Director, Product Management
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
The Director, Product Management is a hands-on product leader who both owns a product domain personally and leads the product managers who own the rest. You will be the accountable expert for one domain — data and analytics, business operations, or user experience, matched to your background — carrying its direction, its decisions, and its delivery work yourself. At the same time you will manage two to three product managers covering Sunny’s other domains, including third-party partner integrations, and mentor one to two more across the function. This is a player-coach role. You are expected to write epics, user stories, and acceptance criteria for your own scope, and to set and enforce the quality bar for everyone else’s. We are not looking for a manager who only directs work. We are looking for someone with real depth in their domain, the judgment to set direction, and the drive to roll up their sleeves and do whatever the team needs to ship well. The role reports to the Chief Product Officer.
SCOPE OF RESPONSIBILITIES
- Team Leadership & Mentorship:
- Directly manage two to three product managers who own Sunny’s other product domains, including third-party partner integrations: set goals, run regular one-on-ones, give candid and specific feedback, and own performance and career development.
- Mentor an additional one to two product managers outside your direct line, raising the craft bar across the function.
- Lead as a player-coach. This role carries its own product domain and does the work alongside the team; directing work from a distance is not sufficient.
- Set and enforce the quality standard for epics, user stories, and acceptance criteria across the team, and review the team’s work directly rather than by summary.
- Lead product managers well in domains where they, not you, are the deepest expert — coaching judgment and craft rather than supplying every answer.
- Participate in hiring, onboarding, and ramping product managers as the function grows.
- Unblock the team decisively — make the call when a decision is stalling, and escalate early when it needs to go higher.
- Personal Domain Ownership:
- Personally own one product domain end-to-end — data and analytics, business operations, or user experience — and be accountable for its outcomes, not only for overseeing it.
- Set direction for that domain: define the problems worth solving, make the calls on scope and sequencing, and defend the tradeoffs.
- Carry the delivery work for your domain yourself — discovery, requirements, acceptance criteria, validation — at the same quality bar you hold the team to.
- Build Sunny’s capability in your domain through standards, tooling, documentation, and shared practice that other product managers can reuse.
- Act as the recognized expert for your domain across the company, and the person other functions come to with questions in it.
- Market, Competitive & User Research:
- Research the competitive landscape and adjacent industries to identify threats, gaps, and opportunities across your domain and your team’s.
- Track emerging technologies, standards, and practices relevant to your domain, and translate them into actionable product decisions.
- Plan and conduct user research (interviews, usability testing, feedback analysis) to ground decisions in real user needs.
- Bring research findings into roadmap and prioritization conversations with the Chief Product Officer and the wider leadership team.
- Cross-Functional Leadership & Executive Communication:
- Build and sustain working relationships across Engineering, Client Success, Sales, Finance, and Compliance — proactively and remotely, without waiting to be introduced or invited.
- Represent product in cross-functional and executive forums, bringing recommendations with the reasoning and tradeoffs made explicit rather than status alone.
- Surface disagreement early and resolve it directly; escalate what genuinely needs escalating and settle the rest.
- Drive alignment in writing: produce decision documents, specifications, and updates that a leader can act on without a meeting.
- Prototyping & Engineering Handoff:
- Partner hands-on with designers and engineers to rapidly prototype concepts and validate ideas early.
- Build functional front-end code and interactive prototypes that demonstrate the intended experience and behavior.
- Hand off working front-end prototypes and clear specifications to engineering for production implementation, scaling, and hardening.
- Champion rapid, prototype-driven ways of working across the full product lifecycle, from discovery through delivery.
- Backlog & Hands-On Delivery Craft:
- Own and maintain the product backlog, ensuring it is clearly defined, prioritized, and aligned with the product vision.
- Personally write epics, user stories, acceptance criteria, and specifications for the domain you own — not only review what others produce.
- Step into whatever the team needs to ship well: drafting requirements, running a working session, testing a build, chasing down a data question, or writing the client-facing explanation.
- Continuously prioritize and reprioritize the backlog based on changing business needs, stakeholder feedback, and team capacity.
- Stakeholder Collaboration & Delivery Execution:
- Act as the primary point of contact between stakeholders and the development team.
- Gather and synthesize input from business leaders, end users, and other stakeholders to inform product decisions.
- Communicate product strategy and progress to all relevant parties.
- Collaborate with the Scrum Master and development team to plan and execute sprints.
- Participate in sprint ceremonies, including planning, reviews, and retrospectives.
- Ensure the team has a clear understanding of goals, priorities, and deliverables for each sprint.
- Translate business objectives into detailed product requirements.
