hard. It can be hard to do, but but but there's a lot that can be done there with existing customers.

SPEAKER_00: 45:05

Yeah, no, I totally get the anxiety around we don't want to scare them off. We really want that big logo, so let's give them a good price. But I think what they don't realize is big companies like that, they're used to paying high prices. So if they get something really low, they're probably gonna question the the you know the service, the quality. So it you should go high with those ones.

SPEAKER_01: 45:26

Yes, yeah, definitely. And that was something because it's really interesting. Something that I learned is like for a lot of sellers, especially the relatively junior, which my team was um uh two companies ago, is like they think of a a lot of money as being or they think of something as being a lot of money if it would be a lot of money for them personally. So they're like, oh well, this is like 50k, that's a lot of money, but it's well, yeah, but this is like Warner Brothers, and that's like 50k is like a rounding error. Yeah, yeah, yeah. It was just, you know, and and so it was like a very interesting thing. But um so yeah, so I think with the with the right sort of account management, like right sizing, but then also finding opportunities for upsells, like can be very like it can dramatically change your revenue trajectory in the early days, yeah.

SPEAKER_00: 46:11

Yeah, yeah, for sure. Um, let's talk about people management. So a lot of um organizations and and a lot of founders, they they talk about hire slow, fire fast. Um do you agree with that? Or do like when you hire salespeople, for example, and maybe you're seeing they're not performing as well as I had hoped, what's your strategy there to, you know, do you think okay, they're not the right fit, maybe we need to fire fast, or do you feel like it's trainable? There needs to be more coaching involved there.

SPEAKER_01: 46:47

That one's sort of tricky. Like I would say that especially early sales team members or early members of any team, I think hiring slow is particularly important because those will be like your like because I've been through this enough times that's like whoever I spend like this disproportionate time with early days, like they're gonna end up being the leaders and they're gonna be the cornerstones of my team. Like they'll probably end up being people managers as well. Like this almost always happens. Like, um, so it's like those people are really, really important. I think that uh what I've learned is that if I know that I need to fire somebody, like if I know like I know that uh that has never changed, I guess. Like, so it's like it's like yeah, yeah. So it's like if you know that you need to let someone go, especially if you're like a if you're sort of newer to people management, I think it it's easy to have pause about that, or it's easy to like it's sort of delay or you know, you because you want to believe in people and like that sort of thing. But I know that as soon as I have the thoughts like I need to fire this person, that it's like I just know experientially, like there's no point in delaying. So I would agree about firing fast with respect to that. Um, the only thing that I would say that has some nuance is that with sales, I'm not overly concerned about what somebody's performance is like today, like what in terms of thinking about retaining them. I'm more concerned about what their trajectory is. And so, like, if somebody has like the right behaviors and the right mindset and they're incrementally improving, then I will not let that person go. Cause it's like I know and I've seen so many people like turn that around. Like, so I care about like their trajectory, whereas like, you know, I uh one of the companies that I joined, um, there's like a small team, and the and um I'll try to anonymize the story, but there there was somebody on the team when I joined and I implemented my daily meetings, and they push back and they're like, Well, I golf in the morning, so I can't make these. And I was just like, Okay, like that's you know, like that's like a pretty basic thing that I just like I don't really want to coach for that. Do you know what I like? And so it's like so like things that are like behaviorally off or pretty basic, or it's like that, you know, their mindset if they're not winning a deal, like the mindset's like, oh, it's the customer, the customers suck, or this demo suck. Like if if they're not like owning these things, like that to me is that to me is like, okay, this isn't gonna turn around. But but if someone's like underperforming and I see that they have the right mindset, behavior, and they're on the right trajectory and they're doing the right inputs, like I I'll definitely keep those folks on my team longer. Um, and generally speaking, that that works out, I would say.

