Straight To Voicemail

Board alignment is harder than ever. Budgets are tight, expectations are high, and every decision feels under a microscope.

In this episode of Straight to Voicemail, Rachel Downey connects with John E. Lepto IV, CRO at Clear Go-To-Market, a buyer intelligence firm serving private equity-backed SaaS companies. With deep experience across sales, healthcare tech, and private equity ops, John shares how strategic clarity helps leaders earn trust in the boardroom even without a formal board himself.

In this episode, you’ll learn:
  • How buyer intelligence builds credibility with executive stakeholders
  • What boards actually want to hear from go-to-market leaders
  • Why clarity is the antidote to boardroom anxiety

Things to listen for:
(00:00) Why we wanted to talk to John
(01:40) From lending to SaaS to PE-backed GTM
(02:20) What Clear Go-To-Market actually delivers
(03:00) Why win-loss is more than “why we lose”
(04:10) Why John bets on service, not SaaS
(05:20) The two converging shifts in PE and SaaS
(07:00) What trust really means in boardroom settings
(08:40) Bringing clarity to win-loss and GTM strategy
(10:15) How Clear helps clients validate or challenge assumptions
(11:30) One piece of advice for CROs walking into the boardroom


Straight to Voicemail is for CMOs, CEOs, and Heads of Marketing in B2B tech who want insights from the people who’ve been there. Each episode centers on one big question answered like a voicemail you’ll want to play again.

Don’t miss this conversation! Follow Straight to Voicemail and explore Genius Cuts for more B2B content strategy insights.

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At Share Your Genius, we have the same questions, so we're tapping the best in the space for their answers—one voicemail at a time.

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[00:00:09] Rachel Elsts Downey: Every CRO or leader of any company actually wants autonomy, but you don't get to do what you want until your board trusts you, and trust doesn't come from charm or confidence might get you there, but it won't keep you there. It comes from results, comes from clarity, comes from alignment. That's where John Lepto comes in.

[00:00:30] He is the Chief Revenue Officer at Clear go-to-market, where he helps PE-backed B2B companies execute and keep their boards bought in while they do it, specifically, what they do what they want. So I asked him that question, how do you build trust with your board so you can do what you want? Here's what he had to say.

[00:01:01] John Lepto: Hey Rachel. This is John Lepto with Clear go-to-market. Currently CRO over here.
[00:01:07] It's a great question. I'll start by just saying in this era of AI, I take a different approach kind of lends a hand to what we're doing at Clear. So we are a services firm, so we're not SaaS, at least today. So there is little AI in what we're doing and a lot of people raise an eyebrow over that.

[00:01:25] I wouldn't say I'm anti AI. There's a way to do it correctly, and I think personally, people should use AI to enhance their job, enhance their responsibilities. I'm not a big proponent for cutting people just to replace them with artificial intelligence, machine learning, et cetera.

[00:01:43] But anyways, back to the question of how do you actually build trust? So I think it's bringing back the human to human connection. So there's a way to do that properly. You know, when you step into a board meeting there's lots of different people with lots of different hats

[00:01:57] But at the end of the day, the board wants to know, what are we doing efficiently? How are we doing it effectively, and how is that gonna be helping to grow the company? You know, before I get into how to do that, you have to think about the two shifts that are happening right now that are converging at the same time, which lends another hand for why Clear is a great value creation lever.

[00:02:16] But there's a shift in private equity that's going on, which obviously, is attached to boards, but the shift from the old playbook of PE, which is to have the ability to financially engineer a deal for good returns for the developmental partners. That is gone due to all of the things that have happened in the recent economy and market. High interest rates, et cetera. Money is not cheap anymore.

[00:02:40] And then, private equity is really trying to understand go-to-market. The other shift that's already been happening in SaaS is the shift from growth at all costs to profitable, efficient revenue growth. And now there's a little bit of a slight shift back to growth. So I'm calling that profitable responsible revenue growth.

[00:02:59] So we still have to sell within our ICP as it makes sense, right? CAC and efficiency and everything else, but we still have to grow or we need to grow.

[00:03:08] But anyways, you look at those two shifts. People within private equity specifically, I think what the board is gonna care about is how do you do it fast, but efficiently and effectively. The one thing you can do to build trust is come prepared with certain metrics that are actually gonna move the needle.

[00:03:24] So I'm a CRO, so if I were to step into a board meeting, I need to make sure all my numbers are spot on. You know, it's going beyond just the typical like, here's the deck, here's the numbers, here's the metrics. Figuring out, okay, here's what these actually mean and here's how we can use maybe a specific one or two to actually move the needle in cost change.

[00:03:44] Because there's so many board meetings where it's just. the typical mundane, let's go over this, let's go over that. You have to switch it up a little bit. Having the ability to not only just come prepared, but come at the board with a different angle. You know, maybe one of those things is win-loss, right?

[00:04:02] We are coming in and helping teams go-to-market teams, not just salespeople understand, yes, surface level, why you win, lose and churn. But through our deep qualitative primary market research, we're synthesizing this data and providing concrete insights that are gonna help move the needle within the go-to-market motion.

[00:04:20] So that's like the, what I would call buyer intelligence. That buyer intelligence is what you can bring as a CRO or even A CMO or CEO to a board meeting and say, look, this a hundred k or 120 k deal we just signed with a third party vendor. Like, Clear, look what we've gathered from an insights perspective with our buyers.

[00:04:37] Like this is stuff that our buyers never would've told us. And the thing is, I think in this market where these shifts are happening, the biggest thing that is important is clarity.

[00:04:48] Clarity around go-to-market. Everybody wants to understand go-to-market. It's all splashed all over LinkedIn. the two biggest things I hear as I sit on some of these delivery calls are a, that's extremely validating that we're doing the right stuff or right things.

[00:05:01] Within our go-to-market motion. And then B, we had no idea our buyers thought about X, Y, Z. But regardless, it's clarity. And that's the biggest thing that I think we can provide. So I think that kind of sums it up of how do you create or build trust so you can do what you want in the company. How do you build trust with your board is to just provide clarity.

[00:05:21] Providing clarity around what your function is within the go-to-market motion is huge and will go a long way. So thank you.