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Senior Director, Support Operations
evermore · Remote
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Senior Director, Support Operations
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About evermore
evermore is a technology company that administers Smart Benefits to connect people to products and services they need, when they need them, so they can live healthier lives. We partner with payers and retailers to deliver expansive benefits for things like healthy foods, OTC medications, or transportation. evermore is reinventing benefits administration so that everyone benefits with more value for each and better outcomes for all. evermore is a Series B stage company, backed by leading investors including General Catalyst, Define Ventures, Lightspeed Venture Partners, Pinegrove Capital Partners, and Qiming Venture Partners.
The Job at a Glance
Reporting to the COO, you will own the end-to-end member and customer experience across three connected functions at evermore: the Care team (frontline member support across phone, chat, and email), Customer Success (client retention, expansion, and the executive relationship with each health plan and retail partner), and Print/Ship Operations (the fulfillment engine that gets physical materials: cards, kits, and member communications to the right member at the right time. This is a senior leadership role with full accountability for service quality, operational throughput, and the unit economics of delivery.
What makes this role distinct is its breadth. You will own how the member-facing operation scales: the workforce model, the vendor strategy, the technology stack, the client-facing motion, and the fulfillment supply chain, and you will build the team that runs each of those pillars day to day. You will set the multi-year roadmap, own the operating budget and unit economics, and represent these functions in client QBRs, executive reviews, and new business pursuits. You will partner closely with peers across Product, Engineering, Implementation, Finance, Commercial, and People.
The right person for this role is a seasoned operations leader who has run a multi-function service organization at scale: contact center, customer success, and physical fulfillment in a regulated, B2B2C environment where service quality, compliance, and unit economics all have to hold at the same time.
What You Will Do
Working within an organization created at the intersection of health care, retail and financial technology, no two days will look the same. Typical responsibilities of the role include:
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
While every candidate brings a unique resume and prospective, an ideal candidate will include:
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
Commitment to building a psychologically safe environment and diverse culture that is highly collaborative, strives to set and achieve goals together, and embraces transparency, innovation, and accountability
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
Other Requirements
Travel may be required from time to time as part of the role, for company events and business needs
evermore 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. evermore will provide a work laptop, and mouse/keyboard upon request
Legal authorization to work in the US is required. At this time, evermore will not consider candidates who need sponsorship, now or in the future
All offers for employment are contingent upon successful completion of a background check
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 we are a fully distributed team from coast to coast
evermore is not currently offering visa sponsorship for this position. Candidates must be legally authorized to work in the United states at the time of application and maintain work authorization throughout employment.
evermore is an equal opportunity employer, Minority/Female/Disability/Veteran/LGBTQIA+ – proudly embracing diversity in all its manifestations. Applicants requiring reasonable accommodation for the application and/or interview process should notify a representative of the People Operations Team via careers@evermoreoutcomes.com.
evermore participates in E-Verify, the federal program for electronic verification of employment eligibility.
To all recruitment agencies: evermore does not accept agency resumes, please do not forward them to any evermore employees.
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evermore is committed to providing Equal Employment Opportunities. We would appreciate it if you could answer the following questions, although it is not required. Please note that this information will not be used to make employment decisions and will only be utilized in compliance with federal and state regulations. We request this information to assess the effectiveness of our outreach and adjust our recruitment efforts to ensure that we reach all communities in the US.
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Listed by evermore for a position based in the United States. Employers on this board attest they are hiring domestically.
Senior Manager, Care Operations
evermore · Remote
Pay
Not listed
Setting
Remote
Senior Manager, Care Operations
Remote
Apply
About evermore
evermore is a technology company that administers Smart Benefits to connect people to products and services they need, when they need them, so they can live healthier lives. We partner with payers and retailers to deliver expansive benefits for things like healthy foods, OTC medications, or transportation. evermore is reinventing benefits administration so that everyone benefits with more value for each and better outcomes for all. evermore is a Series B stage company, backed by leading investors including General Catalyst, Define Ventures, Lightspeed Venture Partners, Pinegrove Capital Partners, and Qiming Venture Partners.
The Job at a Glance
Reporting to the Sr. Director, Member Operations, you will help operate and continuously improve the operating model for evermore’s Customer Care function. This is a hands-on build , and uniquely modern operations role: you will help design, deploy, and continuously improve the agentic Care system: voice and chat AI agents, agent-assist for human reps, automated knowledge retrieval, and AI-driven QA, alongside the human workforce that handles what AI cannot.
