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In a dynamic, high-pressure role like Chief Revenue Officer (CRO), job security isn’t a given, it’s earned. In this recent webinar, Alex Ollie, Co-Founder and CRO of Reachdesk, joined Adam from Ebsta to share his hard-earned lessons from the trenches.

With CRO tenure now averaging just 18 months (down from 24, according to Harvard Business Review), this conversation provided timely and candid insights on how to not only survive but thrive in one of the toughest executive roles in SaaS.

The Five Pillars to Avoid Getting Fired as a CRO

If you’re looking for a framework to guide your thinking and execution as a CRO, these are the five essential pillars Alex laid out:

  1. Board Management
    • Align revenue goals with reality, not fantasy. Don’t accept numbers you don’t understand or believe in.
    • Communicate clearly and consistently, without overloading your board with noise.
    • Share bad news early, it’s a trust builder when done with transparency and purpose.
    • Focus your team and board on the same top three initiatives. Avoid dual narratives.
  2. Data and Insights
    • Move from reactive to proactive. It’s not enough to know what happened, you need to know why.
    • Centralize data to eliminate blind spots. Fragmented tools hide critical funnel insights.
    • Monitor pipeline risk and obsess over sales velocity, broken down by channel, to drive strategy.
  3. Consistency and Accountability
    • Design your sales process around how buyers actually buy, not how sellers want to sell.
    • Set clear exit criteria tied to key behaviors like identifying economic buyers and defining critical events.
    • Use your top performers’ behavior to shape scalable processes for the rest of the team, without turning everyone into robots.
  4. Ultimate Alignment
    • Shared goals are non-negotiable. Marketing, sales, and CS must own the same revenue target.
    • Incentivize cross-functional teams around outcomes, not vanity metrics.
    • Embed a “first team mindset”. Optimize for the company’s success, not departmental wins.
  5. People
    • Talent is everything. As Alex put it: “People are 90% of your problem and your solution.”
    • Be constantly hiring, networking, and spotting potential, especially when times are good.
    • Build hiring scorecards that assess curiosity, coachability, and execution.
    • Promote diversity of thought to avoid groupthink and drive innovation.
    • Create a performance culture without toxicity – be radically candid, structured, and supportive.

Highlights from Avoiding Getting Fired as a CRO

  • Don’t be a one-trick pony. Your credibility with the CEO and board depends on breadth, not just sales expertise. Know marketing. Know CS. Know product impact.
  • Walk the floor. Dashboards won’t tell you everything. Get firsthand insights from your frontline teams, your best strategies will often come from their ideas.
  • Align incentives to outcomes. Marketing with MQL targets? That’s yesterday’s thinking. Tie marketing comp to revenue and drive real collaboration.
  • Design processes for the 80%. Your champions will find a way to win. Your job is to bring the rest of the team up, not build for unicorns.

Standout Quote

“People are 90% of your problem and your solution. The other 10% is pure luck.”
Alex Ollie, CRO of Reachdesk

This statement sums up the reality of leadership in revenue roles. Strategy matters. Data matters. But if you don’t have the right people in the right seats, your risk of joining the 18-month CRO club skyrockets.

Final Thoughts

The CRO seat is more precarious than ever, but it’s also more critical. Those who thrive will do so not because they avoided mistakes, but because they learned from them quickly, communicated transparently, and surrounded themselves with top-tier talent. Alex Ollie’s lessons provide a blueprint for CROs who want to win – sustainably.

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