Sales Manager

Pilot.com•San Francisco, CA

9d•Remote

About The Position

Pilot is seeking a hands-on Sales Manager to lead and develop a team of 5-8 inside sales representatives who sell Pilot's accounting and advisory services. This is a player-coach role focused on daily execution, data-driven coaching, and helping each representative reach their full potential. The Sales Manager will act as a liaison between the sales team and the Director of Sales, translating strategy into actionable day-to-day tasks. The ideal candidate is detail-oriented, enjoys reviewing call recordings, analyzing pipeline data, conducting effective 1:1 meetings, and assisting reps with challenging deals.

Requirements

4-6+ years of experience in sales.
At least 2 years of experience managing a team of inside sales reps.
A proven track record of developing individual reps into consistent quota-attainers.
Strong analytical skills, including comfort with sales data, forecasting, and using metrics for coaching.
Excellent communication and interpersonal skills, with the ability to provide direct, caring feedback.
Proficiency with a modern CRM (Salesforce, HubSpot, or similar).
Organized, detail-oriented, and consistent in following through on commitments.

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 (e.g., Claude Cowork, Codex).
Prior experience building or iterating on a sales playbook or onboarding program.

Responsibilities

Coach and develop the sales team through structured weekly 1:1s focused on skill development, pipeline review, and goal-setting.
Provide specific, actionable feedback to improve rep performance by listening to call recordings.
Identify individual rep strengths and growth areas to create personalized development plans.
Onboard new hires to ensure a quick and confident ramp-up.
Drive team performance by monitoring and managing metrics such as activity volume, conversion rates, pipeline health, and quota attainment.
Utilize CRM and sales analytics data to identify trends, flag risks, and inform coaching strategies.
Hold the team accountable to daily and weekly activity targets in a constructive and motivating manner.
Deliver clear and consistent performance and forecast reports to the Director of Sales.
Lead weekly team meetings to maintain team energy and alignment.
Partner with reps on live deals, offering coaching, handling escalations, and assisting with closing.
Ensure CRM hygiene standards are met for data accuracy and pipeline visibility.
Coordinate with Sales Leadership and Marketing on messaging, campaigns, and tooling.
Foster a high-performance and high-care team environment where reps feel both challenged and supported.
Recognize achievements and provide constructive coaching for areas of improvement.
Advocate for the team's needs, including tools, process enhancements, and career growth opportunities.