Dear SaaStr: I run a 30M arr software company — operating as both CEO and CRO. I feel like I failing at both – what is a better option?
At $30M ARR, you’re at a stage where the demands of both the CEO and CRO roles are too significant for one person to handle effectively. It’s not that you’re failing—it’s that the roles themselves are designed to be full-time, high-stakes jobs. Trying to do both is setting yourself up for burnout and suboptimal results.
The better option? It’s time to hire a strong CRO or VP of Sales.
And yes, this is even true if you’ve failed at this hire several times in the past.
At this stage, you need someone who can build scalable, predictable revenue processes and align your sales, marketing, and customer success teams. A great CRO will take ownership of the revenue engine, freeing you to focus on being the CEO—driving vision, culture, and long-term strategy.
Here’s what I’d recommend:
1. Hire a Proven CRO or VP of Sales
Look for someone who has successfully scaled a company from $30M to $100M+ ARR. They’ll know the pitfalls and have the pattern recognition to avoid them. Be clear about your expectations—align on revenue targets and the roadmap to get there. Don’t settle for someone who’s just chasing the title, you need a veteran who can own the full function.
2. Stay Involved in Sales, But Differently
As CEO, you shouldn’t vanish from the sales cycle entirely. Stay involved in strategic or executive-level deals—spend 10-20% of your time here. This keeps you connected to the market and ensures alignment with your CRO.
3. Focus on Hiring and Scaling Leadership
Beyond a CRO, you might need to bring in other experienced VPs—Marketing, Customer Success, etc.—to build a leadership team that can scale with you. At $30M ARR, you’re big enough to attract top-tier talent. Invest in hiring the right people and empower them to own their functions.
4. Take a Step Back to Recharge
If you’re feeling overwhelmed, take a short break to reset. Even a few weeks can give you clarity and perspective. When you come back, focus on hiring the right leaders and delegating effectively.
You’ve already built something incredible to get to $30M ARR. Now it’s about scaling smartly by bringing in the right people to help you go from $40M to $100M+. You don’t have to do it all yourself—nor should you.
