Head of Fulfillment Operations – Support

Second Nature

. Own enrollment and fulfillment functions for resident benefit services .

Posted 10/31/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing enrollment and fulfillment functions for resident benefit services, with a strong focus on operational leadership in customer support and BPO operations. Proficient in implementing digital-first self-service solutions and optimizing workflows through automation and AI.

Highest-signal resume keywords

Enrollment AdministrationBPO Operations ManagementDigital-First Self-Service ImplementationWorkforce PlanningVendor Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Claims ProcessingBenefits OperationsBilling OperationsContact Volume ForecastingSLA EnforcementProcess RedesignAutomation WorkflowsAI-Driven WorkflowsData AnalysisUnit Economics

Soft Skills

LeadershipCollaborationCoachingQuality AssuranceCommunication

Tools & Technologies

ZendeskSalesforce Service CloudGorgiasAPIsCRM Ticket Routing Tools

Industry Keywords

B2B2CPropTechMarketplaceSaaSMulti-Site Operations

Tech Stack

Tools & technologies

Cloud

About the role

Key responsibilities & impact

Own enrollment and fulfillment functions for resident benefit services
Own the end-to-end resident and Property Management Company support experience
Ensure accurate and timely resident enrollment, billing charges, benefit fulfillment, and partner data exchange
Operate enrollment workflows using resident data from thousands of property management companies through APIs, flat files, and other channels
Move enrollments to external benefit providers and ensure correct PMC billing
Collaborate with product and engineering teams to redesign and automate enrollment and fulfillment workflows
Own multi-channel phone, chat, and email support for PMC staff and residents
Lead workforce planning, forecasting, and queue/channel architecture for internal and BPO support resources
Manage BPO partner operations, SLA compliance, quality assurance, coaching, volume forecasting, and QBRs
Design and launch segment-specific support models for enterprise, mid-market, and small business accounts
Execute digital-first support through self-service, AI/automation, and chat deflection
Analyze contact drivers and build an automation and deflection roadmap
Maintain quality and accuracy standards for automated and AI-driven workflows
Reduce costs through process redesign, automation, and AI-enabled workflows while protecting CSAT and SLA performance
Optimize unit economics across support channels

Requirements

What you’ll need

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 with strict SLA enforcement
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
Systemic, process-oriented operating approach focused on scalable infrastructure
Availability and engagement during core working hours aligned with the Eastern Time Zone
Quiet, professional, distraction-free work environment
Reliable high-speed internet connection
Legal right to work in the United States after hiring

Benefits

Comp & perks

Medical, Dental, Vision, Life Insurance, & 401K Plan
Open PTO and sick days
Remote work from anywhere in the US
Company reimbursement for bi-annual in-person meeting business travel
Supportive team and training to help grow your career
Opportunity to join a fast-growing startup
Diverse, inclusive culture