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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