VP Travel

Vice President of Strategy & Product

Do not wait to apply after reading this description a high application volume is expected for this opportunity.

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’re kind, biased towards action, and sweat the details to create great experiences for those we serve.

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 whats 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. 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.

You’re a strategic, customer‑obsessed product leader with deep expertise in the benefits, HR tech, or healthcare space. 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. Role Model innovation and modern thinking about managing benefits in an AI driven world. Work closely with executive leadership on roadmap priorities, partnerships, and growth plays.

Serve as a trusted voice with brokers, consultants, HR leaders, and partners—translating insights into action.

Bring a deep understanding of the benefits landscape, including regulatory, ecosystem, and competitive dynamics. 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.

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.

~ 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.

~ Experience influencing executive stakeholders and building high‑trust partnerships across and beyond the org.

~ Strong executive presence with the ability to influence cross‑functional leaders, customers, and external partners.

~ Deep experience in customer discovery, validation, and translating insights into market‑ready solutions.

~ In this role, you’ll help redefine what’s possible in the space, using your industry expertise and product chops to lead lasting change. xklufbp If youre a strategic thinker with strong relationships and a passion for building what matters—we want to talk.

Location : Remote

This position is bonus and equity eligible

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.