Chief of Staff, Summer
+ Equity
Student loan management & repayment platform
Open for applications
Student loan management & repayment platform
101-200 employees
Open for applications
+ Equity
101-200 employees
Company mission
To act as a “trusted advisor” to student loan borrowers.
Role
Who you are
- This role requires a strategic thinker and sharp communicator who can create clarity, elevate decision-making, and keep critical initiatives moving
- The position is ideal for a high-level operator who learns quickly, thrives in ambiguity, and can act as a trusted partner at the center of the organization
- At least 5 years of experience in consulting, strategy, operations, business analysis, or similarly demanding roles at a startup or high-growth company; experience supporting founders or C-level leaders strongly preferred
- Bachelor’s degree or equivalent experience required; advanced degree a plus but not necessary
- Exceptional communication, research, and organizational skills; detail-oriented, fast learner, resourceful problem-solver
- Experience running complex, cross-functional workstreams and influencing without formal authority in fast-moving, high-growth environments
- Proven ability to operate with urgency, juggle shifting priorities, and deliver consistently excellent work under tight timelines
- Highly data and tech fluent; able to build models, interpret dashboards, and quickly master new tools (decks, docs, workflows, CRMs, PM systems) to make metric-driven recommendations
- Executive presence and judgment, capable of acting as an extension of the CEO in meetings, written communications, and external interactions
What the job involves
- The Chief of Staff will serve as a force multiplier to the CEO, driving company priorities, strengthening executive alignment, and accelerating progress across the business
- Serve as a true strategic partner to the CEO, conducting deep research, synthesizing insights, and producing sharp, decision-ready briefing materials while helping shape priorities, evaluate tradeoffs, and pressure-test strategies
- Prepare the CEO for every interaction, anticipating questions, risks, stakeholder dynamics, and strategic opportunities to ensure flawless execution in high-stakes settings
- Lead executive communication and relationship management, acting as a trusted point of contact for investors, partners, and advisors while owning board materials, investor updates, and strategic memos
- Own the operating cadence for the CEO, including creating pre-reads, agendas, follow-ups, decision frameworks, and communication workflows, ensuring every meeting and touchpoint is structured, aligned, and high-impact
- Drive cross-functional alignment to ensure the organization is fully prepared for and responsive to the CEO’s top external priorities, removing roadblocks, and translating external opportunities into actionable work
- Represent the CEO with discretion and professionalism, managing confidential information and sensitive communications with absolute trustworthiness
Our take
Nearly two trillion dollars in outstanding student loans has pulled more than 45 million US students, and the country at large, into a student debt crisis. The company has attracted the attention of a slew of fintech startups and investors looking to build solutions - some are available for companies to offer their staff as employee benefits. Summer is one of them, but doing something unique.
Summer scans multiple sources to compile a directory of student loan forgiveness and repayment opportunities, and utilises these options to develop a personalised debt management program for eligible employees - all managed digitally. Not only is this a savvy way for employers to enhance benefits packages for top-tier graduates in a competitive labour market, but it’s also something for which they've recently begun to receive tax incentives.
Summer has seen good sign-ups, and it's helped tens of thousands of borrowers save millions of dollars. Through a partnership with Credit Karma, the company has also been broadening its service beyond being a simple employment benefit. It has also raised significant funds that will expand the platform's reach.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
39% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Apr 2024
$9m
EARLY VC
Apr 2023
$6m
SERIES A
Total funding: $32.8m
Company benefits
- Significant equity allocations
- Healthcare coverage
- 401(k) plans with an employer match
- Contribution toward student loan repayment
- Flexible vacation/PTO
Company HQ
Union Square, New York, NY
Leadership
Will Sealy
(Co-Founder & CEO)Has held various Washington positions, including White House business council, policy analyst and special assistant to Elizabeth Warren at the US Department of the Treasury. Was also an advisor and student loan policy expert at the Consumer Financial Protection Bureau.
Vincent Tran
(Co-Founder & Advisor)Previously an investment analyst at Loews Corporation, before moving into senior product roles at Orchard Platform and then Pave. Subsequently returned to investment with the Partnership Fund for New York City.
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