Director of People, Summer
$165-185k
+ Equity
Student loan management & repayment platform
Be an early applicant
Student loan management & repayment platform
21-100 employees
Be an early applicant
$165-185k
+ Equity
21-100 employees
Company mission
To act as a “trusted advisor” to student loan borrowers.
Role
Who you are
- 8+ years of progressive HR/People experience, including 3–5 years in a leadership role within a high-growth or scaling organization
- Proven ability to build and lead People programs across talent management, performance, compensation, and employee engagement
- Demonstrated success advising executives and managers on organizational design, workforce planning, and change management
- Experience implementing and optimizing HR systems (HRIS, ATS, payroll) and scalable processes in remote-first or distributed environments
- Strong knowledge of employment law, compliance, and HR best practices across multiple U.S. states
- Track record of developing and managing equitable compensation and total rewards programs
- Ability to analyze people data and leverage insights to inform operations and decision-making
- Excellent communication, facilitation, and relationship-building skills; able to influence across functions with empathy and clarity
- Passion for culture, equity, and employee growth — and for creating workplaces where people can do their best work
- Bachelor’s degree in Human Resources, Business Administration, Organizational Development, or a related field preferred
- SHRM-SCP, SPHR, or similar senior-level HR certification preferred
What the job involves
- As Director of People, you’ll lead the day-to-day operations of Summer’s People function, overseeing the full employee lifecycle from recruitment to retention.
- You’ll design scalable processes and programs that support Summer’s growth, while ensuring our People practices reflect our mission and values
- This is a hands-on leadership role ideal for someone who enjoys balancing strategic thinking with execution, partnering closely with the COO and executive leadership team to build an exceptional employee experience as we scale
- Serve as a trusted advisor to managers and employees on organizational design, team development, and people strategy
- Partner with leadership to develop and implement People strategies that align with company goals, support growth, and strengthen overall organizational effectiveness
- Lead all aspects of the employee lifecycle, including recruitment, onboarding, retention, and workforce development
- Oversee all Talent functions, including recruiting, employer brand, and workforce planning — ensuring Summer attracts and retains top talent to meet business goals
- Build and manage scalable onboarding, performance management, and feedback frameworks — including employee review cycles and career development programs
- Design and implement learning and development initiatives that promote skill growth, leadership readiness, and career mobility
- Oversee compensation benchmarking, benefits administration, and vendor relationships to ensure equity and competitiveness
- Strengthen Summer’s culture through engagement, recognition, and initiatives that foster connection, inclusivity, belonging, and well-being
- Manage HR operations and systems (HRIS, ATS, payroll) while partnering with Finance on headcount planning and budgeting
- Lead all HR compliance and employee relations by ensuring alignment with federal, state, and local employment laws in collaboration with legal counsel and proactively mitigating risk through consistent policies and procedures
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. It’s attracted the attention of a slew of fintech startups and investors looking to build solutions - some of them 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 uses these options to build a personal debt management program for eligible employees - all managed digitally. Not only is this a savvy way for employers to improve benefits packages for top-tier graduates in a hot labor market, it’s also something for which they've recently begun to receive tax incentives.
Summer's seen good sign-up, and has helped tens of thousands of borrowers save millions of dollars. Through a partnership with Credit Karma, the company has also been broadening its service out beyond being a simple employment benefit. It has also raised significant funds towards expanding the reach of the platform.
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
Midtown East, New York, NY
Leadership
Will Sealy
(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
(CPO)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.
Paul Joo
(COO)Consulted with TechnoServe and BCG before working as a law associate at Davis Polk & Wardwell LLP.
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