Head of Fulfillment Operations & Support

Second Nature

6d•Remote

About The Position

The Head of Fulfillment Operations & Support owns enrollment and fulfillment for Second Nature’s resident benefit services, along with the end-to-end support experience for residents and Property Management Company (PMC) clients. The role is accountable for accurate, timely enrollment and fulfillment, high-quality support, and reducing unit cost to serve without sacrificing customer satisfaction or service-level performance. It is a builder’s role focused on establishing repeatable operations through process discipline, vendor accountability, and scalable systems. Leveling as Director or VP will depend on candidate qualifications, executive leadership track record, and scope of experience. The role leads a data- and queue-intensive operation that processes variable-quality resident data from thousands of PMCs across channels such as APIs and flat files. It owns enrollment, PMC billing, benefit-provider data exchange, and fulfillment outcomes, and partners closely with product and engineering teams to redesign and automate workflows. It also leads multi-channel support for PMC staff and residents, including workforce planning, internal and BPO operations, segment-specific support models, and digital-first self-service, AI, and automation initiatives. This is a remote-first, work-from-home position. The employee must be available during core hours aligned with the Eastern Time Zone, have a quiet professional workspace and reliable high-speed internet, and attend bi-annual in-person company meetings. Business travel for those meetings is reimbursed according to company guidelines.

Requirements

At least 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 are critical.
At least 7 years of progressive operational leadership in customer support, vendor management, or BPO operations within a fast-growing B2B2C, PropTech, marketplace, or SaaS environment.
Ability to lead a broad span of control and work.
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 such as Zendesk, Salesforce Service Cloud, Gorgias, or similar.
Advanced analytical capability in workforce planning, unit economics, contact-volume forecasting, and vendor scorecards.
Strong ability to distinguish signal from noise.
Systemic, process-oriented operating approach and ability to thrive in unstructured environments while building scalable infrastructure rather than relying on manual workarounds.
Availability and engagement during core working hours aligned with the Eastern Time Zone.
Quiet, professional, distraction-free work environment and reliable high-speed internet access.
Ability to attend bi-annual in-person company meetings.

Responsibilities

Own accurate and timely resident enrollment, PMC billing, and benefit fulfillment processes and outcomes.
Manage the operation that converts resident data from thousands of PMCs, received through APIs, flat files, and other channels, into accurate enrollments.
Move enrollments to external benefit providers and ensure residents receive benefits on time and PMCs are billed correctly.
Partner with internal product and engineering teams to redesign and automate error-prone, high-latency, and labor-intensive enrollment and fulfillment workflows.
Own multi-channel phone, chat, and email support for PMC staff and residents, with distinct service levels, tones, and workflows for each audience.
Lead workforce planning, forecasting, and queue and channel architecture for internal and BPO support resources.
Manage BPO partners’ day-to-day performance and accountability, including SLA compliance, QA scoring, coaching, volume forecasting, and Quarterly Business Reviews.
Design and launch segment-specific support models for enterprise, mid-market, and small business accounts.
Develop and execute a digital-first support strategy using self-service, AI, automation, and chat deflection to resolve routine contacts effectively without human intervention.
Analyze contact drivers, identify opportunities to eliminate, deflect, or automate contacts, and manage the rollout roadmap.
Maintain quality and accuracy standards for automated and AI-driven workflows to protect CSAT and first-contact resolution.
Reduce costs through process redesign, automation, and AI-enabled workflows without degrading enrollment quality, support CSAT, or SLA performance.
Optimize unit economics across support channels.
Track and improve enrollment and fulfillment speed and quality, issue resolution time, first-contact resolution, fulfillment and support costs per enrollment, and resident and PMC satisfaction.
Establish operational visibility through dashboards, scorecards, queue management, data-quality improvements, and partner performance standards.