Account Executive - Director

Candidly

5h•Remote

About The Position

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. 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. Director AEs are expected to personally generate pipeline through outbound, run disciplined sales cycles, and close large, multi-stakeholder deals with rigor. This role carries significant autonomy—and equally significant accountability—especially during periods of funnel rebuild and growth.

Requirements

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
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

Nice To Haves

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

Responsibilities

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