Lead Upwards. Sarah E. Brown
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willing to take that chance on you,” says Rand. “Once you've had the title, everybody else sees you as that from then on.”
Rand was given her first executive role, which involved owning a business line with profit and loss (P&L), because she had proven herself successful as a manager and the mentors around her helped her succeed and believed in her ability to learn and grow into an executive role.
“One of the key things of being successful is having a close group of people around you who support your growth,” says Rand. “I had a group of people around me who were very generous with their support and their advice.”
Rand once had a global controller let her know she'd behaved in a meeting in a way that didn't land well. She would start meetings jumping right into the work without making small talk, which he said didn't align with the organization's mode of operating and culture.
“He told me to take time to connect with everybody who's in the room and have a human conversation,” says Rand. “I thought that we're all under this time pressure and how I'm being judged is what I get done, and people are expecting me to deliver results. I don't want to waste people's time.”
Rand's mentor helped her realize that leadership wasn't just about delivering results, but about establishing the relationships in the organization, building trust, not just in your own team, but your peers and others. Everybody wants to be seen.
By taking in feedback from mentors around her and applying it, she ended up being promoted to take over an organization of more than 80 people with tens of millions in revenue.
“The CEO didn't believe that I should be given the role because it was such a big jump for me,” says Rand. “I'd only ever led a single‐digit team, but my mentor convinced him I would perform.”
Rand's first executive role at a large company led her to become a startup executive, and she faced some of the growing pains discussed earlier of mapping her “big company” experience to a highly different startup culture. She says her friends and even some of her supporters at her larger company doubted her ability to successfully transition.
“You're like Ms. Corporate,” they told me. “Oh, you're going to hate it. You're not going to be good at it,” says Rand.
Rand ignored the naysayers and found a group of peers in Silicon Valley focused on women's empowerment in business who encouraged her to talk about her contributions rather than her role. When she met a startup founder who had an open operations leadership role, she was able to successfully describe how her experience at a big company would support his scaling startup.
“Instead of saying I was a senior director of global services, I would say, ‘I figure out how to build organizations that don't exist or break down and rebuild organizations that need to be rebuilt in a fast‐moving way.'”
Upon transitioning from big‐company executive to startup executive, Rand says it took time to “knock the corporate off (her).” Rand learned to integrate more of her personal life with her professional persona at a startup, becoming more vulnerable with her team, and even befriending them on social media. While acclimatization to startup culture required effort, she also found that her skills and “big company” knowledge were highly valuable in the startup environment and she found success by leaning on those early on.
She quickly found a home for her honed operations skills based on the startup's needs. Rand was very comfortable with board meetings and prep due to lots of early exposure at her large company.
“In my first leadership role at a startup, I saw what they were sharing with the board. I was like, ‘what the F‐‐‐ are you doing? This is a mess. How can this be what you're sharing with the board?”
Rand spent the week prior to her first board meeting re‐doing all of the company's materials, including the financials and reporting structure. The board was “very happy” with the results of her efforts, and that the founder had someone who could communicate in the way the board expected and who could structure the information in a way they could understand and give feedback on much more efficiently.
Rand says she had a “really firm wall” between her personal and professional lives. In her larger company environment, she learned it was “unprofessional” to blend the two. When she started getting social media invitations from her global team members at the startup, she was nervous. One of her direct reports told her they wanted to know her and for her to know them, and she took that feedback to heart.
“Now, I understand there's never anything more important than the people around you, so it doesn't matter what deadline you're on. If someone comes up to your desk and wants to talk, you just stop and you talk. You don't make them feel like you're rushed,” says Rand.
NAIL THE LEAP: START AS A “HEAD OF” AND MAKE THE TITLE OFFICIAL ONCE YOU'VE PROVEN YOUR SUCCESS
In Matt Mochary's book The Great CEO Within, contributor Alex MacCaw advocates that CEOs bring on “heads of” to start in their new ventures. “Call everyone ‘head of x.’ That way, when it's finally time to hire senior VPs, they can slot easily into the organization without ‘demoting’ anyone.”1
Here's where the biggest opportunity lies for first‐time startup executives, particularly those looking to level up within their current organizations. Go for the head of role, use the guides in this book (and lots of elbow grease) to earn your first executive seat.
CONSULTING AS A PATH TO DE‐RISKING YOUR FIRST EXECUTIVE ROLE
On my path to becoming a startup executive, I inadvertently stumbled upon a career accelerant: consulting. Underrepresented minorities who aren't seen with perceived potential due to systemic bias and don't yet have past performance track records need to find a way to bridge that gap. Consulting can be that bridge.
I'd been a multi‐time director at several startups when I was in between companies after an exit and decided to do some consulting while looking for my next opportunity. I applied for director level as well as head of marketing jobs on a whim. In some companies, “head of” is the stand‐in that can mean everything from senior manager up to CMO, so I wasn't necessarily applying for executive roles.
This was also around the time when I had that fateful VC conversation mentioned in the introduction. After that, I started billing myself as a “fractional marketing leader for hire,” which many early‐stage startups interpreted as startup marketing executive. Without anyone's permission, I started doing executive‐level marketing work for startups, building their go‐to‐market strategies from the ground up. There were things I didn't know how to do and I got paid as a consultant to learn how to do them for my clients without any of the pressure of “being an executive.” I just did the role!
My consulting journey involved learning how to create marketing budgets and annual planning spreadsheets (thank you, former boss and spreadsheet guru Matt Harada, for coaching me through this!). I learned how to build and scale‐up marketing functions quickly for my clients in order to earn their repeat business. One of my consulting clients was acquired by a public company after we worked together for about four months, and then I began working with three new clients, all three of whom eventually offered me full‐time roles at the “head of marketing” or “VP of marketing” title. Just like that, my clients saw me as a head of the department, and I joined one of them. Six months later I asked for and got a promotion to vice president after proving I was already succeeding in that role.
“If you can afford to consult, you can do a three‐month trial to see if you really love the job before you take it. I appreciate the approach of trying an opportunity first as you find your executive fit,” says customer success executive Emilia D'Anzica.
If you're a director and/or a “head of” and want to be a true executive, consulting can be a great way to “live the