Sales Manager

About Pilot

The Role

Were looking for a hands-on Sales Manager to lead and develop a team of 58 inside sales reps selling Pilots 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.

Youll 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 Youll 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 reps 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 teams needs: tools process improvements and career growth opportunities

What Were 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 3000 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 Fintechs 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 additional wellness benefits
• Parental leave for birthing or non-birthing parents 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is between $163000 - $214000 in San Francisco CA. Final offer amounts depend on multiple factors such as candidate experience and expertise geographic location total compensation and market 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 Pilots 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.