SMB Field Development Representative (3 month contract)

Pilot.com • San Francisco, CA

71d • $20

About The Position

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.

Requirements

• 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.

Responsibilities

• Visit small businesses throughout assigned neighborhoods in San Francisco to promote Pilot's financial services (bookkeeping, tax, and CFO support).
• Spend 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.

Benefits

• Base pay: $20/hour
• Commission-led structure with uncapped earning potential.
• Competitive commission rates for new customer sign-ups.
• Performance bonuses and incentives for top performers.
• All federal holidays are observed.
• 401(k) plan.

What This Job Offers

• Career Level: Entry Level
• Industry: Professional, Scientific, and Technical Services
• Number of Employees: 251-500 employees