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New Series: When and How to Hire Each CXO

November 1, 2021

About ten years ago I started the blog, “Only Once,” written primarily for first-time CEOs because you’re only a first-time CEO once—and you either succeed at that or get pushed out. While there are tons of books, blogs, podcasts, Ted Talks, and mentors that cover the broad topic of leadership, there are a lot of nuances to being a CEO that aren’t covered in any textbook. What I learned since then is that the same situation holds true for any Chief Executive “X,” especially for the true startup where everybody is pitching in to make things work, titles are basically for people outside the company to know who to contact, and tasks within the startup gets divvied out to the person with a little bit of extra time. You’re only a first-time CXO once, and after that you’ll share the same fate as the first-time CEO—you either succeed or fail.

After my colleagues and I sold our first company, Return Path, we figured out that each of us could share our experience in scaling up a company and we assembled all our ideas and published them in Startup CXO: A Field Guide to Scaling up Your Company’s Critical Functions and Teams. This series of blog posts highlights four common challenges that CEOs and the leadership team face as they scale:

  1. When is it time to hire your first CXO?
  2. What does “great” look like for each CXO?
  3. Signs your CXO isn’t scaling
  4. How to engage with each CXO

The series is intended for any C-level executive or board member involved with startups. After all, the success of a team isn’t wholly determined by whether or not the CEO can understand these four critical factors, but whether any C-level executive can learn about these factors and put into practice the skills needed to level-up themselves.

-Matt Blumberg, November 2, 2021