Strategic Marketing Lead, Pilot
Accounting Firms
$159-250k
+ equity
3 days a week in office
Bookkeeping services for startups
Be an early applicant
Bookkeeping services for startups
201-500 employees
Be an early applicant
$159-250k
+ equity
3 days a week in office
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 senior, but you're hands-on. The work is the point
- 10+ years of B2B marketing experience, including time in enterprise or multi-stakeholder sales environments
- Strong foundation in demand generation and account-based marketing, including pipeline ownership and conversion metrics
- You should be able to hold a strategic narrative as your own and shape how a category gets understood
- Experience partnering closely with sales leadership on account prioritization and pipeline goals
- AI-fluent in your own workflow. You're already using LLMs and AI tools to compress research, draft, iterate, and run plays at scale. You have a view on what AI is good at, what it isn't, and your work shows it
- Comfortable operating as a senior IC. You build, you run, you write, you don't hand off the interesting work to a team
- Open to managing one or two senior ICs if the coaching fit develops. Equally comfortable staying purely IC if it doesn't. Either path is real here
- Writes and communicates clearly
What the job involves
- The motion is enterprise B2B—longer cycles, multiple stakeholders, relationships that close deals. Your primary segment is mid-market accounting firms adopting Meridian, the AI operating system Pilot developed for accounting firms
- Meridian is a sub-brand of Pilot, built specifically for firms that want to run their clients' books on agentic AI to fundamentally change their firms’ unit economics and service delivery model. Different product, different go-to-market, different buyer
- The never-compete promise that anchors the brand is what makes this segment investable. Your job is to take that trust to market and turn it into pipeline at scale
- This role is built for a senior marketer who wants to operate as a high-leverage individual contributor. You're not looking to scale through a dedicated team immediately. You're looking to build the programs, write the messaging, and own the pipeline yourself, with shared specialists to make you faster
- You'll also partner closely with our Franchisor motion, run by a dedicated IC, and our Partner Marketing & Events function. If the right coaching relationships develop with the ICs adjacent to this role, you'll grow into managing them. If they don't, you stay focused on your own work and we're all fine with that
- You'll report to the VP of Marketing and work with a shared team of senior specialists across lifecycle marketing, marketing operations, product marketing, content, and partner marketing. You'll have the support to build full-funnel programs without building a large team from scratch
- The marketing team has grown 3x in the last year and comprises of a group of senior channel experts: growth marketing, lifecycle, product marketing, partner marketing, content, and ops. They operate with high ownership and drive a significant share of Pilot's revenue. The team is collaborative, moves quickly, and takes its craft seriously
- We operate by values worth stating plainly: own your work, care more than expected, build things well, and fight for every opportunity. We invest in our people and take wins seriously
- Segment strategy and execution. You'll define how Pilot wins mid-market accounting firms and you'll be the one running the plays. Strategy is the half that points the work. The other half is in your hands
- Pipeline. You're accountable for what your segment produces. 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
- Messaging. You'll shape how Pilot speaks to mid-market accounting firms, 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 for Meridian, with repeatable demand and partner programs in market
- Meridian moving from launch awareness to sustained pipeline, with growing and measurable contribution to the segment number
- Positioning that holds up under scrutiny from skeptical firm owners, internal sales, and competitive pressure
- Working relationships with the Franchise IC and the Partner Marketing & Events Lead that are either operating well as collaboration or have moved into a reporting structure based on real coaching fit
- Direction set for year 2, including team shape
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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