Head of Fulfillment Operations & Support

Second Nature; United States; Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Health insurance

Dental

Vision

Life Insurance

401K Plan

Open PTO

Remote work

Job summary

Second Nature seeks a visionary Head of Fulfillment Operations and Support to own enrollment and fulfillment of resident benefits, including PMC billing. You will run a data-driven, scalable operation across multi-channel support, partner management, and digital-first strategies.

You will lead a remote-first team, partner with product/engineering, and drive cost reductions while preserving service quality and CSAT.

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 within a fast-growing environment.
• Proven track record managing multi-site or nearshore/offshore partners with strict SLA enforcement.
• Experience implementing digital-first self-service, AI agent workflows, and CRM ticket routing tools.
• Advanced analytical capability (workforce planning, unit economics, forecasting) and ability to delineate signal from noise.
• A systemic, process-oriented operator who thrives in unstructured environments and builds scalable infrastructure.

Responsibilities

• Own enrollment management for resident benefits and PMC billing and ensure timely, accurate fulfillment.
• Collaborate with product and engineering to redesign and automate high-latency enrollment workflows.
• Lead multi-channel support (phone, chat, email) with distinct SLAs for B2B and B2C stakeholders.
• Oversee workforce planning, forecasting, and BPO partner management including QBRs.
• Design and launch digital-first support models with AI-driven resolutions and deflection.
• Identify cost-curve reductions through process redesign and automation without sacrificing quality.

Skills

Operations leadership

Vendor management

BPO management

Digital-first support

Data-driven decisions

Tools

Zendesk

Salesforce Service Cloud

Job description

Today, we live in a world where everything has become convenient. Now you can get a ride anywhere, buy anything, answer any question with just a couple clicks on your phone. Convenience isn’t a luxury, it’s an expectation.

So why not renting? It’s still a chore to get utilities set up, buy renters insurance, get air filters changed, handle pest control, and more.

That’s why we’ve 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. That way renting can be easy and rewarding for everyone.

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.

Metrics This Role Is Accountable For

This is an outcome-driven build role. You will directly own and be evaluated on the following core 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 % 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.

Scope & 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, so every resident receives their benefit on time and every PMC is billed correctly.

• Collaborate in lock-step with dedicated internal product and engineering platform teams to identify and exploit opportunities to redesign and automate error-prone, high-latency, labor-intensive enrollment and fulfillment workflows..

Support Operations (B2B2C)

• Own multi-channel support (phone, chat, email) for both client segments: PMC staff/admins (B2B) and residents (B2C), managing distinct SLAs, tones, and workflows for each.

• Lead workforce planning, forecasting, and queue/channel architecture for internal and external support (BPO) resources.

• Manage day-to-day operations and accountability for BPO partners: SLA compliance, quality assurance (QA) scoring, coaching, volume forecasting, and Quarterly Business Reviews (QBRs).

• Scope, design, and launch segment specific support models tailored for enterprise, mid-market, and small business accounts. This is a new motion with no existing playbook to inherit.

Zero-Touch & Digital-First Support

• Formulate and execute a digital-first support strategy (self-service, AI/automation, chat deflection) to resolve routine contacts faster and at higher quality without human intervention.

• Conduct contact-driver analysis to identify candidates for elimination, deflection, and automated resolution; build and manage the rollout roadmap over time.

• Maintain strict quality and accuracy standards for automated and AI-driven workflows to protect CSAT and FCR.

Cost Optimization & Process Engineering

• Identify and execute cost-curve reduction through process redesign, automation, and AI-enabled workflows, without degrading enrollment quality, support CSAT, or SLA performance.

• Optimize unit economics across all support channels.

What Success Looks Like

• 60 Days:

  • Full visibility into enrollment and fulfillment performance, including intake volume by channel, queue aging, error and exception rates, and billing accuracy; top data quality issues by PMC and source documented and ranked; zero degradation in enrollment timeliness or accuracy during onboarding.

  • Full visibility into current BPO performance with live scorecards; Enterprise Support model scoped and documented; zero CSAT/SLA degradation during onboarding.

• 100 Days:

  • Live enrollment and fulfillment dashboards driving daily queue management and accountability; first data quality improvement shipped for the highest-volume exception driver (e.g., intake validation or PMC feedback loop); accuracy and turnaround targets defined and tracked with external benefit providers. End to end roadmaps in place and active for highest leverage opportunities on the pareto.

  • Vendor scorecards actively driving operational accountability; first major cost-curve reduction initiative shipped; Segment specific support models piloted with key segmented accounts; digital-first deflection live for top contact driver.

• 180 Days:

  • Measurable improvement in enrollment accuracy, time to enroll, and billing accuracy; a meaningful share of enrollments processed with no manual touch; exception volume trending down across API and flat file channels; partner data exchange operating to agreed accuracy and timeliness standards.

  • Measurable downward trend in cost per resolution while CSAT/SLA hold or improve; Enterprise Support fully operational; zero-touch channel handling a meaningful share of volume without FCR or accuracy loss.

Qualifications & Experience

• 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. Ability to command 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 (e.g., Zendesk, Salesforce Service Cloud, Gorgias, or similar).

• Advanced analytical capability (workforce planning, unit economics, contact volume forecasting, and vendor scorecards). Strong intellectual wherewithal and ability to delineate signal v. noise

• A systemic, process-oriented operator who thrives in unstructured environments and prefers building scalable infrastructure over manual workarounds. High say:do ratio.

REMOTE WORK STATEMENT

This position is a remote-first, work-from-home position. Second Nature is committed to creating a culture and workplace where remote work fosters collaboration and connections and is a vital part of our company story and success. To be successful in a remote work role at Second Nature, you must:

• 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)

Why Second Nature?

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

We get it. Requirements can sometimes hold people back from applying to a job, but don’t let that be the case here. If you believe you have the skills it takes to elevate this role, team, and company, we encourage you to apply for this role.

Second Nature is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. We take action to ensure equal employment opportunities for all candidates and employees and to provide employees with a workplace free of discrimination and harassment. Our hiring decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, family or parental status, or any other status protected by federal and/or state law.