SMB Field Development Representative (3 month contract)

The Role

Pilot.com helps small and medium-sized businesses grow confidently by providing world-class bookkeeping, tax, and CFO services powered by technology. We combine expert finance professionals with smart automation to deliver accurate, timely financial insights — empowering entrepreneurs to make better business decisions.

As we expand our presence in the Bay Area, we’re looking for ambitious, entrepreneurial sales professionals to help bring Pilot’s trusted financial services to more local business owners. As a Door-to-Door Sales Representative, you’ll be the face of Pilot in the San Francisco small business community. You’ll engage directly with local business owners, introduce them to Pilot’s financial services, and drive new customer sign-ups — all while enjoying unlimited earning potential based entirely on your performance.

This role is ideal for someone who thrives in face-to-face sales, loves connecting with people, and is motivated by results and rewards.

This is a temporary, 3-month position.

Key Responsibilities

• Visit small businesses throughout assigned neighborhoods in San Francisco to promote Pilot’s financial services (bookkeeping, tax, and CFO support). 
• This role requires spending the majority of your time working in the field.
• Build relationships with business owners, identify their needs, and explain how Pilot can help streamline their financial operations.
• Generate qualified leads and close new accounts through direct engagement and follow-up.
• Maintain detailed records of interactions, leads, and conversions in Pilot’s CRM tools.
• Collaborate with the broader sales team to refine messaging and share field insights.
• Represent Pilot with professionalism, integrity, and enthusiasm in every interaction.

About You

• 1–3 years of experience in door-to-door, field, or outside sales — ideally B2B or small business.
• Strong interpersonal and communication skills — you’re approachable, confident, and persuasive.
• Highly self-motivated, goal-oriented, and comfortable working independently.
• Must be based in or near San Francisco and able to travel locally daily.
• Multilingual candidates strongly preferred — especially those fluent in Spanish, Cantonese, or Mandarin, to connect with the diverse local business community.

Compensation

• Base pay: $20/hour
• Commission-led structure with uncapped earning potential — your income reflects your effort and success.
• Competitive commission rates for new customer sign-ups.
• Performance bonuses and incentives for top performers.

Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. 

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?

• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Drive impact and change the trajectory of Pilot - we’re small enough that your work makes a big difference in Pilot’s success.
• All federal holidays are observed
• 401(k) plan

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.