Location: Remote (U.S.)
Reports to: CEO (Allison Whalen)
Type: Full-time

About Parentaly

Paid parental leave is critical. It’s encouraging to see more companies offer expanded leave benefits. At the same time, parental leave introduces real operational risk for employees, managers, and teams: How does work get covered? How is knowledge transferred? How does an employee return without disruption or career penalty?

Parentaly exists to solve these problems. Through structured programming, coaching, and practical tools, we support expecting employees and their managers before, during, and after leave.

Our clients include some of the world’s most admired companies. Our mission is to ensure no one has to choose between growing their career and growing their family.

As we scale, we are investing in a founding Customer Success Manager (CSM) who will ensure Parentaly consistently delivers on its promise of business continuity while building long-term advocates across HR, employee, and manager stakeholders. 

About the Role

The Enterprise Customer Success Manager is the single accountable owner of the Parentaly client experience post-sale for our most important clients. This role owns retention, growth, and value realization for Tier 1 clients by ensuring employees and managers meaningfully engage with Parentaly programs and complete the behaviors required for business continuity. The CSM is ultimately accountable for clients achieving ROI through effective coverage planning and successful re-onboarding.

The CSM acts as the quarterback across Program Design, Implementation, Coaches, and client stakeholders. They ensure the program progresses end-to-end, utilization and awareness gaps are addressed early, and execution breakdowns are resolved quickly.

This is a senior, hands-on role. It requires comfort with ambiguity and the ability to influence without authority.

Key Responsibilities

Client Ownership and Value Delivery 

• Own a book of Tier 1 accounts (up to $3M in ARR) from kickoff through renewal. 

• Serve as the primary point of contact and trusted advisor for HR buyers and internal champions.

• Be the voice of Parentaly to clients. Share best practices, benchmarks, and insights that reinforce value and drive advocacy.

• Lead renewals and expansion conversations. Forecast growth based on utilization and outcomes.

• Monitor client health and proactively mitigate churn risks through multi-threaded relationships.

Program Progression and Business Continuity

• Own end-to-end program progression across the leave lifecycle - from employee sign-up through re-onboarding.

• Monitor employee activation, coaching attendance, toolkit usage, coverage plan completion, and manager engagement.

• Identify drop-off or execution gaps early and drive corrective action across internal teams and client stakeholders.

• Track coaching session attendance and required deliverables. Share trends and performance feedback with Coaches and the Head of Program Design.

• Lead regular client check-ins and business reviews. Report on business continuity KPIs, utilization trends, and qualitative feedback.

Utilization, Awareness, and Engagement

• Partner with clients to track utilization goals and clarify shared responsibilities for achieving them.

• Develop and execute tailored enrollment awareness plans per client spanning launch, steady-state, and renewal.

• Create or oversee creative assets that drive awareness and sign-ups including emails, intranet content, Slack messages, newsletters, videos, and flyers.

• Serve as the client-facing lead for events such as webinars, open enrollment sessions, family days, or thought leadership programming.

• Attend client events or launches when appropriate as the Parentaly representative. (Travel required up to 5%)

Cross-Functional Coordination and Feedback Loop

• Serve as the single coordinating owner of value delivery across Program Design, Implementation, Coaches, and HR stakeholders.

• Drive alignment when ownership is unclear and intervene when execution breaks down.

• Act as the client and end-user voice back to Program Design, sharing feedback, surfacing trends, and informing program evolution.

• Partner with Marketing to surface client stories that demonstrate business continuity outcomes and ROI.

You’ll Thrive in This Role If You…

• Have experience owning outcomes across complex, multi-stakeholder journeys

• Are comfortable holding partners accountable without direct authority

• Are highly organized, analytical, and disciplined about follow-through.

• Can identify risk signals early and translate them into decisive action.

• Excel at relationship-based influence and communication across executives, HR, managers, and end users.

• Enjoy putting structure around ambiguity and building repeatable playbooks.

• Understand how your role drives outcomes for both the business and the client.

• Are a compelling storyteller who can turn data into insight and impact.

• Have exceptional attention to detail and strong cross-functional project management skills.

Success in This Role Looks Like…

• Increased employee and manager participation across Parentaly programs.

• Consistent progression of participants through coaching and toolkit milestones with improved pre-leave coaching attendance and toolkit activation.

• Higher completion of coverage plans and re-onboarding plans.

• Strong engagement, retention, and expansion driven by demonstrable business continuity outcomes.

• Documented playbooks and scalable frameworks that make business continuity value delivery repeatable.