Summer Opportunities - Retirement Sales AE

Gusto•Denver, CO

1d•Hybrid

About The Position

At Gusto, the mission is to grow the small business economy by handling payroll, health insurance, 401(k)s, and HR, allowing owners to focus on their craft and customers. Gusto supports over 400,000 small businesses nationwide with teams in Denver, San Francisco, and New York. All full-time employees receive competitive base pay, benefits, and equity (RSUs). AI is integral to Gusto's work, and team members are expected to engage with AI tools and grow their fluency. As a Mid-Level Retirement Account Executive, you will assist small and mid-sized businesses in adopting, expanding, and converting 401(k) and retirement plans. This role involves acting as a consultative retirement advisor, engaging customers through inbound opportunities and targeted outbound outreach to high-propensity accounts within Gusto’s existing customer base. You will lead structured, compliant sales conversations, guide customers through decision-making, and close opportunities using defined workflows and AI-enabled tools. The focus is on high-volume SMB deal cycles, with support for more complex mid-sized customers requiring deeper discovery and coordination. You will educate business owners on plan options, compliance, tax advantages, and employee benefits to drive ARR growth and build strong sales fundamentals.

Requirements

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
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
Motivation to thrive in a fast-paced, metrics-driven role while helping small businesses support their employees’ financial futures

Nice To Haves

Experience in SaaS, benefits, fintech, or financial services preferred
Interest in or exposure to 401(k), retirement, or benefits sales is a plus

Responsibilities

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 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