endeavorai.com
AI & Machine LearningDirect Ashby career site

Deployment Strategist

Location
Chicago, IL · On-site
Job type
Full-time
Level
Director
Experience
4+ years
Listed
30 days ago

Skills & highlights for this role

  • enterprise sales
  • ROI modeling
  • stakeholder management

Also useful

  • AI/ML fluency
  • LLMs
  • computer vision

About the role

Endeavor is real-world enterprise AI.

We are the AI partner for the physical world serving factories, warehouses, job sites, and the enterprises that run them.

We are building the last mile for AI, deploying into organizations, earning C-level buy-in, and becoming their exclusive partner for business transformation. Our software combines LLMs, voice AI, and vision models to make physical operations intelligent. We are helping companies make better decisions, automate manual processes, and drive real revenue.

While labs build the models of the future, we build the last-mile delivery for them. We must model complex environments, deliver reliable results, and bridge the gap between models and the antiquated ecosystems in which they must operate.

Our Principles

  • We are bold, especially when the world tells us what we’re doing is impossible.
  • We are truth-seeking, choosing clarity over comfort.
  • We will win. And we work really hard to win.

The Role | Deployment Strategist

This is a client-facing role where you’ll run complex agreements, earn trust in the boardroom, and turn a beachhead into a long-term partnership. You’ll own the client relationship from kickoff through expansion by running executive steercos, aligning internal and external stakeholders, and making sure we deliver outcomes that justify deeper investments. To do this, you’ll be working closely with Forward Deployed Architects and their engineering teams who will write the code and help deliver what you prioritize.

What We Require

  • 4+ years of experience in management consulting (i.e., McKinsey, Bain, BCG), enterprise technology, or a high-growth B2B environment with an MBA.
  • Proven track record running executive-level relationships and growing accounts.
  • Comfortable owning a room - steercos, QBRs, board updates - and driving decisions.
  • Ability to build a credible ROI case from scratch and understand what drives that forward.
  • Technical fluency to hold a real conversation about AI, data, and software.
  • Ability to travel.
Read the original posting

From endeavorai.com's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

Where is the Deployment Strategist job at endeavorai.com located?

This Deployment Strategist position at endeavorai.com is located in Chicago, IL (On-site). Always check endeavorai.com's application page for specific state eligibility or relocation policies.

What qualifications are required for Deployment Strategist at endeavorai.com?

For the Deployment Strategist role, endeavorai.com highlights 4+ years of relevant experience; experience with enterprise sales, ROI modeling, stakeholder management. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Deployment Strategist position at endeavorai.com?

This listing links directly to endeavorai.com's Ashby application page. You can apply directly on endeavorai.com's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.