# Benefits Escalation Services Manager

**Company:** [Gusto](https://hotfix.jobs/companies/gusto)
**Location:** Denver, CO, Phoenix, AZ, Chicago, IL, Las Vegas, NV
**Role:** Other
**Salary:** $87k – $113k/yr
**Experience:** 3+ years
**Skills:** Benefits Administration, health insurance, benefits broker, AI Tools, LLMs, ChatGPT, Claude, gemini, Salesforce, sfdc, Tableau, Excel, Change Management
**Posted:** 2026-07-22

> Lead a team of 15 Operations Specialists handling benefits administration and health insurance enrollments for small businesses. Combine industry expertise, people management, AI fluency, and data-driven problem solving to drive operational excellence, automation, and scalability.

## Job Description

## Responsibilities
- Directly manage a team of ~15 Operations Specialists, including weekly 1:1s, real-time mentoring, and actionable feedback.
- Ensure benefit enrollments are processed timely and accurately within SLAs; manage daily workflows balancing speed and quality.
- Identify opportunities to leverage AI tools and automation to reduce manual work; coach team on adopting technologies to streamline carrier interactions.
- Own team performance against monthly, quarterly, and annual objectives; monitor using scalable systems and data.
- Serve as primary escalation point for high-impact cases; conduct root cause analysis for systemic improvements.
- Lead change management by translating company initiatives and OKRs into daily actions; foster customer-first culture.

## Requirements
- 3+ years of experience in Benefits Administration, Health Insurance (Carrier side), or with a Benefits Broker (e.g., ADP, Rippling, Aetna, Cigna); understand the lifecycle of a benefit order.
- 3+ years of experience leading projects, mentoring peers, or serving as a Team Lead/Subject Matter Expert.
- AI fluency: comfortable using LLMs (e.g., ChatGPT, Claude, Gemini) and modern tools to draft communications, summarize data, and solve problems; seek ways to automate processes.
- Data-driven: comfortable with Excel, Salesforce (SFDC), Tableau to measure performance and make decisions.
- Experience with change management; able to inspire buy-in amid competing priorities.
- Creative problem solver using first-principles approach to complex enrollment issues with customer-first mentality.
- Bachelor’s degree preferred or equivalent relevant work experience.

## Nice-to-Haves
- Experience in a high-growth startup environment.
- Specific experience with Salesforce (SFDC) reporting and dashboards.
- Experience with prompt engineering or optimizing workflows using generative AI.
- Proven track record of hiring or training top talent.

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