Sales Manager, Pilot

• 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

Desirable

• 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
• 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