Enterprise GTM

Enterprise Gtm Leader

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 reductionsnot 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 challengeshow engineering teams diagnose firmware issues, how finance teams run due diligence, how consultants build client deliverablesand 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 objectsnot 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 Productand business buyersCFOs, 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 softwareenough 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