Who is Sunny?

Sunny is changing the world by leveraging digital technologies to help people live healthier lives. Using a digital first strategy, Sunny is helping health plans and employer groups to engage consumers with innovative, integrated health and wealth tools to improve outcomes and drive quantifiable results.

Sunny Payments & Benefits solution helps consumers capitalize on their health benefits by making it easy to spend smarter via directed spend technology for supplemental and specialized benefits. Sunny Rewards, an integrated Reward Dashboard, pairs high-value actions with appropriate financial incentives. Sunny’s simplified consumer experience is designed to maximize rewards, improve health outcomes, and drive quantifiable results.

Sunny’s team of experienced leaders is what truly sets them apart. The elite team represents all corners of the market, ensuring a comprehensive and holistic understanding of the dynamics at play. Drawing from their collective insights, extensive knowledge, and expertise in the field of consumer engagement, the team knows what works and what doesn’t with today’s consumers.

WORKING HERE

Invaluable lessons learned is the genesis of Sunny, which has led to a fine-tuned product-to-market fit that caters to a range of stakeholders in the healthcare space. Whether it’s payers, employers, or individual consumers, Sunny has refined its solutions to meet their unique requirements. Sunny is unmatched in its ability to customize and employ refreshing levels of creativity, adaptability, and inventiveness. This is crucial in an industry where trends and demands change rapidly and calls for a very nimble team.

Sunny is fully committed to revolutionizing consumer engagement. Finally, alignment of valuable actions with financial incentives, a knowledgeable and diverse management team, and a keen understanding of customization and market trends have been brought together to make a significant impact on the way consumers interact with their health and well-being – we hope you consider taking this journey with us!

OPPORTUNITY

As Director, Client Implementation, you will play a critical role in ensuring the successful onboarding and launch of Sunny’s employer and health plan clients. You will lead the end-to-end implementation process—serving as the bridge between clients, vendors, and internal teams to deliver seamless launches that delight our clients and set the foundation for long-term success.

You will build and lead a high-performing team of client implementation specialists, oversee all aspects of implementation, and drive continuous improvement in how Sunny brings new clients live.

SCOPE OF RESPONSIBILITIES

• Own end-to-end client implementations, managing onboarding timelines, deliverables, and integration milestones to ensure successful launches.
• Serve as the primary implementation lead and client-facing expert, partnering closely with Client Success to deliver an exceptional launch experience.
• Facilitate implementation meetings and coordinate regular touchpoints with clients, vendors, and internal stakeholders.
• Gather and translate client requirements into actionable plans, ensuring all details are accurately documented and disseminated.
• Lead data collection, file transfers, and integration efforts with client vendor partners to ensure clean, accurate setup.
• Proactively identify and resolve risks/issues during implementations, escalating when necessary to keep launches on track.
• Build strong relationships with client stakeholders, becoming a trusted partner throughout their onboarding journey.
• Develop best practices and standardized implementation playbooks to ensure consistent, repeatable excellence across all client launches.
• Recruit, mentor, and lead a team of client implementation specialists, cultivating a culture of ownership, accountability, and client-first delivery.
• Partner cross-functionally with Product, Engineering, and Client Success to improve implementation processes and feedback loops.
• Turn every client implementation into a showcase success story—creating raving fans of Sunny.

REQUIRED CANDIDATE QUALIFICATIONS

• Bachelor’s degree or equivalent experience.
• 5+ years of client implementation experience, preferably within healthcare or fintech.
• Proven success leading client-facing implementations that include data integration, vendor coordination, and system onboarding.
• Strong relationship-building skills and a track record of exceeding client expectations.
• Exceptional communication and facilitation skills—adept at guiding clients and internal teams through complex processes.
• Ability to manage multiple implementations simultaneously in a fast-paced environment.
• Experience working cross-functionally to drive problem resolution and continuous process improvements.
• Detail-oriented mindset with strong organizational and prioritization skills.
• Passion for Sunny’s mission and delivering best-in-class client experiences.
• Willingness to travel as needed.

PREFERRED CANDIDATE QUALIFICATIONS

• Project management certification (e.g., PMP or similar) is a plus.
• Experience implementing healthcare technology, services, or member engagement platforms.
• Background in startup or high-growth environments where adaptability is key.
• Demonstrated ability to innovate and build scalable processes for client onboarding.
• Comfortable managing technical and operational aspects of implementations, including data workflows and system integrations.

COMPENSATION & BENEFITS

Sunny has an ambitious vision to empower people to live healthier and happier lives. We are committed to delivering an outstanding culture and experience for every employee. We offer comprehensive benefits and perks, as well as a high level of flexibility.

• A competitive compensation package of $120,000–$150,000 per year, plus a 15% target bonus and an equity grant
• Flexible PTO with manager approval
• An extra day of PTO to volunteer for a cause you feel passionate about
• Employer-sponsored healthcare, dental, vision, short- and long-term disability, and life insurance opportunities
• A company-sponsored rewards and benefits plan with a potential value of $2,100 annually in 2025
• Health account savings plans (HSA, FSA, Dependent Care FSA)
• 401k retirement savings plan company matched up to 5%

SUNNY’S COMMITMENTS

Sunny Rewards is an Equal Opportunity Employer. We’re passionately dedicated to providing the ultimate consumer engagement solution, so please send us a note with your comments or questions at [email protected].

TO APPLY

Please include in your application email to John Chandler, Director of Recruiting:  Job title on subject line, and attach your resume/CV and cover letter.