How to Build an Early Stage Sales Team Beyond the First Five Reps (Miles Kane, Tenderly)

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1. 14:34

   take to stand up a CRM and get all of our data under one roof and actually have a central source of truth. I had buy-in going into it, thankfully, and it took me a couple of times to get there, but I think it's a key critical piece to think about so that it's not just, okay, great. I got the job. I got hired. And then you turn to your founder and say, this is what I got to go do and hire. And they're going to say, well, what do you mean? Like, I thought that's your job. “So like the alignment piece before you jump, if you can control that, super critical.” Listen, I can't tell you how many times I've heard people tell me, well, just recreate your best rep. I can't tell you how many times I sold at outreach, outreach helps you recreate your best rep until I realized that's not really what it does, right? But I bet there's a few mistakes that you commonly see people make in doing this, Miles, or mistakes that you've made.

   In Team and roles

2. 23:44

   4 million in ARR, you start to have the leading indicators of how many conversations do you need to have with a prospect to turn it into an evaluation? How long does it take to move an evaluation through to close one? How many of those deals are you winning and losing on your average selling price? Once you start to get those to an a core basics, now you can go to your team. “To me early on, the importance of introducing the metrics is it starts to shine the light” on like, which part of the funnel are you good at? Which part of the funnel are you maybe having a blocker at, and you need to really double down on. And so ultimately, if you can introduce them as early as possible, and continue to explain, especially to your team, the why behind it, and that metrics actually are a leading cause of helping them be successful.

   In Metrics

3. 24:29

   was like, all right, you need this many opportunities, this many meetings, yada, yada, yada. And that stuff happened really, really early on. So we knew how to make pipeline, and we knew how much pipeline we needed to make. And those were two metrics that we tracked upfront. Leading indicators on pipe gen, how much pipe gen we had. “And obviously the inverse of that is win rates.” How much pipeline did you need to have based on a certain win rate to get your revenue? But then as you start to get more sophisticated, you start to track where that pipeline falls off because you're not on top of every single deal. You track the conversion from stage one to two, stage two to three, stage three to four.

   In Outbound funnel conversion assumptions

4. 25:11

   product or CS, or whoever it is, for example? Because at the beginning, it's just like, dude, build what I tell you to build. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. This is bullshit. Build it, trust me, everyone's asking for it. And then eventually like three reps say one thing, two reps say another thing. And oftentimes market feedback is conflicting against each other. So how do you deal with that whole situation? “I think the metric that I'm currently tracking now” that is helpful in that regard is sales cycle length from qualified opportunity through to close one. I think early stage companies, especially like, it's one thing to think that you have product market fit in the sense that you're talking to lots of customers and you got leads and that's all well and good. The question that I have and what a lot of companies I see

   In Inbound and outbound attribution

5. 26:25

   the more people you're getting in there, you're getting to that point of thinking that scale is really near and that will also help the internal conversations, I think of going to those product folks and saying, hey, if we build XYZ feature, we can see that it's gonna shorten our sales cycle by one to two weeks or two to three months, whatever it is. And you've got the data to show it if you've adopted a metrics first mindset “and adopting things like your call intelligence” or recorders so that you can surface that up and show not only anecdotal feedback of customers asking for XYZ features, or just at an aggregate level on a weekly, monthly, quarterly basis, documenting those close one and close last deals. You're trying to surface up more and more of that to help your cause. But I would say like that's to me is like

   In Dialers and call tools