Retirement Sales Account Executive, Gusto
Summer Opportunities
1-2 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
1-2 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 2-4 years of quota-carrying sales experience as an Account Executive, Account Manager, or similar role
- Prior experience with outbound prospecting, including calls and email-based outreach
- Experience in SaaS, benefits, fintech, or financial services preferred
- Interest in or exposure to 401(k), retirement, or benefits sales is a plus
- Familiarity with Salesforce CRM and sales engagement tools
- Strong communication, organization, and time-management skills
- Learner's mindset with a deep commitment to continued growth and development
What the job involves
- As a Mid-Level Retirement Account Executive at Gusto, you will support small and mid-sized businesses by helping them adopt, expand, and convert 401(k) and retirement plans
- In this role, you’ll act as a consultative retirement advisor, engaging customers through a blend of inbound opportunities and targeted outbound outreach into high-propensity accounts within Gusto’s existing customer base
- You’ll lead structured, compliant sales conversations, guide customers through decision steps, and move opportunities toward closure using defined workflows and AI-enabled tools
- This role focuses on high-volume SMB deal cycles, while also supporting slightly more complex mid-sized customers that require deeper discovery and coordination
- You’ll guide business owners through retirement decisions by educating them on plan options, compliance basics, tax advantages, and employee benefits—driving meaningful ARR growth while building strong sales fundamentals
- Manage a mix of consultative inbound retirement opportunities and targeted outbound outreach into high-propensity customer segments
- Execute a structured, insight-led outbound motion into Gusto’s customer base, tailoring outreach based on company maturity, payroll signals, benefits footprint, and prior engagement history
- Own high-volume SMB retirement sales cycles from discovery through close, with exposure to moderately complex mid-size customer deals
- Own the end-to-end sales process for high-propensity SMB accounts, from initial discovery of retirement needs to final plan adoption and "Plan Sponsor" authorization
- Leverage AI-powered tools to prioritize opportunities, personalize follow-ups, and reduce administrative work
- Conduct daily consultative retirement conversations to understand customer goals related to hiring, retention, tax strategy, and compliance
- Educate customers on 401(k) basics, plan design options, pricing, employer match considerations, and conversion timelines
- Clearly articulate the value of Gusto’s retirement solution as a simple, modern alternative to legacy providers
- Partner with customers who maintain existing 401(k) plans with external providers and are seeking to migrate to Gusto’s Retirement platform
- Lead discovery to collect and review existing plan documentation, contracts, and service agreements, ensuring a clear understanding of plan structure, pricing, and fiduciary obligations
- Collaborate closely with Gusto’s Legal, Compliance, and Retirement Operations teams to design a compliant switcher strategy that meets regulatory requirements and platform capabilities
- Guide customers through the end-to-end plan switcher process, setting clear expectations, mitigating risk, and ensuring a seamless transition to Gusto’s retirement offering
- Maintain an organized retirement sales pipeline in Salesforce, including accurate call notes, opportunity updates, and follow-up tasks
- Support forecasting accuracy by keeping pipeline stages and close dates up to date
- Partner cross-functionally with Retirement Product, Marketing, Operations, and Compliance to ensure smooth deal handoff and onboarding
- Capture complex customer questions, objections, and competitive insights from daily conversations
- Share feedback with leadership and cross-functional partners to help refine messaging, sales plays, and enablement
- Own and work toward achieving a monthly ARR quota driven by new 401(k) sales, plan switchers, and customer expansion
- Operate with consistency and urgency in a high-activity, high-expectation sales environment
- Participate in daily team huddles and 1:1s to review priorities, pipeline, and skill development areas
- Actively seek coaching and apply feedback to improve discovery, objection handling, and close rates
- Contribute to team success by sharing learnings, talk tracks, and wins
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 400,000 customers and a multi-billion dollar valuation. And 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 has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & 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
(Co-Founder & 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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