Chief of Staff

November 25

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Summer

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Fintech • HR Tech • Education

Summer is a company that partners with organizations, including employers, retirement providers, and financial institutions, to offer customized student loan and education assistance benefits. Their solutions aim to improve employee retention by offering savings through loan optimization, forgiveness programs, tax-free contributions, and retirement matching for student loan payments. Summer helps manage the entire process, including participant enrollment and reporting, ensuring efficient delivery of benefits. Their platform is particularly beneficial for HR teams in public sector and government entities, and aims to promote diversity, equity, inclusion, and belonging (DEIB) by supporting a diverse employee base.

11 - 50 employees

💳 Fintech

👥 HR Tech

📚 Education

📋 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.

🎯 Requirements

• 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.

🏖️ Benefits

• 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!