Senior Product Manager, Contractor Products

The Wrap; Boston, New York (MA, NY); Hybrid; USD 152,000 - 230,000; Full time

Job summary

Gusto is seeking a Senior Product Manager to own contractor products and drive end-to-end growth. You’ll lead long-term strategy, define customer and market positioning, and align cross-functional teams to deliver high-impact solutions.

You’ll use AI to turn complex challenges into durable, customer-loved products while guiding investments for scale. Join a team that values experimentation, rapid iteration, and a strong customer focus across offices in multiple cities with a flexible hybrid

Qualifications

• 5+ years of hands-on Product Management experience.
• Proven track record of building 0-to-1 products from discovery through launch.
• Strong customer discovery and product research skills.
• Solid data acumen to inform decisions, set goals, and measure success.
• Experience with AI tools and a vision for transforming product experiences.
• Exceptional cross-functional collaborator and leader.
• Ability to build business cases, define product vision, and roadmaps.
• Entrepreneurial mindset with empathy for small business owners and contractors.
• Proven track record of building products customers love.

Responsibilities

• Ownership: Lead long-term strategy, research, positioning, and investments; translate strategy into guidance.
• North Star: Define long-term vision for contractor products and durable competitive advantage.
• Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations.
• Make it happen: Drive execution using AI as a co-builder to deliver customer-loved solutions with urgency.

Skills

Product management

0-to-1 product building

Customer discovery

Data-driven decisions

AI tools

Cross-functional leadership

Opportunity identification

Entrepreneurial mindset

Product-market fit

Tools

AI tools

Job description

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff - payroll, health insurance, 401(k)s, and HR - so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) - because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

By the Numbers:

• Named #1 best software for small business of 2024 by G2

About the Team:

Contractors is one of Gusto's fastest-growing business segments. The Contractor Products team owns end-to-end contractor management for SMBs—from onboarding to payments to compliance, across domestic and international contractors. With massive white space ahead, you'll have the chance to take products from 0-1 and beyond, solving real problems for hundreds of thousands of small businesses. We're looking for someone with experience building 0-1 and able to own and drive growth levers for the contractors business.

Here's what you'll do day-to-day:

• Ownership: Lead long-term strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You'll translate this strategy into actionable guidance that informs company-wide planning and execution.
• North Star: Build a long-term vision for how Gusto invests in contractor products - defining how we can simplify contractor management for SMBs and create durable competitive advantage
• Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You'll help create shared understanding and ensure cross-functional teams are set up to deliver.
• Make it happen. Be the pace setter. Drive execution as a boundaryless builder - doing whatever it takes to achieve outcomes. You will use AI as your co-builder to turn complex problems into durable, customer-loved solutions with urgency and care.

Here's what we're looking for:

• 5+ years of hands-on Product Management experience
• Proven track record of building 0-to-1 products - taking ideas from discovery through launch and iteration
• Strong customer discovery and product research skills with the ability to translate insights into actionable product strategies
• Solid data acumen with the ability to use data to inform decisions, set goals, and measure success
• Experience with AI tools and a vision for how AI can transform product experiences
• Exceptional cross-functional collaborator and leader - a great listener who naturally brings teams and stakeholders along, yet doesn't hesitate to make hard decisions when needed
• Ability to identify emerging opportunities, build business cases, define product vision, and create supporting roadmaps
• Entrepreneurial mindset, driven by our mission, with deep empathy for small business owners and their contractor workforce challenges
• A proven track record of building products that customers love

Our cash compensation amount for this role is $152,000/yr to $190,000/yr in Denver & most major metro locations, and $184,000/yr to $230,000/yr for San Francisco, Seattle & New York. 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.