The Billion-Dollar Mistake. Why Most Companies Hire the Wrong CRO
What founders and CEOs get wrong when choosing their top revenue leader
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In today's market, hiring the wrong Chief Revenue Officer isn’t just a setback—it’s a multi-million-dollar mistake. However, many companies continue to make bad hires by relying on outdated, ineffective playbooks for what is arguably one of the most critical roles married to business success.
The traditional approach is a flawed metric
For years, the CRO hiring playbook has looked the same:
Prioritize candidates with impressive past revenue achievements.
Look for leaders who have scaled sales teams and hit aggressive revenue targets.
Assume that if they drove big results before, they’ll do it again.
But revenue leadership isn’t about repeating past success—it’s about building what’s next. I’ve met countless revenue leaders who start a new role thinking that their past experience will carry over into the new role but that isn’t always the case.
Every company is different and today, the way revenue leaders sell, market, and drive growth has fundamentally changed. AI, automation, and shifting buyer behaviors have made old playbooks obsolete. Yet, most companies are still hiring CROs as if the landscape hasn’t changed.
A CRO who thrived five years ago—before technology transformed demand generation, before automation reduced SDR headcount before data dictated every customer interaction—may be completely irrelevant today.
What companies get wrong about CRO hiring
1. They mistake past company experience for future growth potential
Too many CEOs are enamored by well known brands that have scaled. They default to hiring revenue leadership from these companies with the assumption that past success at a high-growth company will translate.
But as all business leaders know, there are many factors that go into success and it is essential to unpack if the growth was really driven by the CRO. We know nobody does it alone and success includes the strength of the product, timing, pricing, product market fit, tailwinds, and more.
A leader who rode the wave at an already dominant company may struggle to build a revenue engine from the ground up in a different environment.
2. They overvalue past experience in a market that shifted
The go-to-market models that worked a decade ago have changed across most industries. AI is automating large portions of the sales funnel, self-service and product-led growth models are reshaping B2B sales, buyers have more control and more options, and relationship selling is over as data, efficacy and transparency take center stage.
A CRO who built their career on yesterday’s playbook may be the worst choice to lead a next generation revenue strategy.
3. They overestimate a candidate’s ability to be adaptable
The best CROs today are operators who understand how to build revenue strategies that evolve with technology advancements. They know how to align sales, marketing, and customer success into a single, unified revenue engine. They make bold moves when old strategies stop working. And they know how—and when—to lean into their most human traits, like empathy and judgment, to lead effectively.
Three things to look for when hiring a CRO:
There are many things to consider when hiring a CRO but here are three things to keep top of mind.
1. Prioritize candidates who have built in unpredictable markets
A great CRO isn’t just someone who scaled a business when the wind was at their back. They’ve led through downturns, market disruptions, and radical shifts in buyer behavior.
An easy question to ask during the interview process is: "What was your biggest sales success?" What is more telling though is:"Share with me a time your entire go-to-market stopped working. How did you manage it? What actions did you take?"
A CRO who can answer that question by walking you through the ups and downs of the decisions they had to make, how they influenced the corporation at large to gain alignment, and the actions they took to lead their team will give you greater insight as to if your prospect hire can adapt when challenges head their way.
2. Hire for revenue strategy, not just sales leadership
A CRO isn’t just the head of sales—they influence the entire revenue engine. Note the word influence not ownership. The distinct lanes of revenue ownership are over. Divisions are merging, organizational design is shifting, and revenue leadership requires more influence to ensure success.
Today’s CRO must:
Align sales, marketing, and customer success into one cohesive strategy.
Understand where AI fits into revenue operations—and where it doesn’t.
Know when to scale teams—and when to lean on automation instead.
Be humble and transparent about what they do and don’t know so the CEO can design a leadership team that is complimentary and collaborative.
3. Stop defaulting to safe hiring and take calculated risks
The worst CRO hires often feel like the safest choice. It’s hard not to lean into candidates that have big name logos on their résumés but this is when CEOs need to double down on their interview process and fully examine if a candidate can deliver on their vision.
A calculated risk means:
Deeply interviewing candidates against “must have” knowledge and criteria.
Using technology and 3rd party assessment tools to measure capability and adaptability
Learning about past failures as much as examining past successes.
Reference checking to the highest level to understand personality traits, motivators, triggers, and more.
Always having a project during the interview process which allows you to get to know your candidate, how they work, the vision and skills they have, and if you are compatible.
Hiring a CRO in today’s landscape can be terrifying for many CEOs. The wrong hire can set your company back by months or even years. The companies that continue to hire CROs based on outdated criteria will struggle to scale in a world where revenue growth is changing faster than ever. The companies that rethink their hiring strategy—who prioritize adaptability, strategic thinking, and AI fluency—will own the next decade of growth.
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