Mechanical Orchard builds Imogen, a mainframe modernization platform for rewriting the most critical and complex business applications—the systems that quietly run the world as we know it—so they can continue operating reliably while adapting to new challenges and opportunities. These are business-critical systems where reliability, safety, and correctness are paramount.

Selling at Mechanical Orchard means selling change to organizations that have lived with their legacy systems for decades and have good reason to distrust modernization. The risk is real, the buyers are senior and technical, and the cost of getting it wrong is high. Our go-to-market motion earns trust through proof rather than promises, and pairs commercial ownership with deep delivery credibility.

We value strong fundamentals, pragmatic use of AI, and close collaboration across roles and organizations. Our values are simple: Do the right thing. Do what works. Be kind.

The Role

The Sales Director owns the commercial relationship for a portfolio of enterprise accounts—from first conversation through closed deal and expansion. You'll lead complex, consultative sales cycles for mainframe modernization, selling to senior business and technical buyers (CIO, CTO, VP Engineering) where the decision involves many stakeholders, real risk, and long evaluation timelines.

This role partners closely with Delivery and our Sales Engineers. You own the deal; Delivery owns execution. Your job is to align customer goals, the Imogen platform, and our partner ecosystem into a credible path the customer trusts enough to commit to—and to keep that relationship healthy as engagements grow.

This is a senior, client-facing, quota-carrying role that combines commercial ownership, executive relationship-building, and the technical fluency to be credible in the room.

What You'll Do

Own a portfolio of enterprise accounts and a revenue number, from pipeline generation through close and expansion
Lead long, complex, multi-stakeholder sales cycles, building consensus across business and technical buyers up to the C-suite
Develop account strategies that map customer modernization priorities to Imogen's capabilities and our partner ecosystem
Partner closely with Delivery and Sales Engineering leadership on scoping, delivery planning, and expansion, ensuring what you sell is what we can deliver
Build and maintain trusted relationships with senior executives, navigating high-stakes conversations and tradeoffs
Run a disciplined, well-forecasted pipeline, and communicate risk and progress honestly to internal leadership
Work with system integration partners to structure deals that set engagements up for durable, partner-led execution
Represent Mechanical Orchard credibly in technical and business conversations, and bring field insight back to inform product and go-to-market strategy

What You'll Bring

A track record of closing complex, high-value enterprise deals with long sales cycles and multiple stakeholders
Experience selling technical or platform products to senior technical buyers (CIO, CTO, VP Engineering)
The ability to build credibility in technical conversations without overpromising
Strong consultative selling skills—you diagnose before you pitch, and you sell outcomes rather than features
Disciplined pipeline management and accurate forecasting
Comfort operating in ambiguity, in a category where the buyer may not yet believe the problem is solvable
Excellent communication and executive presence across seniority levels

Nice to have: experience in enterprise modernization, mainframe, or legacy systems; experience selling alongside delivery teams or system integrators; familiarity with consumption- or outcome-based commercial models.