# Summer Opportunities - Retirement Sales AE

**Company:** [Gusto](https://hotfix.jobs/companies/gusto)
**Location:** Denver, CO, San Francisco, CA, New York, NY
**Role:** Account Executive
**Experience:** 2+ years
**Skills:** Salesforce, SaaS, Outbound Prospecting, 401(K), Retirement Plans, Fintech, Sales Engagement Tools, AI Tools
**Posted:** 2026-04-20

> Supports small and mid-sized businesses adopting Gusto's 401(k) retirement plans through inbound/outbound sales, consultative advising, plan migrations, and pipeline management in Salesforce. Requires 2-4 years quota-carrying sales experience, preferably in SaaS/benefits.

## Job Description

## Key Responsibilities

### Inbound & Targeted Outbound Retirement Sales Motion
- 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

### Consultative Retirement Engagement
- 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

### Competitive Plan Migration & Switcher Management
- 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

### Pipeline Management & Sales Execution
- 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

### Market Insight & Customer Feedback
- 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

### Quota Ownership & Performance Accountability
- 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

### Continuous Improvement & Team Contribution
- 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

## What We’re Looking For
- **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
- Motivation to thrive in a fast-paced, metrics-driven role while helping small businesses support their employees’ financial futures

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