Summer

Build and optimize revenue processes, systems, and data infrastructure to support scalable growth across marketing, sales, and customer success. | 7-10 years in Revenue or Sales Operations within SaaS or tech, with deep HubSpot CRM expertise, and proven success in scaling revenue processes. | 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 Director of Revenue Operations will serve as the operational backbone of Summer’s go-to-market team, responsible for building the systems, processes, and data infrastructure that support scalable, predictable revenue growth. This role owns how revenue works at Summer, across marketing, sales, and client success, by translating company goals into clear operating models, rigorous forecasting, and actionable insights. You will partner closely with executive leadership and GTM leaders to ensure alignment, accountability, and visibility from first touch through renewal and expansion. This is a hands-on role for a strategic operator who thrives in ambiguity, brings structure to complex environments, and uses data to drive clarity and decision-making. What You’ll Do Develop and own a unified revenue operations strategy aligned with company goals, in partnership with executive leadership and GTM leaders. Design, implement, and continuously improve end-to-end revenue processes, including lead management, funnel stages, handoffs, renewals, and expansion across marketing, sales, and client success. Build and manage a rigorous forecasting, pipeline management, and performance reporting framework to support executive and board-level decision-making. Define, track, and operationalize key revenue KPIs across the funnel (e.g., conversion rates, velocity, CAC, LTV, retention, expansion), translating insights into clear recommendations and action plans. Own GTM systems and data strategy (including HubSpot CRM and related tools), ensuring data integrity, seamless integrations, and effective usage across teams from prospect through launch. Partner with GTM leaders on territory design, quota setting, routing rules, and coverage models to support scalable and efficient growth. Serve as a cross-functional partner to Sales, Marketing, Client Success, Product, Finance, and People to ensure alignment on revenue processes, metrics, and incentives. Build and maintain scalable enablement processes and documentation (playbooks, SOPs, training materials) that equip sales, marketing, and client success teams with the knowledge, tools, and best practices needed to execute consistently and effectively. Support executive and board reporting with clear, accurate, and timely revenue insights that highlight risks, opportunities, and progress against goals. Identify bottlenecks and friction in the revenue funnel and drive cross‑functional initiatives to improve efficiency, productivity, and customer experience. You Might Be a Fit If You Have 7-10 years in Revenue Operations, Sales Operations, or a related role within B2B SaaS or technology-driven companies. Proven experience operating in a scaling startup environment (Series B or similar growth stage). Deep hands-on expertise with Hubspot CRM, including reporting, automation, and system integrations. Strong analytical skill set with the ability to turn data into clear insights and actionable recommendations. Demonstrated success partnering with senior leaders and supporting executive- and board-level reporting. Track record of designing and implementing scalable revenue processes across sales, marketing, and customer success. Exceptional cross-functional communication, stakeholder management, and change leadership skills. Comfort operating with ambiguity, working autonomously from strategic goals, and driving continuous improvement. The Details Compensation: $170-190k base + 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.

Lead company-wide financial planning, reporting, and controls to support growth and strategic decision-making. | Over 8 years of progressive finance experience, strong financial modeling skills, experience with GAAP and SaaS revenue recognition, and managing external accounting partners. | 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 Summer is hiring a Director of Finance to lead the financial backbone of the business and play a meaningful role in shaping Summer’s growth. This role reports directly into the COO and partners closely with Summer’s leadership team owning financial execution, forecasting, and reporting, while also supporting the executive team on board, investor, and long-term strategic initiatives. This role blends hands-on ownership with strategic influence. The Director of Finance will professionalize financial operations, strengthen controls, and build scalable reporting and forecasting infrastructure while helping leadership evaluate tradeoffs, prioritize investments, and prepare the organization for its next phase of growth. What You’ll Do Lead company-wide FP&A, including budgeting, forecasting, variance analysis, and scenario modeling to support growth and resource planning. Partner closely with the executive team as the day-to-day finance lead, translating strategy into clear financial plans and decision-ready insights. Build and own financial models and reporting that inform executive decisions, product investment, organizational tradeoffs and as needed fundraising scenarios. Own day-to-day financial operations, including A/P, A/R, employee reimbursements, corporate cards, cash movement, and monthly close. Prepare monthly financial reporting for the executive team and support quarterly board and investor reporting. Strengthen financial controls and approval workflows across contracts, spend, and payments, serving as the internal point of accountability. Manage and hold accountable external partners (controller, bookkeepers, tax advisors), providing direction and pushing back when needed. Develop team-, product-, and revenue-level reporting to improve visibility into performance, unit economics, cost of sales, and sales efficiency. You Might Be a Fit If You Have 8+ years of progressive finance experience, including FP&A, forecasting, and operational finance. Bachelor’s degree in Finance, Accounting, Economics, Business, or a related field (or equivalent practical experience), Master’s degree in related field preferred. Experience in a VC-backed SaaS, fintech, benefits, or GovTech company, ideally including at least one scaled startup (100–1000 employees). Strong financial modeling skills and the ability to translate complex data into clear insights for executives. Hands-on experience managing accounting operations and external partners (controller, auditors, tax providers). Solid understanding of GAAP, with hands-on experience supporting revenue recognition in a SaaS or recurring-revenue business (ASC 606 familiarity strongly preferred). A builder mindset; comfortable creating structure, improving processes, and operating in ambiguity. Strong judgment and communication skills, with the ability to present financial insights clearly to executive and non-finance stakeholders. Prior background in consulting, venture capital, investment banking, or large enterprise finance before moving into startups is a plus. CPA a plus, not required The Details Compensation: $160-190k base + 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.