Head of Growth - Insurance

About Sunny

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

Today, getting care means navigating insurance rules, searchinginaccurate provider directories, calling offices, waiting forappointments, and coordinating across systems that were never designedaround 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, manageprescriptions, and navigate the healthcare system. For many commonconditions, Sunny can deliver the entire care experience over text,including prescriptions when appropriate. When in-person or specialtycare is necessary, Sunny finds and schedules the right care.

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

The Role

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

This is a senior individual contributor role. You will not manage asales 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 businessscale.

You'll work directly with the CEO and founding team. You should becomfortable going from cold outreach in the morning to abenefits-leader meeting in the afternoon to rewriting the pitch basedon what you learned that night.

We want someone who gets energy from personally winning customers, notmanaging people who do.

What You'll Own

Personally own employer revenue from pipeline creation through closeand expansion.

Prospect and sell directly to employers, from technology startupsthrough large self-insured organizations.

Develop relationships with founders, CFOs, People leaders, benefitsleaders, and other economic buyers.

Build distribution through benefits brokers, consultants, PEOs,benefits platforms, and other channel partners.

Determine which customer segments, messages, pricing models, andchannels produce the fastest and most efficient growth.

Build and execute a disciplined outbound motion while developinginbound, referral, and partner-driven acquisition.

Run demos, commercial conversations, negotiations, and contractingyourself.

Turn early customer deployments into compelling ROI stories,references, and case studies.

Work directly with product to translate employer and employeefeedback 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 onwhat you learn in the market.

What Success Looks Like

You build a repeatable employer growth engine through your ownexecution.

Sunny knows exactly which employers to target, how to reach them, whatmessage converts, how to close them, and how to expand deploymentsafter launch.

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

Who You Are

You are an exceptional seller and commercial operator who wantsautonomy, 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 B2Bstartup.
• Experience personally selling to employers or working within theemployee-benefits ecosystem.
• A strong understanding of how employers purchase healthcare andbenefits products.
• A track record of sourcing and closing business yourself.
• The ability to sell both a strategic vision and a measurable economicoutcome.
• Strong quantitative instincts and a habit of measuring funnelsinstead of relying on anecdotes.
• High agency and comfort creating opportunities from scratch.
• The ability to operate effectively in an early-stage company wherethe product, pitch, and go-to-market strategy are evolving quickly.
• Experience working with benefits brokers, consultants, PEOs, healthplans, or self-insured employers is particularly valuable.

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

Why Sunny

Healthcare has accumulated enormous amounts of administrativecomplexity between a person deciding they need care and actuallyreceiving it.

AI gives us an opportunity to remove much of that complexity ratherthan 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 haveunusually high ownership over a major part of the company's growth.

See how AI-powered navigation can lower costs and improve outcomes.

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