Sarah E. Brown - Lead Upwards

Startup executives are accountable for delivering business results to company shareholders, including your co‐founders, fellow executives, the board and investors (your founders' bosses), and other employees. As an executive, you have the most ownership (including, likely, equity) and accountability of anyone on your team. Unlike individual contributors or mid‐level management, startup executives must build business strategies and execute them. Pavilion leader Jennifer Rice refers to the concept of building business opinions (vs. being an order taker) as “having a theory of business.”

As a marketing executive I am expected to form and communicate data‐driven opinions on how to generate demand within target accounts to increase my startup's market share and grow revenue. My CEO and cross‐functional peers can help and my team will provide input, but, ultimately, I own and put my name on a plan. I need others to believe in the plan, but first I have to believe in it and champion it. When it succeeds or fails, I am the one who's responsible. No one will hand these plans to us to go execute as startup leaders as they did when we were mid‐level managers (although great ideas can and do come from anyone on the team). It's on us to strategize and enable our teams to deliver results.

As business leader Peter Drucker would say, there is a difference between doing the right work and work done right. Your job is to make sure that the programs, tactics, and tools your team uses roll up to the overall business goals of your organization. Own the “why” of the work—not just “should I run this PR campaign?” but “should we run *any* PR campaigns, and is that the best investment of our limited budget, and why?” This is how executives need to think. You'll constantly be making tradeoffs.

How will your department's strategy and tactics lead to the business achieving goals? What have you learned in previous quarters or even recent weeks and days that informs the work you're doing? These are the types of questions executives are expected to answer. Continuing to think through “why” is just as important as “how.” The best startup leaders constantly learn to improve and achieve faster, better results.

As an individual contributor or a manager of a small team, you can get away with having depth of expertise in one area without much breadth across the department. Your remit may be narrow. Being an executive comes with an expectation that you understand the fundamentals of many areas of your department, not just one specific area of functional expertise. This includes things like knowing about front‐end engineering vs. full‐stack, and how to manage multiple technical teams running multiple products, etc. While you aren't expected to know everything (that's what hiring your team is all about), you'll need to expand the breadth of your functional area expertise in order to hire, retain, and effectively manage a team of high performers who execute across your function.

You can be a “team of one” as a “head of” at a startup for longer than you'd think. I did it for several quarters before hiring my team in a recent executive role. But you can't reach any kind of scale without growing your organization. If you can't hire a team, that can be a dealbreaker impediment to your success. First‐time executives often fail to attract the best talent, because candidates may feel that their abilities as a leader are yet to be proven.

We'll dig into how first‐time startup executives can succeed at hiring in later chapters, including how to build an inclusive, high‐performing team that will support each other's success. If you want to be an executive (or already are one), be prepared to adopt a “servant leader” mindset and stretch your skills in effective management as one of your highest priorities.

Startup executive and Diversity and Inclusion (D&I) expert Aubrey Blanche says that while it's possible to live a balanced life as an executive, we shouldn't underplay the lifestyle impact. It really is a bigger commitment than a non‐executive role.

“There is often discussion that you don't have to give up some of your life to be a leader. We do a disservice to people when we're not honest about the big life impact that comes with taking on leadership roles,” says Blanche. “There certainly are unique situations where you can work part‐time and be a VP, but it really does require you to put your job relatively central to your life. I think we should go into that choice with eyes wide open,” says Blanche.

While you'll enjoy camaraderie with your fellow executives, don't expect to be chummy with your team in the same way, especially if you were promoted from within the ranks. Being the team leader gives you power and a position of authority that won't allow you to act as you did before, even as a manager. That power is significant. You can't expect to be on “even footing” when you could fire, promote, or give pay rises to your people. Their livelihood is now tied to your decision‐making, and that puts you in a position of power that shifts the dynamics within your relationships.

You're also dependent on your team. No startup executive would be successful if they didn't have a high‐performing team rallied around them, but it's inherently imbalanced and skewed by authority dynamics. It's much harder for a report to get their boss fired than vice versa. If you fail, your team may stay on and you may see the door, but it wouldn't be them making that decision. Because of this power imbalance, you must act accordingly.

We must not abuse this power imbalance or put our direct reports in positions that could hurt them (for example, dating them, or engaging in behavior that's inappropriate for the hierarchy). Some startup executives have too much power over their teams and reports. Unlike at big companies, some startup leaders can get away with a lot without oversight, which is thankfully becoming less the norm thanks to movements to increase equity and inclusion and expose and enforce consequences for bad behavior. The checks and balances within the startup ecosystem have been lacking for too long. Thankfully, many startups are creating opportunities for employees to have a real voice in giving feedback on their managers and supporting a healthy, inclusive culture on teams.

Acknowledging inherent imbalances, we can still create strong, positive relationships with individuals on our teams. Even though we can't be peers while we're managing our reports, we can get to know them as individuals, help them be stewards of their own careers, give them growth opportunities, and support their contributions and productivity. We can do our best to treat everyone with the kindness and respect they deserve and ensure they have a psychologically safe and affirming work environment that honors their individual needs as well as the collective team needs.

If you're signing up for an executive role, embrace the fact that your ability to consistently perform these management responsibilities makes a true difference in people's lives. Aspire to do this well, knowing even with good intentions you can and will make plenty of mistakes along the way. We'll talk about how to deal with this later in the book in the section on team management.