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Director, Customer Success

United States (Remote)

Espresa is the only personal benefits platform that delivers a global and all-in-one experience for HR, people teams, and employees. With a core focus on Lifestyle Spending Accounts (LSAs) and a complimentary, modular suite of solutions focused on total wellbeing, recognition, and community, Espresa powers Great Places to Work® while making heroes out of HR teams.

Join our growing team of tenacious builders, designers, and people igniters, and help transform the industry of personal benefits for good.

The opportunity

The Director of Customer Success is a key leadership role responsible for driving the vision, strategy, and execution of the Customer Success department at Espresa. This role oversees large-scale initiatives, accounts, and teams while partnering closely with the VP of Customer Success to align departmental goals with broader business objectives.

As one of two Directors within the department, this individual must be highly collaborative, working closely with their peer Director to ensure a consistent experience across all Customer Success Managers (CSMs) regardless of reporting lines. They will also work in tandem with the Head of Account Management to align on commercial outcomes, ensuring renewals are secured and expansion opportunities are enabled.

This is a role for a leader who operates at multiple altitudes: equally comfortable setting strategy, building scalable processes, and getting into the details when it matters. The ideal candidate brings strong technical fluency with the Espresa platform, a sharp eye for detail, and the ability to be a credible, informed voice with both customers and the Product team.

The role

Leadership & Strategy

  • Take ownership of establishing a structured strategic planning process for the CS team, including goal-setting cadences, segment-level planning, and alignment with broader business objectives -- in close partnership with the VP of Customer Success.

Strategic Collaboration

  • Work hand-in-hand with the peer Director of Customer Success to standardize processes, tools, and methodologies, ensuring a unified and consistent experience for all CSMs and customers.

Product Partnership & Customer Advocacy

  • Serve as the primary voice of the customer and admin with the Product team, synthesizing technical feedback from across the portfolio into clear, prioritized input on roadmap decisions.
  • Build a deep, functional understanding of how Espresa is configured and used at the admin level to diagnose issues, identify patterns, and advocate for product changes that reduce friction for customers and the CS team.
  • Maintain a close feedback loop with Product on escalations, bugs, and systemic gaps, ensuring customer and admin pain points translate into actionable product improvements.
  • Work across departments to solve key business challenges, maintaining a clear perspective on team gaps and opportunities. Engage with leadership to gain executive buy-in for advancing strategic initiatives.

Technical Depth & Platform Fluency

  • Develop expert-level knowledge of the Espresa platform, including configuration options, integration capabilities, and admin workflows.
  • Support CSMs on complex technical questions, configuration challenges, and escalations that require platform depth.
  • Evaluate technical processes and tooling used by the team, identifying gaps and recommending improvements that increase efficiency and reduce errors.

Commercial Alignment

  • Partner closely with the Head of Account Management to support a seamless commercial strategy. Ensure the CS team provides the necessary support to secure renewals and identify and enable growth and expansion opportunities managed by the AM team.

Team Development

  • Attract, hire, and mentor top talent, fostering a culture of leadership, accountability, and continuous improvement.
  • Proactively coach team members and drive operational standards for day-to-day tasks and customer outcomes.
  • Build a team culture where attention to detail and operational rigor are as valued as strategic thinking.

Operational Excellence

  • Adopt and enforce best practices in Salesforce and other CS platforms, leveraging dashboards and data to drive portfolio insight and team accountability.
  • Design and implement processes that scale with the team without creating unnecessary manual overhead.

What you bring

  • Collaborative Leadership: Proven ability to partner with peer leaders to drive organizational consistency and shared goals.
  • Technical Aptitude: Able to develop and maintain deep fluency in complex SaaS platform functionality. Comfortable operating in a technical environment and bridging customer needs with product capabilities. Capable of supporting CSMs on configuration, integrations, and admin-level challenges.
  • Detail Orientation: Equally comfortable in the details as in the strategy. Able to review data, spot anomalies, catch process gaps, and build systems that don't let things fall through the cracks.
  • Product Partnership: Experienced in translating customer and admin feedback into structured, credible product input. Knows how to prioritize and escalate effectively without crying wolf.
  • Commercial Acumen: Solid understanding of the renewal and expansion lifecycle, with the ability to support Account Management in achieving commercial targets.
  • Team Management: Strong ability to manage large, multidisciplinary teams and complex projects with high visibility and impact.
  • Mentorship: Proven track record building, mentoring, and developing senior team members.
  • Problem Solving: Highly skilled in conflict resolution, breaking down barriers, and building cross-functional collaboration.
  • Operational Skills: Exceptional delegation and process-building skills, with the ability to manage up and across the organization effectively.
  • Integrity & Influence: Significant gravitas as a leader with strong internal influence and a commitment to confidentiality and integrity.

Espresa’s benefits

Espresa offers a comprehensive benefits package that is competitive with Silicon Valley/Bay Area employers, including health, retirement, a Lifestyle Spending Account, generous PTO, and more.

We are an equal opportunity employer and do not discriminate on the basis of race, religion, national origin, gender, sexual orientation, age, veteran status, disability or any other legally protected status.

For US Based Candidates: Pursuant to the San Francisco Fair Chance Ordinance, we will consider qualified applicants with arrest and conviction records.

We are committed to providing reasonable accommodations to applicants with disabilities.

Show us you and how our mission and vision shine in you. We welcome wonderful, kind, and bright humans!

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