Senior Customer Success Director - Strategic Accounts

What We Do

Wagmo is a new type of pet health company focused on empowering and inspiring responsible pet parenting through top-tier pet benefits provided by employers. From everyday care to rainy-day emergencies, we offer tech-enabled solutions that are optimized for value and flexibility so that our pet parents always feel confident that they are giving their pets the care they deserve.

What's Important To Us

We solve hard problems all day long but hang out with dogs while we do it. We value authenticity and efficiency and have no time for egos. We prioritize performance over pedigree, compensate fairly, and never take ourselves too seriously. Our values are core to who we are and how we operate. We talk about them all the time. These are not just things posted on a wall. We will interview for them, hold each other accountable to them, and make sure we work with every single person we interact with in a way that's consistent with these values.

About The Role

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, and influencing the employer's HR, Communications, and executive teams to drive adoption they ultimately control. You will partner closely with Sales on every new-logo handoff and with Implementation on every launch, and you will stay 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

Account Management

• 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

What You'll Need To Be Successful

• 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

Why Consider This Role?

• Own a book of enterprise relationships where your work shows up directly in enrollment, renewal, and NRR, with a comp plan that rewards it

• Shape how some of the largest employers in the country deliver pet benefits, and see the full arc from launch to multi-year renewal

• Build the playbooks that define how Customer Success operates as Wagmo scales

• Join a rapidly growing, VC-backed startup where ownership, impact, and collaboration drive success

• Work in a fast-paced, high-performance environment. This is not a traditional 9-to-5 job, but one that offers flexibility and autonomy in exchange for dedication and impact

Key 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