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:
As a Leader of Expansion Account Management, you will coach, motivate, and scale a high-impact team, driving sales execution, pipeline growth, and revenue expansion. You will also optimize processes, implement data-driven strategies, and work cross-functionally to improve customer loyalty and maximize revenue.
About the Team:
The Account Management team at Gusto is dedicated to helping small businesses maximize their success by driving engagement, retention, and expansion. We are looking for a high-performing sales leader to manage and develop a team of Expansion Account Managers focused on expansion revenue and customer retention. This team is responsible for proactively identifying growth opportunities within our existing customer base—upselling and cross-selling Gusto’s suite of products while ensuring long-term customer value and retention.
Here’s what you’ll do day-to-day:
Leadership & Team Performance
- Lead and develop a high-performing Expansion Account Management team focused on revenue growth and retention.
- Drive goal setting, sales strategy, and hands-on coaching to exceed expansion and retention targets.
- Foster a culture of accountability, continuous learning, and data-driven performance.
Revenue Growth & Sales Execution
- Drive expansion revenue through proactive outreach and product-driven insights across Gusto’s customer base.
- Lead pipeline management, forecasting, and team quota attainment while refining upsell playbooks.
- Optimize sales processes and KPIs to scale cross-sell efforts and improve engagement strategies.
Operational Excellence & Strategic Execution
- Leverage customer data to refine segmentation, targeting, and sales strategies.
- Implement tools and workflows to boost sales productivity and efficiency.
- Use CRM and analytics to track performance, uncover trends, and guide strategic decisions.
Here’s what we're looking for:
- Revenue Growth & Sales Execution – 3+ years leading high-performing SaaS/tech account management or sales teams; proven in driving expansion revenue, retention, and quota attainment
- Operational Excellence & Strategy – Leverages customer data, tools, and CRM analytics to refine targeting, boost productivity, and guide strategic decisions
- Data & Analytics Expertise – Advanced in Excel modeling, data analysis, and identifying key performance metrics
- Skilled in outbound sales motions, upsell, and cross-sell strategies
- Strong analytical mindset; uses data to optimize sales motions and measure impact
- Expertise in sales coaching, pipeline management, and consultative selling
- Thrives in fast-paced, high-growth environments with strong change management skills
- Excellent cross-functional communication and influence abilities
- Proficient in CRM tools (Salesforce preferred) and sales enablement platforms
- Proven, day-to-day experience integrating AI into how you work - across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes.
Our cash compensation range for this role is $144,000 to $176,000 OTE in Denver, Atlanta & Chicago. $127,000 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.
Similar Jobs at Gusto
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