SPEAKER_00: 49:29

Yeah. Well, that's a good point, actually, because we're so focused on the numbers sometimes. Like, you know, Peter didn't get his targets in these in this month, um, or three months or quarter. Um but if he's great mindset, positive, team player, you know, has all the right features, the mindsets, and um, you're right, they can turn things around. Um, you mentioned a few things there that to me sounded like red flags.

SPEAKER_01: 49:56

Um, what are some of the guys about my rate?

SPEAKER_00: 50:00

Yeah, just the ones that um the ones that you mentioned, like he didn't want to come to the morning meeting, he was blanking the customers, maybe it's marketing's fault. Yeah, QLs are not quality.

SPEAKER_01: 50:12

Yeah, yeah. I think like a general bucket would be like, does the person have ownership of what's going on? Like I think that's the biggest thing. And so um, like if if the reason that they're giving for their lack of success is external, then I know that that's not going to change, right? Like you have to you have to be internally looking, and and it's hard, right? Like it's hard to be like, I'm not doing well and this is my fault, right? Like it's it's not like nobody wants to say that, but the thing is, is like things don't improve unless you have like unless you it's like okay, it's my like thing, right? And and the and that's sort of what I talk about with like high care is like if someone's like, hey, like my discovery's not going really well, or it's like I'm having a really hard time saying next steps at the end of my demos, like can you help me with that? I'm like, yeah, like absolutely. Like that to me is great, right? As opposed to like it's like, oh, this like demo sucked and you know, they weren't ready to buy. Like that, you know, like that sort of thing.

SPEAKER_00: 51:15

Sleep deadline.

SPEAKER_01: 51:16

Yeah, yeah. So I think that like a lot of behavior that to me would be problematic would be like externalizing things as opposed to like having a sense of control. Um, I think I'm not quite sure how to say this, but like I think being realistic about what's going on, you know, like which once again can be really hard, but like sometimes like salespeople will be like, you know, they're like in a slump or things aren't going well, and then they'll be like, yeah, but my forecast over the next three months is like, you know, it's just all sunshine and rainbows, and you know, there's a pot of gold like over the you know, in in the next month or in the next quarter, like and um, and sometimes that can happen, to be clear, but I think like if I get the sense that they're not like being real about what's going on, like um, or they're not like steeped in reality, like that can be problematic. Um and and sometimes if you just have a conversation with somebody, like they will like sort of get back on the right track. So it's not like, oh, somebody has unrealistic expectations, you should fire them or something. But but if that if that perpetuates, I think that can be a problem. Um, I think just like generally not wanting to participate in the things that are making people successful. Um, so like I'm really big on coaching. Um, early days with my teens, if they're small, I do one-on-one. Later on, I tend to do more group. Like if somebody's not like vulnerable or they're like, I'm good, like I have nothing to work on, like that sort of thing. Like that to me is is problematic. Yeah, yeah, yeah, yeah. Like I I think that I'm quite good at sales, but like every call I get off of, I know there's different, like, it's like, oh, I talk too much, or I could have said something, you know, and like and that sort of thing. And maybe I'm like too hard on myself, but like there's all like with sales, like there's always something you could be like it's human interaction. Like there is no 10 out of 10 in sales, right? Like there's always things we can be doing better. And so I think that um people who are coachable and have the vulnerability and are willing to look within, I think can be really helpful. Like, um, but if somebody's like really guarded or they're not coachable or they're not willing to change or they're really defensive about stuff, like like those to me are the signs that's like this is not going to change, you know, like this is just gonna perpetuate.

SPEAKER_00: 53:30

Yeah. I love that. These are exactly the traits I'm trying to teach my children, actually. I'm like, you have to take responsibility, just say it's my fault. How can I do how can I not do that again?

SPEAKER_01: 53:42

Yeah, yeah.

SPEAKER_00: 53:42

Um, it's definitely a hard one, I think, for adults as well.

