Sarah E. Brown - Lead Upwards

2 2.“Why Women Don't Apply for Jobs Unless They're 100% Qualified,” Harvard Business Review (2021, November 2). Retrieved November 6, 2021, from: https://hbr.org/2014/08/why-women-dont-apply-for-jobs-unless-theyre-100-qualified.

3 3.Scott, K. I. M. (2021). Just Work: Get Sh*t Done, Fast and Fair. Essay, Macmillan, p. 195.

4 4.“How Apple Is Organized for Innovation,” Harvard Business Review (2021, August 27). Retrieved November 6, 2021, from: https://hbr.org/2020/11/how-apple-is-organized-for-innovation.

If you want to be a startup executive, there are several skill and experience gaps you'll likely need to address to make the transition. Here's how some successful startup leaders did it .

The skills and experience gaps you'll need to address to transition to an executive are within your reach. To be a strategic leader who can scale, you'll need to operate differently from how you did in prior roles. In this chapter, we'll discuss how leaders landed their first startup roles and how they successfully bridged the transition.

“I think we have this story that we need to wait to be knighted with a K to be in leadership,” says VC and executive coach Sue Heilbronner. “Instead, just go identify an objective and start working towards it until you're doing it. Deciding to do leadership is that simple.”

Rachel Beisel spent years as a marketing manager in the outdoor industry before pivoting to technology marketing, eventually becoming promoted from Director to VP at her company (she's since become a C‐level executive at another technology company). She credits the help of a mentor in making the leap, including learning how to navigate the startup environment and become an executive.

Samantha McKenna is an accomplished sales leader, former VP of Sales at LinkedIn and On24, and now runs a consulting firm called Sam Sales. In her first executive role, she was promoted from within her organization. She said one of the challenges to making the leap from individual sales contributor to sales executive was, ironically, her high performance as a rep.

“In many organizations that lack forward‐thinking growth, they do not want to lose the revenue that you, as an individual contributor, bring for the organization,” says McKenna. “They want to keep you in your role, with the millions of dollars that you bring in every year.”

McKenna says the key to getting promoted was to master doing her current job while also starting to take on the ownership and “stretching” beyond the role simultaneously.

“For anybody that wants to get promoted, ask yourself, how do I do the job that I was hired to do very well, and then how do I stretch myself beyond that? I needed to prove that I could proactively do more, not just by taking instruction, but by looking for gaps in the business and ways that I could contribute my skill set to fix those issues,” says McKenna.

For McKenna, after two‐and‐a‐half years of being highly successful, coming in first place numerous times for crushing her sales quota, she decided to go for the executive seat.

“I really had my sights set on leadership and I had a leader in October of a particular year who promised me that if I finish the year off successfully that I could get promoted. In November of that year, the executive was fired,” says McKenna.

McKenna says that when she went to his replacement the following January, it took her three months to even get the conversation on the books. Despite having finished the previous year as the second highest performing member of the sales team, by April she had fallen behind in her quota and was told that she couldn't get promoted given her Q1 performance, and would need to prove herself. Again. The lesson she learned: regardless of the relationship you have with leadership, get commitments in writing. Further, this was a call to action to leadership. Promotions and honors shouldn't only be based on an individual having proven themselves; it should also be based on the potential one sees in someone.

“I had to hustle, but I had to carve out this role for myself. So I had to not only carve the role out for myself but then prove I was worth it twice,” says McKenna.

Mindy Lauck, CEO of Broadly, has been in two situations where she's not the founder but made her way up to CEO. She's been a non‐founder CEO both times she's been CEO (at About.me and Broadly), and by being promoted to suddenly inheriting a board, executive team, and company.

“I inherited my executives, the team, everything was pre‐made,” says Lauck. “Founders don't have to deal with this,” says Lauck.

Lauck assessed the startup phase they were in, understanding the state of the startup and whether certain executives and programs were right for their stage.

“I tried to really think about what phase are we in, what phase are we going to, and are these the right people for the right phase?” says Lauck.

Lauck had to adapt the mindset of executives who are non‐founders and make the best of the situation she inherited while focusing on contributing her strengths to grow the business.

“You're not doing the business a favor if you wait too long to make those decisions, especially when it's at the executive level,” says Lauck. “I let go of the executives that weren't the right fit, and focused on building trust and communication as well as aligning around values with the team that stayed.”

Lauck credits her swift action with her success in the role, and being promoted again to CEO, since she had a proven track record.

On her path to her first executive role, entrepreneur and sales leader Sam McKenna was a director and then promoted to senior director before being promoted to Vice President. McKenna said she learned to advocate for herself while acknowledging that she was hired instead of a few team members who never quite accepted her in her new role.

McKenna overcame obstacles around this by focusing on empowering her team and proving she could build and manage a high‐performing sales organization. Knowing she “had their back” created a lot of trust and the foundation for her team to consistently exceed their goals.

“I really made a point of building my brand around success not at the expense of others,” says McKenna. “I let my team know, it's not a dog‐eat‐dog situation; it's we‐win or we‐die as a team.”

McKenna also had to work on building new relationships cross‐functionally thich she did not have to do as an individual contributor.

“As a top performer, I know I made a lot of demands of our legal team, including ‘I want it and I want it now.’ Patience is a word I still don't understand,” says McKenna.

In her leadership role, she had to make new inroads with that team, taking time to invest in cross‐functional leaders in a way she had not before.

McKenna says a common mistake she sees in scaling leaders who are trying to make the leap from director to VP is focusing on the wrong things to get promoted and/or letting their performance in their current roles slip.

“The sales reps that I speak to say, ‘Well, I hit 75 percent of quota the last three years, but I also created a birthday club last year … shouldn't that get me promoted,'” says McKenna. “I tell them, what matters first is the consistency at which you exceed your goals. You have to nail the job you were hired to do first, before you highlight anything else you've done above‐and‐beyond. Once that's underway, what you do to stretch yourself has to address the goals your executives are focused on; take the time to understand what your executives are trying to solve and then help them get there,” says McKenna.