About Gusto
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.
Here’s what you’ll do day-to-day:
- 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.
Here’s what we're looking for:
- 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.
Our cash compensation amount for this role is $143,675 to $176,000 OTE for Denver, Atlanta, Chicago & Las Vegas. $163,265 to $200,000 OTE for San Francisco & New York. $126,530 to $155,000 OTE for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.
Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.
When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
What the Team is Saying
Gusto Compensation & Benefits Highlights
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Healthcare Strength — Health coverage is described as robust and inclusive, with multiple plan choices, relatively low employee premiums for some plans, and offerings like mental-health support and gender‑affirming care. Coverage extends to dependents and is consistently portrayed as a strong part of the package.
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Leave & Time Off Breadth — Time away includes paid vacation, sick leave, holidays, bereavement, various paid leaves, and sabbaticals, with some roles using flexible or unlimited PTO. Usage of multiple weeks off annually is described for certain teams, reinforcing the breadth in practice.
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Parental & Family Support — Family-forming benefits such as fertility support and adoption assistance, alongside robust parental leave, are highlighted. Inclusive care elements and supportive resources around family needs are emphasized as part of the core offering.
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What We Do
Gusto is a modern, online small business platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses. Our customers come from all walks of life, and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Why Work With Us
We help small businesses—the backbone of the economy—thrive. Everything we do ladders up to empowering entrepreneurs and supporting their teams. Gusto empowers builders at every level to take initiative and make things better. You'll be solving meaningful challenges that shape the future of work.
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