Head of Sales Management

Sales Manager
com provides bookkeeping, CFO, and tax services powered by a combination of expert teams and intelligent software. We work with thousands of startups and growing businesses, giving them the financial clarity and confidence they need to scale. Backed by top investors and loved by founders, we're on a mission to be the financial back office for every business.
We're looking for a hands-on Sales Manager to lead and develop a team of 5–8 inside sales reps selling Pilot's suite of accounting and advisory services. This is a player-coach role focused on the fundamentals: daily execution, data-driven coaching, and helping each rep reach their full potential.
You'll sit between the reps and our Director of Sales, translating strategy into day-to-day action. The right person for this role loves being in the details — reviewing call recordings, digging into pipeline data, running tight 1:1s, and rolling up their sleeves to help reps work through tough deals.
Run structured weekly 1:1s with each rep focused on skill development, pipeline review, and goal-setting
Listen to call recordings and provide specific, actionable feedback to improve rep performance
Drive Performance Through Data

Own team-level metrics including activity volume, conversion rates, pipeline health, and quota attainment
Use CRM and sales analytics data to spot trends, flag risks early, and surface coaching opportunities
Deliver clear, consistent reporting to the Director of Sales on team performance and forecast
Execute Day-to-Day Operations

Partner with reps on live deals — provide deal coaching, handle escalations, and help close
Maintain CRM hygiene standards across the team to ensure data accuracy and pipeline visibility
Coordinate with Sales Leadership and Marketing on messaging, campaigns, and tooling rollouts
Create a team environment that is high-performance and high-care — reps should feel challenged and supported
Advocate for your team's needs: tools, process improvements, and career growth opportunities
4-6+ years of experience in sales, including at least 2 years managing a team of inside sales reps

• Strong analytical skills — comfortable digging into sales data, building a forecast, and using metrics to make coaching decisions
• Proficiency with a modern CRM (Salesforce, HubSpot, or similar)
• Familiarity with accounting, bookkeeping, or financial services

Experience with advanced AI tools and processes for sales (Claude Cowork, Codex)
Prior experience building or iterating on a sales playbook or onboarding program
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.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 3,000 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. 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
• The on-target earnings (OTE) range target for the role seniority described in this job description is $163k - $269k 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, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.