Head of Strategic Marketing, Pilot
$172-260k
+ equity
Bookkeeping services for startups
Be an early applicant
Bookkeeping services for startups
201-500 employees
Be an early applicant
$172-260k
+ equity
201-500 employees
Company mission
To help small businesses and startups to achieve their commercial goals by taking care of the CFO services, tax preparation and bookkeeping.
Role
Who you are
- You’ve marketed to complex B2B buyers before—multi-stakeholder, longer sales cycles, relationships that matter. You understand the difference between selling to a partner and selling through one, and you’re comfortable building programs that support both. You’re ready to take on broader ownership across segments, pipeline, and strategy—and operate through a team to make it happen
- 10+ years of B2B marketing experience, including time in enterprise or multi-stakeholder sales environments
- Experience managing and developing direct reports
- Strong foundation in demand generation and/or account-based marketing (ABM), including pipeline ownership and conversion metrics
- Experience partnering closely with sales leadership on account prioritization and pipeline goals
- Exposure to partner or channel marketing (direct ownership or close collaboration)
- Writes and communicates clearly
- Ideally, previous experience marketing to franchisors or accounting firms
What the job involves
- Most marketing leaders inherit a playbook. This one gets to write and scale it
- The motion is enterprise B2B—longer cycles, multiple stakeholders, relationships that close deals. Pilot has that motion working. Your job is to point it at 2 distinct segments and build everything behind it. The segments are distinct:
- Franchisors are corporate buyers whose vendor decisions cascade across entire franchise systems—win one, and you've won dozens of locations
- And Mid-market accounting firms adopting Pilot as the platform they run their clients' books on, at scale
- We’re building a partner-led growth model that scales through relationships rather than ad spend. This role is about extending that model across new segments in a way that drives consistent, measurable pipeline
- This role is ideal for a senior marketing leader who has built and scaled demand programs in complex B2B environments and is ready to take on broader ownership. You’re equal parts strategist and experimenter—excited to unlock new growth channels, test bold ideas, and deepen a partner ecosystem as a meaningful driver of acquisition
- You'll report to the VP of Marketing and manage a direct report: a Partner Marketing and Events Lead. You'll also work with a shared team of senior specialists across lifecycle marketing, marketing operations, product marketing, and content—giving you the support to build full-funnel programs without building a large team from scratch
- Segment strategy. Each segment requires a distinct motion—but they share the same enterprise foundation. You’ll define how we approach each and make that strategy actionable
- Pipeline. You’re accountable for what these segments produce. In close partnership with sales, you’ll align on account prioritization and build programs that move the right prospects from first impression to signed contract
- Partner pipeline. You’ll build on and scale our partner-led motion—working with our Partner Marketing and Events Lead to turn relationships into a consistent source of pipeline through referral programs, co-marketing, and field engagement
- Messaging. You’ll shape how Pilot speaks to each of these audiences—externally and in the materials our sales team uses every day
- What Success Looks Like in Year 1:
- A clear, defensible go-to-market strategy across all three segments
- Repeatable demand and partner programs in market
- Growing, measurable pipeline contribution
- A team aligned around a clear roadmap and direction for year 2
Our take
Back office operations such as bookkeeping can be an unwelcome distraction and expense for businesses. Pilot is the largest provider of back office services for startups and small businesses in the US, aiming to take care of a company's back office so they can focus on their core activities.
Founded in 2016. Pilot has attracted an impressive range of customers including Bolt, r2c and Pathrise. The company's proposition is more than just bookkeeping software, providing services that would ordinarily be provided by a fractional CFO. This empowers small businesses and startups to make better budgeting and spending decisions without the need of an expensive finance department hire.
The company evidently excels in customer service, with the vast majority of its business driven by customer referrals and organic interest. Going forward, Pilot aims to become to startups and medium-sized firms what AWS is to cloud computing - a comprehensive, easily scalable solution that prevents the need to reinvent a necessary but non-core function from scratch.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2021
$40m
SERIES C
Jan 2021
$60m
SERIES C
Total funding: $158.3m
Company benefits
- Development opportunities & employee happiness initiatives
- 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
- Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
- Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
- 401(k) plan
Company HQ
Financial District, San Francisco, CA
Leadership
Waseem Daher
(Chair & Co-Founder)They studied at MIT before founding Ksplice, where they spent 3 years as COO, and working at Oracle and Dropbox. Having founded Zulip in August 2012, they co-founded Pilot in January 2017.
Jessica McKellar
(CEO & Co-Founder)Previously, they were the founder and the VP of Engineering for a real-time collaboration startup acquired by Dropbox, where they then served as a Director of Engineering.
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