Sales Team Lead

Sales Team Lead

San Francisco, California, United States

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 58 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

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 $163k - $269k in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In 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.