Demo

Senior Product Manager

SageSure
Chicago, IL Full Time
POSTED ON 8/25/2026
AVAILABLE BEFORE 9/23/2026
Overview:

If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a Senior Software Product Manager to help drive the strategy, development, and delivery of critical software products and platforms, including inspection and onboarding experiences, that support our business, customers, and partners. This role will work closely with design, engineering, QA, and data partners on a cross-functional software product team, while collaborating with stakeholders across the organization to identify opportunities, solve complex business challenges, and shape how our customers experience SageSure at every step.

This is a highly collaborative and technical role, working closely with engineering on system architecture and API design, that owns product outcomes for our customers, not just for the business. We're looking for someone who thinks in systems, builds real empathy for the people affected by their decisions, and holds themselves to a high bar for what a great customer experience actually feels like, not just what's technically correct or contractually required.

What you’d be doing:

  • Build a deep, evidence-based understanding of our customers: their needs, frustrations, and what a genuinely great experience looks like for them
  • Define and communicate a product vision and roadmap that treats customer trust as a measurable outcome, not a byproduct
  • Apply systems thinking to translate complex business problems into product solutions that hold up across the full customer journey
  • Identify business needs and customer needs independently, not only in response to stakeholder requests, while still partnering closely where it counts
  • Collaborate closely with design, engineering, QA, and data teams throughout product discovery, delivery, and iteration
  • Lead product discovery through direct user research and clear problem definition, not assumption
  • Use data to tell a clear, honest story about what's working, what isn't, and why, both to leadership and through the product itself
  • Drive alignment across stakeholders and facilitate decision-making in complex or ambiguous situations


We’re looking for someone who has:

  • 5-7 years of product management experience, preferably in software or technology-focused environments
  • Deep customer-focused mindset: a track record of treating the end user's experience as a first-order design constraint, not an afterthought
  • Passion for solving meaningful problems and a bias toward measurable value over activity
  • Strong storytelling ability, both internally to make the case to stakeholders, and through the product itself in the experience a customer has using what you build
  • Comfort using AI tools to move faster and think more clearly, balanced with sound judgment on what shouldn't be automated away
  • Experience managing products throughout the full product lifecycle, from discovery and strategy through delivery and optimization
  • Strong analytical and problem-solving skills with the ability to synthesize information from multiple sources and make data-driven decisions
  • Ability to navigate ambiguity and balance competing priorities in a fast-paced environment
  • Strong stakeholder management skills with the ability to influence and drive alignment across cross-functional teams
  • Ownership mentality with the ability to operate strategically while also diving into execution details when needed
  • Ability and willingness to travel periodically for team meetings, stakeholder engagement, office visits, and company events, estimated at approximately 10–15% annually


Highly preferred candidates also have:

  • Background in hospitality, travel, consumer tech, or other industries built around delivering a great end-to-end experience
  • A track record of pushing AI usage further than most, without losing sight of the human being on the other end of the product
  • Experience building products that support customer experiences, operational workflows, or enterprise business processes
  • Experience working closely with software engineering teams and modern product development practices
  • Familiarity with agile product development methodologies and product management best practices
  • Experience leveraging data, analytics, and experimentation to inform product strategy and measure impact


Software at SageSure:

Originally founded as a software and analytics business, SageSure's proprietary technology has always been a key source of competitive advantage. We offer agents and policyholders best-in-class, modern capabilities to quote and bind insurance, service policies, and submit and track claims. We operate a microservices-based SaaS platform and conduct a substantial share of our business through our API. Our software product, engineering, and operations teams set the bar for talent in our industry. We work remotely from numerous states across the country and are always looking for exceptional individuals to join us.

We are continually innovating with modern tools and technologies, and we welcome new perspectives. An ideal candidate will have a passion for some of our key technologies and advocate pragmatic industry practices around availability, scalability, security, and automation. A cloud-based infrastructure, continuous integration and delivery, and a quality-first approach help us to better deliver software. A metrics-driven mindset has become part of our DNA and helps us make data-driven decisions. If you have interests across these domains, we want to help grow and foster them.

About SageSure:

Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed property in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 110 home, flood, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $3.2 billion of inforce premium and helps protect more than 970,000 policyholders. 

 We have more than 1,000 employees in a distributed workforce environment across 12 offices—Fairfield, CA; Mountain View, CA; Cheshire, CT; Jacksonville, FL; Tallahassee, FL; Tampa, FL; Chicago, IL; Jersey City, NJ; Marlton, NJ; Cincinnati, OH; Houston, TX; Sheboygan, WI—who are tackling the industry’s toughest challenges.    

SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, age, veteran status, ability status, gender, and country of origin, striving to create a culture where all individuals feel valued, respected, and empowered to bring their authentic selves to work.

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. Come join our team! Visit sagesure.com/careers to find a position for you.

California Applicants: View SageSure’s Workforce Members’ Privacy Notice - CA Privacy Policy & Notice of Collection

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