Director of Insurance (Insurtech)

TL;DR

Director of Insurance (Insurtech): Shaping insurance strategy and managing carrier relationships to make health benefits accessible for small businesses with an accent on product roadmap design, regulatory compliance, and vendor negotiation. Focus on optimizing benefit value, ensuring 100% compliance with ACA/ERISA, and simplifying the customer experience.

Location: Remote (United States)

Company

hirify.global is a remote-first company on a mission to make health benefits simple, affordable, and accessible for small businesses.

What you will do

• Design and execute the insurance product roadmap to improve benefit value and expand insurance lines.
• Negotiate with carriers and build strong relationships with TPAs and other strategic partners to secure competitive rates.
• Ensure full compliance with ACA, ERISA, and state and federal regulations, overseeing regulatory filings and licensing renewals.
• Collaborate with Sales, Client Success, and Product teams to simplify the customer experience and strengthen client outcomes.
• Mentor internal teams on insurance best practices and translate complex "insurance-speak" into accessible language.
• Lead audits and contribute to broader company compliance and risk management efforts.

Requirements

• Must be based in the United States.
• 7–10 years of experience in health insurance or employee benefits.
• Deep knowledge of group health plans and regulations (specifically ACA and ERISA).
• Proven track record of negotiating with carriers and TPAs and scaling insurance products.
• Strong cross-functional leadership and communication skills.
• Ability to operate effectively in a fast-moving, remote-first environment.

Nice to have

• Experience with level-funded, self-funded, or captive health plans.
• Active insurance broker license.
• Actuarial background or an MBA/relevant graduate degree.
• Previous experience at a benefits or insurtech startup.

Culture & Benefits

• Remote-first culture with annual in-person offsites.
• Equity through stock options.
• Employer-paid health benefits and 401(k).
• Discretionary time off for better work-life balance.
• Collaborative environment with significant room for leadership growth.