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Director Insurtech Jobs in Chicago, IL (NOW HIRING)

Convr

Director, Customer Strategy

Schaumburg, IL · On-site

... insurtech, or enterprise financial services where underwriting or risk workflows are central ... Direct experience packaging, pricing, and delivering advisory services, including contributing to ...

Convr

Director, Customer Strategy

Schaumburg, IL · Remote

Director, Customer Strategy About Convr:Convr is an AI underwriting, data, and intelligent document ... insurtech, or enterprise financial services where underwriting or risk workflows are central.

Convr

Director, Customer Strategy

Schaumburg, IL · On-site

... insurtech, or enterprise financial services where underwriting or risk workflows are central ... Direct experience packaging, pricing, and delivering advisory services, including contributing to ...

Convr

Director, Customer Strategy

Schaumburg, IL · Remote

Director, Customer Strategy About Convr:Convr is an AI underwriting, data, and intelligent document ... insurtech, or enterprise financial services where underwriting or risk workflows are central.

Cccis

Director, Corporate Strategy

Chicago, IL · On-site

The Role CCC is seeking a Director of Corporate Strategy to serve as a core member of CCC ... Insurtech experience a plus * MBA from a top tier business school strongly preferred * Growth ...

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All JobsDirector Insurtech JobsDirector Insurtech Jobs in Chicago, IL

Director Insurtech information

What is the difference between Director Insurtech vs Product Manager Insurtech?

AspectDirector InsurtechProduct Manager Insurtech
ResponsibilitiesOversees strategic initiatives, manages teams, and aligns insurtech innovations with business goals.Focuses on developing, launching, and managing specific insurance products within the insurtech space.
Required CredentialsBachelor's or Master’s in Business, Insurance, or Technology; extensive industry experience.Bachelor's in Business, Marketing, or Tech; experience in product development preferred.
Work EnvironmentLeadership role in corporate or startup settings, collaborating with cross-functional teams.Product-focused teams, working closely with engineering, marketing, and sales.

The main difference is that the Director Insurtech leads strategic initiatives and manages teams, while the Product Manager Insurtech concentrates on developing and executing specific insurance products. Both roles require industry knowledge, but the director has broader oversight and strategic responsibilities.

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What are popular job titles related to Director Insurtech jobs in Chicago, IL? For Director Insurtech jobs in Chicago, IL, the most frequently searched job titles are:
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Director Insurtech jobs near you
Director, Customer Strategy

Director, Customer Strategy

Convr

Schaumburg, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 8 days ago

Job description

Director, Customer Strategy
About Convr:Convr is an AI underwriting, data, and intelligent document automation workbench built for commercial P&C insurers. We help carriers, MGAs, and brokers accelerate premium growth, improve risk insights, and drive operational efficiency. Founded in 2016, Convr transforms outdated, manual processes into structured, decision-ready workflows. Our modular platform manages underwriting from submission through quote with a purpose-built AI decisioning context engine - grounded in a commercial insurance ontology -ensuring complete data and smarter decisions, faster, while enabling a frictionless experience and superior performance. As we scale, we're building a team shaping the future of commercial underwriting. Join us in modernizing commercial insurance with modern AI.
Role Overview: The Director, Customer Strategy is a foundational role at Convr that operates at the intersection of executive strategy, customer outcomes, and commercial expansion. Positioned within the Customer Experience organization, this role is distinct from Activation and Customer Success, focusing on driving strategic outcomes, roadmap development, and high-value deal expansion. Serving as Convr's "Echo," the Director is embedded in strategic accounts and qualified pre-close prospects to bridge the gap between platform capability and measurable business value. This role will establish the Customer Strategy playbook from the ground up, bringing deep deployment experience and strategic credibility to both existing clients and sophisticated buyers.
What You'll be Doing
  • Serve as the strategic point of contact for named accounts, operating at the business and executive level to steer account growth and direction.
  • Lead billable client engagements packaged as fixed-fee or retainer deliverables, including roadmap workshops, value measurement reviews, and solution advisory sessions.
  • Define and track value metrics post-go-live, using documented outcomes to anchor future renewal and expansion conversations.
  • Partner closely with Customer Success Managers (CSMs) to extend coverage to the strategic layer, ensuring Customer Strategy owns the ongoing business case while CSMs manage adoption and relationships.
  • Coordinate directly with the Activation team during handoffs to ensure value measurement begins immediately at go-live.
  • Participate selectively in qualified sales cycles and complex deals to demonstrate strategic delivery capability, solution depth, and deployment roadmaps to prospects.
  • Build the foundational Customer Strategy playbook, establishing the processes and methodology for this newly created function.

Experience Requirements
  • 7-12 years of experience in Customer Success, solution consulting, or strategic advisory roles -
    preferably within commercial insurance, insurtech, or enterprise financial services where underwriting or risk workflows are central.
  • Demonstrated understanding of commercial insurance operations - specifically how underwriters evaluate risk, structure submissions, and make coverage decisions.
  • Proven comfort operating at the executive level, with an ability to connect platform capabilities directly to business outcomes without relying on a product demo.
  • A strong commercial awareness with a track record of identifying and building toward account expansion opportunities seamlessly.
  • Direct experience packaging, pricing, and delivering advisory services, including contributing to or establishing a formal delivery methodology.
  • A workflow-obsessed mindset that prioritizes understanding how underwriters actually work over simple technical integration success.
  • Comfort with building operational structure where none exists, thriving in a founding role capacity.

Benefits & Compensation
  • Remote work opportunities
  • Flexible Paid Time Off
  • Company Paid Holidays
  • Insurance Coverage (medical, dental, vision, short-term & long-term disability, life insurance, and accident coverage)
  • 401K
  • Paid Parental Leave

Why Join Convr? Joining our team means becoming a vital part of a high-growth, entrepreneurial mission to redefine the commercial insurance industry. We've traded corporate silos for radical transparency and a shared ownership mentality, ensuring that every voice is heard, and no one is just a number. We believe in the power of flexibility because we know life happens, and we empower our people with the autonomy to maintain a genuine work-life balance. As a team of experts striving for excellence, we will challenge you to develop your career and sharpen your craft alongside passionate colleagues who are committed to your success as they are to our collective impact.

Apply