The Role

This is an outbound AE role where you’re responsible for building and maintaining a pipeline of prospective customers. Top of funnel will come from several places; lead and target account lists from our existing database, partner channels, current customer expansion, and cold outbound. Your role requires you to generate opportunities and revenue from these leads using various tactics, such as emailing, social selling, calling, etc. 
 
Hires will be founding members of a new team at Pilot. You’ll have resources at your disposal, but will be working with your manager & others within the org to build out processes, playbooks, and workflows. 
 
You’ll be successful if you are a builder, are curious, work well out of structure, are hungry and motivated. You bring a consultative approach to every prospect interaction, are detail-oriented and have impeccable pipeline management skills. 

Key responsibilities

  • Achieve and consistently exceed sales goals by closing new business
  • Own the full cycle of pre-signature sales, including nurturing leads & partners, creating opportunities through prospecting efforts, and winning the deal
  • Present and demonstrate the value of Pilot’s products and services to prospective buyer
  • Deeply understand and own the information regarding Pilot’s financial and bookkeeping service offerings
  • Rigorously manage and maintain lead queues and opportunity pipeline 
  • Work cross-functionally with our marketing, product, and service delivery teams—echoing the voice of the customer and providing constructive and actionable feedback to the team
  • Work closely with our executive and founding team — this is a highly visible role that comes with executive sponsorship and collaboration. 

About You

  • 2+ years in a quota-carrying role in either a pre-sales or post-sales setting 
  • Proven track record of consistent quota achievement 
  • General aptitude in how money moves in and out of a business
  • Gritty, determined, self-starter mentality
  • Previous fintech experience preferred
  • Exceptional oral and written communication skills
  • Highly organized and detailed with an eye towards process
  • Excellent prioritization and time management skills
  • Experience using Sales tech tools like Salesforce, Outreach.io, Gong, etc.

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 1,000 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 such as Spring Health and One Medical
  • Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
  • 401(k) plan

The on-target earnings (OTE) range target for the role seniority described in this job description is $142k - $214k for San Francisco, CA (base pay is 50% of OTE). 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.

Apply for this Job

* Required

resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)


Our system has flagged this application as potentially being associated with bot traffic. Please turn off any VPNs, clear your browser cache and cookies, or try submitting your application in a different browser. If this issue persists, please reach out to our support team via our help center.
Please complete the reCAPTCHA above.