How the Startup CEO Serves Their Executive Team
It’s always interesting how certain topics or themes pop into my mind. On some level, the ambiguity and constant iteration inherent in the startup CEO role creates a constant churn of ideas, most of which are aimed squarely at questions like “how do we grow bigger, faster?” and “how do we scale our company culture to support this growth?” Thinking about the future path of Remind inevitably brings my thoughts back to our team, our people. The team within our full team that I think of most — and spend the bulk of my time with directly — is our executive team, or “e-team”.
Reflecting recently on how I think about my role leading and managing (yes, two different elements) our e-team, I came up with five layers that define how I view the important role each e-team member plays in a startup. In parallel, these five elements describe the way I best serve and support each e-team leader. For the purposes of the framing below, I’ll speak interchangeably in the context of both my role as a card-carrying e-team member, and as the “coach” for each of our e-team members. Of course, like any relationship, it’s critical that a healthy dialogue flows in both directions, so I’m always open to feedback from my e-team colleagues whenever they feel I can be more helpful to them individually or to all of us as a unified e-team.
It begins with an alignment on the vision, mission, values, and goals that we live by as a company and an e-team. While our vision, mission, and values persist over longer periods of time, our goals have shorter timeframes (e.g. annual and quarterly), and by definition they create the common north star — and sense of urgency — over these discrete periods that bring every functional group together. The e-team must ensure that clearly defined and measurable goals exist for the impact we strive to deliver for our users and customers, the sustainability we strive to create as a business, and the performance and belonging we strive to engender within every team member at Remind.
Next, each of our e-team members must be experts. They are the domain champions for product, engineering, sales, marketing, customer success, finance, and people operations — as well as for many sub-areas of expertise that evolve within these organizational groups. By extension, the people that our e-team leads are themselves even more expert at the important slices of what happens in each of these areas. While it might be the case early on in a startup that a CEO plays a dual role as CEO and functional expert (e.g. product or engineering), once the company has shifted into the “1 to X” phase, the CEO by necessity must shift fully into the “jack of all trades, master of none” mode.
Third, e-team members are not only domain experts, but they perform the equally important (and in some contexts, more important) role as people manager to those team members who report to them. So, not only is our e-team marketing leader or product leader asked to be experts in those domains, they are also asked to be great people managers or “coaches” to the individuals on their teams. As CEO, an important role I play is as a “coach” for my e-team colleagues in helping them as managers, an always challenging role given the constant forces that push and pull on a startup every day.
While the expertise and manager contributions from an e-team member are critical to a company’s success, it actually rests below the fourth ask made of every e-team member, that being they view the e-team as their “first team”. This by no means diminishes the importance of their work as experts and people managers, rather it represents an ask on behalf of the company that they bring their functional focus together with our unified goals in a way that enables us to continually evaluate our performance, processes, and priorities in the most objective way possible. When our head of sales voices the importance of an engineering investment and our head of finance highlights the need for a customer success initiative, these are the examples that illustrate how e-team leaders are collaborating with each other in a way that’s about putting the needs of the company and our collective team ahead of the needs (or wants) of any single department.
Finally, the layers above — and most certainly the fourth area just highlighted —rest firmly on a foundation of trust. If there’s one thing a CEO can most bring to an e-team (and by extension to an entire company) it’s a clear and continuous commitment to building trust. There’s no magic formula to building trust. It starts with being vulnerable across the e-team — sharing openly our backgrounds, our talents and strengths, and our lesser talents and strengths, including even our weaknesses. Trust also requires familiarity and repetition. This means spending more time together (yes, more Zoom meetings together five days a week post COVID), and being willing as an e-team to rely on the collective trust across the team when our work requires us to engage in hard conversations, work through conflict, and make difficult decisions.
It’s true, a startup CEO has too much to do — just like everyone else — yet nothing’s more important than how we show up to serve our e-teams. It begins with being aligned around a core set of shared goals, and then being there to help your e-team experts be great managers for their functional teams. From there it then requires setting a clear expectation that each e-team leader’s first team is the e-team, and that trusting each other on every level — and in every situation — is how executive leadership teams become the force multiplier for company success, as well as team member growth and development, for every individual in the company.
