Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese

**Ray Rike** (0:00)
Hello, I'm Ray Reich, Founder and CEO of RevOpSquared, and your host of the Metrics that Measure Up podcast. We talked to a wide variety of B2B, SaaS and Cloud thought leaders, executives, investors, and people just like you to discuss the metrics and benchmarks they use to make metrics-informed decisions. Now on to today's show. Welcome to today's episode of the Metrics It Measure Up podcast. Today, we are joined by Scott Leese, six-time SaaS sales leader, three-time founder, and two-time author. Today, we'll be covering three main areas with Scott. First, pattern recognition from being a six-time SaaS sales leader, plus all from his several SaaS clients. Two, the catalyst of transforming and transitioning from sales executive to strategic advisor, and now to full-out sales influencer. And third, sales rep hero to sales leadership. Kind of the pitfalls, the promise, and the reality. Scott, please take a moment to give a brief background overview of your journey to becoming a guest on the Metrics that Measure Up podcast.

**Scott Leese** (1:18)
Thanks for having me here, Ray. I've been building and scaling sales teams for the better part of the last 20 years, either as an operator or as a strategic advisor. And I've started a couple companies. I run my own sales consulting firm. I run a business called Surf and Sales, and that has a podcast called the Surf and Sales Podcast. I run another business called Thursday Night Sales, which is the world's largest virtual sales happy hour. And we have a Slack community over there. And like you said, I've written a couple books. I got another book coming out soon. So I got my hands in a lot of different cookie jars, Ray.

**Ray Rike** (1:51)
Well, let's double click on the first thing. And that is when I first met you and I was doing some research on your LinkedIn profile, I noticed that you have over 10 years of VP of Sales experience for five different SaaS companies. And by the way, when I dug into that, you actually averaged almost three years for four of those companies, which in a world where VP of Sales life is about 14 to 16 months, you had to be doing something right. What were some of the common trends or patterns that you identified that informed your decision to pivot your career and launch your own strategic advisory sales services company for SaaS?

**Scott Leese** (2:27)
You know, I just think that getting into a good rhythm of how to build something from the beginning that is set up to scale was really, really critical. You know, I think a lot of companies fail because they can't get a process out of their head and onto paper. And if you can't do that, you can't transfer that knowledge beyond yourself over to, you know, 5, 10, 15, 500 sales reps. And so that was something that I kind of picked up on really early on, that building and scaling these orgs out, there was a bit of a playbook to it. It was, let's identify our ICP. Let's figure out who our buyer personas are. Let's build a cold call script, inbound script, a resurrection script if we're trying to win back old customers. What's our objections and rebuttals? And I just built all these things out and set it up like that from day one. The next thing I would mention is, I've been a huge supporter and believer in the sales ops and rev ops function.
From the get go, that function hasn't been around forever. But about 2011, I got budget approval to have a sales ops hire as my first hire. And from that moment on, I'm like, I'm never taking a head of sales role ever again, without getting approval to have a head of sales ops or a head of revenue ops be my first hire. So just having a really good partner there who can build all these reports and dive into Salesforce and manage all the vendors and the tools. So I don't have to, so I can focus on coaching, recruiting, training, developing, mentoring, all of these other things. Those are two patterns right there. And the last pattern I'd say is, you learn how to pick better horses as you go. I didn't necessarily pick the greatest horses early on. I'd consider five of the six companies I've been a head of sales at to be successful. Four of them have had staying power, but the last three have been really, really strong. And the last one in particular is a full blown unicorn working on a multi-billion dollar valuation. And so just learning to find a company that has a better product, that has maybe less modern kind of competitors, old antiquated kind of industries right for disruption, and then looking for founders that give you a little more autonomy, they let you do things and trust in your experience rather than being all up in your business when they don't have sales leadership experience and whatnot. So those are the three things that I would give you there for that answer, Ray.