Senior Director, Support Operations

About the Opportunity

The company is a technology organization that administers Smart Benefits to connect people to products and services they need, when they need them, so they can live healthier lives. The organization partners with payers and retailers to deliver expansive benefits for things like healthy foods, OTC medications, or transportation. The company is reinventing benefits administration so that everyone benefits with more value for each and better outcomes for all. The organization is a Series B stage company, backed by leading investors.

Role at a Glance

Reporting to the COO, this senior leadership role oversees Customer Care, Customer Success, and Print/Ship Operations, ensuring an exceptional end-to-end member and client experience. The position is responsible for scaling operations, managing service quality, fulfillment, vendor strategy, technology, budgets, and operational efficiency. The role also partners with cross-functional teams and represents these functions in executive client meetings and business development efforts.

What You Will Do

• Setting strategy and leading the Support Operations Organization

• Defining the multi-year operating model across Care, Customer Success, and Print/Ship Operations: the channel strategy, the vendor footprint, the technology stack, and the quality framework, and translating it into a quarterly roadmap with clear owners, milestones, and success metrics

• Building and leading a team of managers across the three functions: hiring, developing, and holding the bar for a leadership bench that scales with the business

• Owning the operating budget and unit economics across human handling, vendor spend, and fulfillment cost-to-serve, modeling where to invest, where to consolidate vendors, and where to renegotiate

• Serving as the executive operational voice for Support Operations: representing the function in ELT reviews, board materials, client QBRs, and new business pursuits

• Running the Care Function

• Owning service levels across phone, email, and chat: response time, resolution time, first-contact resolution, and CSAT against forecasted volume and seasonal patterns

• Directing the workforce model: staffing, scheduling, intraday operating standards, and the cross-channel playbook for peak events, launches, and recovery scenarios

• Establishing the quality program: calibration cadence, coaching frameworks, and the link between QA outcomes and reinforcement learning for agents

• Owning the Care knowledge architecture and the tooling that lets agents resolve issues at first contact

• Leading Customer Success

• Driving retention for the existing book of health plan and retail partner clients

• Defining the health-scoring framework, EBR cadence, and the early-warning system for at-risk accounts, with a clear escalation path into the exec team

• Partnering with Commercial on expansion opportunities and with Product on what each client needs from the roadmap

• Owning Print/Ship Operations and the Fulfillment Supply Chain

• Driving throughput, on-time ship rate, and defect rate across all printed and shipped materials: cards, kits, and member communications

• Setting the vendor strategy for print, mail, and fulfillment partners: selection, scope allocation, commercial terms, SLAs, and the periodic RFPs and renewals that follow

• Owning the cost per unit and the operating budget for fulfillment, and the capacity model tied to client launches and seasonal volume

• Personally owning the most senior fulfillment vendor relationships at the principal or VP level

• Driving the Data, Technology, and Integration Agenda

• Defining the metrics that matter across all three functions: service levels, NRR, fulfillment SLAs, cost-to-serve and ensuring the analytics function produces a defensible, accurate narrative for every audience

• Owning the technology roadmap for Support Operations: contact center platforms, CRM, WFM tooling, knowledge platforms, and fulfillment systems, and partnering with IT, Engineering, and Product on selection, implementation, and continuous improvement

• Designing the handoffs between Care, Customer Success, and Print/Ship Operations so the member and the client experience is cohesive, not three disconnected teams

• Serving as a credible, senior operational presence for health plan and retail clients: leading client-facing performance conversations, contributing to large new client onboardings, and acting as the executive escalation point for operational issues

About You

• 10+ years of experience in operations, customer success, or service delivery leadership, including 5+ years leading multiple functions or a function with 50+ people, with demonstrated experience managing managers and building a multi-layer team

• Proven track record of running a contact center or high-volume service operation against SLAs in a regulated or compliance-heavy environment

• Direct experience owning a P&L or a multi-million-dollar operating budget, including the unit economics and the trade-offs across human handling, vendor spend, and technology

• Vendor management experience at scale: selecting, contracting, holding vendors accountable, and personally owning the most senior relationships

• Customer Success leadership experience in a B2B2C model where the buyer (health plan or retail partner) and the end user (member) are different people

• Prior ownership of a physical fulfillment, print, or mail operation, or demonstrated ability to learn the supply chain quickly

• A track record of building and scaling operations in healthcare, Medicare Advantage, Medicaid, benefits administration, or another regulated industry where PHI handling, member communication, and audit requirements are non-negotiable

• Demonstrated experience setting and executing an operating strategy: defining the model, building the roadmap, owning the budget, and reporting on results to executive and board audiences

• Strong analytics orientation: you build the dashboard yourself before you ask someone else to, and you know your numbers cold

• A senior operator who can move fluently between altitude and execution: board-ready strategy on Tuesday, a vendor escalation on Wednesday, a service-level review on Thursday, and brings the same rigor and care to all three

• A systems thinker who connects dots across operations, quality, technology, and finance: you build the case for change with data, sequence the work realistically, and drive sustainable improvements rather than one-time fixes

• Strong written and verbal communication skills: you can write a board-ready operating review, run a tense vendor governance meeting, walk a health plan client through a service issue, and translate operational tradeoffs into clear business language

• A clear passion for, if not direct experience in, addressing health inequities: you understand that benefits access is a health equity issue and that the work you do leading Support Operations has a direct impact on real people’s lives

• A leader of leaders who invests in the people around them, hires and coaches with the same standards they expect of others, and holds the bar for the function

Additional Information

• Travel may be required from time to time as part of the role, for company events and business needs

• The organization is a remote-first, distributed workforce. Candidates should be comfortable with, and equipped to work within, a distributed remote team, including having reliable internet access and basic home office equipment

• The company will provide a work laptop, and mouse/keyboard upon request

Legal Authorization

Legal authorization to work in the US is required. At this time, the organization will not consider candidates who need sponsorship, now or in the future

What We Offer

• Competitive base salary ranging from $212,108 to $221,760, discretionary bonus, and equity; depending on experience/qualifications

• Benefits:

  • Medical, Dental, and Vision insurance with 90% paid employer premium contributions for all tiers

  • 100% Employer Paid Short-Term & Long-Term Disability

  • 100% Employer Paid Basic Life Insurance Policy

  • Employee Assistance Program (EAP)

  • 401(k) Program

  • Discretionary PTO

  • Paid holidays

  • Parental Leave

  • Flexible work schedule within core hours

  • Work anywhere in the USA as the organization is a fully distributed team from coast to coast