Sales Manager

Pilot.com•San Francisco, CA

5d•Hybrid

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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.