Chief of Staff

Who We Are Summer is a Certified B Corp® on a mission to restore financial freedom for the 46 million Americans burdened by student debt. We combine deep policy expertise with powerful technology to simplify every step of college cost planning and loan repayment. We have helped people save an average of $278 per month and more than $1.8 billion in total savings to date. By partnering with leading employers, cities, and financial institutions, including ADP, the City of New York, Banc of California, Norton Healthcare, and the American Federation of Teachers, Summer helps millions of Americans move closer to a debt-free future. Backed by $30 million in funding from top investors including Rebalance Capital, SemperVirens, QED Investors, General Catalyst, and Flourish Ventures, we’re building the infrastructure that powers student loan relief and education affordability in America. Your Role 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. 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. What You’ll Do 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. You Might Be a Fit If You Have 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. The Details Compensation: Base salary + equity + comprehensive benefits Work Setup: Remote (U.S.) Status: Full-time Work Environment Summer is a remote-first company with team members across the U.S. We collaborate asynchronously and meet virtually each week, with in-person gatherings for key moments during the year. Why Join Summer Summer is on a mission to help borrowers navigate and eliminate student debt. We partner with financial institutions, employers, and government agencies to provide digital tools that simplify the loan experience for millions of borrowers. We’re a mission-driven team that believes in solving real problems with real empathy. We care deeply about our users and each other. If you’re excited about building technology that changes lives, we’d love to meet you. How We Support You Equity grant to share in Summer’s success 100% employee-covered medical, dental, and vision insurance 401(k) plan with 3% match, fully vested day one Home office setup reimbursement Monthly lunch credits Direct contributions toward your student loans Up to 11 paid holidays + flexible PTO Paid leave for family, health, or personal needs Annual in-person events including Summer Camp and Summer Wonderland And more! Equal Opportunity Summer provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination or harassment of any kind. This policy applies to all employment terms and conditions, including recruiting, hiring, promotion, termination, compensation, and training.