Before you hire a CRO: learn how your company sells first

If you are hiring your first chief revenue officer, you probably want two things at once: faster revenue growth, and day-to-day selling off your own desk. Both are reasonable. The trouble starts when the new leader is expected to work out how the company sells while also running and growing it.

A CRO or VP of Sales can do a great deal with a sales process that already works: hire, coach, fix the weak stages and take it into new markets. Turning a sale that lives only in the founder's head into one a team can run is a different and much harder job. A new leader can be handed it without anyone saying so, and then be measured as if the process already worked.

This post explains why that happens, what to write down before you start the search and how to hand over sales once the leader arrives. It draws on two attempts I made to hand off sales at Lead Cookie, my former LinkedIn prospecting company: the first failed, the second worked. I wrote about both in a 2020 essay and talked them through on my podcast in 2019. Both were about a small company's first salesperson, not a CRO; what follows applies those lessons to a CRO search.

DisclosureJake Jorgovan co-founded Alpha Apex Group, which this essay links to.

Why hiring a salesperson to fix a sales problem goes wrong

In an October 2019 episode with Damian Thompson, a sales trainer and the founder of Salesability, I described a sentence I kept hearing from people running consultancies and agencies: "I've got a sales problem, and so I'm going to go hire a salesperson." In my 2020 essay I admitted it was the big mistake I had made myself.

A peer once pushed back on me: you can hire a developer without knowing how to code, so why not a salesperson? Damian's answer on that episode was this. You can hire a developer because you hold the vision for the product, the market and the roadmap. With sales, founders often want one person to set the vision, build the systems and the processes, and also do the daily work. If the system and process are in place, he said, you can absolutely hire someone to do the daily work in sales. His first question to anyone planning the hire was why: it should come because you are ready to scale, and wanting to stop selling because you dislike it is almost always the wrong reason.

The same holds for a senior hire. A CRO will build more than a first salesperson does, but they still need to know who the company sells to, why those customers buy and what a good deal looks like. If nobody can tell them, the first months go on discovering it, and the targets don't wait.

What happened when I handed off sales too early

At Lead Cookie, I first tried to hand off sales roughly ten months into the business. In the essay I listed what went wrong. It was too early: we still had a lot to learn about our own sales process. The process was far too ambiguous and lived in my head; I had tried to document some of it, but what I handed over was vague. I called that probably the biggest mistake. I also went too fast, trying to offload it completely in about a month and a half, and handed over everything at once: sales calls, inbound leads and account management.

The result showed up in the deals. As I said on the 2019 episode, the salesperson made some sales to people he should have turned away, and turned away some people who were a good fit. After about two and a half months sales slumped, and I had to lay people off. In my words then: "it was me trying to hand things off way too early. Just didn't have it figured out yet."

The salesperson was overwhelmed and failed at the role, but the failure was mine. Every mistake on that list was a decision I made.

Image

Zoom

Jake’s historical account, summarized from this article. These results describe his experience and are not a performance forecast.

What changed the second time

After that, I kept the sales seat for the next full year. I refined the process, automated as much as I could in our CRM, closing, invoicing and follow-ups, and documented it in a sales playbook. The goal I set in the essay was that before you hand off sales, "you want it to become robotic. You want it to be a system and a process that someone else is simply taking over."

When I did hand it over, the difference was that there was something to hand over. As I put it on the 2019 episode, our new salesperson "didn't have to build a process. He just had to learn what existed there." He then went on to make it better than I had it, which is what you want from a good hire. He also came with years of running outbound campaigns himself, which is what let him act as the gatekeeper, filtering out leads who were a bad fit.

The handover itself was slow on purpose. While he trained for sales, he spent about one to two months working across the company's other roles, from account strategy to the simplest tasks, so he saw how the whole business and its systems worked. His 90-day goal was to handle closing deals from inbound to operations on his own. He took on one or two pieces a week: first scheduling calls with inbound leads while I stayed copied on the emails, then the CRM and follow-ups, then entering closed deals and handing them to the operations team. He shadowed my calls, then ran calls with me listening, then ran them alone.

Image

Zoom

Jake’s handover at Lead Cookie: responsibilities moved across gradually, with a 90-day goal of handling a deal from inbound lead to operations.

One thing took longer to transfer. Some of our deals had closed on the first call partly because I could improvise, pulling up a client we had succeeded with who was just like the prospect. Early on, our new salesperson couldn't always do that, and when he wasn't sure he told prospects he would check with the team and come back. That accidentally raised his close rates. Damian's point on the same episode was that a founder can't hand their experience to a sales rep. "What you can give them is a winning process."

What to write down before a CRO search

A CEO hiring a CRO doesn't need to be the best seller in the company. You do need enough grasp of how the company wins to brief the search, judge the candidates and manage the person you hire. Writing it down is the test. If you can't fill in the page below, that is the work to do before the search, or the first thing to agree with the leader you hire.

The "run, fix or build" line matters most. A candidate who has run a mature sales organization and one who has built a first team are different hires. As I wrote in the essay, citing Damian, who was then my sales coach, you can't just hire anyone to build your sales process: anyone capable of it is going to be either extremely expensive or already working somewhere making a lot of money. If that is the job, say so in the brief and pay for it.

Decide who owns lead generation

The second handover taught me something the first one hadn't. Handing off sales is not the same as handing off marketing. Once sales ran without me, I stepped back too far and let our existing marketing momentum carry us, until lead flow slowed. Only then did I see that generating leads was still on my plate. As I put it in the essay: "Sales is closing deals. Marketing is generating them."

Decide whether this leader will own sales alone or also marketing and customer success. Put that scope in the brief before the search and agree it with the marketing leader. A new sales leader who inherits a shrinking pipeline nobody owns will look like the problem.

Hand over in pieces and watch the numbers

Three parts of that second handover carry over to a senior hire, adapted to the role:

1. Hand the work over in pieces.
2. Stay close to the early decisions, so questions about existing accounts, pricing exceptions and past deals come to you while the new leader is still learning the answers.
3. Keep weekly one-on-ones going after the handover, because the person running sales is the first to see when lead volume drops and when sales pick up.

At Lead Cookie we tracked three numbers every week: new leads, sales calls held and deals closed. When new leads dropped, the other two soon followed. The point, as I wrote, is that "you need data so you can know if the salesperson is the problem, or if something else is." For a senior hire, record those numbers before the leader arrives and agree which measures fit the role. They show where to look when results dip, alongside the revenue outcomes the leader was hired to deliver. Without that starting point, the first dip in their tenure has nothing to be measured against.

Image

Zoom

The approach described in this article, shown as a visual guide.

How my rule changed between 2020 and 2025

In 2020 I put the rule strictly: build your sales process yourself, then hire someone else to operate it. By 2021 I described it as learning a skill to a level where you can do it, not mastering it. "Even if you want to hire someone for sales for your business," I said on an episode about systems, "you need to be able to do sales first." My own pattern was to work in an area for a while, build and document its systems, then hire someone to replace myself.

Talking to Alex McClafferty in a May 2025 interview (opens in a new tab), I said I had almost updated a rule from a list I had written down, never to hire someone to solve a problem you haven't solved yourself. I said founders were still making the same mistake, deciding they have a sales problem and hiring a salesperson, over and over. In that interview I put it more softly: "there's some level of competency you need in all aspects of the business to be able to hire someone effectively." You have to get decent at it, then hire someone, so you can manage them.

Applied to a CRO search, that is the bar. You don't need to outsell the person you hire. You need to understand your sales process well enough to tell them how it works today, and to see whether it is getting better.

Could you fill in that page today, with every line answered?