Head of Fulfillment Operations & Support

Today, we live in a world where everything has become convenient. Now you can get a ride anywhere, buy anything, answer any question with just a couple clicks on your phone. Convenience isn’t a luxury, it’s an expectation. So why not renting? It’s still a chore to get utilities set up, buy renters insurance, get air filters changed, handle pest control, and more. That’s why we’ve built the world’s first Resident Experience Platform that makes resident onboarding, resident services, and ancillary revenue effortless for property managers. We’re passionate about turning friction into triple win experiences for residents, property managers, and investors. That way renting can be easy and rewarding for everyone. And now you can join us. Apply today to join 300 passionate, creative people who strive to make a difference each day so residents, property managers, and investors all win; creating the ultimate Triple Win. ROLE OVERVIEW The Head of Fulfillment Operations and Support will own the enrollment and fulfillment functions for Second Nature’s resident benefit services, as well as the end-to-end resident and Property Management Company (PMC) support experience. The core mission: ensure accurate and timely resident enrollment and fulfillment, while continuously elevating service quality and driving down unit cost to serve. This is a builder’s role, not a caretaker’s. The ideal leader is an operator at the core and deeply service-oriented. They recognize that high-quality service at scale isn't only delivered through hustle. It's delivered through control: process discipline, vendor accountability, and systems that make flawless fulfillment and excellent service repeatable rather than heroic. Note: Leveling (Director vs. VP) will be determined based on candidate qualifications, executive leadership track record, and scope of experience. METRICS THIS ROLE IS ACCOUNTABLE FOR This is an outcome-driven build role. You will directly own and be evaluated on the following core metrics: - Enrollment and Fulfillment Speed & Quality: High-accuracy thresholds for timely resident benefit enrollments, billing charges, benefit fulfillment, and partner data exchange management. - Speed of Resolution & First Contact Resolution (FCR): Mean time to resolve (MTTR) and % of issues closed on first contact across BPO and internal support channels. - Fulfillment Cost per New Enrollment & Support Cost per Active Enrollment: Unit cost to enroll residents and resolve support issues across all channels, driven downward without sacrificing customer quality, CSAT or SLA performance. - Resident & PMC CSAT: Resident-side satisfaction and likelihood-to-recommend, tracked distinctly from PMC-side satisfaction given the two-audience model. SCOPE & RESPONSIBILITIES ENROLLMENT MANAGEMENT - Own the processes and outcomes for accurate, timely resident enrollment, accurate PMC billing, and error-free benefit fulfillment. Run the data- and queue-intensive operation that turns variable-quality resident data from thousands of PMCs (API, flat file, and more) into clean enrollments. - Serve as the operational engine that moves enrollments to external benefit providers, so every resident receives their benefit on time and every PMC is billed correctly. - Collaborate in lock-step with dedicated internal product and engineering platform teams to identify and exploit opportunities to redesign and automate error-prone, high-latency, labor-intensive enrollment and fulfillment workflows.. SUPPORT OPERATIONS (B2B2C) - Own multi-channel support (phone, chat, email) for both client segments: PMC staff/admins (B2B) and residents (B2C), managing distinct SLAs, tones, and workflows for each. - Lead workforce planning, forecasting, and queue/channel arc