Sales Manager

About Pilot Pilot.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. The Role 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. What You'll Do Coach and Develop Your Team 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 Identify each rep's strengths and growth areas, and build individualized development plans Onboard new hires and ensure they ramp quickly and confidently 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 Hold the team accountable to daily and weekly activity targets in a constructive, motivating way Deliver clear, consistent reporting to the Director of Sales on team performance and forecast Execute Day-to-Day Operations Lead weekly team meetings that keep the team energized and aligned 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 Build a Winning Culture Create a team environment that is high-performance and high-care — reps should feel challenged and supported Recognize wins loudly and coach through misses constructively Advocate for your team's needs: tools, process improvements, and career growth opportunities What We're Looking For Required: 4-6+ years of experience in sales, including at least 2 years managing a team of inside sales reps A track record of developing individual reps into consistent quota-attainers Strong analytical skills — comfortable digging into sales data, building a forecast, and using metrics to make coaching decisions Excellent communication and interpersonal skills; you give direct, caring feedback Proficiency with a modern CRM (Salesforce, HubSpot, or similar) Organized, detail-oriented, and consistent in following through on commitments to your team Nice to Have: Experience selling professional services, fintech, or SaaS products 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 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 3,000 customers and has raised over $170 millio