HERstory: Anne Fleshman, Director of Marketing, Autopilot
Anne Fleshman is the Director of Marketing at Autopilot, the visual marketing software that makes it easy (and fun!) to automate customer journeys. Anne joined Autopilot in 2014 to take the company from startup to scaleup and can be credited with driving top-of-funnel acquisition to maintain 21% month-over-month revenue growth. Prior to Autopilot, Anne ran marketing programs at Work4 and received her BA in Peace and Conflict Studies from UC Berkeley.
How did you break into marketing leadership?
I was accelerated into a leadership role much sooner than I was ready.
My first job out of college was at a startup company in San Francisco. I was an HR Manager, responsible for writing company policies, tracking vacation hours, and submitting payroll. The job had nothing to do with what I studied and it certainly wasn’t something I could see myself doing forever. I wanted to contribute more.
I had fallen in love with marketing during high school when my family opened a Korean restaurant. It felt natural to me—that drive to introduce people to something that would make their lives better, or easier, or happier. So, I started volunteering for marketing projects. The marketing team was overextended already, and I had a lot of ideas to share.
I took the initiative. I listened actively. I learned fast. And I put my best effort forward every day. I voiced my desire to be on the marketing team full time and, eventually, was able to make a successful transition.
It was hard work, and I made a lot of mistakes. I sent oops emails, lost an entire event booth in the mail, and had to find a last-minute replacement for a speaker who didn’t show up on webinar day.
Fast forward two years, and I was managing a team and running all marketing programs at that company. It was a humbling experience.
When I switched jobs in 2014 to join Autopilot, I wasn’t ready to continue being in a leadership role. While I had developed a strong foundation in early-stage B2B startup marketing, I was still green in my field. Rather than launch myself into management, I chose to be an individual contributor and focus on demand generation as a specialty. The small team and pre-beta days put me in a position where I could make a big impact. At the same time, I could learn new skills on the job and absorb insights from experienced mentors around me.
Holy moly, I felt like I hit the jackpot. Every day I got to use and market beautifully simple and fun marketing software to other marketers just like me.
I took advantage of the opportunity. I stepped up to the plate and straight-up hustled. I planned and executed 100+ events and webinars, increased website traffic 1400%, spent over $1M in advertising and demand generation programs, and launched countless automated journeys and integrated marketing campaigns.
It wasn’t easy. My team and I sometimes joke about this concept of “pull and glide”. The early days were all about pull, pull, pull. Never glide.
Autopilot grew and, in November 2016, I was promoted to Director of Marketing. I didn’t think it was the right time to be a team leader again, but is it ever the right time, really? I’m still learning when it’s appropriate to delegate or take ownership, how to tactfully manage up and down, and the difference between empowering a team versus being a bottleneck. There’s lots of room for growth.
What unique obstacles or challenges have you faced as a woman in a tech leadership role?
The tech space is dominated by men. Even in marketing, where gender diversity is somewhat more even, there is an overwhelming number of men in leadership roles.
Gender gap challenges are inevitable and it’s prevalent. You’re going to walk into a meeting as the only woman representative in the room. You’re going to overhear inappropriate comments and opinions that make you feel uncomfortable. You’re going to face situations where you have to squash gender bias and stand up for yourself.
I’m fortunate to have not experienced sexual harassment in the workplace, but I know plenty of women who have. This is a real problem.
My unsolicited advice to professional women is to support each other. When faced with sexism and unfair treatment, seek mentorship from other women, be an agent for inclusivity, speak up for the respect you deserve, and keep the conversation alive.
How do you negotiate a higher salary?
I negotiated a 30% salary increase when I switched jobs.
When I was doing HR, I noticed male candidates asked for more money compared to women, who often accepted the offer given to them without negotiation. The truth is, most companies build cushion into their offers and are willing to pay more if asked! Negotiating is almost an expectation as part of the hiring process.
Asking for more doesn’t make you greedy, ungrateful, or entitled. Any smart hire should know what they’re worth and be straightforward about what will make them happy. The last thing you want is to be in a position where you are unhappy with your pay. That’s a distraction from your work that will foster more resentment over time.
So how did I do it? I prepared. I wrote a list of transferable skills and interpersonal qualities I’d bring to the table. I researched market data on the average compensation for my level of experience in my role, industry, and location. I considered other parts of the compensation package beyond my base salary, like health care, a bonus plan, stock options, and a flexible work schedule. I understood my BATNA - Best Alternative to a Negotiated Agreement. In other words, I knew my walk-away point. I had a back-up plan if the hiring manager didn’t play ball.
When it comes to timing, you have the most negotiating power after you’ve received a written offer. At this point, you know they want you, and you’ve got a small window of time to accept or deny. While it’s tempting to celebrate and just say “yes”, negotiating your salary during the initial offer is much easier than having the conversation after you’ve started.
I recommend a verbal conversation with the hiring manager rather than email. Make your ask as clear as possible. Don’t ramble, lie, or lose your cool. Be open minded and see what happens. You’ll never know if you don’t ask.
If you could do it all again, what would you do differently?
Seek more mentorship. Ask more questions. Be more confident. Focus on compounding long-term impact instead of chasing quick wins.
What’s been the highlight of your career thus far?
One recent highlight was speaking onstage in front of an audience of 1,000 people for the first time!
Share something valuable or interesting with the community.
“Stop being so afraid! That’s really what strikes me when I look back—the sheer amount of time I spent tangled up in fears and doubts that were entirely of my own creation […] Focus more on learning than on succeeding—instead of pretending that you understand something when you don’t, just raise your hand and ask a question. You’re a smart girl, and chances are if you’re confused, plenty of other students are too. And for heaven’s sake, let yourself really fail once in a while—not some tiny little mistakes here and there, but big, glaring, confidence-shaking, dark-night-of-the-soul-inducing failures. Understand that no one—especially folks who are truly successful—simply coasts from achievement to achievement. The most accomplished people in the world fail and fail big. That’s how they learn so much and grow so quickly and become so interesting and wise. In short, stop trying to be someone who will impress everyone else, and just focus on being and becoming fully, sincerely, and passionately yourself.”