Enterprise GTM

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 an Enterprise GTM leader at Context AI, you'll drive revenue growth by bringing AI agents that execute complex, high-stakes work to Fortune 100 enterprises. Your mission is to identify, engage, and close transformational deals with organizations seeking 30-40% productivity improvements and 90%+ cycle time reductions—not through simple automation, but through AI that performs production-quality work knowledge workers do every day.

You'll own the full sales cycle for enterprise accounts, from initial prospecting to contract close and expansion. You'll partner with C-suite executives, VPs of Engineering, CFOs, and operational leaders to understand their most pressing challenges—how engineering teams diagnose firmware issues, how finance teams run due diligence, how consultants build client deliverables—and demonstrate how Context AI agents can execute that work with institutional intelligence: the tribal knowledge, business rules, and quality standards that define their organization.

In this role, you'll need strategic thinking, deep business acumen, and the ability to sell transformational technology. You'll navigate complex enterprise buying processes, build executive relationships, and orchestrate technical evaluations that prove Context delivers real business impact. You'll work alongside Deployment Strategists, Forward Deployed Engineers, Product, and Engineering to craft winning proposals, drive pilots, and expand strategic accounts.

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

• Own enterprise pipeline and quota—prospect, qualify, and close deals with Fortune 500 companies across telecommunications, finance, consulting, biotech, and technology sectors

• Build C-suite relationships—engage with CEOs, CIOs, CTOs, CFOs, and VPs to position Context as strategic infrastructure for AI-powered knowledge work

• Lead discovery and qualification—understand customers' critical workflows, execution bottlenecks, and business outcomes to identify where AI can deliver measurable impact

• Orchestrate technical evaluations and pilots—partner with Deployment Strategists and Engineers to design proof-of-value engagements that demonstrate 30-40% productivity gains

• Navigate complex enterprise sales cycles—manage multi-stakeholder buying processes, procurement, legal, security reviews, and executive approvals

• Present business cases and ROI—articulate value propositions to audiences ranging from individual contributors to C-suite executives, demonstrating productivity gains, cycle time reductions, and strategic impact

• Build and deliver executive demos—showcase Context agents executing real work (analyzing engineering logs, running financial analysis, generating client deliverables) tailored to customer use cases

• Drive account expansion—identify new use cases, departments, and workflows within existing customers to expand footprint and revenue

• Partner cross-functionally—work with Product, Engineering, and Deployment teams to incorporate customer feedback, shape product roadmap, and ensure customer success

• Scope new market opportunities—identify whitespace across industries, verticals, and use cases to help expand Context's enterprise footprint

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

What We Require

• 5+ years of enterprise sales experience selling complex, transformational software to Fortune 500 companies

• Proven track record closing deals >$500K ACV, ideally $1M+ ACV

• Experience selling to technical buyers—CTOs, VPs of Engineering, VPs of Product—and business buyers—CFOs, COOs, business unit leaders

• Strong business acumen and ability to articulate ROI, productivity improvements, and strategic value

• Comfort with technical concepts—AI/ML, data integration, APIs, enterprise software—enough to engage credibly with technical stakeholders

• Executive relationship building—demonstrated ability to build trust with C-suite and navigate complex buying processes

• Consultative selling approach—curiosity to understand customer workflows deeply and craft tailored solutions

Nice to Have

• Experience selling AI/ML, data infrastructure, or developer tools to enterprises

• Prior work in consulting, professional services, or customer-facing technical roles—you've been in customers' shoes

• Familiarity with specific verticals—telecommunications, finance, consulting, biotech, engineering systems

• Track record of driving pilots and proofs-of-value that convert to strategic deals

• Experience with product-led or technical sales motions—demos, technical evaluations, proof-of-concept engagements

• Network in target industries—existing relationships with Fortune 500 executives or decision-makers

• MBA or advanced degree in business, engineering, or related fields