Summer Opportunities - Retirement Sales AE

Denver, COOn-site 4d ago

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.

Mid-Level Retirement Account Executive (401k Sales)

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.

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.
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