Sales Leader Jobs in Chicago, IL

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.

About the role

This role's scope is the equivalent of a Director, PMM in many organizations. We're looking for an experienced, customer-obsessed, and AI-fluent Product Marketing leader to lead the go-to-market strategy and execution for Gusto's core products, spanning payroll, time & attendance, contractors, and HR experiences and services.

In this highly strategic and cross-functional leadership role, you'll define how Gusto shows up to target audiences—translating customer and market insights into compelling positioning, clear messaging, and actionable plans. You'll guide how we prioritize opportunities, shape go-to-market plays, and ensure each product is brought to market in a way that drives impact for the entire Gusto portfolio.

Reporting to the Head of Product Marketing, this role will lead a team of full-stack product marketers and partner closely with leaders across Product, Sales, Growth, and Marketing to align strategies and drive measurable results.

We're looking for someone who thrives in both strategy and execution: equally comfortable identifying market opportunities, shaping cross-product narratives, and rolling up their sleeves to turn strategy into action.

If this sounds like you, and you're passionate about helping small businesses succeed, we'd love to meet you.

Lead Product Positioning & Strategy: Own and evolve Gusto's product- and portfolio-level positioning and messaging across our target audiences. Ensure we show up as a clear, differentiated, and valuable solution in the market.

Architect & Execute GTM Strategy: Lead go-to-market strategy and execution across product areas—partnering with Product and Marketing to shape customer segmentation, pricing, and GTM motions that drive adoption and growth.

Turn Insights Into Action: Synthesize market research, customer insights, usage data, and cross-functional input to identify opportunities and inform strategy. Translate strategy into actionable plans and ensure GTM execution lands with excellence.

Lead & Grow a High-Impact Team: Manage and develop a team of product marketers. Create clarity and focus, raise the bar on craft, and foster a culture of insight-driven thinking, collaboration, and results.

Drive Cross-Functional Alignment & Accountability: Act as the connective tissue across Product, Sales, Marketing, and Customer Experience to align on shared goals and orchestrate execution across teams. Bring structure, momentum, and accountability to complex initiatives.

Own Performance & Optimization: Define success metrics and track performance across initiatives. Drive regular reviews of GTM performance and lead iteration to improve outcomes over time.

Here's what we're looking for:

• 10+ years in marketing, product marketing, or product management, with 6+ years focused on product marketing
• Proven success leading portfolio-level GTM strategy and execution across multiple products and audiences
• Strong leadership and people management experience, with a track record of coaching and building high-performing PMMs
• Ability to move between strategic planning and hands-on execution—comfortable with ambiguity and bias toward action
• Excellent cross-functional collaboration and communication skills; adept at influencing across Sales, Product, and Marketing
• Deep experience with customer segmentation, positioning, pricing, and GTM planning
• Experience in SMB, fintech, HR/benefits/payroll tech, or a complex multi-audience business is a plus

Compensation

Our cash compensation amount for this role is targeted at $190,000 - $235,000/yr in Denver & most remote locations, $220,000 - $280,000/yr for San Francisco & New York, and CAD 175,000-230,000 for Toronto. Final offer amounts are determined by multiple factors including candidate 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.