What makes this role distinct is its breadth. You will help drive how Care scales, contributing across the vendor strategy, the AI agent stack, the workforce model across humans and agents, the technology infrastructure, the learning system, and the analytics layer. You will help shape the annual roadmap for Care, including deflection and automation targets, the AI safety and compliance posture, and the cost-to-serve trajectory. You will support budget planning and unit economics, and contribute to client QBRs and operating reviews. You will partner closely with peers across Operations, Implementation, Finance, Product, Strategy and Solution Development, Marketing, Engineering, and Account Management, and especially closely with AI/ML and Product on the agentic Care roadmap.
The right person for this role is a Care operator who has worked inside a multi-vendor contact center AND has built or operated production AI agents in a customer support setting: someone who can move fluently between operations, regulated-environment requirements, and the technical realities of deploying LLM-based systems against real members.
What You'll Do
Working within an organization created at the intersection of health care, retail, and financial technology, and at a moment when AI is reshaping what Care can look like, no two days will look the same. Typical responsibilities of the role include:
Driving Care Operations Programs
Helping shape the Care operating model, the mix of internal teams, BPO partners, and AI agents; the channel strategy; the technology stack; and the quality framework, and translating it into a quarterly roadmap with clear owners, milestones, and success metrics.
Leading cross-functional program teams across operations, AI / agentic Care, training and knowledge, and quality, partnering with team leads, coaching individual contributors, and holding the bar on execution
Modeling Care unit economics: cost-to-serve across human and AI handling, programs, and channels, and recommending where to deploy AI, where to keep humans, where to consolidate vendors, and where to renegotiate
Serving as an operational voice for Care, contributing to internal operating reviews, client QBRs, and new business pursuits, including the AI Care agenda
Designing and Operating the Agentic Care System
Owning the AI agent roadmap for Care: voice and chat agents for member and caregiver self-service, agent-assist copilots for human reps, automated triage and routing, AI-driven knowledge retrieval, and AI-led QA , and partnering with Product and Engineering on what to build vs. buy
Defining the human + AI operating model: what gets routed to an AI agent, what escalates to a human, how handoffs happen, how AI agent capacity and confidence thresholds are managed alongside human workforce planning, and how the experience stays cohesive to the member
Establishing the evaluation and quality framework for AI agents: offline eval sets, online metrics, red-teaming, human review sampling, and the calibration cadence between AI QA and human QA so the bar is the same regardless of who (or what) handled the contact
Owning the safety, compliance, and policy posture for agentic Care, including the guardrails, escalation triggers, audit logging, and PHI handling required to operate AI agents inside CMS-regulated programs such as Medicare Advantage and Medicaid
Leading the change management for AI in Care: how human agents are trained to work alongside AI, how their roles and incentives evolve as automation scales, and how the vendor partnerships are restructured as the human/AI mix shifts
Driving the AI agent improvement loop: pulling failure cases out of production, partnering with AI/ML and Product on prompt, policy, retrieval, and model updates, and shipping measurable quality gains release over release
Owning the Vendor Strategy and Human Workforce Performance
Setting the vendor strategy: partner selection, scope allocation, geographic mix, and commercial terms, and leading periodic RFPs, contract renewals, and SOW negotiations with BPO partners as their scope evolves alongside AI deflection
Establishing the performance framework across ACT, Startek, and other partners: SLAs, scorecards, governance cadence, and escalation paths, and owning day-to-day vendor relationships at the operations and director level
Directing Workforce Management strategy across humans and AI agents: joint forecasting and capacity planning, intraday operating standards, AI fallback plans, and the cross-channel playbook for peak events, launches, and recovery scenarios
Leading the most complex operational initiatives: platform migrations, AI agent rollouts, large new client launches, market entries, and turnaround plans, and owning the cross-functional execution with Product, Implementation, Engineering, and Customer Success
Building the Learning, Knowledge, and Quality System for a Hybrid Workforce
Setting the strategy for how Care builds capability across humans AND AI agents: the onboarding model, the ongoing development curriculum, and the certification standards that govern who (or what) is qualified to handle each program and channel
Owning the Care knowledge architecture: recognizing that the knowledge base is now both human-facing documentation and the retrieval source for AI agents, and ensuring content governance, structure, and freshness meet the bar for both audiences
Defining the unified quality program: calibration cadence, coaching frameworks, and the link between QA outcomes and reinforcement learning for humans, plus the analogous loop of failure analysis and model/prompt/policy updates for AI agents
