Business Insurance Sales Producer Lead

Gusto•Chicago, NY

15d

About The Position

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . About the Role: Gusto is actively searching for a dynamic and inspiring commercial P&C insurance sales leader to further accelerate Gusto's growth in the business insurance space. You will be responsible for driving new revenue by cross selling Gusto’s insurance solutions to both prospects and our existing client base, with a focus on Commercial Property & Casualty policies. The pace in Gusto sales is fast and the landscape we’re playing in is ever-changing. We’re looking for someone who is motivated by that and who will bring their experience, creativity, and passion for empowering sales professionals to the table every single day. You align with our company values and have a knack for building for the long haul. If you’re passionate about developing people, shaping processes, and you’re excited to roll up your sleeves and lead by example, let’s talk. About the Team: You will initially manage one licensed P&C sales agent hired for this critical pilot, with a path to leading a larger team in the near future. This team is central to evolving Gusto’s business insurance strategy and is crucial to solving customer experience gaps and optimizing our offline insurance channels. Your team will serve as Subject Matter Experts (SMEs), performing the "human-in-the-loop" workflows required to train and optimize the AI Insurance Advisor, Gus. Our collective vision is to be an expert advisor that supports small businesses through every stage of growth, with this pilot and the team you lead being key to establishing our digital insurance agency and licensed agent integration.

Requirements

P&C Insurance Expertise: 4-6 years of experience as a national producer for the small commercial P&C market
Management Experience: 3+ years of people management experience in a sales organization.
Licensing: An active Property & Casualty insurance producer’s license , or the ability to obtain upon hire.
Results-Oriented: Consistent track record of establishing and exceeding measurable goals.
Sales Acumen: Experience with start-up environments and SMB SaaS sales models, and excellent working knowledge of inbound and outbound SaaS sales methodologies.
Coaching Passion: A passion for coaching advisors on discovery, objection handling, and soft skills.
Collaboration: Ability to interact effectively with multiple teams; excellent social and interpersonal skills.
Education: Bachelor’s degree from an accredited university.
Technical Proficiency: Working knowledge of carrier quoting systems, proficiency in insurance software, and Salesforce.com (SFDC) experience required.
Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving.

Responsibilities

Lead a team of P&C sales advisors to achieve and exceed weekly/monthly/quarterly targets for P&C policies.
Encourage and empower your team to perform to their full potential.
Build a world-class consultative sales team by investing in and developing the existing sales team while at the same time attracting top sales talent to Gusto.
Coach and support the team in their role as subject matter experts (SMEs) providing "human-in-the-loop" support to optimize the AI Insurance Advisor, Gus, and assisting customers with complex P&C needs.
Collaborate with Sales, Marketing, and Product leadership to identify market opportunities, drive leads and pipeline progression, and help shape the product vision and strategy.
Use data to inform decision-making and focus areas - ranging from advisor skill development (e.g., coaching conversations, email campaign usage) to team initiatives (e.g., staffing to seasonality, piloting new activities).
Track, measure, and report-out on sales effectiveness against targets and adjust programs and strategies as necessary.
Build a culture of fun and excellence within the team.
Cultivate each individual’s skill set development and guide career pathing as they grow within the organization.
Ensure the team maintains compliance with all state licensing and continuing education (CE) requirements for P&C insurance.