[Hiring] Head of Fulfillment Operations & Support @Second Nature

Role Description

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.

Metrics This Role Is Accountable For:

• 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.

Qualifications

• 5+ years leading high-volume, transaction-driven operations such as claims processing, enrollment administration, or benefits and billing operations, where accuracy, queue management, and data quality across multiple intake channels determine the outcome.
• 7+ years of progressive operational leadership in customer support, vendor management, or BPO operations within a fast-growing B2B2C, PropTech, Marketplace, or SaaS environment.
• Proven track record managing multi-site or nearshore/offshore BPO partners and third-party fulfillment vendors with strict SLA enforcement.
• Demonstrated experience implementing digital-first self-service, AI agent workflows, and CRM ticket routing tools (e.g., Zendesk, Salesforce Service Cloud, Gorgias, or similar).
• Advanced analytical capability (workforce planning, unit economics, contact volume forecasting, and vendor scorecards).
• A systemic, process-oriented operator who thrives in unstructured environments and prefers building scalable infrastructure over manual workarounds.

Requirements

• Be available and engaged during core working hours aligned with the Eastern Time Zone to ensure effective collaboration and timely completion of responsibilities.
• Have a quiet, professional, distraction-free environment in which to complete your work.
• Have access to your own reliable high-speed internet connection.
• Attend our bi-annual in-person company meetings (Second Nature will reimburse the cost of your business travel per company guidelines).

Benefits

• Health First: Medical, Dental, Vision, Life Insurance, & 401K Plan.
• Location: Work remotely from anywhere in the US.
• Flexibility: Open PTO and sick days.
• The Product: Beyond the awards and 5-star reviews, our clients and customers love what they can do with a fully managed RBP.
• Diverse, Inclusive Culture: We embrace employees from all backgrounds with openness and respect.
• Training: A supportive team to help you grow your career and unlock your full potential.
• Growth: The opportunity to get in on the ground floor of a fast-growing startup that’s designing and developing an exciting category.