What surprised us?
Katelyn: Both of us showed up to truly share the CEO seat—which is materially different from acting as Sales and Ops/Content working in partnership. We’d talked about this changing element of our dynamic before stepping into our new roles, but actually living it was surprising. I think on some level I was still thinking of each of us having domains, and sure, we each specialize. But because we have the same job now, I found myself thinking differently about business problems and saw the same happening with Tony. It kicked us into a different headspace that I think will be super productive for the company. It’s been really cool to see what we come up with when we apply our complementary but very different strengths to problems that have historically been the other’s territory.
Tony: I totally went into the year thinking of us still having our specific domains, but it didn’t take long to see the benefit that Steyer would receive from both of us bringing fresh perspectives. While I still love the idea of specialization and mastery, there is a huge advantage in taking in the opinion of a partner with less emotional attachment to a certain area of the business. Being guarded and defensive around fresh ideas on how to drive sales, improve operational efficiency, reduce costs, etc., would be a big detriment to any partnership and the team. I am super happy with how it worked out and hope to expand on this in 2025!
Katelyn: I didn’t expect to get as much time with Tony as I ended up typically getting on any given week. I knew our twice-weekly 1:1s would be essential to our partnership, and I expected them to be perhaps even our only time together each week, out of respect for the work both of us need to get done outside of meetings time (especially out of respect for Tony’s heads-down prospecting time). Some weeks, that was the case, but more often than not we would meet ad hoc throughout the week as questions, issues, or ideas bubbled up, joining each other’s calls sometimes. We’d then cancel our formal 1:1s or use them to debrief on other meetings.
Tony: For those that don’t know, I am very guarded with my time, specifically meeting time – sometimes to a fault! The financial part of my brain quickly starts calculating the cost, and opportunity cost, of each meeting, which often leads me to decline the meetings altogether or to multitask. As we went about the year, the value of the time we spent together far outweighed those costs which allowed me to free up my brain for those ad-hoc conversations and I believe they led to strong results. One thing that was a huge help in this is how aware Katelyn was of this blocker for me and the care in which she approached us spending our time.
What went as expected?
Katelyn: I’m finding it hugely important, as I expected, to be able to talk with Tony super openly as a peer about business leadership challenges and dilemmas and get his super open takes in return. We are in such a tough business environment and we’ve had to make such difficult, in some cases painful decisions—I truly felt, over the course of the year, that I was in the best of company with Tony talking through our perspectives, our options, and how our choices played out.
Katelyn: I also expected we’d disagree on some things, and we did. I’m glad for it, too, because the decisions we made were so much stronger and better informed than they would have been with either of us tackling it solo. This benefit is also, honestly, as expected… and it’s been really satisfying to see that hope/expectation come to fruition. If we don’t agree yet on a course of action, we’re not done talking about it–or letting it simmer, or gathering our research–yet.
Tony: This! If we never disagreed, then why would we even want to have a Co-CEO model? I found our disagreements to be a great balance in the decisions we would ultimately land on. When Kate approached us with the idea of a Co-CEO model, I was mainly hesitant because of this aspect of the partnership, but as the year progressed it became crystal clear that we would land on a much better decision/outcome by putting our heads together with all the facts and assumptions vs. one of us making the call. There still are many decisions that each of us just trust the other to make, which is crucial, but for the big “iceberg” (major) decisions we listened to each other’s perspectives and came out with an agreed-upon path forward. There is nothing like a healthy business “argument.”
What are we going to do differently in 2025?
Katelyn: We are leaning into the benefits of Co-CEOing when it comes to sparking new ideas and trying new approaches. We’ve changed up a few responsibilities and rethought structure so that we can more easily give input where we can contribute best.
Tony: I am really looking forward to continuing to blur the lines of each other’s territories and collaborating to lead the company to new heights!
For more about our business expectations for this year versus reality, here’s a recent Workings on that very subject. We’d love to hear from you, and we can be reached at kreilly@steyer.net and/or tbatista@steyer.net.
Thanks,
Katelyn and Tony
Photo of the Steyer systems and deals team, circa October 2024. Katelyn’s in the flowered blouse and Tony’s in the grey hoodie. From left to right, top to bottom: Jen Carlston, Genevieve Jacobsen, Katelyn Reilly, Josh Krenz, Tony Batista, Kiersten Kieran, Jon Francis-Landau, Jordyn Hatch.