Sales Team Lead

Responsibilities

• Coach and develop a team of 5–8 inside sales reps through weekly 1:1s and call reviews
• Drive performance using CRM and sales analytics to monitor conversion rates and pipeline health
• Execute day-to-day operations including weekly team meetings and maintaining CRM hygiene
• Partner with reps on live deals to provide coaching and handle escalations
• Build a high-performance culture by recognizing wins and advocating for team needs

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
• Experience selling to SMB or mid-market customers

Preferred Qualifications

• Experience selling professional services, fintech, or SaaS products
• Familiarity with accounting, bookkeeping, or financial services
• Experience with advanced AI tools for sales (Claude, Codex)
• Experience building or iterating on sales playbooks

About the Company

Pilot provides small businesses with dedicated finance experts, custom software, and integrated systems for bookkeeping, CFO, and tax services. Backed by top investors like Sequoia and Stripe, Pilot is a fintech unicorn helping startups scale with financial clarity.