Head of Customer Success

Esper•Austin, TX

32d•$140,000 - $160,000

About The Position

Esper is looking for an experienced Head of Customer Success to serve as a long-term partner to our customers. The customer journey doesnât stop at launch. Our goal is durable adoption, measurable outcomes, and partnerships that grow over time. This is a hands-on individual contributor role for the first 6 months, with the opportunity to build and scale the Customer Success team as Esper grows. As Head of Customer Success, youâll lead Esperâs next-stage CS evolution: moving from effective generalist motions to a specialized, scalable organization with clear ownership, consistent customer experiences, and predictable retention outcomes. Youâll be accountable for our retention and renewal performance, strengthen adoption and customer health, and build the operating system (people, process, and tooling) that supports growth. Youâll thrive here if youâre resourceful, decisive, highly organized, and comfortable operating in a fast-moving startup environment with a strong bias for execution and continuous feedback. As a bonus, weâd love it if you have a strong interest in policy making and Government! We believe policy shapes our daily lives more than most realize, and central to the role is helping us build software for transforming how policy is created through better data and transparency.

Requirements

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 âwhatever it takesâ mentality
Ability to travel domestically (up to 30%) depending on business need

Nice To Haves

Bonus: public sector or govtech experience

Responsibilities

Become an âEspertâ and trusted advisor by building a deep understanding of Esperâs product, our customers, and their goals
Lead and scale Esperâs 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 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

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