Oyster set out to close that gap - building a global employment platform that lets companies hire, pay, and care for brilliant people anywhere. We're proof that a high-performing culture doesn't need an office. Named one of America's Greatest Startup Workplaces 2026 by Newsweek A G2 Spring 2026 Leader across Employer of Record, Global Employment, Multi-country Payroll, and HR Compliance global employment platform independently verified since 2023 They landed in the same place ~ because at Oyster, culture and performance aren't separate conversations.

If you want to do the best work of your career alongside people who care as much as you do, we'd love for you to apply. Fully remote. To create the best experience for you and to meet our business needs, this role requires you to be based within the EMEA or AMER regions.

You’ll join Oyster as a Senior AI Solutions Engineer, reporting to the AI Director and partnering closely with functional leadership across Oyster. You’ll help make Oyster’s business functions AI native, initially across areas such as People & Legal, Finance, and Operations. This means rethinking how people work with AI, where agents can take on operational work, and where human judgement creates the most value to build a more effective AI enabled organization.

You’ll be part of a connected group of Senior AI Solutions Engineers transforming different departments across Oyster. Together, you’ll establish shared standards, reuse successful approaches, and ensure Oyster’s AI transformation is coordinated rather than siloed. This is a senior, hands on role.

You’ll independently identify high value opportunities, decide where AI should and should not be used, and lead complex solutions from discovery through adoption and measurable business impact. Successful candidates will be aligned to the business function where their experience, strengths, and interests can create the greatest impact,



with the flexibility to support different functions as Oyster’s transformation priorities evolve. Core ResponsibilitiesMake business functions AI native Reimagine how teams work with AI.

Move teams from manually operating tools and workflows toward humans orchestrating AI powered ways of working, with human judgement where it matters. Shape the AI roadmap Partner with functional leaders to identify, prioritize, and frame high impact transformation opportunities. Own complex initiatives from an ambiguous problem through design, build, deployment, adoption, and improvement.

Build best in class AI agents and solutions Design, build, test, and continuously improve reliable AI agents, agentic workflows, automations, and integrations using LLMs, orchestration platforms, APIs, tools, and enterprise data sources. Balance value, feasibility, risk, data quality, maintainability, and human oversight. Recognize when AI is not the right solution.

Drive AI adoption and self sufficiency Partner with functional leaders, managers, and champions to embed AI into everyday work. Help teams move beyond consuming AI outputs toward confidently creating reusable prompts, workflows, and AI powered ways of working. Measure adoption, quality, reliability, and business impact after release.

Build trust with functional leadership, share reusable patterns with AI Solutions Engineers supporting other departments, mentor colleagues, and help teams develop the skills and confidence to operate effectively in an AI enabled environment.



3+ years of hands on AI and automation experience, supported by broader experience delivering complex solutions in business operations, functional transformation, Solutions Engineering, systems integration, or a related field. Strong hands on experience designing, building, deploying, and improving production AI agents and agentic workflows using LLMs, APIs, tools, and enterprise data. Strong experience in at least one complex business function such as People, Legal, Finance, Operations, or a related area.

Strong judgement about where AI can create value, where processes need deeper redesign, and where automation should not be used. Ability to influence functional leaders, challenge assumptions constructively, and align technical and nontechnical stakeholders.

Bonus Experience

Experience with enterprise systems and platforms used across functions such as People, Legal, Finance, or Operations. JavaScript, Python, or SQL experience. Familiarity with RAG, MCP, AI evaluation, observability, governance, or security controls.

Our mission is to create a more equal world of work: helping companies everywhere hire, pay, and care for talent anywhere. We embrace asynchronous, cooperative work and share how we operate in the Oyster Public HQ so other global teams can learn from us. a program supporting your whole human experience at Oyster: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.

Flexible parental leave: WFH stipend: Receive a stipend for your laptop and home office equipment to get you set up quickly. Oyster is committed to ensuring equal opportunity of employment for qualified persons with disabilities and actively fosters an inclusive work environment. If you receive a suspicious email about Oyster jobs or are directed to a site other than please report it via our Compliance and Ethics Helpline. #

📌 Senior Ai Solutions Engineer (Winnipeg)
🏢 Oyster
📍 Winnipeg