Being a CRO is hard. Not only do you have to deliver quarter after quarter, but the average tenure is around 2 years. Of those that leave, 70% are shown the door involuntarily.1 Oof.
That means most CROs are hired into a situation where the last person was dismissed because things weren’t going well. You start day one with a ticking clock and the expectation that you’ll quickly turn it all around.
In summary, only a small set of CROs succeed. The ones that do are great at quickly solving today’s problems while building teams that can scale for tomorrow. That’s where this week’s interview with Amy Volas comes in.
Amy’s been a successful seller and sales leader. Now she’s the CEO and Founder of Avenue Talent Partners, making it her mission to help companies hire the sales leaders they need to succeed. Beyond that, she’s also a LinkedIn top voice and an all-around delightful person.
We sat down for a fantastic conversation about the lifecycle of the CRO—from before you take the job, through the first 90 days all the way to successfully delivering at scale. While we mostly focused on hiring and team building, Amy delivered words of wisdom on many other parts of the role as well.
You can watch the interview2 right here on Substack, but it’s also on YouTube if you prefer that. Read on for some key takeaways using old-fashioned text.
On the mistakes that get CROs fired
“It’s one thing to get the seat, it’s another thing to keep it.”
Amy hits us with two primary reasons why CROs get the axe—and it starts from day one.
First, they rely too heavily on their “rinse and repeat” playbook, failing to adapt their past success to the true jobs to be done that exist in their new role. (More on that below.)
Second, they don’t fight for (and earn) the seat at the table. CROs have to set realistic expectations—with data and transparency—or they won’t last. The smartest CROs aren’t just trying to keep their job; they’re actively managing their relationship with the CEO, other leaders and the board.
Amy shared a real-life story to illustrate the point.
The CEO comes down and says, look, we have this number, we've got to hit this number and commits that number to the board without really a lot of discussion. […] The number is like $85 million. The CRO says there's no way we're gonna get to that $85 million. We're gonna get to like $43 if we're lucky and here's why. Had the data, had all of the information. Also was communicating with this operating partner that I know from this VC and was like, if I'm missing something, let me know. Was super transparent about here's why. And the CEO said, that's not your problem to manage that, that's mine, just go get the number. Well, what do you think happened? They hit like $42 and a half.
Guess who got fired? The CEO—not the CRO! They’d taken the time to be transparent, built trust, and managed expectations. CROs who treat board and stakeholder management as an ongoing, proactive process—rather than reactive damage control—are the ones who stay in the role.
Amy notes that this starts during the hiring process. She suggests identifying the most influential member of the board, understanding their expectations and making sure that aligns with everything else you’ve heard about the plan. If there are mismatches, address it head on or else you’re in for pain.
On jobs to be done, playbooks and “the big guns”
"Your ‘read, rinse, repeat’ playbook is going to get you fired. It’s not about whether you have a playbook—it’s about knowing which pieces to pull out, when to use them, and when to throw the whole thing out and start fresh."
You get hired for a role because you’ve been successful in the past. You also get hired for a role because you’ve got a network of folks you can bring with you. Why not run it back? Bring the same plays with the same people to the new gig and get rolling.
Amy’s seen this go sideways way too many times. Just because the thing you did last time worked then, it doesn’t mean it’ll work this time. Your first job to be done is is to determine the jobs to be done that are specific to the current situation.
Average CROs just open the old playbook without fully considering those jobs to be done. The best CROs keep an open mind and combine information about the new role with their existing playbooks to learn and adapt. (This might remind some of you of the OODA loop.)
Rushing into a situation by bringing in the old team or running the old plays often alienates the talent you already have and signals that you’re making changes before you even understand the problems. You might overlook some great players that can actually help you ramp faster and execute better.
Make sure you’re setting yourself up to do this job, not the last one.
On evaluating your current team
“We all have data. But do you actually know the story behind it?”
Once a CRO has mapped the jobs to be done, the next challenge is determining whether they have the right people in place (before bringing in the “big guns”). Amy notes it’s very tempting to just look at the raw data and decide who stays and who goes. If Team A is hitting and Team B isn’t, get rid of the Team B’s manager. If Rep A’s last 3 gong recording are bad, send ‘em packing.
It might not be so simple. You need to put away the spreadsheet, talk to people and deeply inspect deals.
I love that Amy gave two super tactical callouts here.
Sales stage clarity - New CROs often need to fix forecasting. (After all, missing the number is why got the last person fired.) In her experience, it’s incredibly common to find out that reps don’t even have a common definition of the existing sales stages. Fix this and watch the forecast improve.
Time studies - Spend two weeks having everyone (including you) log their time. Make it fun with a slack channel. It’s a shortcut to rooting out inefficiencies.
On building a leadership team that scales
“The best way to build an external bench is to actually take care of your internal team.”
CROs need to be proactive, not reactive, about leadership hiring. That means building and continuously maintaining a bench of good people so that you’ve got folks to tap when the time is right. She had some great advice here:
Take care of your people - A leader that shows up and works for their team creates a flywheel. Fulfilled team members will recruit for you. Unhappy team members will send people running in the opposite direction. Amy puts it succinctly: “people talk.”
Build the internal bench - Identify high-potential ICs and managers who can grow into bigger roles. If you’re always looking outside for leaders, you’re failing to build a sustainable team.
Build the external bench - Keep a running list of top talent—people you’ve met at conferences, through referrals, or past hiring processes. Make sure to regularly stay in touch so you’re not coming in cold when an opening arises.
Manage your pipeline - Keep a list of short, near and long-term hiring prospects so you’ll always have folks to reach out to when you need it.
The strongest revenue organizations are intentional about leadership hiring, not just backfilling gaps.
On IC hiring that focuses on quality over quantity
“You hired for the ‘what’ and missed the ‘how’ and the ‘why.’”
The old days of just hiring to hit a headcount plan are long gone. Instead, Amy says to focus on impact. Here are a few of her recommendations:
Audit job descriptions quarterly to ensure they reflect the actual work.
Hire based on pipeline needs, not territory coverage. Adding reps without careful consideration here just leads to wasted payroll.3
Challenge hiring managers: Are they hiring people they like, or people who can actually do the job?
As the ROI on reps has declined, it’s never been more important to get this right.
On building a sales hiring system that works
“Most hiring plans operate from a reactive place—weakness is reaction, strength is being proactive and strategic.”
Amy left us with some specific takeaways for creating better interviewing processes. Here’s her simple, but effective, blueprint:
Scorecards - Define success upfront so gut instincts don’t derail hiring decisions. Use a scorecard.
Real-world scenarios - Have candidates engage in actual work challenges, not generic roleplay. Amy offers a great example of this when she talks about having a rep go through the exact process they’d use to prioritize their territory. She’s also kind enough to give Gradient Works a shoutout here.
Hiring committee alignment - Everyone should understand what “good” looks like—not just interview for likability. The scorecard helps tremendously here.
Great hiring processes minimize gut feelings and subjectivity—they’re about building a system that drives alignment on what good looks like and then rigorously enforces it.
And yes, I know it’s not actually a podcast since it’s not available on, you know, podcasting services. I may change that in the future.
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