Head of Collections

In Person in New York City, NY

About Us

Obligo is a fast-growing FinTech / Real Estate Tech startup on a mission to build trust between renters and landlords worldwide. By leveraging open banking, data, and AI, Obligo eliminates traditional security deposits and replaces them with a fair, flexible, and transparent renter experience while streamlining operations and reducing risk for property managers.

At Obligo, we believe that clear communication, thoughtful user experience, and trust-building design are just as important as strong risk models and technical execution. We build financial products that people can understand, trust, and feel confident using.

The Role

As Head of Collections, you'll lead Obligo's collections function, combining hands-on collections expertise, people leadership, data, and technology to improve recovery performance while delivering a thoughtful renter experience.

About the Position

We are looking for an experienced, analytical, and hands-on collections leader to own and continuously improve Obligo's collections operation. You will manage a team of four collectors as well as external first- and third-party collection resources and AI agents, while serving as Obligo's internal collections subject matter expert.

This role combines day-to-day leadership with strategy and execution. You'll coach the team, handle complex escalations, track and improve performance, develop new collection strategies, and lead projects that make the organization more effective and scalable.

Working in a hybrid model from our NYC office in Union Square two days per week, you'll collaborate closely with Risk, Customer Support, Legal, Product, Data, and other teams across Obligo.

Responsibilities

• Lead, coach, and develop Obligo's internal collections team, setting clear goals and driving individual and team performance.
• Own Obligo's collections strategy, including account segmentation, prioritization, outreach, negotiation, escalation, and resolution strategies. Lead projects and experiments to improve recovery rates, operational efficiency, renter experience, and team productivity.
• Help design and implement the use of AI agents, automation, and other technologies across the collections lifecycle. Develop and maintain collections playbooks, workflows, scripts, training, QA standards, and operating procedures.
• Use data to understand renter behavior, evaluate collection strategies and team performance, and identify opportunities for improvement. Identify recurring issues and emerging trends from collections activity and translate them into broader product, policy, or operational improvements.
• Serve as Obligo's collections subject matter expert and personally handle Tier-3, sensitive, unusual, and high-value collection cases when needed.
• Manage the performance of external first-party and third-party collection partners and determine how work should be allocated across internal, external, and automated resources.
• Partner closely with Support, Risk, Legal, Product, Data, Finance, and Operations on complex cases, new initiatives, product improvements, and collections policies.

Requirements

• 5+ years of relevant experience in collections, customer operations, or a 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, and turning insights into coaching and action.
• Strong analytical skills and comfort working hands-on with dashboards, spreadsheets, BI tools, and operational data to make decisions and measure results.
• Demonstrated ability to improve processes and team productivity, from identifying opportunities 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 the ability to lead and execute in a fast-moving startup environment.
• Nice to Have: Experience in fintech or consumer finance; managing outsourced collection partners; implementing AI or automation in operations; SQL or hands-on BI experience.