Strategic Enterprise Account Executive

WHAT WE DO

The company 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

The company 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 the company 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 the company'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 the company 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 the company pet wellness and insurance plans

• Regular company-wide events and team gatherings