Senior Product Manager, InsureTech

At mature, pre-IPO HR Tech company with mission helping SMBs

Location: Hybrid 2-3 days/week in NYC (FiDi – with sweeping bay views!)

Comp: $165,000–202,500K base + options

Visas: Sorry, no visa sponsorship or transfers available

About the company:

Chances are, if you've worked for a tech startup or an established small-to-medium-sized business, you're probably already familiar with our client!

They're a late-stage Benefits / Payroll platform tech company (Series E, pre-IPO, 1300 people) in an exciting stage of substantial but responsible growth, and with great name recognition. They provide SMBs - including many in the tech industry - high-quality, enterprise-level health insurance and payroll tools that smaller businesses and their employees wouldn’t otherwise have access to.

They’re known for a standout culture rooted in honesty, openness, integrity, friendliness, no-ego, and inclusion – “collaboration” isn’t just a word on a cheesy poster in a hallway – it represents their values at their core. 

Their cred:

Fortune magazine named them to their Best Workplaces in New York list 5 times, and are one of BuiltIn’s “NYC Best Large Companies to Work For".

They’ve been in business for 10+ years and are an important player in the $40B HR Tech industry. They’re secured $160M in funding from many top VCs including Bain, Thrive, FirstMark Capital, and Union Square Ventures.

Their star continues to rise rapidly; it’s a great time to get in the door! They recently expanded into global markets and have grown consistently and intelligently year over year.

They have doubled their Product org in the last 2 years, now ~50 Product Managers strong, and growing. They’re now adding a full suite of products to their already well-known core product, so they’re in a great place for continued growth and visibility.

About the role:

Senior Product Manager, InsureTech

This Product Team is responsible for safeguarding customers through seamless, compliant, and transparent management of complex risk and regulatory workflows, with a focus on state unemployment insurance and workers’ comp. The team underpins the systems and experiences that ensure every aspect of risk coverage—from onboarding and policy administration to claims and audits—is efficient, accurate, and trustworthy.

As a Senior Product Manager, you’ll play a high-impact role driving the roadmap for one or more pods aligned around a single mission. You’ll scope and prioritize new initiatives through research-backed case development and guide work through the full product development lifecycle. Across your initiatives, you’ll balance both customer-facing and internal platform needs, ensuring we meet a high bar for quality and reliability.

As a champion for your team’s focus and productivity, you’ll remove obstacles, build alignment, and support smooth execution toward business objectives. You’ll operate with a high degree of independence and clearly articulate the reasoning behind your decisions to peers and cross-functional partners.

You’ll be joining a team at the intersection of technology, compliance, and customer impact—where thoughtful product work directly helps businesses stay compliant and confident. You’ll have the autonomy to shape meaningful solutions in a complex space, surrounded by peers who value curiosity, collaboration, and continuous learning.

What You’ll Do:

• Guide the product lifecycle (PDLC) from discovery and definition through delivery and iteration, grounded in a deep understanding of user needs and regulatory complexity.
• Create and refine PRDs that articulate clear problem statements, requirements, and success measures, enabling Engineering and Design to execute effectively.
• Influence cross-functional collaboration across Engineering, Design, Compliance, and Operations to align on solutions that balance compliance, usability, and scalability.
• Synthesize data, insights, and feedback to inform prioritization, roadmap adjustments, and iterative improvements.
• Conduct research and interviews with customers and stakeholders to uncover pain points in filing, reporting, and communication—translating findings into actionable opportunities.
• Contribute to a supportive, outcome-focused product culture, helping improve team processes, rituals, and alignment across product pods.

Who you are:

• Minimum of 4-5 years of Product Management experience in a modern technology business, preferably in a highly regulated industry.
• Familiarity with risk or insurance domains (e.g., workers’ comp, unemployment insurance, underwriting) is a major plus!
• At least some experience from midsized tech companies (~500-2000 people)
• If you also have large corporate and/or small scrappy startup experience, that’s great.
• Experience tackling complex areas to use technology and automation to simplify and streamline into reliable, user-friendly experiences.
• Ability to own mission-critical operations with lots of data and limited margin for error.
• Proven track record owning projects end-to-end, navigating ambiguity, and driving initiatives forward.
• Skilled at simplifying complex problems and communicating clearly without jargon.
• Solid business acumen and ability to influence effectively across cross-functional stakeholders in Marketing, Design, Finance, Engineering, and Operations
• Comfortable in fast-changing, regulated environments where legislation and compliance influence product choices.
• Thrive in a high-ownership culture: independent, resourceful, and proactive
• Low-ego, team-first mindset - you are excellent at building camaraderie, setting a north star that people can rally around, and contribute to a collaborative, healthy culture 
• Senior-level experience preferred; seeking someone seasoned and strategic with natural leadership qualities- you’re probably on the mid to upper end of “Senior”.
• Able to start quickly.​​ They’ve got some juicy work on deck that needs some love asap! 

Why this role matters:

At its core, this team builds the systems that make work work — ensuring people everywhere get paid, taxed, and supported accurately and on time. You’ll be solving real-world problems at scale, in a space that’s both technically challenging and emotionally resonant.

If you’re excited by the idea of contributing to a high-caliber team through a pivotal platform transformation — and doing it in a company that values collaboration, humility, and impact — this could be the next big chapter in your career.

TO APPLY:

Apply here online, or send us your resume, portfolio, openness to hybrid onsite in NYC, and salary range to: team@joanneweavergroup.com

*** $1,000 REFERRAL BONUS ELIGIBILITY ***

If this isn't for you, but you recommend someone to us who we place in the job longterm, you can earn up to a $1000 referral bonus. Recommendations can be sent to team@joanneweavergroup.com - and are very appreciated!