Head of Growth, Employer

About Sunny

Sunny is building the AI-native operating layer for healthcare.

Today, getting care means navigating insurance rules, searching inaccurate provider directories, calling offices, waiting for appointments, and coordinating across systems that were never designed around the patient.

Sunny changes that.

Members can text or call Sunny to get care, understand their benefits, find high-quality in-network providers, schedule appointments, manage prescriptions, and navigate the healthcare system. For many common conditions, Sunny can deliver the entire care experience over text, including prescriptions when appropriate. When in-person or specialty care is necessary, Sunny finds and schedules the right care.

Our goal is simple: make accessing healthcare as easy as sending a text.

The Role

We're hiring a Head of Growth to personally own and grow Sunny's employer business.

This is a senior individual contributor role. You will not manage a sales team.

You will be responsible for identifying prospects, opening doors, running sales processes, closing customers, developing partnerships, expanding accounts, and figuring out what makes the employer business scale.

You'll work directly with the CEO and founding team. You should be comfortable going from cold outreach in the morning to a benefits-leader meeting in the afternoon to rewriting the pitch based on what you learned that night.

We want someone who gets energy from personally winning customers, not managing people who do.

What You'll Own

• Personally own employer revenue from pipeline creation through close and expansion.
• Prospect and sell directly to employers, from technology startups through large self-insured organizations.
• Develop relationships with founders, CFOs, People leaders, benefits leaders, and other economic buyers.
• Build distribution through benefits brokers, consultants, PEOs, benefits platforms, and other channel partners.
• Determine which customer segments, messages, pricing models, and channels produce the fastest and most efficient growth.
• Build and execute a disciplined outbound motion while developing inbound, referral, and partner-driven acquisition.
• Run demos, commercial conversations, negotiations, and contracting yourself.
• Turn early customer deployments into compelling ROI stories, references, and case studies.
• Work directly with product to translate employer and employee feedback into improvements that increase adoption and retention.
• Own your pipeline, forecasts, conversion rates, sales-cycle analysis, and revenue targets.
• Continually refine Sunny's employer go-to-market playbook based on what you learn in the market.

What Success Looks Like

You build a repeatable employer growth engine through your own execution.

Sunny knows exactly which employers to target, how to reach them, what message converts, how to close them, and how to expand deployments after launch.

Most importantly, you are personally responsible for creating meaningful new revenue and distribution for Sunny.

Who You Are

You are an exceptional seller and commercial operator who wants autonomy, ownership, and a number to hit. You likely have:

• 5+ years in growth, sales, partnerships, or business development, ideally in healthcare, benefits, insurance, or a high-growth B2B startup.
• Experience personally selling to employers or working within the employee-benefits ecosystem.
• A strong understanding of how employers purchase healthcare and benefits products.
• A track record of sourcing and closing business yourself.
• The ability to sell both a strategic vision and a measurable economic outcome.
• Excellent written and verbal communication.
• Strong quantitative instincts and a habit of measuring funnels instead of relying on anecdotes.
• High agency and comfort creating opportunities from scratch.
• The ability to operate effectively in an early-stage company where the product, pitch, and go-to-market strategy are evolving quickly.
• Experience working with benefits brokers, consultants, PEOs, health plans, or self-insured employers is particularly valuable.

You should not take this role if your ideal next step is managing a large sales organization. This role is designed for someone who wants to remain close to customers and personally drive growth.

Why Sunny

Healthcare has accumulated enormous amounts of administrative complexity between a person deciding they need care and actually receiving it.

AI gives us an opportunity to remove much of that complexity rather than simply build better software for administering it.

Sunny is building the infrastructure to do exactly that.

You'll join a small team, work directly with the founders, and have unusually high ownership over a major part of the company's growth.

Interested? Connect with us

Email us at [email protected] and tell us how you can contribute to Sunny's mission and team.