Senior Account Executive

Candidly 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 Candidly 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. 

Candidly 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.

This is a closing role for someone who builds their own pipeline and wins complex, high-value deals. You'll own the full sales cycle — from outbound prospecting through procurement, legal, and close — across all employer segments, financial institutions, and retirement record keepers.

If you've spent your career waiting on inbound or inheriting accounts, this isn't the right fit. If you know how to build from scratch, navigate multi-stakeholder buying committees, and close six-figure ARR deals with discipline, keep reading.

• →Build and maintain outbound-driven pipeline across priority accounts and buyer personas — this means prospecting from scratch, not inheriting a book
• →Develop and execute targeted outbound motions using a mix of direct outreach, technology, and creative sequencing to break into new accounts
• →Partner with Marketing and Partnerships to amplify your efforts, but own your own number — inbound alone won't get you there
• →Maintain sufficient pipeline coverage to support predictable, consistent closes quarter over quarter
• →Run complex, full-cycle sales from first touch through close — you're not handing off to a closer, you are the closer
• →Navigate executive buying committees across HR, finance, legal, and C-suite with confidence and commercial rigor
• →Build compelling ROI narratives and business cases tailored to each stakeholder's priorities
• →Own procurement, legal, security, and contracting workflows end-to-end without dropping the ball on deal momentum
• →Forecast accurately and maintain clean CRM hygiene — pipeline visibility is non-negotiable
• →Collaborate cross-functionally with internal teams to remove blockers and accelerate deal cycles
• →Represent Candidly in client-facing meetings and presentations with executive presence and professionalism

• 7+ years of SaaS closing experience with a quota-carrying track record
• Demonstrated ability to build pipeline through outbound — not just close inbound
• Experience closing six-figure ARR deals with multi-stakeholder buying processes
• Strong executive communication and negotiation skills
• Salesforce fluency and structured approach to pipeline management

• Background in financial wellness, HR tech, employee benefits, or retirement
• Familiarity with benefits brokers, retirement record keepers, or financial institutions
• Experience in a partner-led or channel sales environment
• Prior experience at a growth-stage startup

Consistent quota attainment driven by self-sourced pipeline. High close rates on complex deals. A trusted, no-ego presence — internally and with clients. 

Candidly 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).

Candidly 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.