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Pilot provides small businesses with dedicated finance experts.
The Role
The Role: Key Areas of Ownership:
We're building something special in the fintech space, taking the headache out of back-office financial operations for startups and SMBs. As we expand our reach, we’re looking for a growth-minded marketer to lead strategy and execution for one of our most important audiences: newly formed startups and SMBs—businesses typically in their first 12 months, navigating the complexities of getting off the ground.
In this role, you’ll be responsible for raising awareness of Pilot’s services for newly formed businesses, generating qualified demand, and working closely with our R&D and marketing team to shape a go-to-market engine. You’ll lead full-funnel marketing efforts—from awareness to conversion—by creating campaigns and experiences that meet founders and SMB owners where they are. You'll do this by finding ways to drive conversions without relying on sales, using self-serve and marketing-led approaches that let buyers take action on their own.
Success in this role means:
- Building and executing a full-funnel marketing strategy that drives demand among newly formed startups and small businesses
- Designing programs that drive conversion with minimal sales involvement, whether through landing page experiences, product-led flows, or educational nurture
- Serving as the marketing voice of the customer, bringing feedback from the field to influence product direction
- Acting as a founder and SMB owner whisperer—earning trust through credible, helpful content and programs
Go-to-Market Strategy & Execution
- Partner with R&D, product marketing, and GTM leadership to understand pain points, product priorities, and messaging that would resonate with newly formed businesses
- Design and lead integrated campaigns across paid, owned, and earned channels that engage prospects at every stage of the funnel
- Collaborate with product marketing to develop compelling, educational content: blog posts, videos, tools, guides, and case studies
- Act as a feedback loop between newly formed businesses and R&D, translating customer needs and objections into actionable product insights
- Find opportunities for frictionless conversion that don’t require sales intervention, and experiment with conversion levers across marketing channels
Demand Generation & Activation
- Launch and manage regional marketing plans, including digital campaigns, outbound and referral programs, as well as entrepreneur-focused events
- Build demand gen programs that show up in the right channels at the right time, from community to content to paid
- Develop self-serve journeys and digital touchpoints, e.g. conversion-optimized landing pages, content flows, onboarding sequences, or interactive tools that drive commitment without a sales touch
- Ideate and test creative new initiatives that educate founders and SMB owners while driving measurable ROI
Marketing Infrastructure & Ops
- Partner with MarketingOps and RevOps to implement right-sized tools, automations, and tech stack enhancements
- Establish repeatable workflows to scale programs and performance
Measurement & Optimization
- Track and analyze program performance with an eye toward improving efficiency, conversion, and CAC
- Drive a culture of test-learn-optimize across all efforts
- You’ve built something from scratch either as a startup founder, small business owner, or early-stage operator
- You’re high-grit and hands-on, comfortable working independently and iterating quickly
- You blend creative instincts with strong analytical chops so you know what great looks like and how to measure it
- You think like a builder: you love spotting a low-friction path to conversion and crafting buyer journeys that don’t rely on sales
- You’re an excellent communicator who knows how to tailor your message to founders, owners, teammates, and executives
- You bring empathy and credibility to your work because you understand what it’s like to start and run a business
- Experience with either product-led growth or marketing for service-based businesses is a strong bonus
- Own a critical growth initiative for a fast-growing fintech startup
- Significant equity opportunity
- Direct impact on company strategy and growth
- Freedom to experiment with new formats and approaches
Think you've got what it takes? We'd love to hear your story.
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 2,000 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
- Competitive benefits package including wellness 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 $159,000 - $215,000 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.
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The Company
What We Do
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.
Why Work With Us
Pilot is truly a diverse company. We embrace people from all backgrounds including those who were formerly incarcerated. In addition, with our high growth environment we love to promote people within and offer them great career opportunities.
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