Sr. Customer Success Manager

The Role

At Pilot, we're building the back office for every business. Our dedicated bookkeepers and finance experts help owners and founders make sense of their finances, giving them the clarity and confidence to make decisions and grow. Those teams are the customer’s focus, and they own the direct customer relationship.

That makes the CSM role here different. Instead of being the main face to the customer, you're the strategist, often behind the scenes, who helps our service delivery teams succeed at scale. You'll focus on the most critical moments in the customer journey—particularly smooth, on-time renewals—by interpreting a large array of inputs to create cohesive retention and expansion strategies, and then partner with Operations and other teams to execute them with customers.

That means you’ll use both customer-facing empathy and a grounding in accounting and finance to spot patterns, solve problems, and support a frictionless customer experience. If you love being the strategic operator who connects the dots across data, operations, and customer outcomes—without needing to be the relationship hero—this role lets you have massive impact by making the team and our customers more successful.. A successful CSM in this role is adept at working cross-functionally, analytical and strategic, organized and detail-oriented, and thrives in a fast-paced environment.

This is a hybrid position with the expectation to work in our San Francisco or Nashville office on Mondays, Tuesdays, and Thursdays.

Key Responsibilities

• Proactively manage a monthly portfolio of renewing customers by leveraging customer insights, CSAT, health score, QBRs, and more, collaborating with Operations on customer engagement to drive optimal outcomes
• Identify and address churn risks by aligning closely with Operations to set appropriate customer expectations, and supporting customer calls as needed
• Own and execute win/win contract negotiation strategies for renewals and retention that protect and maintain customer trust and satisfaction
• Maintain a deep understanding of Pilot’s products and features, to identify the most relevant solution for a customer’s specific milestones and business needs
• Uncover any add-on or cross-sell opportunities, coordinating with product-line owners to demonstrate value for the customer
• Serve as an advocate for customer needs when partnering with internal teams and sharing insights to drive product, process, and service improvements
• Help Pilot achieve accurate net revenue targets by accurately maintaining churn pipeline and communicating all churn risks to appropriate internal stakeholders
• Support financial and strategic analyses by ensuring timely off-boarding for all churned customers and complete data collection to surface trends

About You

• 3+ years experience in customer-facing roles in public accounting or finance; OR Customer Success, Sales or Account Management
• Education/experience in accounting or finance preferred
• Strong verbal and written communication skills with an ability to convey critical information across our customers and our service teams
• Highly self-motivated and autonomous, demonstrating ownership over business results
• Demonstrated aptitude to learn quickly, including an interest in accounting, finance, and/or financial technology
• Analytical skills and the ability to interpret customer data, compile reports, and make insightful, data-driven decisions
• Positive attitude and ability to stay calm and solution-focused under pressure, including when working outside of defined processes
• Organization and prioritization of competing tasks independently and with light guidance from your manager
• Experience with Salesforce, Looker, or ClickUp is a plus

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 2,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

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 wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is between $86,000 - $164,000 in Nashville, TN, and between $108,000 - $204,000 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.

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, recruitment agency policy, recruitment scam notice, and important E-Verify information.  You may view our job candidate privacy policy here.