About Okareo
Our mission is simple: make it safe to rely on AI.

AI-native companies and enterprise teams are innovating faster than ever. But while it’s easy to start building with a foundational model, taking an AI project to production is full of friction, risk, and uncertainty.

Okareo gives developers the tools they need to build, test, and trust LLM-powered software—through behavioral evaluation, fine-tuning, and real-time feedback. Our wedge is an Agent simulation environment that evaluates behavior and creates guardrails so you can trust your agents in production.

We’re a critical building block for production-grade LLM applications—from complex agents to retrieval-augmented generation (RAG) systems.

Why This Role Matters
Okareo is redefining how GenAI developers build and debug complex systems—LLM chatbots, RAG pipelines, multi-agent workflows, and beyond.

In this Founding GTM role, you won’t just be carrying a quota—you’ll be building the go-to-market function from the ground up. You’ll help shape our sales strategy, brand voice, and market position while working directly with the CEO and founding engineers.

This is an opportunity to sell a new category of tooling—combining simulation, error intelligence, synthetic data, and evaluation—while influencing how the next generation of AI software is built, tested, and monitored.
Ideal backgrounds include technical sales, developer relations, or technical marketing—anything that blends deep technical fluency with customer-facing skills.

What You’ll Do

• Own the full sales cycle—from outbound prospecting to closing deals with mid-market and enterprise accounts.
• Lead technical demos and live debugging sessions, showing how Okareo pinpoints LLM failures, hallucinations, and evaluation blind spots.
• Translate developer pain into actionable product insights, influencing our roadmap.
• Prototype and test GTM experiments—from pricing and packaging to outreach and content plays—to find repeatable motions.
• Represent Okareo at hackathons, AI conferences, podcasts, and online communities (Twitter, Slack, Discord).
• Collaborate with Marketing and Product to create use-case-driven content—case studies, integration guides, and success stories that establish credibility.
• Lay the foundation for a scalable sales org—from CRM setup and reporting to onboarding materials and hiring support.

You Might Be a Fit If You…

• Have 5–7+ years of full-cycle sales experience, ideally with developer tools, infrastructure, observability, or AI/ML platforms.
• Are deeply technical and comfortable speaking with CTOs, engineers, and product leaders. (Bonus: experience with LLMs, RAG, or evals.)
• Thrive in zero-to-one environments—you move fast, embrace uncertainty, and create playbooks where none exist.
• Bring a founder’s mindset—resourceful, accountable, and eager to own outcomes.
• Build trust through insight and empathy, not scripts—your discovery, storytelling, and follow-up are world-class.
• Want to be part of something big and early—helping define a category, not just selling a product.

Why Join Okareo

• Category-defining product in one of the most exciting spaces—GenAI infrastructure.
• Early-stage momentum—real customers, real use cases, and a team that moves fast.
• Backed by builders—you’ll work directly with the founding team, not layers of management.
• Impact from day one—your fingerprints will be on every deal, every iteration, every decision.

Compensation & Benefits

• Competitive startup salary + meaningful founding equity
• Full health, dental, and vision benefits
• On-site in the San Mateo area (with flexibility as needed)
• Budget for learning, conferences, and travel to represent Okareo
• The chance to help build the Sentry + PostHog for GenAI

Our Team
We’re a small, fast-moving team of multi-hat wearers who value:

• Diversity of thought and background, because better products come from varied perspectives.
• Transparency and independence, balanced by collaboration and a bias for action.

CEO & Co-founder – Matt Wyman
CTO & Co-founder – Boris Selitser
Let’s build the future of AI Agents together.