Director of Product Management

Sunny is hiring a Director of Product Management to personally own one product domain and lead product managers responsible for other domains. The role sets product direction, guides research and delivery, builds cross-functional alignment, and advances Sunny’s digital health benefits and engagement products.

Responsibilities:

• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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

Requirements:

• Bachelor's degree in business, computer science, or a related field
• 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
• 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
• 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
• 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
• 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