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 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 additional wellness benefits

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 …