Dear SaaStr: What Does a CEO’s Typical Week Look Like at $5m-$10m ARR?
Here’s a typical week for a CEO at $5M-$10m ARR. It’s all about balancing recruiting, customer engagement, team alignment, and strategic planning.
Let’s break it down day by day:
Monday
– Morning: Kick off the week with a leadership team meeting. Review key metrics (ARR growth, churn, pipeline, etc.), align on priorities, and address any blockers. Make sure everyone is clear on what needs to happen this week.
– Midday: Spend 1-2 hours recruiting. This could be interviews, sourcing candidates, or working with your recruiting team to refine the pipeline.
– Afternoon: Customer calls or Zooms. Aim for 2-3 calls with top customers to check in, gather feedback, and strengthen relationships. These are critical for retention and upsell opportunities.
Tuesday
– Morning: Deep dive into product strategy. Meet with your VP of Product (if you have one) or your product team to review the roadmap, prioritize features, and ensure alignment with customer needs.
–Midday: More recruiting. Block another 1-2 hours for interviews or outreach. At this stage, you should be spending at least 20-30% of your time on recruiting.
– Afternoon: Meet with your VP of Sales to review the pipeline. Focus on deals that need your involvement and ensure the team is on track to hit targets.
Wednesday
– Morning: Customer visits or Zooms. If possible, dedicate the morning to meeting with customers in person or virtually. Aim for at least 3-4 touchpoints this day.
– Midday: Team 1:1s. Check in with your direct reports (VPs of Sales, Marketing, Customer Success, etc.) to provide support, remove roadblocks, and ensure alignment.
– Afternoon: Strategy session. Use this time to work on long-term planning—whether it’s fundraising, market expansion, or scaling operations.
Thursday
– Morning: Recruiting again. By now, you’re seeing the pattern—recruiting is a daily activity. Focus on key hires like VPs or other leadership roles.
– Midday: Marketing review. Meet with your VP of Marketing to review campaigns, lead generation efforts, and brand strategy. Ensure the team is driving enough pipeline to support sales growth.
– Afternoon: Product or engineering sync. Check in on progress, address any technical debt, and ensure the team is aligned on priorities.
Friday
– Morning: Customer success focus. Meet with your VP of Customer Success to review retention metrics, churn risks, and upsell opportunities. Ensure your biggest customers are happy and engaged.
– Midday: All-hands meeting. Share updates with the entire company—progress, wins, challenges, and priorities for the next week. This keeps everyone aligned and motivated.
– Afternoon: Wrap up the week with more recruiting or customer calls. Use this time to tie up loose ends and prepare for the following week.
Saturday
– Morning: Reflect and plan. Spend a few hours reviewing the week’s progress and planning for the next. This is also a good time to catch up on emails or other admin tasks.
– Afternoon: Personal time. Recharge and spend time with family or hobbies. You need to stay sharp, and that means taking care of yourself.
Sunday
– Morning: Light work. Review key metrics, prep for Monday’s leadership meeting, and finalize your priorities for the week.
– Afternoon: Rest and recharge. Scaling a company is a marathon, not a sprint. Take the time to reset so you can hit the ground running on Monday.
This agenda isn’t rigid of course ;)—it’s a framework.
And yes, it’s a lot. But the world is so much more competitive now than it used to be in B2B. Especially in the Age of AI.
The key is to prioritize recruiting, customer engagement, and supporting your team while carving out time for strategic thinking.
