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Pilot.comPilot.comSan Francisco, CA

Sales Team Lead

Lead and coach a team of 5-8 inside sales reps selling accounting and advisory services. Focus on daily execution, data-driven coaching, and helping reps exceed quota in a player-coach role.

163k – 269k
On-site5+ YOESales Enablement

About the role

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

Compensation & Benefits

  • The on-target earnings (OTE) range target for the role is $163k - $269k in San Francisco, CA
  • Full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits
  • 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

Skills

SaaS SalesConsultative SalesPipeline ManagementForecastingCRMDeal StrategyCoachingMentoringQuota AttainmentSales Analytics
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