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Salary: USD 140,000 - 160,000 / annual
Obligo is a fast-growing fintech and real estate tech startup building trust between renters and landlords by eliminating traditional security deposits through open banking, data, and AI. The company replaces deposits with a fair, flexible, and transparent renter experience while streamlining operations and reducing risk for property managers.
As Head of Collections, you will lead Obligo's collections function, combining hands-on expertise, people leadership, data, and technology to improve recovery performance while maintaining a thoughtful renter experience. You will manage a team of four collectors, oversee external first- and third-party collection resources and AI agents, and serve as the organization's internal collections subject matter expert.
The role blends day-to-day team leadership with strategic execution. You will coach and develop your team, handle complex escalations, track and improve performance metrics, develop new collection strategies, and lead projects that enhance organizational effectiveness and scalability. You'll work in a hybrid model from the NYC office in Union Square (two days per week) and collaborate closely with Risk, Customer Support, Legal, Product, Data, and other cross-functional teams.
Key responsibilities include: leading and developing the internal collections team with clear goal-setting and performance management; owning collections strategy including account segmentation, prioritization, outreach, negotiation, and resolution approaches; designing and implementing AI agents, automation, and technologies across the collections lifecycle; developing playbooks, workflows, scripts, training, QA standards, and operating procedures; using data to understand renter behavior and identify improvement opportunities; personally handling Tier-3, sensitive, unusual, and high-value cases; managing external collection partners and allocating work across internal, external, and automated resources; and partnering with support, risk, legal, product, data, finance, and operations teams on complex cases and policy improvements.
REQUIREMENTS:
- 5+ years of relevant experience in collections, customer operations, or similar operational environment, including 3+ years managing a team
- Strong track record of data-led performance management: setting targets, identifying performance gaps and root causes, translating insights into coaching and action
- Strong analytical skills and comfort working hands-on with dashboards, spreadsheets, BI tools, and operational data
- Demonstrated ability to improve processes and team productivity from identification through implementation and measurement
- Experienced people manager who can set clear expectations, coach and develop employees, and address underperformance
- Meaningful collections expertise including collection strategy, negotiation, escalations, and customer communication
- Self-motivated and adaptable with strong judgment and ability to lead and execute in a fast-moving startup environment
Nice to have: fintech or consumer finance experience; managing outsourced collection partners; implementing AI or automation in operations; SQL or hands-on BI experience.
