Sep 30, 2026 · 54 min · 10 segments
Most SaaS founders think scaling sales means hiring more salespeople. Kevin Wilson thinks that's exactly how you get into trouble. Kevin is the CRO of Skimmer, the software platform used by…
Yeah, maybe I'll start because most of my experience is kind of an early stage SaaS.
And maybe the underlying question is like, when is it time to scale sales? I've seen it too many times where early stage founders scale when, for example, the board wants more revenue or right after a big series A or when a competitor is like really ramping up, you sort of want to keep up.
And you're ready to scale when you have both one product market fit and so that's our customers succeeding consistently like gdr is the truth here also what's your leading indicator of early retention right so if x happens within y time frame we know we have a customer for life and making that very scientific understanding you know what percentage of your customers by cohort or by months that are kind of achieving that early sign of retention.
And so one is when you have product market fit, and then two, when you have go-to market fit.
So you can acquire and retain them scalably, right? So you can look at the unit economics of
LTV
And so when you have those two things, I think that's when you are ready to scale.
So I've been handed plans in the past where they say, hey, Kevin, we just raised a big round.
And so if I kind of take that example and I kind of put some best practices against it or some like highly probable to work.
things, instead of hiring those 10 AEs out the gate, I would maybe approach it as like, go hire two in month one.
And always, always hire in twos is what I say versus just versus just the one because then you know, you'll be able to understand is that the rep or the process or the systems that's not working or working.
And then watch that speedometer, right? So those are those those are those metrics I was talking about.
So retention, and that might be too late based on your sales cycles, but things like especially checking to see if these customers are completing onboarding, if they're happy with onboarding, if they're hitting those leading indicators of success.
Yeah, maybe I'll start because most of my experience is kind of an early stage SaaS.
And maybe the underlying question is like, when is it time to scale sales? I've seen it too many times where early stage founders scale when, for example, the board wants more revenue or right after a big series A or when a competitor is like really ramping up, you sort of want to keep up.
And you're ready to scale when you have both one product market fit and so that's our customers succeeding consistently like gdr is the truth here also what's your leading indicator of early retention right so if x happens within y time frame we know we have a customer for life and making that very scientific understanding you know what percentage of your customers by cohort or by months that are kind of achieving that early sign of retention.
And so one is when you have product market fit, and then two, when you have go-to market fit.
So you can acquire and retain them scalably, right? So you can look at the unit economics of
LTV
And so when you have those two things, I think that's when you are ready to scale.
So I've been handed plans in the past where they say, hey, Kevin, we just raised a big round.
And so if I kind of take that example and I kind of put some best practices against it or some like highly probable to work.
things, instead of hiring those 10 AEs out the gate, I would maybe approach it as like, go hire two in month one.
And always, always hire in twos is what I say versus just versus just the one because then you know, you'll be able to understand is that the rep or the process or the systems that's not working or working.
And then watch that speedometer, right? So those are those those are those metrics I was talking about.
So retention, and that might be too late based on your sales cycles, but things like especially checking to see if these customers are completing onboarding, if they're happy with onboarding, if they're hitting those leading indicators of success.
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