Strategic Enterprise Account Executive

Strategic Enterprise Account Executive

Wagmo is looking for a Strategic Enterprise Account Executive to own a defined, named list of 25–50 Fortune 500 accounts — the large majority greenfield prospects, with a small number of existing Wagmo clients mixed in. This is a full-lifecycle ownership role, not a "close and hand off" seat. You will prospect and close net-new logos from your list, then personally remain the accountable relationship owner through onboarding (in close partnership with our Implementation/Technical team), enrollment performance, upsell and cross-sell expansion, and renewal. You're not just accountable for signed ACV — you're accountable for whether that ACV turns into a durable, growing, multi-year relationship. If you've built a career owning a strategic account list end-to-end — sale, expansion, and renewal, on the same named accounts — we want to talk to you.

Core Responsibilities

• Own the full lifecycle — prospecting, closing, onboarding, enrollment, expansion, and renewal — for a fixed list of 25–50 named Fortune 500 accounts
• Build and maintain a living strategic account plan for every named account, whether it's a cold prospect or an existing client
• Run complex, multi-stakeholder enterprise sales cycles with HR, Benefits, Total Rewards, Finance, Procurement, Legal, and broker/consultant partners at Fortune 500 companies
• Partner closely with Wagmo's Implementation/Technical team on every closed deal to ensure a clean, on-time onboarding — while remaining the single accountable executive owner of the relationship
• Own enrollment outcomes post-launch: work with the employer's HR/Comms team (and internally with Wagmo Marketing) to drive employee awareness and adoption during open enrollment windows
• Proactively identify and execute upsell and cross-sell opportunities within the existing book — new product lines, expanded eligible populations, additional coverage tiers
• Own the renewal motion for every account in the book: get ahead of renewal risk early, build the business case for continued or expanded investment, and lead renewal negotiations
• Serve as the senior, trusted point of contact for named accounts across the entire lifecycle — including at the executive level — so relationships don't reset with every internal handoff
• Forecast and report accurately across three concurrent pipelines: new bookings, enrollment/adoption health, and renewal/expansion
• Collaborate cross-functionally with Implementation, Partner/Customer Success, Marketing, Product, and Finance to ensure named accounts succeed pre- and post-sale
• Lead RFP/RFI responses and renewal negotiations with the same rigor as new-business pursuits

What You'll Need To Be Successful

• 7+ years of B2B/SaaS sales experience, with proven experience owning a named strategic account list end-to-end — sale, expansion, and renewal, on the same accounts — not primarily a new-logo hunter with occasional account touches

• Demonstrated success selling to, and maintaining long-term relationships with, Fortune 500 / large enterprise HR, Benefits, and Total Rewards leaders

• Experience working with brokers/consultants in a benefits or similarly regulated, cyclical buying environment

• Proven track record of defending and growing revenue at renewal, not just winning net-new logos

• Comfort partnering with technical/implementation specialists on delivery without either micromanaging the work or disengaging from the account

• Strong executive presence — credible operating with VP/C-level stakeholders inside Fortune 500 organizations

• Excellent forecasting discipline across a mixed pipeline (new bookings + enrollment health + renewal/expansion)

• Experience with CRM and account-planning tooling (e.g. Salesforce, Gainsight, or similar)

• Track record of top performance in both new-business and account-growth motions (President's Club, Rep of the Year, or equivalent recognition in either)

Why Consider This Role?

• Own a career-defining book of Fortune 500 relationships — not a rotating cast of one-and-done logos

• Shape how the largest employers in the country deliver pet benefits, and see the full arc of impact from first cold email to multi-year renewal

• 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