Principal, Enterprise Growth

We deliver applied enterprise AI solutions that help organizations modernize their products and operations using AI. Our work spans AI strategy, product development, and hands-on implementation, taking customers from idea to production-ready systems that run in real environments. We work through a Forward Deployed model, with senior engineers embedded directly inside client environments, working against real systems and real data.

Responsibilities

• Land net-new enterprise logos among organizations with $500M to $5B or more in revenue
• Own revenue, expansion, and the executive relationship in the accounts you land
• Sell to CTO, CIO, COO, and Chief Transformation Officer buyers through account-based, consultative engagement
• Grow entry engagements into full multi-year transformation and delivery programs
• Partner with delivery and executive leadership to keep accounts expanding
• Bring founder-level presence into an account when it matters, and run everything else yourself

Requirements

• Track record closing enterprise deals at $2M or more per year with real multi-year expansion, not one-time bookings
• Experience selling services-led or solutions-led offerings on consultative, enterprise deals
• Forward Deployed or enterprise services background strongly preferred; adjacent enterprise software backgrounds considered if you have carried deals at this size and complexity
• Strong ability to hold a serious conversation about production systems, integration reality, and organizational resistance, not a feature pitch
• Experience with AI, data, or enterprise technology is a strong plus

Mindset

We expect precision over volume. Ten qualified enterprise conversations beat massive reach. This role requires the confidence to be deliberately clear about who we are for and who we are not, and the judgment to build trust with the one person accountable for AI outcomes rather than selling to an organization in the abstract.

Our Expectations

This is not a transactional sales role. You will own accounts end to end, from the land through years of expansion, and you will be accountable for the relationship long after the first contract is signed. You will work directly with founders and executive leadership on the accounts that matter most. We value intellectual rigor, independent thinking, and the ability to sell without hype. This role requires comfort with complexity, long enterprise sales cycles, and a long-term mindset.

Why This Role Matters

You will directly drive revenue, expand our most important accounts, and help build a serious, execution-first AI company with long-term ambition. This is the role that proves our growth does not depend on the founders. What you build in your first two accounts becomes the model for the next twenty, scaling us from a handful of founder-led relationships into a repeatable enterprise motion that compounds.

Schedule

This position is based in Chicago, IL with a hybrid working model requiring an average of 3.5 days per week in the office. Candidates must reside within the Chicagoland area.