year end tips for CEOs

Good morning, and Happy Holidays from your friends at the SaaS Playbook! It’s been a fantastic year, and we thank you for tuning in to our playbook every week. As we come up on the end of the year and began to reflect on the past 12 months, we thought we’d offer some CEOing tips to help get you thinking on how to have an even better 2020.

Cheers, and see you next year!


📋 CEOs usually reserve quarterly presentations for their board, where they update the group on what’s been accomplished over the past 3 months as well as their plan for the next period. But let’s take a step back for a second. Who is more important to your company’s success, your board, or your own employees? Front CEO Mathilde Collin knows the answer, and spends two weeks every quarter also putting together a deck just for her team. Her decks have all the classic metrics and anecdotes, but revolve around a story, which involves the team and helps them find meaning in their work. While it takes a lot of time to put together (and an hour from employee’s days to hear it), Collin insists it’s well worth the benefits.

🧪 Mark Coopersmith has spent his life in entrepreneurship and innovation, first founding and exiting an Ecommerce business to Google, and now teaching the subject at UC Berkeley. One of the first (and most important) lessons he teaches his students is that the startup motto of “failure is not an option” is a conflicting statement. New ideas are bound to not work out, and if you can’t detach yourself from an idea and move on to the next, you will continue to fail! If he could offer one takeaway from his course, it would be that developing a more productive relationship with failure will foster a better environment for innovation, engagement, and long-term success.

💼 A company’s board of directors is there to make sure it’s getting guidance from the best equipped people to help it succeed. But those people are really there for the business as a whole, and not just you as a CEO. A great way to make sure you’re also getting helpful advice from people dedicated to your development and wellbeing is what we call a personal board. There are 4 main roles you will want to have filled on your board:

  1. Professional Mentor - Try to find a mentor who has led a business in your space, and if possible, at a company similar in scale to yours. They’ll understand the problems you face better than anyone else, and likely be thrilled to share their experiences.

  2. Mental Health Coach - Nearly half of founders struggle with mental health at some point, so it’s important to have someone to help you with coping strategies. This doesn’t have to be a professional—a close friend who has some experience is also great.

  3. Bigger Picture Person - This should be a person who can take a step back and put things in perspective for you, so someone not involved in your business at all like a spouse or one of your old friends is an ideal candidate for the role.

  4. Pressure Release Valve - Lastly, it always helps to have someone else you can vent to. Try looking for another founder dealing with similar issues or that at least can put themselves in your shoes.


🧘 There’s an unfound belief in many tech startups that consistently working all nighters and focusing on nothing but your business is “just a part of the grind.” We acknowledge that working hard obviously pays off, but as Megan McNealy argues in her recently published Reinvent the Wheel, your output will generally be better (and more sustainable) if you can do well while also being well. We don’t necessarily see eye to eye on every one of her “well-being wheel spokes,” but the book’s interviews with entrepreneurs who have struck an admirable work-life balance while also increasing their production are inspiring.