[Hiring] Customer Success Lead @Esper

Role Description

Esper is looking for an experienced Customer Success Lead to serve as a long-term partner to our customers. The customer journey doesn’t stop at launch. Our goal is durable adoption, measurable outcomes, and partnerships that grow over time.

As the Customer Success Lead, you’ll lead Esper’s next-stage CS evolution:

• Moving from effective generalist motions to a specialized, scalable organization with clear ownership, consistent customer experiences, and predictable retention outcomes.
• Accountable for retention and renewal performance, strengthening adoption and customer health, and building the operating system (people, process, and tooling) that supports growth.

You’ll thrive here if you’re resourceful, decisive, highly organized, and comfortable operating in a fast-moving environment with a strong bias for execution and continuous feedback.

As a bonus, we’d love it if you have a strong interest in policymaking and government!

What you'll do:

• Become an “Espert” and trusted advisor by building a deep understanding of Esper’s product, our customers, and their goals.
• Lead and scale Esper’s Customer Success function, including specialization, role clarity, and operating rhythms.
• Own renewals end-to-end across our U.S. customer base, including renewal strategy, pricing/terms, negotiation, and close.
• Drive adoption and outcomes post-launch through onboarding reinforcement, enablement, success plans, and ongoing check-ins.
• Build strong relationships with government employees at multiple levels of seniority through regular meetings, proactive outreach, and in-person engagement.
• Identify and lead expansion opportunities (upsell/cross-sell) in partnership with the Professional Services, Sales, and Executive teams.
• Establish and iterate CS playbooks (onboarding reinforcement, stakeholder changes, at-risk recovery, renewal prep, customer advocacy motion, EBRs/QBRs).
• Improve customer-facing collateral (help center articles, user guides, in-product comms, release comms).
• Manage customer support coverage and ensure issues are prioritized, communicated, and resolved with urgency.
• Serve as the internal voice of the customer, partnering cross-functionally with Product and Engineering to translate feedback into improvements.
• Report on customer health, adoption, renewal status, and key risks/opportunities for leadership.

Success in this role looks like:

• Renewals are predictable and strong: accurate forecasting, proactive risk management, and consistently high retention (>95%).
• CS roles are specialized with crisp handoffs; customers experience “one Esper” despite internal specialization.
• Measurable increases in adoption and time-to-value across the customer base.
• Trusted customer champions and referenceable accounts.
• Repeatable CS processes, playbooks, and a foundation that can scale.

Qualifications

• 6+ years in Customer Success or Account Management with at least 2 years managing/leading programs through scale and specialization.
• Track record of owning retention outcomes and leading complex renewals with senior stakeholders.
• Strong analytical and operational chops, can build process and run it.
• Excellent written and verbal communication (recaps, success plans, exec updates).
• Comfort working cross-functionally with Product/Engineering on feedback and fixes.
• Bias for action and focus on customer outcomes.
• Team player with a “whatever it takes” mentality.
• Bonus: public sector or govtech experience.
• Ability to travel domestically (up to 30%) depending on business need.

Benefits

• Being a part of an innovative and collaborative team that will both support and challenge you.
• Significant opportunity for growth and ownership and to shape Esper for the long-term.
• Competitive salary and equity at a growing early-stage company.
• Paid holidays & unlimited PTO.
• Medical, dental, and vision insurance.
• Generous parental & sick leave.
• 401(k) retirement plan with employer match.
• Short/Long term disability & life insurance.
• Flexible spending account (FSA).
• Work anniversary equity grants.
• Monthly stipend to offset remote work expenses.
• Office equipment allowance.
• Paid Time Off to participate in volunteer/community events.