Enterprise Account Executive

At August Health, our mission is to empower the essential work of caring for our elders.

We achieve this by providing a modern operating platform and electronic health record (EHR) that enables senior living operators to deliver high-quality care with confidence.

Caregivers are the heart of senior living communities, embodying care, compassion, and well-being. Yet, they face increasing challenges—higher resident acuity, complex workflows, and staffing shortages. At August Health, we build tools that simplify their tasks, eliminate inefficiencies, and provide the insights they need to focus on what truly matters—caring for residents.

At August, we strive to live our values each day, in every interaction with our customers and with each other.

• Be responsible – leave things better than you found them

• Take ownership – be decisive and take action

• Be ambitious – build something great

• Keep an open mindset – communicate candidly and welcome new ideas

• Be humble – celebrate each others’ successes and learn from our mistakes

• Stay positive – assume best intent

We’re looking for an experienced Enterprise Sales Executive to help us scale and build a durable, repeatable enterprise motion.

This role offers the opportunity to deeply embed yourself in the senior living ecosystem — working closely with operators, executives, and clinical leaders to ensure residents, caregivers, and communities are set up for success.

You’ll partner closely with our founders and executive team early, with growing ownership as the sales motion matures. The sale is competitive, relationship-driven, and complex — and you thrive in turning that complexity into momentum to win new communities.

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  Build and own pipeline across a defined list of named Senior Living communities and operators

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  Develop trusted relationships through a mix of cold outreach, warm introductions, and in-person engagement

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  Quarterback complex, multi-stakeholder sales cycles — aligning executives, operators, and clinical leaders around the value August delivers

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  Architect and run the sales process end-to-end, from discovery through close

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  Partner closely with founders and internal SMEs to navigate nuanced deal dynamics and relatively long sales cycles

• 8+ years of experience in B2B SaaS sales, with a focus on complex, multi-stakeholder deals

• Direct experience selling into Senior Living (or closely adjacent healthcare markets)

• Specific experience in hunting net-new opportunities; starting a year from $0 and consistently exceeding a 7-figure quota.

• Strong existing relationships in the industry, or a proven ability to build them quickly and credibly

• Highly personable, professional, and organized — trusted by both customers and internal teams

• Comfortable owning and expanding relationships across executives, operators, and frontline stakeholders

• Ability to operate effectively in an early-stage environment with ambiguity, tradeoffs, and evolving processes

• Clear, concise communicator with strong judgment and follow-through

• Solutions-oriented self-starter with strong intuition for deal progression and customer validation

• Interest in helping shape company culture and how it shows up in our sales motion

• Willingness to travel ~25–50% to be present with customers and industry events

Our team brings together deep expertise in technology, healthcare, and company-building. We’ve led teams at Apple, Google, Landmark Health, and Adobe, co-founded and exited multiple companies, shipped products used by hundreds of millions of users, and managed clinical teams caring for thousands of patients.

Backed by top-tier Silicon Valley investors, we are partnering with some of the largest senior care organizations in the U.S. to transform the future of senior living.

We offer market-competitive compensation based on experience and ability, including significant equity option grants. Our benefits prioritize your well-being with 100% company-paid premiums for health, dental, and vision coverage, along with company contributions to your HSA. We help you plan for the future with a 2% 401(k) match, and support your physical and mental health through services like Rightway Health Advocacy and Spring Health Mental Wellness. Beyond traditional benefits, we offer a flexible time off policy, 100% paid family leave, and all-expenses-paid, in-person company offsites twice a year.