Vice President of Strategy & Product

Who we are

Jellyvision ALEX®, is on a mission to improve lives by helping people choose and use their benefits. We are raising the bar—for benefits and the employee experience (for our employees and those of the customers we serve) – by scaling personalization, compassion and an earnest intent to be helpful in all that we do.

Jellyvision people are a group of creative problem solvers who use good judgment, give each other honest feedback, engage in real debate, and snack frequently. We are curious, hungry, and humble—because we know this is how we’ll continue to make an impact. We’re kind, biased towards action, and sweat the details to create great experiences for those we serve.

We are an inclusive, human-first workplace. Respect and trust for each other are foundational, and our equitable total rewards offerings support the lives and holistic well-being of our unique people. At Jellyvision, expect career experiences that challenge you, empower you to have a direct impact on our mission, and enable you to learn, try, and do while having fun along the way.

What’s the role?

We’re on a mission to simplify benefits and empower employers, brokers, and employees with smarter, more human technology. As Vice President of Strategy & Product, you’ll lead the vision for where we go next—crafting product strategy, deepening our market position, and building solutions that modernize the benefits experience. You’ll also serve as a trusted connector across the industry, leveraging your domain expertise and relationships to shape what's next.

The Vice President of Strategy & Product is a key member of the Senior Leadership Team, directly responsible for shaping and executing our product strategy in alignment with market dynamics, customer needs, and company growth goals. You will lead a high-impact product team tasked with owning the roadmap, prioritizing across a complex ecosystem of stakeholders, and building products that measurably reduce the cost and complexity of benefits for employers and their employees.

This role requires a strategic thinker with deep domain expertise in the benefits space and a strong orientation toward cross-functional partnership. You’ll collaborate closely with:

• Technology leadership to ensure our product vision is supported by scalable, forward-looking architecture.
• Creative leadership to deliver intuitive, differentiated user experiences.
• Customer Operations leadership to ensure implementation, support, and service models reflect our promise of simplicity and clarity.
• Revenue leadership to bring new solutions to market and ensure our go-to-market motion aligns with customer pain points and business outcomes.
  
  

What Are We Looking For?

You’re a strategic, customer-obsessed product leader with deep expertise in the benefits, HR tech, or healthcare space. You know how to craft a vision, align stakeholders, and execute at pace—balancing long-term strategy with the urgency of delivering value now.

• Strategic and hands-on – You move seamlessly between big-picture thinking and in-the-weeds execution. You’re as comfortable mapping market strategy as you are navigating sprint cycles and release plans.
• A strong people leader – You build high-performing, motivated teams. You coach, develop, and inspire others to do their best work and grow with the company.
• Commercially minded – You’re fluent in build/buy/partner decisions and have a sharp eye on where the market is going. You understand how products drive growth—and how to make smart bets.
• Executive savvy, team-first – You can influence at the highest levels while staying grounded in the needs of your team. You advocate for your people and keep alignment clear across all layers of the org.
• Comfortable with ambiguity – You thrive in fast-moving environments with legacy complexity and new greenfield opportunities. You know how to push forward even when the data’s incomplete.
• Curious and driven – You’re energized by learning, solving real problems, and making things better—for users, customers, and the business. You bring grit, heart, and momentum to everything you lead. You are ready to make and own big bets that drive business growth.

What you’ll do to be successful

• Define and drive product strategy grounded in real market needs—balancing near-term impact with long-term differentiation.
• Role Model innovation and modern thinking about managing benefits in an AI driven world. Take AI product strategy beyond the buzzwords to meaningful impact.
• Lead product development: Own the full product lifecycle, ensuring delivery of intuitive, value-driven experiences for employers, brokers, and employees.
• Shape company strategy: Work closely with executive leadership on roadmap priorities, partnerships, and growth plays.
• Build strong industry relationships: Serve as a trusted voice with brokers, consultants, HR leaders, and partners—translating insights into action.
• Be a domain expert: Bring a deep understanding of the benefits landscape, including regulatory, ecosystem, and competitive dynamics. Represent Jellyvision in the market at conferences and speaking engagements.
• Scale and lead the product team: Hire, develop, and inspire a team of product managers and strategic thinkers.
• Foster cross-functional alignment: Collaborate across engineering, sales, marketing, and customer success to deliver outcomes.
• Balance data and intuition: Use metrics, customer feedback, and industry trends to inform smart, decisive prioritization.

Experience & skills you’ll need

• 10+ years of experience in product leadership and/or strategic roles for SaaS businesses—ideally within benefits tech, HR software, or adjacent spaces (healthcare, insurance, payroll, etc.).
• Exposure to building AI driven products with a keen understanding of where to apply AI to solve customer problems.
• Deep domain knowledge of the U.S. benefits ecosystem—ERISA, ACA, open enrollment workflows, broker networks, etc.
• A strong network in the benefits or HR space, with a reputation for thought leadership, integrity, and collaboration.
• Strategic clarity paired with operational grit—you can both chart the course and drive the work.
• Experience influencing executive stakeholders and building high-trust partnerships across and beyond the org.
• Proven ability to lead with vision and drive execution in complex, fast-moving environments.
• Exceptional communicator—able to align technical and non-technical stakeholders and elevate thinking across the org.
• Strong executive presence with the ability to influence cross-functional leaders, customers, and external partners.
• Skilled in setting strategy and team priorities that deliver clear business impact—even with imperfect information.
• Deep experience in customer discovery, validation, and translating insights into market-ready solutions.
• Partner to revenue teams—able to bring product strategy to life in the market and support go-to-market success.

Why This Role Matters
Benefits should be easier—for everyone. In this role, you’ll help redefine what’s possible in the space, using your industry expertise and product chops to lead lasting change. If you're a strategic thinker with strong relationships and a passion for building what matters—we want to talk.

Core Competencies

• Communicates Effectively
• Cultivates Innovation
• Drives Results
• Leads with Trust
• Mission Focus
• Strategic Mindset
• Drives vision and purpose
• Leads and develops talent

The Details

• Location: Remote
• Starting Salary: $215,000 - $230,000
• Additional Compensation: This position is bonus and equity eligible

What Jellyvision will give you

Check out our benefits here!

Jellyvision is committed to continuous evolution and fostering a more diverse and inclusive workplace where everyone is welcomed, valued, and respected. It doesn’t matter your race, ethnicity, religion, age, disability, sexual orientation, gender, gender identity/expression, country of origin, genetic information, veteran status, marital status, pregnancy or related condition (including breastfeeding), criminal histories consistent with legal requirements or any other basis protected by law...we just want amazing people who are willing to grow along with us.

Although we have a Chicago-based HQ that employees are welcome to work out of whether they’re local or just visiting, this position is also eligible for work by a remote employee out of CA, CO, FL, GA, IL, IN, KY, MA, MI, MN, NC, NJ, NY, OH, OR, PA, SC, TN, TX, UT, VA, WA or WI.