Posted last month
Senior Staff Applied AI Engineer
@ OpenLoop Health
Toronto, Ontario
Overview
OpenLoop Health is hiring a Senior Staff Applied AI Engineer to be one of its first technical AI leaders. The role sets direction for agent runtimes, evaluation, model access, observability and grounding on the company's platform. Full-time, with salaried benefits including medical, dental, vision and 401(k) match.
Responsibilities:
- Set technical direction for agent runtime, orchestration and failure handling
- Build evaluation systems and regression tests for AI quality
- Manage multi-provider model access, routing and fallbacks
- Trace agent behavior and attribute AI spend with budgets
- Protect PHI and control agent access to data
Requirements summary:
- 12+ years of software engineering, at tech lead or staff scope
- 2+ years running LLM systems in production
- Deep expertise in agent runtime or evaluation
- Track record measuring AI quality with evaluation sets
- Experience leading a team from zero in a greenfield setting
Tools & skills
Benefits mentioned
Source and dates
Employer career site / ATS feed · ashby
- Employer posting date
- 2026-09-30
- First seen by our source
- 2026-10-08
- Source record updated
- 2026-10-09
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Senior |
| Department | Software development |
| Experience | 12+ years |
| Hours per week | 40 (estimated) |
| Work setting | Office |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Languages | English |
| Education | Bachelor’s degree (required) |
| Fields of study | Computer Science, Engineering |
| Perks mentioned | Generous paid time off, Flexible hours, Retirement plan |
Summary and details written by AI from the posting; the employer’s posting is the authority.
OpenLoop Health
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
Powering superior telehealth from end-to-end. #HealingAnywhere
Full company description
OpenLoop is the nation’s top white-label digital health infrastructure provider, powering virtual care delivery for healthcare organizations, employers, retailers, and consumer brands. We make it simple to launch and scale virtual care by delivering the complete clinical and operational backbone behind the scenes—you control your brand, and we handle everything else. Our end-to-end stack includes: - Pharmacy & Diagnostic - Platform & AI - RCM & Billing - RPM Fullfilment - Built-In AI Solutions Trusted by organizations nationwide, OpenLoop supports 300K+ patient visits per month and serves 3M+ patients annually, earning a 4.9★ Trustpilot rating. You focus on your brand and growth—we’ll power the care delivery.
- LinkedIn followers
- 38,021
- People associated on LinkedIn
- 591
- Reported office locations
- 317 6th Ave, Suite 400, Des Moines, Iowa 50309, US
- Business categories
- Service Industry
- Health Care
- Telehealth
- Medical
- IT Infrastructure
- Staffing Agency
- Other recorded names
- OpenLoop Health Partners
- OpenLoop Health
- OpenLoop
- Specialties
- Telehealth
- Revenue Cycle Management
- Practice Management
- Provider Staffing
- Payer Coverage
- and Clinician Licensing
- Profile identifies a recruitment agency
- No
- Reported total investment
- 26,620,000
Currency and observation date were not supplied; this is not a current valuation or a funding round.
OpenLoop is the nation’s top white-label digital health infrastructure provider, powering virtual care delivery for healthcare organizations, employers, retailers, and consumer brands. We make it simple to launch and scale virtual care by delivering the complete clinical and operational backbone behind the scenes—you control your brand, and we handle everything else. Our end-to-end stack includes: - Pharmacy &…
| Field | Value |
|---|---|
| Industry | Hospitals and Health Care |
| Company size | 201-500 employees |
| Headquarters | Des Moines, Iowa |
| Organization type | Privately Held |
| Year founded | 2020 |
| Specialties | TelehealthRevenue Cycle ManagementPractice ManagementProvider StaffingPayer Coverageand Clinician Licensing |
| Open jobs on Jobsy | 8 |
| View page |
About OpenLoop
OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.
About the Role
OpenLoop is building the future of healthcare infrastructure. We are hiring a Senior Staff Applied AI Engineer to be one of the first technical leader for AI at OpenLoop .
As one of the earliest hires, the decisions you make become the foundation everyone else builds on: how our AI agents run, how we prove they are good, how we keep them safe and affordable, and how other teams build agents on our platform.
What You'll Do
Agent Runtime & Orchestration: Set the technical direction for how agents run, call tools, hold context and hand off work, including failure handling, retries, timeouts and sandboxing. Decide when to build and when to adopt frameworks.
Evaluation: Build the systems that prove our AI is actually good, including regression tests and AI-graded evals, and help each team define what "good" means for their agents.
Model Access & Operations: Set up access to models from multiple providers, route between them, manage version upgrades and plan fallbacks for when a provider fails.
Observability & Cost: Trace what agents did and why, monitor behavior in production, and attribute AI spend to each agent and use case with budgets and guardrails.
Grounding & Retrieval: Connect agents to real, messy company data and documents through retrieval (RAG), context design and prompt engineering, so answers are based on facts.
Workflow Design: Partner with operations teams to turn human workflows, such as patient support, into agent workflows, and decide which steps should stay with a person.
Security, Privacy & Safety: Keep patient data (PHI) protected in every AI system, control what agents can access, and defend against misuse such as prompt injection.
Cloud & Data Foundations: Make sound infrastructure decisions on GCP and partner with the Data Platform teams who provide the governed data agents use.
Technical Leadership: Set and document direction when the right answer is unclear, make build-versus-buy calls and revisit them as tools change, keep the platform general enough for many teams, and mentor engineers who are new to AI through code and design review.
Cross-functional Work: Explain AI trade-offs in plain language to product, operations and clinical stakeholders, including when the honest answer is "the AI isn't ready for this yet."
Other duties as assigned.
Who You Are
Required Qualifications:
Bachelor's degree in Computer Science, Engineering, or a related technical field
Proven Technical Leadership: 12+ years of software engineering experience, with a track record at tech lead, staff or principal-level scope.
Production LLM Experience: 2+ years building and running LLM-based systems in production that real users relied on, not only demos, prototypes or personal projects.
Core AI Depth: Deep, hands-on expertise in agent runtime or evaluation, a second area of real depth, and working knowledge across the rest of the AI engineering stack.
Evaluation Rigor: A track record of measuring AI quality with real evaluation sets and test harnesses, and reporting results with numbers.
Zero-to-One Leadership: Experience leading a small team's technical direction from zero, or close to it, in a greenfield setting.
Excellent communication skills with the ability to explain complex technical concepts and trade-offs to non-technical stakeholders
Preferred Qualifications:
Regulated-Industry Experience: Healthcare (PHI, HIPAA), finance or insurance.
GCP Experience: Running production services on Google Cloud.
Internal Platforms: Built a platform used by other engineering teams.
Team Scaling: Helped grow a single pod into multiple teams.
Our Benefits
In addition, for salaried positions you would also be eligible for:
Medical, Dental, and Vision plans
Flexible Spending/Health Savings Accounts
Flexible PTO
401(k) + Company Match
Life Insurance, Pet insurance, and more
Our Company
We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.
Sound like a good fit? We’d love to meet you.
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