[Hiring] Account Executive - Director @Candidly

Role Description

Director-level Account Executives at Candidly are elite, hands-on closers responsible for building pipeline and closing the most complex, high-impact deals in the business. This is not a strategy role and not an inbound-only role.

• Personally source and build pipeline through consistent, high-quality outbound activity
• Execute targeted outbound motions across priority accounts and buyer personas
• Partner with Marketing and Partnerships, but do not rely on inbound
• Maintain sufficient pipeline coverage to support predictable closes
• Lead complex, high-value sales cycles from first touch through close
• Navigate executive buying committees and multi-stakeholder decision processes
• Build clear business cases and ROI narratives
• Own procurement, legal, security, and contracting workflows end-to-end
• Close fewer, larger, more complex deals with discipline and follow-through
• Maintain exceptional CRM hygiene, pipeline visibility, and forecast accuracy
• Run structured deal processes with clear next steps and accountability
• Collaborate cross-functionally to move deals forward
• Model best-in-class execution and professionalism

Qualifications

• 7–10+ years of enterprise SaaS closing experience
• Proven track record of driving adoption and fulfillment in a partner-led or channel sales environment
• Exceptional organizational skills with experience tracking performance against contractual commitments
• Comfort leading product demos, handling sales objections, and engaging in customer-facing deal support
• Strong communication and presentation skills, with the ability to influence without direct authority
• Experience generating and managing upsell opportunities within a partner portfolio
• Ability to thrive in a fast-paced, high-growth environment with evolving processes
• Experience in the financial wellness, retirement, or employee benefits space
• Familiarity with retirement recordkeepers, financial institutions, or benefits brokers
• Previous work in a high-growth startup or scaling partner program
• Experience with Salesforce, partner portals, and enablement tools
• Demonstrated success building pipeline via outbound, not just closing inbound
• Proven ability to close large, complex six-figure ARR deals
• Comfort navigating procurement, legal, and security reviews
• Strong negotiation and executive communication skills
• High accountability, resilience, and bias toward action
• No-attitude mindset—focused on outcomes over titles

Company Description

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.

• Achieved incredible results — helped users eliminate more than $1.8B in student debt
• Pay off loans 175,000 years quicker
• High-growth, Series B startup, funded by leading investors
• Fully remote, international team of 70 (and counting)
• Includes alumni from Google, UBS, Twitter, Plaid, Prudential, LendingTree, Morgan Stanley, Deutsche Bank, and more

Background and EEOC

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.