Head of Fulfillment Operations & Support - Second Nature

Second Nature has 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.

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.

Core Accountabilities & 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 percentage 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.

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 on time while ensuring correct billing.
• Collaborate closely with product and engineering teams to automate error-prone, high-latency, labor-intensive workflows.

Support Operations (B2B2C)

• Own multi-channel support (phone, chat, email) for both PMC staff/admins (B2B) and residents (B2C), managing distinct SLAs, tones, and workflows.
• Lead workforce planning, forecasting, and channel architecture for internal and BPO support resources.
• Manage day-to-day operations and accountability for BPO partners (SLA compliance, QA scoring, coaching, forecasting, and QBRs).
• Scope, design, and launch segment-specific support models tailored for enterprise, mid-market, and small business accounts.

Zero-Touch & Digital-First Support

• Formulate and execute a digital-first support strategy (self-service, AI/automation, chat deflection) to resolve routine contacts faster.
• Conduct contact-driver analysis to identify candidates for elimination, deflection, and automated resolution.
• Maintain strict quality and accuracy standards for automated and AI-driven workflows.

Cost Optimization & Process Engineering

• Identify and execute cost-curve reduction through process redesign, automation, and AI-enabled workflows without degrading CSAT or SLAs.
• Optimize unit economics across all support channels.

60 / 100 / 180 Day Success Milestones

• 60 Days: Establish full visibility into enrollment/fulfillment performance and BPO scorecards; document top data quality issues by PMC; scope Enterprise Support model with zero CSAT/SLA degradation.
• 100 Days: Operationalize live queue management dashboards; ship first data quality improvement for top exception driver; pilot segment-specific support models and launch digital-first deflection for top contact driver.
• 180 Days: Achieve measurable improvements in enrollment accuracy and turnaround time; reduce cost per resolution while maintaining or improving CSAT/SLA; fully operationalize Enterprise Support and zero-touch volume deflection.

Qualifications & Experience

• 5+ years leading high-volume, transaction-driven operations (claims processing, enrollment administration, or benefits/billing operations) where accuracy, queue management, and data quality determine outcomes.
• 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).
• Advanced analytical capabilities in workforce planning, unit economics, contact volume forecasting, and vendor scorecards.
• A systemic, process-oriented operator comfortable building scalable infrastructure in unstructured environments.

Remote Work Requirements

• Available and engaged during core working hours aligned with the US Eastern Time Zone.
• Distraction-free home workspace with reliable high-speed internet.
• Willingness to attend bi-annual in-person company meetings (travel expenses reimbursed).

Benefits & Perks

• Comprehensive health coverage: Medical, Dental, Vision, Life Insurance, and 401(k) plan.
• Open PTO and sick leave policy.
• Fully remote workplace within the US.
• Career growth and training support in a fast-scaling startup culture.