- Collaborate with design teams to create user-friendly interfaces and experiences.
- Validate and test features to ensure they meet quality standards and user needs.
- Data, Risk & Customer Focus:
- Analyze product performance metrics and user feedback to identify areas for improvement.
- Use data insights to guide prioritization and feature development.
- Identify potential risks and dependencies across your domain, your team’s roadmaps, and shared capacity.
- Work proactively to address challenges and ensure smooth delivery of features.
- Advocate for the user at every stage of the product lifecycle.
- Continuously seek opportunities to enhance the user experience and deliver customer value.
REQUIRED CANDIDATE QUALIFICATIONS
- Education:
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- Bachelor’s degree in business, computer science, or a related field.
- Experience:
- 8+ years of experience in product management and/or product ownership in an agile environment, including at least 2 years directly managing product managers.
- Product management experience at a SaaS company, with a track record of shipping and iterating on a multi-tenant platform used by enterprise clients
- Proven track record of delivering successful products or features.
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- Deep domain expertise in at least one of: data and analytics, business operations, or user experience.
- Hands-on experience building front-end prototypes or working with front-end code.
- Experience in healthcare, health insurance, payments, or regulated financial technology.
- A track record of personally authoring epics, stories, and acceptance criteria at the quality bar the rest of the team is held to.
- Experience managing product managers in domains where they, not you, hold the deepest expertise.
- Experience conducting competitive and user research, and translating the findings into product decisions.
- Experience leading a distributed, fully remote product team.
- Availability to work core hours aligned to US Eastern Time (EST/EDT).
- Skills:
- Strong understanding of agile methodologies (Scrum, Kanban) and tools (e.g., Jira, Monday.com).
- Exceptional communication and collaboration skills.
- Ability to balance user needs with business goals and technical feasibility.
- Strong problem-solving and decision-making abilities.
- Familiarity with user experience (UX) principles and product design.
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- Ability to synthesize market, competitive, and user research into a clear product direction, and to document complex product logic well enough that another team can execute from it without a meeting.
- Working knowledge of front-end technologies (HTML, CSS, JavaScript/React) sufficient to build and iterate on prototypes.
- Fluency with AI-assisted development tools (for example, Claude) to accelerate prototyping and documentation.
- Comfort working through technical detail directly with engineers rather than relaying it.
- Ability to give direct, specific feedback and have difficult conversations without delay.
- Exceptional written communication — the primary leadership instrument in a remote team.
PREFERRED CANDIDATE QUALIFICATIONS
- Certifications such as Certified Scrum Product Owner (CSPO) or SAFe Product Owner/Product Manager.
- Knowledge of accessibility standards and compliance requirements.
- Experience establishing product standards, templates, or playbooks that other teams adopt and reuse.
- Demonstrated fluency with rapid prototyping and design tools.
- Experience owning a data, business operations, or user experience domain at a B2B2C or healthcare platform.
- Experience scaling a product function through standards, documentation, and coaching rather than headcount alone.
WHAT SUCCESS LOOKS LIKE
- By day 30: you have met every stakeholder who touches your domain and your team’s without being prompted, you can explain how Sunny’s health plan clients use the platform, and you know each of your product managers’ strengths and gaps firsthand.
- By day 60: you own your domain outright and are shipping in it, and the team’s epics and stories visibly meet a higher bar than when you arrived.
- By day 90: your team ships predictably across their domains, your own domain has a direction others can articulate back to you, and at least one product manager is demonstrably better at the craft because of your coaching.
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.
As a full-time employee, you can expect:
- A competitive compensation package in line with leading technology companies
- Flexible PTO with manager approval
- Employer sponsored healthcare, dental, vision, short and long term disability, and life insurance opportunities
- A company sponsored supplemental benefits plan worth over $1,800 annually
- 401k retirement savings plan company matched up to 5%
SUNNY’S COMMITMENTS
Sunny 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]
8+ years product management in agile environment, 2+ years managing product managers, SaaS experience, deep domain expertise in data/analytics/business ops/UX, front-end prototyping skills, healthcare/payments experience, US Eastern core hours.
Key Responsibilities
- managing product managers
- owning product domain
- writing product requirements
Skills & Tools
Jira, Monday.com, HTML, CSS, JavaScript, React, Claude
Job Details
- Category: Product Management
- Seniority: Senior Level
- Commitment: Full Time
- Workplace: Remote — United States
- Languages: English
Benefits
- 401k matching
- Generous paid time off
- Retirement plan
About Sunny Benefits, Inc.
A digital health and benefits company helping consumers maximize rewards and improve health outcomes. — Industry: Information Technology