Senior AI Solutions Engineer - GTM

✨ One platform, a whole world of opportunity

The best jobs have always clustered in a handful of the world's wealthiest cities. But talent is everywhere. 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. Distributed across 60+ countries since 2020, we've built something the industry keeps noticing:

• Ranked #10 of 250 on TIME and Statista's 2026 list of America's Top WorkTech Companies
• 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
• The only B Corp-certified global employment platform ~ independently verified since 2023

Role Overview

You’ll join Oyster as a Senior AI Solutions Engineer: Go-to-Market, reporting to the AI Director and partnering closely with GTM leadership.

Your mandate goes beyond automating individual tasks. You’ll help make Sales, Marketing, Customer Success, Partnerships, and Revenue Operations AI native. 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 GTM 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.

Core Responsibilities

• Make GTM AI native: Reimagine how GTM teams work with AI. Move teams from manually operating tools and workflows toward humans orchestrating AI-powered ways of working.
• Shape the AI roadmap: Partner with GTM leaders to identify, prioritize, and frame high-impact transformation opportunities.
• Lead solutions from start to finish: 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.
• Apply sound judgement: 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 GTM leaders, managers, and champions to embed AI into everyday work.
• Own solutions beyond launch: Measure adoption, quality, reliability, and business impact after release.
• Connect the organization and raise capability: Build trust with GTM leadership, share reusable patterns, mentor colleagues, and help teams develop skills.

Minimum Requirements

• 3+ years of hands-on AI and automation experience, supported by broader experience delivering complex solutions in GTM Engineering, Solutions Engineering, Revenue Operations, systems integration, or a related field.
• A track record of redesigning workflows or operating models, rather than only automating isolated tasks.
• Experience independently leading complex, cross-functional initiatives from an ambiguous problem to measurable business impact.
• Strong automation capability using tools such as n8n, Zapier, Make, or comparable orchestration technologies.
• Strong hands-on experience designing, building, deploying, and improving production AI agents and agentic workflows using LLMs, APIs, tools, and enterprise data.
• Strong understanding of B2B GTM operations across Sales, Marketing, Customer Success, Partnerships, and Revenue Operations.
• Experience integrating business systems through APIs, webhooks, and authentication mechanisms.
• 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.
• A track record of mentoring others, sharing expertise, and raising standards across a team.

Bonus Experience

• Experience with Salesforce, HubSpot, Gong, Clay, or similar GTM platforms.
• JavaScript, Python, or SQL experience.
• Familiarity with RAG, MCP, AI evaluation, observability, governance, or security controls.

How YOU work

• Work from anywhere: Oyster has no borders or HQ. As long as work is timely, your team is supported, and you're authorized to work where you live, you can work from anywhere.
• Paid time off: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.
• Mental health support: Access Plumm, our mental well-being service.
• Wellbeing allowance: Each month, receive a wellbeing allowance in your ThanksBen wallet to spend on a wide range of options.
• Flexible parental leave: All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months.
• WFH stipend: Receive a stipend for your laptop and home office equipment.