Deployment Strategist

About Context

We're on a mission to unlock the next frontier of productivity for knowledge workers.

Context AI is building the future of enterprise AI—systems that don't just answer questions or automate simple tasks, but execute the complex, judgment-heavy work that drives real business outcomes. The constraint blocking AI from creating true enterprise value isn't model intelligence anymore; it's institutional intelligence: understanding how your organization operates, where information lives, what quality standards matter, and how work actually gets done.

Our platform solves this by automatically learning each organization's unique context—the tribal knowledge, business rules, internal lexicon, and tacit expertise that defines production-quality work. Each Context task can connect to gigabytes of data across entire codebases, data rooms, and operational systems, enabling AI agents to perform real work that knowledge workers do: engineers analyzing firmware logs to identify root causes, bankers running due diligence on multi-terabyte data rooms, analysts refreshing deliverables with live market data, and consulting teams creating client presentations and websites.

We've proven our system with Fortune 100 customers, achieving 30-40% productivity improvements, reducing cycle times by over 90%, and deploying solutions in days rather than months. Context AI operates 24/7/365 across global teams, freeing knowledge workers to focus on strategic initiatives and new growth frontiers.

Why Context

• Massive Impact: The potential of enterprise AI is unbounded, and we're at the frontier. At Context, you will build software that transforms the nature of work for thousands of engineers, bankers, analysts, consultants, product managers, lawyers, and more

• Real Technical Challenges: Design systems no one else has ever built in order to tackle problems that no one else has ever solved

• Ownership That Matters: We trust our team members to direct influence on product direction and own entire systems. At Context, you propose, build, and ship features with full autonomy and ownership

• Elite Technical Team: We've assembled a superstar team hailing from Apple AI, Microsoft Research, Google, Stripe, Ramp, and more. Work with and learn from the best

What You'll Do

As a Deployment Strategist at Context AI, you'll work alongside a driven team of Engineers, Product Designers, and fellow Deployment Strategists to deploy AI agents that execute complex, high-stakes work for Fortune 100 enterprises. Your mission is to understand the institutional intelligence that makes organizations tick—the tribal knowledge, business rules, workflows, and quality standards—and translate that into AI systems that perform production-quality work knowledge workers do every day.

You'll immerse yourself in our customers' most complex workflows. You'll partner with subject matter experts to understand how engineering teams diagnose firmware issues, how finance teams run due diligence, how consultants build client deliverables. You'll explore gigabytes of data across codebases, data rooms, and operational systems to identify where AI can execute real work, not just assist with it. In this role, you'll need a curious and analytical approach, sharp product intuition, and deep user insight to empower our customers to achieve 30-40% productivity improvements and 90%+ cycle time reductions.

No two days are the same, but you can expect to:

• Go onsite to meet with knowledge workers—engineers, analysts, consultants—to understand their critical workflows and locate their biggest execution bottlenecks

• Map institutional intelligence through deep engagement with customer problems, identifying the tribal knowledge, business rules, and quality standards that define production-quality work

• Partner with Forward Deployed Engineers to ground our AI agents in customer data—integrating codebases, operational systems, and proprietary datasets into stable, extensible pipelines

• Design AI workflows that learn from subject matter experts and execute complex tasks: analyzing engineering logs, running financial analysis, generating client deliverables, shipping code

• Present results and proposals to audiences ranging from individual contributors to C-suite executives, demonstrating productivity gains and cycle time reductions

• Build and deliver demos showcasing Context agents executing real work for new and existing customers

• Scope new engagements across industries—telecom, finance, consulting, biotech, technology—and help expand Context into new verticals and use cases

What We Value

• Agency: Innovation happens when team members think from first principles and go above and beyond in order achieve objects—not by simply completing tasks

• Digging Deep: Surface-level understanding won't cut it when AI needs to execute production-quality work with institutional knowledge

• Low ego: We understand that the outcome matters more than who gets the credit. Team members share wins and don't play politics.

• Extraordinary Problem-Solving Ability: You'll confront open-ended problems in unstructured environments where "how we do things" isn't documented

• Adaptive and Introspective: We operate in a fast-moving environment and accordingly iterate rapidly; team members must be able to learn from their mistakes and improve constantly