How to move from VP of Sales to CRO with leading exec recruiter David Ives

It wasn’t so long ago that sales meant just showing up with a deck and a smile. These days, it seems that sales leaders almost need a PhD in statistics just to get through the typical day managing a sales funnel. From SQLs and MQLs to NDRR and managing overall retention, the roles of VP of Sales and Chief Revenue Officers (CROs) are evolving rapidly in tandem with the best practices of SaaS startups.

Few people know this world better than David Ives, who is a partner at True Search, one of the top executive recruiting firms in the country where he co-leads the go-to-market practice. David has led countless CRO and VP of Sales searches, and in the process, has learned not just what CEOs and boards are looking for, but also the kinds of skills that candidates need to shine in these important career inflection points.

In our conversation, we talk about the evolving nature of the sales org, how leaders can best position themselves for future advancement, what companies are looking for today in new executive sales hires, and compensation changes in the industry.

This interview has been extensively edited and condensed for clarity

Introduction and background

Danny: Why don’t we start with your background — how did you get into recruiting?

David: So my background was definitely unique. I started as an enterprise sales rep of the truest form selling subscription-based data analytics and systems into capital markets, so into investment banks, trading desks, hedge funds, asset managers, portfolio managers — you name it. Then I drifted purposely, intentionally away from capital markets and did about four different growth technology companies. I landed at NewsCred, and it was a neat time — it was really the birth of the startup landscape with the whole Flatiron district in New York.

Later, I was looking for my next CRO opportunity and was networking with some of the investor folks that I knew. I had a friend of mine who was a talent partner at a private equity firm who said to me, “I’ve always thought that you’d be really good at this and we’re starting to push for our search firms to have operators.” I went and met with Brad and Joe [founders of True], and three weeks later I was in the seat.

Danny: That’s great. And what do you do at True?

David: Well, we moved to a specialization model right when I got here. I don’t know if I was the test case or not, but I didn’t know search, so my skillset was that I knew the role. I run our go-to-market practice with another partner, and we have probably 40, 45 people in that group. We focus exclusively on sales, marketing, customer success, we’ll do biz dev. I probably skew more to CRO than anything else, but I do CMO and VP of marketing as well, and then I do a handful of business development, chief client officers, and VPs of customer success a year. That’s my mix basically.

What is the skillset of a modern CRO?

Danny: You’ve been in the sales leadership space for a long time, and you’ve been in the recruiting space for a couple of years. What are some of the changes that you’re seeing today in terms of candidates, skills, and experiences?

David: I think a big change has been from what I call a backend pipeline manager to what I would call a full funnel manager.