Sales Team Lead

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 high-performing sales professional ready to take the next step into leadership. As a Sales Team Lead, you'll 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.

This role is ideal for a Senior Account Executive who consistently exceeds quota, enjoys mentoring peers, and wants to expand their impact beyond individual production. 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

About You

5+ years of SaaS, technology, or consultative sales experience.

Consistent track record of achieving or exceeding quota.

Experience managing complex sales cycles and multiple stakeholders.

Demonstrated success mentoring, onboarding, or coaching peers.

Strong forecasting, pipeline management, and deal strategy skills.

Excellent communication and presentation abilities.

Highly organized, data-driven, and results-oriented.

Desire to grow into formal people leadership over time.

Experience serving as a team lead, pod lead, or peer mentor.

Experience helping onboard or train new Account Executives.

Experience selling to SMB or mid-market customers.

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).

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