Director / Head of Customer Success

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.

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.

Wagmo is looking for a strategic, hands-on Director of Customer Success to architect and lead a world-class post-sale experience. Reporting directly to COO, Jessica Bryant, you’ll own the entire Customer Success lifecycle—from onboarding and implementation through renewal, expansion, and long-term retention.

As the Director of Customer Success, you will build the strategy, team, and infrastructure to scale our rapidly growing B2B customer base. You’ll be responsible for ensuring success across our employer and PEO channel partners, driving value from Open Enrollment onward. Your mission: turn customers into champions by proactively delivering exceptional experiences for both employers and their employees.

You’ll inherit a small but mighty team and be charged with building the org design, playbooks, and KPIs required for scale. This is a foundational leadership role at a high-growth company with strong product-market fit, solid unit economics, and a customer base as loyal as a Labrador.

This role is ideal for someone who thrives in ambiguity, excels at building from zero to one, and rolls up their sleeves to get the job done. You’ll collaborate closely with Sales, Product, Engineering, Marketing, and Customer Operations to drive cross-functional alignment, continuous improvement, and customer outcomes that move the business. The Director of CS is a rare opportunity to take a company with proven traction and build the CS systems, team, and metrics that will support its next phase of scale.

This role is based in New York, requiring 3 days a week in office.

• Own and scale the Customer Success function at Wagmo, driving strategy and execution across onboarding, engagement, retention, and expansion.

• Lead, mentor, and grow a high-performing team of Customer Success Managers and Strategic Account Directors; oversee hiring, onboarding, and team development.

• Define and operationalize key CS metrics, including onboarding success, product adoption, engagement, NPS, and Net Revenue Retention (NRR).

• Build and implement segmentation strategies and coverage models to support SMB, mid-market, and enterprise clients.

• Serve as the sponsor for Wagmo’s employer and PEO clients, deepening relationships and ensuring long-term value.

• Collaborate cross-functionally with Sales, Marketing, Product, Operations, and Support to align on enrollment, lifecycle, and renewal strategies.

• Design and execute scalable QBRs, customer health frameworks, and feedback loops to elevate the customer voice across the business.

• Optimize implementation and onboarding workflows to ensure seamless, efficient, and high-impact client experiences.

• Drive customer advocacy and uncover upsell opportunities through trusted relationships, data insights, and strategic account planning.

• Champion cross-functional excellence by improving collaboration rituals—such as sales-to-CS handoffs and internal feedback cycles—to support customer outcomes and internal alignment.

You’re a strategic, hands-on Customer Success leader who thrives in dynamic, high-growth environments. Equal parts operator and relationship-builder, you bring structure to ambiguity and elevate customer experience into a true growth engine.

• A seasoned CS leader with 8–10+ years of experience across Customer Success, Strategic Accounts, or Client Experience, preferably in B2B, HR tech, benefits, or other high-complexity sales environments.

• Proven track record of building and scaling high-performing teams—you coach, motivate, and hold teams accountable while fostering a culture of ownership, continuous improvement, and cross-functional collaboration.

• Skilled in organizational design and hiring; you bring a clear point of view on how to scale team structure in line with company growth.

• Experience either overseeing or directly managing and growing enterprise and strategic client relationships, acting as a sponsor and trusted advisor.

• Naturally cross-functional—you collaborate closely and effectively with Sales, Product, Marketing, and Customer Ops to align on shared goals and execute flawlessly.

• Highly analytical and outcome-oriented; you tie CS work to business impact, using data to drive decisions, identify opportunities, and improve performance across the lifecycle.

• Passionate about delivering delightful, high-impact customer experiences that drive long-term value for employers and their employees.

• Tech-savvy with strong familiarity with CS platforms and CRM tools; bonus points for experience with implementation tools or HRIS integrations.

• Independent and proactive with a strong sense of ownership—but you’re also deeply collaborative, mission-driven, and motivated by team wins.

• Revolutionize the pet health industry by shaping solutions that improve the lives of pets and their families.

• 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.

• Company paid medical premiums

• Dental, vision, voluntary life, short-term disability and long-term disability

• Unlimited paid time off & extended holiday break

• 12 weeks parental time off

• 401k

• Company paid Wagmo pet wellness and insurance plans

• Pet-friendly office

• Regular company-wide events

We believe pets—and people—thrive when they’re supported and valued. Wagmo is proud to be an Equal Opportunity Employer and is committed to building a diverse and inclusive team.