Head of Consumer Goods & Retail Growth



Sales & Business Development
San Francisco, CA, USA
Posted on Friday, January 26, 2024

The Role

Pilot has significant traction with startups and technology companies. We deeply understand these customers and have built a product that startups know and love. However, the vision for Pilot is not to be the financial back office for startups, it's to be the financial back office for every company. We believe the best way to do this is by expanding in a vertical-specific way, because each verticals have different buyer behavior, go-to-market motions, product needs, and willingness to pay.
We’ve seen significant traction with e-commerce/direct-to-consumer/consumer goods businesses, and we’re excited to double-down there:
  • It’s a huge market
  • They’re used to leveraging technology to solve core operating problems
  • They have unique challenges in bookkeeping, taxes, and finance where they’re not well-served today
It’s one thing to serve these customers well (which we do)—but it’s another thing entirely to acquire them at scale. That’s where you come in. Your job: get more of these customers.
Your levers? Pretty much anything you can think of that yields ROI. Advertising on podcasts that they listen to? Sure. Direct mail? Why not? Specialized events targeted at this audience? Go for it. Cold LinkedIn reachouts? Yes please.
And the scorecard is super-clear: revenue and ROI.
If you like puzzles, like to move fast, and like ownership, you’ll love this role.
We move quickly and are prepared to deploy significant resources to fuel things that are working: this is a big, blank canvas opportunity, backed by an A+ team at a fintech startup with top-tier investors.

Key Responsibilities

  • Work closely with Pilot’s CEO and marketing team to brainstorm and execute on new, out-of-the-box experiments that directly drive revenue and customer adoption in this segment
  • Start, optimize, repeat:
    • Form a hypothesis about how we might get in front of this specific type of customer (presumably informed by, well, talking to them)
    • Try it out, see if it works
    • If it does, scale it up until you hit the point of diminishing returns
    • If it doesn’t, shut it down
    • Come up with the next hypothesis
  • Use your analytical/technical abilities to scalably do things that a traditional marketer wouldn’t successfully do
  • This job is not “sit back in your armchair and articulate the strategy and have other people do the actual work,” it’s “get in the weeds and make it happen”

About You

  • You’re a scrappy, super-quantitative generalist who is eager to roll up their sleeves, own a big, meaty project, and get the job done
  • We’ve seen particular success in this role from former startup founders and from quant traders
  • You’re curious, creative, and extremely self-directed
  • You’re competitive and want to win
  • It’s a huge plus if you already have a deep understanding of business owners of D2C/ecomm/consumer goods companies

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

  • We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
  • The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
  • Flexible vacation/time-off policy
  • All federal holidays are observed
  • 100% coverage of employee only (individual) benefits
  • Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
  • 401(k) plan

The base pay range target for the role seniority described in this job description is $133k - $215k in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.