Sales Manager, Gusto
Expansion Team
$146-220k
OTE
OTE ranges encompass a 60% base salary / 40% commission structure
2-3 days a week in office
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
$146-220k
OTE
OTE ranges encompass a 60% base salary / 40% commission structure
2-3 days a week in office
1001+ employees
Company mission
To create a world where work empowers a better life.
Role
Who you are
- 10+ years of experience leading high-performance account management or sales teams, ideally in a SaaS or tech environment
- Proven success in driving expansion revenue, customer retention, and quota attainment
- Experience in outbound/proactive sales motions, with a strong understanding of upsell and cross-sell strategies
- Strong analytical mindset—able to use data to drive decision-making, optimize sales motions, and measure impact
- Expertise in sales coaching, pipeline management, and consultative selling
- Ability to thrive in a fast-paced, high-growth environment and manage change with agility
- Strong communication and influence skills to collaborate effectively across teams
- Experience with CRM tools (Salesforce preferred) and sales enablement platforms
What the job involves
- 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
- As a Sales Manager oExpansion Team team, 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
- Inspire, lead, and develop a team of high-performing Expansion Account Managers focused on revenue growth and retention
- Set clear goals and drive a sales-first mindset, ensuring the team meets and exceeds expansion revenue and retention targets
- Provide hands-on coaching in sales strategy, consultative selling, and negotiation to optimize performance
- Develop a culture of accountability, continuous learning, and data-driven decision-making
- Recruit, train, and mentor top account management talent to scale the team and sustain growth
- Own and drive expansion revenue across Gusto’s existing customer base through proactive outreach as well as leveraging Product signals and insight
- Develop and refine outbound and upsell playbooks to maximize conversion rates
- Drive pipeline management, forecasting, and quota attainment for the team
- Establish a scalable sales process for identifying and closing upsell and cross-sell opportunities
- Monitor KPIs and team performance, leveraging insights to continuously optimize outreach and engagement strategies
- Analyze customer data and buying patterns to refine segmentation, targeting, and sales motions
- Implement tools and workflows that improve sales productivity and operational efficiency
- Partner with Sales, Marketing, Product, and CX teams to align account management strategies with broader company goals
- Use CRM and analytics platforms to track success, identify trends, and inform strategic decisions
- Develop and report on dashboards that measure revenue impact, pipeline health, and growth opportunities
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 200,000 customers and a multi-billion dollar valuation. In 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that will see it reach key profitability benchmarks. It continues to consolidate its platform, for example by integrating with OpenComp to grant its users access to the company's Compensation Intelligence Platform.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.1m
Company benefits
- Comprehensive medical, dental, and vision benefits, plus a variety of mental health resources
- Flexible vacation - Gusties are encouraged to take the time off they need to continue doing great work
- Fertility treatments, parental leave, pregnancy termination, caregiving, gender-affirming surgery, hormone treatments, transgender-inclusive services, and more
- If you work at one of our homebases, enjoy food, drinks, and good conversation — on us
- Celebrate 5 or 10 years at Gusto and take a month off to recharge
- Take advantage of internet, phone, commuter, and wellness stipends each month, along with a WFH stipend and cash for anniversaries
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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