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Director, Insurance Strategy & Innovation

Paretocaptiveservicesllc · Remote · Posted Jul 6, 2026

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We’re in this for the greater good at ParetoHealth. Our mission is collective greatness, nothing less will do. Our team is a single force united in the drive to transform employee health benefits.

The company was founded in 2011 to help small and medium-sized businesses fight the rising cost of employee health benefits. We blazed the trail with financing innovations that reduce the risks in self-insurance and deliver significant savings—and we continue to lead with a growing ecosystem of partners and world-class cost control solutions.

But success is measured by more than dollars alone and we measure ours by the good that comes from knowing that every client and all their employees can count on effective, affordable healthcare for years to come.

Please note that ParetoHealth does not provide employment visa sponsorship for this position. Candidates must be authorized to work in the United States without sponsorship both now or in the future.

Position Summary:

ParetoHealth is seeking a Director of Insurance Strategy Innovation to lead the evolution of our captive-based stop-loss solutions and drive innovation across our risk-sharing model. This role is responsible for defining product vision, advancing innovation, and aligning cross-functional teams to deliver competitive, data-driven solutions for self-funded employers.

As a strategic leader, you will shape and execute initiatives that strengthen Pareto’s differentiated approach. This will include assessing alternative risk structures, managing and evolving our overall suite of protections, identifying market pain points, and developing solutions to address those needs.

The ideal candidate brings strategic thinking, creativity, strong analytical acumen, and a demonstrated ability to translate market and customer insights into impactful product strategies. Additionally, strong communication and collaboration capabilities are required to drive alignment across the organization.

Key Responsibilities:

Product Strategy Vision

Define and own the risk product strategy for Pareto’s captive and stop-loss portfolio

Assess alternative risk structures and determine whether/how Pareto should evolve captive structures, contribution models, and risk corridors to optimize performance and member experience

Identify market pain points and associated opportunities through broker feedback, claims analysis, regulatory insights, and assessment of the competitive landscape

Develop and prioritize a roadmap to expand/manage a suite of protections for captive Members aligned with company growth objectives and risk appetite

Market Competitive Intelligence

Understand industry trends, including cost drivers, network strategies, and alternative funding models

Evaluate alternative product designs, pricing approaches, and underwriting methodologies

Partner with sales and marketing to capture voice-of-customer insights from brokers, consultants, and employer groups

Understand risk/ product management capabilities at carriers and TPAs in detail to identify gaps and opportunities

Cross-Functional Leadership

Drive alignment on product priorities and ensure effective execution of key initiatives across underwriting, product, and technology

Support go-to-market efforts in partnership with Product, Sales, and Marketing, including messaging and sales enablement

Required Skills Qualifications:

3-5 years of top-tier consulting experience

3-5 years of experience owning Insurance Product strategy and innovation (e.g., carrier, broker, MGU)

Strong nose for value with ability to translate market pain points into solutions; creative, innovative mindset

Data-driven with strong analytical and financial acumen

Demonstrated ability to lead cross-functional initiatives in a complex, matrixed environment; superior communication skills

Preferred:

Deep understanding of risk-sharing structures and stop-loss mechanics

Experience with captive programs, alternative risk arrangements, or level-funded products

Experience working with mid-market employers (50–1,000 lives)

Exposure to clinical programs, cost containment vendors, and population health strategies

MBA or advanced degree

Core Competencies:

Creative with a focus on value – ability to identify opportunities and develop appropriate solutions

Data-driven – ability to utilize data to validate and size opportunities

Strategic thinking grounded in data and real-world performance

Strong communicator – ability to clearly communicate across all levels and functions to drive alignment

Cross-functional/collaborative – able to work across teams to define a solution and bring it to market (commercial focus)

What Success Looks Like

Continued evolution of Pareto’s captive model as a market-leading solution

Strong adoption and advocacy from brokers, consultants, and employer groups

Tight alignment between product strategy, underwriting, and commercial execution

Perks Benefits:

Fully paid medical, dental, and vision benefits.

F…

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