Sales Team Lead

Pilot.com•San Francisco, CA

1d•Onsite

About The Position

Pilot is seeking a high-performing sales professional ready to transition into leadership. As a Sales Team Lead, you will be responsible for developing a team of 5–8 inside sales representatives who sell Pilot's accounting and advisory services. This is a player-coach role that emphasizes daily execution, data-driven coaching, and individual rep development. It is ideal for a Senior Account Executive who consistently exceeds quota, enjoys mentoring, and wishes to broaden their impact beyond personal sales achievements. You will act as a liaison between the sales reps and the Director of Sales, translating strategic goals into actionable daily tasks. The successful candidate will be detail-oriented, adept at reviewing call recordings, analyzing pipeline data, conducting effective 1:1 meetings, and assisting reps with challenging deals.

Requirements

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 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.