Account Executive

Company Description

The company was founded in 2016 to flip the script on what it means to plan, borrow, repay, and save for college. Today, we’re the category leader with the market’s most comprehensive AI-driven student debt and savings optimization platform. We partner with hundreds of top employers, financial institutions, and retirement record keepers, positioning the company to serve more than 35 million Americans.

We’re already achieving incredible results — to date, we’ve helped our users get on track to eliminate more than $1.8B in student debt and pay off their loans 175,000 years quicker — and we’re seeking movers, shakers, innovators, and problem solvers to help take our mission even further.

The company is a high-growth, Series B startup, funded by leading investors including Altos Ventures, Aflac, Salesforce Ventures, UBS, Equal Opportunity Ventures, Impact Engine, Rethink Impact, Unum, and Cercano Management. Our fully remote, international team of 70 (and counting) includes alumni from Google, UBS, Twitter, Plaid, Prudential, LendingTree, Morgan Stanley, Deutsche Bank, and more.

Job Description

We're looking for an Account Executive to sell across the company portfolio, directly to employers and alongside our financial institution and workplace service provider partners. You'll report to our Chief Commercial Officer and work closely with sales, marketing, product, and customer success.

This is a full-cycle closing role. You'll build pipeline, run discovery and demos, and close deals with HR, Total Rewards, Benefits, and Finance buyers. You'll sell our established solutions, and you'll be among the first to take a new product to market. Because that product is new, there is no inherited playbook. What you learn in the field will shape our positioning, our pitch, and how we sell.

What You'll Do

• Own a new-business quota across the company's existing products and our new product

• Generate pipeline through targeted outbound to employers, and work partner-referred and inbound opportunities alongside it

• Co-sell with partner sales teams, including financial institutions, retirement recordkeepers, and benefits brokers, to move referred opportunities to close

• Run structured discovery and tailored demos that tie the product to the metrics your buyer cares about

• Run multi-threaded deals across HR, Finance, and executive stakeholders

• Feed what you hear in the field back into messaging, pricing, packaging, and the product roadmap

• Work with product and customer success on demos, implementation, and a clean handoff after close

• Keep Salesforce accurate and forecast honestly

What Success Looks Like

• Consistent pipeline from your own outreach, plus strong follow-through on partner and inbound leads

• Early wins on the new product that become repeatable plays and reference customers

• Accurate forecasts and clean CRM data without being chased

Required Skills and Experience

• 4-7 years of B2B SaaS closing experience with a consistent record of quota attainment

• Experience building your own pipeline, not only working inbound

• Experience closing multi-stakeholder deals with HR, Benefits, or Finance buyers

• Comfort selling a mix of established and brand-new products, including a product with limited references and a playbook still being written

• Strong discovery, demo, and storytelling skills

• Discipline with CRM hygiene, pipeline reviews, and forecasting

• A self-starter who works independently and raises problems early

Preferred Skills and Experience

• Experience in benefits, HR tech, or fintech SaaS

• Knowledge of 401(k), recordkeeper, broker, or advisor channels

• Experience co-selling with financial institutions, workplace service providers, or other distribution partners

• Time at an early-stage or high-growth company

• Fluency with AI-assisted sales workflows and modern GTM tools

Background and EEOC

The company offers for employment are conditioned upon satisfactory completion of our employment screening process (including, but not limited to, a review of past employment and education records, background investigation, and/or credit check & fingerprints).

The company strives to foster an environment where every employee can succeed. As an Equal Opportunity Employer we do not discriminate on the basis of race, religion, color, sex, sexual orientation, gender identity, gender expression, national origin, age, non-disqualifying physical or mental disability, veteran status, or any other basis covered by applicable law. All employment is decided on the basis of qualifications, merit, and business need.