Remote Ai Assistant Jobs in Oregon (NOW HIRING)

About the Role

The Founding Head of Customer Success & Operations is a high-conviction hire for Tebra's Innovation team - and one of the most demanding. This is a hands-on, high-touch role that represents the human face to providers through personalized support and onboarding to our innovation features. This role will simultaneously build a scalable CS strategy, PHI protocols, AI agent corpus, and long-term team infrastructure. We are looking for someone who has built a CS function from scratch before and is choosing to do it again at an earlier, higher-stakes stage - a player-coach who finds genuine satisfaction in working directly with customers in Month 1 and writing the playbook that empowers others to do it in Month 6.

Your Area of Focus

• Personally onboard and support every provider in the initial Alpha cohort - handle every inbound question manually for the first 6-8 weeks to build deep product and customer intuition.
• Record and transcribe every provider call to build a structured question taxonomy that will serve as the foundation of the AI agent knowledge base.
• Own the AI CS agent corpus: structure and synthesize rotating engineer inputs weekly, prune and publish the knowledge base, and evaluate agent responses for accuracy and PHI compliance.
• Comfortable owning the AI agent corpus as a product artifact - this is a content and systems ownership function, not just a tooling decision.
• Define and document the PHI routing protocol before the first provider is onboarded - establishing clear rules for what routes to AI, what routes to a human, and what requires immediate clinical escalation.
• Identify and onboard a licensed clinical consultant (LCSW, LPC, or LMFT) on retainer within 30-60 days post-launch to serve as the escalation path for red-line clinical accuracy events.
• Build the Nitro CS runbook, CE rotation handoff documentation, trust-repair scripts, and provider communication playbook - documenting in real time, not after the fact. 
• Own the long-term CS strategy: develop the hiring and integration plan, team structure, metrics framework (CSAT, resolution rate, retention), and CS tool stack decisions. 
• Exchange learnings on best practices with Customer Success Learning and Enablement team to ensure AI knowledge base strategies and AI knowledge protocols are aligned. 
• Lead AI CS agent platform evaluation at Week 4 and manage deployment at Week 6-8 using the question taxonomy built through direct provider interactions.
• Partner with the GTM / Growth Lead on referral generation, surfacing provider satisfaction signals and identifying optimal moments to request introductions.
• Ensure all CS operations and provider interactions maintain strict HIPAA compliance, with particular sensitivity to PHI handling in a mental health documentation context.

Your Professional Qualifications

• 7-10 years in customer success, with at least one "first CS hire" or "built the function from scratch" experience at a SaaS company.
• Has hired and built a CS team before - this is not a first leadership opportunity.
• Healthcare-adjacent experience is strongly preferred; a mental health background or familiarity with clinical workflows is a meaningful differentiator.
• PHI-fluent: understands HIPAA obligations in practice, what can and cannot be communicated over which channels, and what constitutes a clinical escalation versus a product support ticket.
• Player-coach by disposition: genuinely energized by working directly with customers in Month 1, and equally motivated to build the system that scales that work in Month 6.
• Comfortable owning the AI agent corpus as a product artifact - this requires content strategy and systems thinking, not just tooling familiarity.
• Experience with CS platforms, ticketing systems, and AI-assisted support tools; willingness to evaluate and select the right stack from scratch.
• Strong verbal and written communication skills, with demonstrated ability to navigate sensitive clinical or emotionally charged customer interactions with empathy and professionalism.
• Comfortable making judgment calls in ambiguous situations, including routing decisions that sit at the intersection of product support and clinical risk.
• Highly fluent with AI tools in daily workflow - uses AI assistants, automation, and emerging capabilities as a core operating layer, not an occasional shortcut; comfortable evaluating and adopting new tools as the landscape evolves.
• Clear vision for AI-driven CS transformation - understands how AI reshapes support operations, deflection strategy, and provider experience, and can lead that transformation proactively rather than reactively; sees the AI agent corpus as a strategic asset, not an IT project.

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