[Hiring] Customer Success Director @Wagmo

Role Description

Wagmo is looking for a Senior Customer Success Director to own a defined, named book of strategic clients and be the strategic partner their HR, Benefits, and Total Rewards leaders rely on year after year. This is not a reactive support or check-in seat. You are accountable for whether each account's enrollment holds, whether employees keep engaging with Wagmo, and whether the relationship grows into a multi-year, expanding partnership.

You will work as a trusted partner:

• Reading account data, anticipating risk a year before renewal.
• Building the business case for expansion.
• Influencing the employer's HR, Communications, and executive teams to drive adoption.
• Partnering closely with Sales on every new-logo handoff and with Implementation on every launch.
• Staying the single accountable owner of the relationship after both are done.

If you have built a career turning large, complex accounts into growing, renewing, referenceable partners, we want to talk to you.

Core Responsibilities

• Own the post-sale relationship for a named book of enterprise accounts, from onboarding through enrollment, engagement, expansion, and renewal.
• Manage post-sale onboarding and partner with Wagmo’s onboarding team to ensure year 1 enrollment success.
• Build and maintain a living strategic account plan for every account, refreshed at least quarterly, with owners, risks, goals, and next steps.
• Conduct quarterly business reviews with clients to review results, risks, and engagement/enrollment opportunities.
• Serve as the senior, trusted point of contact across the client's HR, Benefits, Total Rewards, Finance, and broker team member.
• Build multi-threaded relationships; no account depends on a single champion.
• Track and improve employee engagement with the benefit: active-user rate, wellness plan usage, claims activity, app and portal activity, and satisfaction (NPS/CSAT).
• Translate account data into a clear value story for the client: employee sentiment, retention and recruiting impact, and benefit ROI.
• Own renewal and expansion. Hold every account to a NRR target and own the plan to get there: expanded eligible populations, additional coverage tiers, and new product offerings.
• Track renewal timelines and account health at least 12 months out.
• Build an ROI narrative grounded in the account's own enrollment and utilization data, and lead renewal negotiations with the same rigor as a new-business close.
• Pursue multi-year renewals, and secure references, case studies, and executive sponsors from healthy accounts.
• Drive year over year account growth.
• Own enrollment % of eligible employees as the leading indicator of account health, and hold each account to its target.
• Partner with marketing to build and execute on a year-round enrollment and communications calendar with the client's HR/Comms team.
• Diagnose low-enrollment risk early and intervene with a specific plan and date.
• Be the strategic voice of the customer inside Wagmo.
• Partner with Implementation on every launch and with Sales on every handoff, while remaining the single accountable owner of the relationship.
• Represent the client's interests to Product, Marketing, and Finance, and turn recurring account feedback into roadmap and process improvements.
• Forecast accurately across three concurrent motions: enrollment/engagement health, renewal, and expansion, each on its own evidence.
• Build and share playbooks (account planning, enrollment, QBR, risk escalation, renewal) that raise the bar for the entire Customer Success team and mentor CSMs on how to run them.

Qualifications

• 8+ years of B2B/SaaS customer success, account management, or client services experience, including 3+ years owning a named strategic book with a retention and expansion number.
• Proven track record of meeting and exceeding NRR targets on a book of strategic accounts, with examples of how you got there account by account.
• Demonstrated success driving adoption and enrollment on products where the customer, not you, controls the rollout (benefits, HR tech, or similar employee-facing programs).
• Experience working with Fortune 500 or large-enterprise HR, Benefits, and Total Rewards leaders, and with brokers/consultants in a regulated, cyclical buying environment.
• Strong executive presence: credible with VP and C-level stakeholders, comfortable delivering a hard message with data and a plan.
• Analytical depth: you build your own account health views from enrollment, claims, and engagement data and can explain what is driving a trend.
• Proven ability to spot churn and contraction risk 6–12 months out and turn an at-risk account around.
• Comfort partnering with Sales, Implementation, Marketing, and Product without micromanaging their work or disengaging from the account.
• Excellent forecasting and operating discipline across renewal, expansion, and enrollment health.
• Experience with CRM and customer success tooling (e.g., Salesforce, Gainsight, or similar).
• Track record of recognition for retention, expansion, or account growth (President's Club, CSM of the Year, or equivalent).
• Nice to have: experience in pet insurance, voluntary benefits, or employee benefits administration.

Benefits

• Comprehensive health, vision, and dental coverage.
• HSA/FSA.
• 401(k) retirement planning with employer matching.
• Unlimited paid time off.
• Annual company holidays.
• Additional company-wide recharge days off.
• 12 weeks parental leave for eligible employees.
• Company paid Wagmo pet wellness and insurance plans.
• Regular company-wide events and team gatherings.