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Enterprise Account Executive

Dataworks
Illinois, IL Full Time
POSTED ON 1/28/2026
AVAILABLE BEFORE 6/7/2026

🚀 Enterprise Account Executive | Series A "AI" Startup

🏣This is a FULLY remote role, within Illinois, ideally, within commuting distance to Chicago


$140/160k and double OTE - Plus Equity


We’re working closely with a Series A AI company as they move from early enterprise traction into their next phase of growth. They’re backed, building something genuinely differentiated, and now need an experienced Enterprise AE to help shape how sales are done as they scale.


This Role Will Suit

An Enterprise AE who’s comfortable operating without a script. Someone who enjoys ambiguity, takes ownership, and wants responsibility for pipeline, messaging, and outcomes, not just quota.

You’ll be trusted to think, challenge, and build, not simply follow a playbook.


What Our Client Is Looking For

  • You ask sharp questions and lead thoughtful discovery
  • You can translate complex AI concepts into clear commercial value for senior marketing leaders
  • You’re practical, resourceful, and comfortable building what doesn’t yet exist
  • You stay resilient through long cycles and incomplete information
  • You take feedback on board quickly and adapt as the product and ICP evolve
  • You engage confidently across technical and non-technical stakeholders


Relevant Experience

  • Building an outbound pipeline in environments with limited marketing support
  • Closing complex enterprise deals, typically $250k ARR
  • Running pilots, proof-of-value engagements, RFPs, and security reviews
  • Multi-threading across Marketing, Data, IT, Finance, and Procurement
  • Owning senior-level conversations and demos end-to-end
  • Establishing technical credibility without being an engineer
  • Strong discovery, qualification, and ROI-led storytelling
  • Experience selling fixed and consumption-based pricing models


Backgrounds That Tend to Fit Well

  • Sellers from credible but non-obvious players in their category
  • People who’ve succeeded without a strong brand tailwind
  • Career paths showing depth and durability rather than frequent moves
  • Experience selling early-category or less differentiated solutions


Why You Should Apply!

  • Early ownership in an enterprise sales motion that’s still being defined
  • Genuine influence over messaging, process, and approach
  • Direct access to founders in a high-trust environment
  • Clear opportunity to grow with the business post-Series A


If you’re an Enterprise AE who values impact over polish and wants to be part of building something meaningful at an early stage, this is worth a conversation.

Salary : $140,000 - $160,000

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