Head of Fulfillment Operations & Support

The role

The Head of Fulfillment Operations and Support will own enrollment and fulfillment functions for resident benefit services and manage the end-to-end support experience for residents and Property Management Companies. This role focuses on ensuring accurate, timely enrollment and driving down unit costs through process discipline and automation.

What you will do

• Own processes for resident enrollment, PMC billing, and benefit fulfillment
• Manage data and queues from multiple PMCs to ensure clean enrollments
• Collaborate with product and engineering teams to automate enrollment workflows
• Own multi-channel support for PMC staff and residents
• Lead workforce planning, forecasting, and channel architecture
• Manage day-to-day operations and accountability for BPO partners
• Scope, design, and launch segment specific support models
• Execute a digital-first support strategy using self-service, AI, and automation
• Identify and execute cost-curve reduction through process redesign
• Optimize unit economics across all support channels

Required qualifications

• 5+ years leading high-volume, transaction-driven operations such as claims processing, enrollment administration, or benefits and billing operations
• 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
• Experience implementing digital-first self-service, AI agent workflows, and CRM ticket routing tools
• Advanced analytical capability in workforce planning, unit economics, contact volume forecasting, and vendor scorecards
• Systemic, process-oriented operator
• Available and engaged during core working hours aligned with the Eastern Time Zone
• Quiet, professional, distraction-free environment
• Access to reliable high-speed internet

Benefits

• Medical
• Dental
• Vision
• Life Insurance
• 401K Plan
• Open PTO and sick days
• Reimbursement for business travel to bi-annual in-person meetings

About the company

Second Nature has built a Resident Experience Platform that makes resident onboarding, resident services, and ancillary revenue effortless for property managers. The company consists of 300 people striving to create a Triple Win for residents, property managers, and investors.