Chief of Staff

Summer

Remote regions

US

Benefits

Unlimited PTO

Job Description

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.

About Summer

Summer is a Certified B Corp® on a mission to restore financial freedom for the 46 million Americans burdened by student debt.

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