Build the Future of Benefits | Outbound Sales Associate (HR Tech / Fintech)

About the Role

A stealth-stage, high-growth startup backed by top-tier investors is building something rare: a benefit that helps employees become homeowners—without giving up equity or waiting for a liquidity event.

This is a chance to get in early with a team reshaping financial wellness from the inside out. You’ll join as an Outbound Sales Associate, owning the revenue motion into HR and Total Rewards leaders at forward-thinking companies. This isn’t a plug-and-play role. You’ll test, iterate, pitch, and close. You’ll build the engine alongside the exec team.

If you’re ready to stop selling just another SaaS tool—and want to open doors that change lives—this is your shot.

What You’ll Do

• Drive top-of-funnel pipeline by researching and prospecting high-fit HR/People targets

• Own the full sales cycle: from first outreach to closed partnership

• Tailor messaging and GTM strategy to a category-defining benefit

• Represent the company at industry events and conferences (~30% travel)

• Partner with leadership on outbound strategy, ICP targeting, and messaging tests

You Might Be a Fit If You Have

• 3–5 years in B2B sales, ideally in benefits, HR tech, or fintech

• Proven track record in outbound prospecting and full-cycle deal management

• Experience selling to HR, People, or Total Rewards leaders

• Comfort with ambiguity, and a bias toward action

• Early-stage or startup sales experience (SDR to AE path or similar)

Bonus Points If You Have

• Past experience at companies like Carrot, Origin, Calm, Modern Health, Ramp, Newfront

• A Rolodex or network in the HR/benefits buyer space

• Founder mindset or early-stage experience where you helped build from zero

This Is Not the Role for You If

• You want to manage people right away

• You prefer structured enablement over building your own process

• You’ve only sold traditional group health plans

• You’re more comfortable analyzing than executing

Compensation and Benefits

We’ve designed our compensation to reward performance—no artificial caps, no buried clauses.

Base Salary: $80,000 to $120,000
On-Target Earnings (OTE): $125,000 to $180,000+

• 65/35 base-to-variable split

• Uncapped variable comp with linear payouts — exceed quota, earn more

• Performance goals are realistic, ambitious, and tied directly to growth

Equity:

• Offered based on seniority and impact

• Benchmarked to the 75th percentile via PAVE

• Designed to reward those who help build early momentum

Benefits:

• Full medical, dental, vision, and life insurance

• 401(k) with company contribution

• Flexible PTO + paid parental leave

• Domestic relocation support available

• Hybrid work model: in-office 3 days/week (San Francisco)

Why Now

This team has already helped dozens of employees access homeownership—often years before they thought it was possible. Now they’re scaling the partnerships engine that powers that impact.

There’s a narrow window to be one of the first hires shaping how this benefit hits the market. You’ll work directly with the CEO and GTM leader, and leave your fingerprint on a benefit that could change the future of work.

If you’ve been waiting for a sales role with real upside—and real meaning—this is it.125