JOB DESCRIPTION

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

We are hiring a Chief Financial Officer to partner directly with the CEO in running and scaling the company.

This is not a traditional CFO role. We are looking for an operator who happens to be a world-class finance leader, not a finance leader who operates from the sidelines. This individual will be deeply embedded in the business, driving performance, enforcing discipline, and ensuring we are operating with clarity and rigor across every function.

The CFO will own the financial strategy of the company while also acting as a central force in how the business runs day to day. They will challenge assumptions, pressure-test decisions, and ensure that resources are allocated effectively. This role is critical to our next phase of growth as we continue to scale both revenue and operational complexity.

SCOPE OF RESPONSIBILITIES

Financial Leadership

• Own all aspects of financial strategy, planning, forecasting, and reporting
• Maintain absolute precision and command of the company’s financials
• Build and evolve financial models that accurately reflect healthcare and SaaS dynamics, including recurring revenue, unit economics, and engagement-based pricing

Operational Leadership

• Act as a core operator within the business, partnering closely with the CEO and executive team to drive execution and performance
• Establish clear visibility into operational performance, inefficiencies, and resource allocation across all departments
• Implement and enforce financial discipline across the organization

Business Performance and Accountability

• Own and drive the Monthly Business Review cadence, setting the standard for accountability and performance management
• Ensure every function is operating against clear metrics, targets, and expectations
• Challenge functional leaders on spend, headcount, and ROI, ensuring all decisions are grounded in data and aligned with company priorities
• Drive measurable improvements in efficiency, forecasting accuracy, and financial performance

Investor and Board Engagement

• Serve as a key financial partner to the CEO in all investor and board interactions
• Build credibility quickly with investors and stakeholders
• Evolve into the primary financial voice in board and investor settings over time

Finance Function Leadership

• Build and lead a high-performing finance organization
• Oversee accounting, FP&A, and financial operations with a focus on accuracy, scalability, and transparency
• Partner closely with existing finance leadership to elevate the function while maintaining continuity

Required Candidate Qualifications

• Bachelor’s degree in finance, accounting, or a related field; MBA or CPA preferred
• 10+ years of progressive financial leadership experience, including senior finance or CFO-level roles
• Deep experience within healthcare, health plans, or healthcare IT, with recent experience in high-growth or early-stage environments
• Strong SaaS financial acumen, including recurring revenue models and unit economics
• Proven experience working with investors, private equity firms, and boards
• Demonstrated ability to operate as a hands-on leader embedded in the business, not just a reporting function
• Track record of driving operational discipline and accountability across cross-functional teams
• Exceptional analytical and problem-solving skills with high attention to detail and precision
• Strong communication skills with the ability to challenge and influence executive stakeholders
• Ability to thrive in a fast-paced, evolving, and sometimes ambiguous environment

Preferred Candidate Qualifications

• Experience helping scale a company through significant revenue growth, ideally in earlier-stage or growth-stage environments
• Background in environments where finance plays a central role in operational decision-making
• Experience building structure and discipline in high-growth, less structured organizations
• Strong executive presence with the confidence to challenge leadership constructively
• No ego, willing to roll up sleeves and do what is needed to move the business forward

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 in line with leading technology companies
• 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 supplemental benefits plan worth over $2000 annually in 2025
• 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]