SPEAKER_01: 53:46

Yeah, yeah. I I remember this is like ingrained in me when I was like 10. I remember I was golfing with my dad and some of his like I think business associates. And um, one of his business associates was trying to like help me, because obviously I was like 10 and I had no idea what I was doing, and I was like refusing his help. And I remember he said to me that I wasn't coachable, and that like stuck, and I don't know why, but that like stuck with me, and I was like, oh yeah, right. Like, and so for me, like any time because it's it's it's hard, right? Because like to be coachable, you have to be you have to have an openness to be like, yeah, here are my flaws, or here's the things I'm struggling with, or here's what's not going, like so it's hard it's hard, right? Like, but if you're not willing to do that, uh you'll just never get better. Like it's not possible.

SPEAKER_00: 54:31

Yeah, yeah. It's it's a very important quality, I think. Being able to accept criticism, um, constructive criticism, and yeah, being open to learn. Um, Thomas, my audience, if they want to find more of you, you mentioned an article. I think you're also excited about a live calling show later in the month. Can you tell us more about that and where they can find you?

SPEAKER_01: 54:53

Yeah, definitely. So my website's TWSales.com. And so I have a bunch of long form articles on there. Um, and they're all they're all free. Like so people can just go check those out, those sorts of things. Um, I have articles for founders, sales management, sales skills, and then mindset. And then something that I'm starting uh this month is a live colon show, which I'm really excited about. And so it's gonna be every other week. Um, I'm gonna be doing it this year, and so um uh it'll be once a month, it'll be for sales leaders, and then once a month it'll be for founders who are doing either the selling themselves or they're uh managing uh sellers or they're managing the sales leader. Um and then they can come bring a question and it'll be really dynamic and and sort of fun.

SPEAKER_00: 55:36

Amazing. I'll happily join that one for sure. Um looking forward to it. My last question for you a bit of a tradition on this podcast is if you could go back in time and give yourself one bit of advice, maybe it's to your 10-year-old self to say, listen. Um, could be at any point in your life, doesn't have to be professional, could be personal. Where would you go back and what would that advice be?

SPEAKER_01: 56:03

Ooh, um good question. I think probably as early as possible, as as early as I would have retained it, like um, but just around having like a growth mindset, I think. Um, and so this is something that I think about a lot. It it actually relates to the stuff around being coachable, is like like as an example, like in my early days of managing sales, it's just like I was like, oh, I'm really good at sales, and so I never read sales books as an example. Because I'm like, someone would only read sales books if they don't know what they're doing. I know what I'm doing, therefore I'm not gonna read sales books, right? And so um, and it's just like which is like a not a good mindset, and and I'm I'm sure I could have progressed even faster. Um and and I've had that mindset about different things over time, whereas now, like I think for me, like I always want to be learning and I always want to be like I'm always trying to pay attention to like what other people are doing or what I can learn from other people. And um, you know, like I've been I've been learning Spanish in the last year, which has been really humbling and fun. And it's like, you know, it's like that I have to be really coachable with my like I have a Spanish teacher that we do one-on-ones with, and I feel really silly because, you know, I'm fairly eloquent or well spoken in English, but certainly not in Spanish, and you know, that sort of thing. But it's like being coachable and being willing to grow and make mistakes um and learn, I think is so, so uh important to just like growing and and being your absolute best and having that humility. So that's like I think having more of a growth mindset earlier, I think would have served me really well.

SPEAKER_00: 57:35

Yeah, I couldn't agree more with that mindset. Although I do question whether we were willing to take that on earlier, you know, in in our 20s or if if we had to mature into that mindset.

SPEAKER_01: 57:48

Yeah. Well, that's what I was thinking. I was like, when would I have like I probably would have rejected that advice at different ages? That's when I would give it to me. Yeah, yeah.

SPEAKER_00: 58:00

Yeah. Thank you so much for being in the show. I think we got some really good insights here into you know, building winning cultures, winning sales teams, alignment. Um, absolutely amazing. I love the metrics you mentioned as well. So absolutely fantastic insights. Lovely to meet you. Thank you so much.

SPEAKER_01: 58:19

Yeah, thank you so much for having me. This is this is wonderful, Joanna.