Driving the Data, Technology, and AI Agenda for Care
Defining the metrics that matter for Care, including the AI-specific layer of deflection rate, AI containment, escalation rate, AI quality, hallucination rate, and cost-per-resolution across human and AI handling, and ensuring the analytics function produces a defensible, accurate narrative for every audience
Owning the Care technology roadmap: Salesforce (Service Cloud), telephony (e.g., Vonage), contact center platforms (e.g., Zendesk), WFM tools, LMS and authoring (e.g.,EasyGenerator), knowledge platforms (e.g., Confluence), and the AI agent / agent-assist / AI QA stack, and partnering with IT, Engineering, Product, and AI/ML on selection, implementation, and continuous improvement
Serving as a credible operational presence for health plan clients: leading client-facing performance conversations, walking clients through the AI Care model and its safeguards, contributing to new client onboardings, and acting as a senior escalation point for operational issues
About You
While every candidate brings a unique resume and perspective, an ideal candidate will include:
7–10 years of experience in contact center or care operations, including time leading programs or small teams of individual contributors
Direct experience deploying and operating AI in a customer support or contact center environment: voice or chat AI agents, agent-assist copilots, AI-driven QA, or automated knowledge retrieval, including ownership of the production quality bar, not just sponsorship of someone else's pilot
A working understanding of how modern LLM-based agentic systems are built and evaluated: retrieval, tool use, guardrails, eval sets, online metrics, red-teaming, human-in-the-loop review, sufficient to be a credible operating partner to AI/ML and Product
Experience owning a multi-vendor BPO environment at scale, and a point of view on how vendor partnerships and human roles evolve as AI scales inside Care
A track record of building and scaling Care operations in a healthcare, Medicare Advantage, Medicaid, or benefits administration environment: including the compliance, PHI handling, member communication, and audit requirements that govern operating AI agents in a regulated setting
Demonstrated experience executing an operating plan: contributing to the model, building the roadmap, helping manage the budget, and reporting on results to executive stakeholders
Experience leading the learning, knowledge, and quality function within a Care organization, with a clear point of view on how the knowledge base, training, and QA programs change when AI agents are part of the workforce
Strong analytics orientation and fluency with the data systems Care runs on, including the AI-specific layer of deflection, containment, AI quality, and cost-per-resolution
An operator who can move fluently between strategy and execution : an internal operating review on Tuesday, an AI failure-mode review with the ML team on Wednesday, a vendor escalation on Thursday, and brings the same rigor and care to all three
A systems thinker who connects dots across operations, quality, training, technology, AI, 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 an operating review for executives, run a tense vendor governance meeting, walk a health plan client through how your AI agents work and stay safe, and translate technical AI 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 Care has a direct impact on real people's lives, and you take the responsibility of deploying AI in that context seriously
Commitment to building a psychologically safe environment and diverse culture that is highly collaborative, strives to set and achieve goals together, and embraces transparency, innovation, and accountability
A leader who invests in the people around them, including the humans whose roles evolve as AI scales, and who coaches and holds the bar with the same standards they expect of others
Other Requirements
Travel may be required from time to time as part of the role, for company events and business needs
evermore 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. evermore will provide a work laptop, and mouse/keyboard upon request
Legal authorization to work in the US is required. At this time, evermore will not consider candidates who need sponsorship, now or in the future
All offers for employment are contingent upon successful completion of a background check
What We Offer
Competitive base salary ranging from $144,630-$154,260, 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 we are a fully distributed team from coast to coast
evermore is not currently offering visa sponsorship for this position. Candidates must be legally authorized to work in the United states at the time of application and maintain work authorization throughout employment.
evermore is an equal opportunity employer, Minority/Female/Disability/Veteran/LGBTQIA+ – proudly embracing diversity in all its manifestations. Applicants requiring reasonable accommodation for the application and/or interview process should notify a representative of the People Operations Team via careers@evermoreoutcomes.com.
evermore participates in E-Verify, the federal program for electronic verification of employment eligibility.
To all recruitment agencies: evermore does not accept agency resumes. Please do not forward them to any evermore employees.
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