SMB Sales Manager

Company: Pilot
Location: Nashville
Posted on: July 1, 2025

Job Description:

Pilot is building a first-of-its-kind, software-centric solution to tackle the financial back office (bookkeeping, tax, CFO, etc.) so that founders and business owners dont have to. We work with 2000 customers and are rapidly expanding to serve the needs of all small and medium sized businesses. As a Sales Manager in Pilot’s SMB segment, youll be responsible for meeting sales targets through hiring and coaching your team of Account Executives. You’ll work closely with stakeholders across the business, ensuring that strategic initiatives externally roll out to market and providing feedback internally to inform go-to-market strategy. We are seeking individuals who have demonstrated success in startup sales in SaaS or services-focused companies. You bring a thoughtful approach to every interaction and you can solve complex problems operating independently. Key responsibilities Consistent achievement quarterly team sales goals and daily/weekly/monthly KPIs Day to day management of 6-8 Account Executives Coaching to a framework from pipeline creation to close Hiring to meet headcount goals Motivation of your Account Executives to learn and grow to prepare them for their next sales roles Understand and own the information regarding Pilot’s numerous financial service offerings Work cross-functionally with our solutions, marketing, product, and finance teams—echoing the voice of the customer and providing constructive and actionable feedback to the team Work collaboratively to build and iterate day-to-day processes within the role About You Located in the Nashville area and able to be in office 4x per week 2 years of sales management experience (ideally fintech, or financial services) Proven track record of success, creating pipeline, quota attainment, and over-achievement Highly organized and detailed with an eye towards process Excellent prioritization and time management skills Exceptional oral and written communication skills Experience with Salesforce 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 such as Modern 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 $147k - $188k for Nashville, TN (base pay is 60% 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.

Keywords: Pilot, Hendersonville , SMB Sales Manager, Sales , Nashville, Tennessee