Benefit Services Senior Leader - Group Fulfillment (HRtech)

TL;DR

Benefit Services Senior Leader - Group Fulfillment (HRtech): Leading the Group Fulfillment operation to deliver health benefits accurately and on time for small businesses with an accent on operational scaling and AI transformation. Focus on redesigning workflows around AI, managing cross-functional dependencies, and coaching leaders to drive operational excellence.

Location: Denver, CO; Chicago, IL; Phoenix, AZ. Hybrid (2-3 days in office if based in Denver, San Francisco, New York, or Scottsdale)

Salary: $119,185 – $154,940 per year

Company

hirify.global is a platform that manages payroll, health insurance, 401(k)s, and HR for over 500,000 small businesses nationwide.

What you will do

• Lead 3-5 managers and approximately 40 specialists within the Group Fulfillment operation.
• Set and own operational objectives, policies, and work plans, including headcount and capacity planning.
• Define the AI vision and execute the automation roadmap to reduce overhead and increase capacity.
• Manage critical cross-functional dependencies with Onboarding, BizOps, and insurance carrier partners.
• Coach and develop leaders through structured calibration, performance reviews, and direct sponsorship.
• Ensure strict adherence to timeliness, accuracy, and completeness standards for benefits delivery.

Requirements

• 5+ years of leadership experience, including at least 2 years leading other managers.
• High AI fluency is a non-negotiable expectation: must have experience redesigning workflows or building automated processes using AI.
• Track record of operating against time-sensitive SLAs in benefits, healthcare, payroll, or insurance environments.
• Proven experience setting operational strategy, owning budgets, and driving meaningful organizational change.
• Ability to make decisive, data-backed decisions and manage high-volume operational tooling.

Nice to have

• Experience in benefits operations, health insurance brokerage, or employee benefits administration.
• Proficiency with Salesforce and carrier portals.

Culture & Benefits

• Competitive base pay, comprehensive benefits, and equity (RSUs).
• AI-native work environment with a focus on digital fluency and tool adoption.
• Hybrid work model with a balance of remote and designated office days.
• Inclusive culture committed to equal opportunity and diversity.