4+ years in product, operations, or deployment roles focusing on AI/automation production
Demonstrated ability to build, prototype, and debug AI systems
Strong understanding of workflows and behavioral data analysis
Ability to critically analyze ambiguous problems and develop solutions
Self-directed with a high degree of ownership
Bonus: experience in healthtech or insurance workflows, proficiency in Python or SQL
Responsibilities
Drive end-to-end AI deployments, including design, testing, and rollout
Translate complex payer and clinical workflows into executable technical specifications
Ensure output quality by measuring accuracy and enhancing reliability of deployments
Document and create reproducible playbooks for prompt and deployment strategies
Define and execute a prioritized AI roadmap
Establish metrics to determine and validate successful outcomes
Benefits
Competitive salary and meaningful equity
Hybrid working model based in Union Square, NYC (3 days/week)
Unlimited PTO along with 9 company holidays
Comprehensive full benefits package
Full Job Description
The Role
This is not a supporting role. You'll own the patient experience end-to-end - the ongoing telehealth relationship, the DME order journey, and every lifecycle touchpoint - with one job: keep patients engaged and drive LTV and retention.
A big part of that is AI. Our SMS and Voice AI systems increasingly are the patient experience, and you'll own their quality - deciding where AI runs the interaction, where it assists a human, and where a human takes over, then proving it works through disciplined evaluation.
You'll work across Patient Experience, Growth Marketing, and Clinical Operations with real autonomy and a high bar. We want someone who reaches for AI before reaching for headcount.
What You'll Own
Retention & LTV - own the metrics and the roadmap that move them.
The end-to-end patient experience - ongoing telehealth, the DME order journey, and lifecycle comms, treated as one system, not a set of screens.
AI-powered support - decide where AI handles patient interactions end-to-end, where it assists a human, and where a human stays in the loop.
LLM evaluation & quality - define what "good" looks like for our SMS and Voice AI, build eval sets from real conversations, catch regressions before they ship, and monitor safety in production.
Experiment velocity - a prioritized backlog of retention experiments and enhancements, shipped and learned from fast.
Metrics - define what "working" means for both retention and AI quality, and prove it.
Who You Are
4+ years in product - with meaningful time owning retention, lifecycle, or growth in a D2C product.
AI-native: you build, prototype, and debug with AI, and you're skeptical of any process that doesn't.
You think in cohorts and behavioral data - and you know when the data is lying to you.
You've evaluated or managed the quality of LLM/AI systems - rubrics, eval sets, regressions, safety - or you're hungry to own it.
Comfortable with high ownership and minimal guardrails - you don't wait to be told what to prioritize.
High-trust judgment - you care about clarity, trust, and safety in a healthcare context.
Bonus: healthtech, fintech, or regulated industries; lifecycle marketing exposure.
The Details
Competitive salary + meaningful equity
Hybrid, Union Square NYC (3 days/week)
Unlimited PTO + 9 company holidays
Full benefits
Location: New York City | Type: Full time | Hybrid | Department: Product | Salary: $170K-$200K. We are willing to go above this range for exceptional candidates with specialized expertise whose background exceeds the requirements.
