Chief Product Officer

Our Company

At Wysh, we’re not your average insurance company—we’re redefining financial protection for the modern world. Our purpose is to empower every person to live life to the fullest, with the confidence of financial protection. As an entrepreneurial team, we thrive on thinking outside the box, experimenting fearlessly, and delivering innovative solutions that challenge industry norms.

What sets us apart is our people: a dynamic mix of math nerd strategists, user-flow-obsessed designers, results-driven developers, and epic storytelling marketers. We love what we do and take work-life balance and professional development as seriously as our products.

At Wysh, we dream big, safeguard futures, and inspire everyone—our customers and team alike—to aim high. Ready to join a company that’s redefining financial protection and making dreams a reality? Join us on this exciting journey, and let’s make an impact, one Wysh at a time.

The Role

Wysh is looking for a Chief Product Officer to define what we build, why we build it, and how it creates value for the people we serve — policyholders, our parent company, distribution partners, and the broader ecosystem we operate in. This is a full-time, remote position based in the U.S. (EST or CST time zones preferred), reporting directly to the CEO, with travel to New York, Durham, and Milwaukee required as needed to support key strategic meetings. The base salary range for this role is $250k – $300k, with final compensation determined by experience, skill set, and region.

You'll own the full product portfolio, from core insurance products to the digital platforms and APIs that power our distribution partnerships. You'll set the multi-year product vision and help us make the bold, well-reasoned bets that deliver long-term economic value and meaningful learnings to our parent, Northwestern Mutual.

We're looking for someone who leads with genuine customer obsession — grounding every decision in a real understanding of what customers and partners need, not just what's easy to build. You'll bring credible, hard-won insurance product expertise, the kind that earns trust with regulators and stakeholders alike. You know how to build and empower a high-performing product organization, and you're not afraid to push the boundaries of what insurance products and platforms can be.

You know how to build and empower a high-performing product organization, and you're not afraid to push the boundaries of what insurance products and platforms can be.

Responsibilities

• Define and own the company's product strategy and multi-year product roadmap — spanning insurance product portfolio, digital platforms, parent company distribution, and product innovation initiatives.
• Collaborate with the Wysh Senior Leadership Team and Northwestern Mutual to define and implement the company's product, distribution, and technology strategy.
• Measure strategy performance against key business outcomes, delivering learnings to the parent company while driving long-term standalone economic value for Wysh.
• Build and lead the Product organization, including external and internal (parent company) relationship management, product strategy, and product design/UX.
• Create and champion a formal product development lifecycle process that leverages emerging technologies and automation to deliver a product development program with industry-leading speed, flexibility and cost efficiency.
• Own the product development lifecycle defining success metrics for each product, building business cases, tracking business outcomes, and making investment and retirement decisions based on evidence.
• Partner with the CTO and CIO to define Technology-Product collaboration models, including development of the company's API product strategy and deployment of the partner API ecosystem that enables distribution, data exchange, and operational integration with our partners.
• Own the company's insurance product go-to-market and filing strategy working closely with Legal, Compliance and Actuarial to develop, file, and maintain policy forms and rates across all licensed states.
• Represent product strategy externally to distribution partners, reinsurers, and regulatory stakeholders in close coordination with Legal, Compliance and Finance.
• Deliver market insights and thought leadership on insurance product and distribution innovation to shape the company’s strategic priorities and deliver key learnings and insights to the parent.

Qualifications

• 12+ years of product management experience, with at least 5 years in a senior product leadership role (VP Product, CPO, or equivalent).
• Direct experience in insurance technology — including knowledge of insurance product design, state filing processes, and policy form development.
• Proven track record building and scaling product organizations in a startup or high-growth environment.
• Strong background in both advisor-facing and and B2B API/platform product development.
• Demonstrated ability to develop and execute product strategy that creates measurable business value.
• Excellent stakeholder management skills — comfortable navigating legal and regulatory requirements as part of the product development process.
• Experience with traditional (e.g., captive, brokerage, IMO) and emerging (e.g., holistic wealth management and embedded) insurance distribution channels. 

Diversity and Inclusion

Wysh is a proud equal opportunity employer that is committed to diversity and inclusion in and outside of the workplace. We strongly believe that everyone deserves a seat at the table and we support a culture where our people are empowered to be their authentic selves each and everyday.

We’re building a team that represents a variety of backgrounds, perspectives, and skills to reflect the world that we live in and the customers we serve. You are welcomed to apply for this role free of biases or discrimination regardless of your race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, national origin, veteran status or any other basis covered by law.

Benefits

A Great Team – We focus on hiring people from diverse backgrounds who are easy to get along with and fantastic teammates.

Flexible Work Schedule – Hybrid or Remote work schedule. We’re interested in what you contribute more so than when you do it.

Work Life Balance – Unlimited PTO, Paid Holidays, along with Paid Summer Fridays and Paid parental leave.

Competitive Compensation – Exact compensation range is determined based on your region, years of experience, and specific skill set using aggregate market data from PayScale.

Health & Wellness – We offer 100% Medical Care Coverage for you and generous contributions for family, Dental and Vision Coverage, Commuter and Parking Reimbursement, 401k with a 4% Match, Health and Wellness Reimbursement, Free talkspace membership, Voluntary Long-term and Short-term Disability, Life Insurance and FSA/HSA.

Career Development – We believe in upskilling our teams, providing each employee a $1,000 annual training allowance.

Friendly office environments – Two modern offices; one in Dumbo, Brooklyn and the other in Durham, NC, offering a variety of working spaces for individual or team collaboration with free meals and snacks.

Social events – Monthly culture events, celebrations, team outings and social hours.