[Hiring] Customer Support Team Lead @Jerry.ai

Role Description

You could lead a team anywhere. Why us?

• Join a pre-IPO startup with capital, traction, and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
• Work with a high-caliber team from companies like Lemonade, GEICO, Bain & Co, and McKinsey.
• Disrupt a massive market and help us scale to a $10B business in the next few years.
• Be immersed in a talent-dense environment that prioritizes first-principles thinking and rapid career acceleration.

About the Opportunity:

Jerry is growing fast, and more than 5 million customers count on us to make car insurance simple. As Team Lead on our Insurance Service team, you’ll work closely with the Manager, Contact Center Operations, to coach a team of 10 insurance agents and make sure every customer gets a white-glove experience.

Behind every great customer experience at Jerry is a team of licensed agents, ready on calls, chats, and digital channels. As their leader, you’ll raise that team’s game:

• Coaching every agent to their best, setting a high bar for service, keeping the team compliant, and solving problems before customers ever notice them.

How You Will Make an Impact:

• Coaching & Performance: Lift team results through regular 1:1s, clear feedback, and performance reviews, and catch performance issues early.
• Operations & Compliance: Own staffing and coverage, quality reviews, timesheets, and PTO, and keep every agent compliant with insurance regulations and Jerry policy.
• Escalations: Resolve complex product, carrier, and system issues, and step in on customer calls when needed.
• Cross-Functional Impact: Work across the business to fix operational problems at the source and help shape the initiatives that scale Jerry’s customer experience.

Qualifications

• A People Leader: You drive results by coaching consistently, not just when something goes wrong.
• An Insurance & Systems Expert: You know policies, regulations, and call center and CRM tools well enough to answer tough questions and troubleshoot complex issues.
• Customer-Obsessed: You hold a high bar for service, sweat the details, and fix issues fast.
• Truth-Seeking: You bring rigor to every part of the job, from your own work to your team’s.

Requirements

• 3+ years of experience in a high-volume contact center in the insurance or financial services industry.
• Demonstrated experience in a leadership or "player-coach" capacity (Team Lead, Senior Rep, or Manager).
• Active Property & Casualty (P&C) license is required (or willingness to obtain one quickly).
• Strong technical aptitude and comfort with CRM tools and omni-channel communication platforms.

Benefits

• Pay: $50,000 - $60,000 annual base
• Workplace: Remote (we will provide you with equipment)
• Benefits: Insurance (health, vision, dental), paid time off, paid parental leave, 401K with employer matching, etc.