Inside Sales Manager

About Pilot
Pilot.com provides bookkeeping, CFO, and tax services powered by a combination of expert teams and intelligent software. We work with thousands of startups and growing businesses, giving them the financial clarity and confidence they need to scale. Backed by top investors and loved by founders, we’re on a mission to be the financial back office for every business.

The Role
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.

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

What We're Looking For
Required

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

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

Compensation
The on‑target earnings (OTE) range target for the role seniority described in this job description is $163k - $214k 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.

EEO Statement
Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E‑Verify information. You may view our job candidate privacy policy here.

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