Director of Delivery

Mechanical Orchard builds Imogen, a 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.

Delivery at Mechanical Orchard is where Imogen meets reality. Delivery teams work directly with customers and system integration partners in real production environments to modernize mainframe systems using Imogen. This work delivers customer outcomes while also shaping how the platform evolves, ensuring Imogen is grounded in real-world constraints, risks, and opportunities.

Our Delivery team operates in complex, ambiguous environments with high stakes. We balance long-term modernization outcomes with incremental, production-ready delivery; validate functional equivalence, performance, and operational readiness; and work closely with partners to enable durable handoff and long-term ownership. 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 Director of Delivery is accountable for the success of customer engagements at Mechanical Orchard. Partnering closely with Account Executives, this role owns delivery outcomes across a portfolio of engagements—aligning customer goals, company strategy, partner capabilities, and the Imogen platform to ensure high-quality execution.

As Imogen adoption grows and our partner ecosystem matures, success in this role increasingly centers on maximizing value delivered through the Imogen platform, enabling effective partner-led execution, and ensuring Delivery effort is focused where it creates the most leverage.

This is a senior, client-facing leadership role that combines delivery accountability, people leadership, and systems thinking.

What You'll Do - As a Director of Delivery, you may be expected to:

• Own the end-to-end success of a portfolio of customer engagements, including outcomes, timelines, quality, risk management, and stakeholder satisfaction

• Serve as the primary delivery owner for senior client stakeholders, including executive leadership

• Partner closely with Account Executives on account strategy, delivery planning, and expansion opportunities

• Lead and mentor cross-functional teams of engineers, product managers, and designers, fostering a collaborative and inclusive environment

• Drive cross-functional execution across Engineering, Product, Sales, and Platform teams

• Ensure Delivery teams are using Imogen effectively to modernize client systems and that engagement learnings inform platform evolution

• Foster strong collaboration with the Imogen platform team, providing timely, actionable feedback grounded in field experience

• Oversee delivery planning, operating rhythms, and execution health across engagements

• Partner with operations and finance to support resourcing, forecasting, and engagement financial health

• Own the transition from MO-led delivery to partner-led execution as Imogen adoption grows, ensuring Delivery effort is focused where MO creates the most leverage

• Develop and evolve partner delivery models, expectations, and success metrics in collaboration with Sales, Platform, and partner leadership

Things to Consider Before Applying

• This is a senior, client-facing leadership role with direct accountability for delivery outcomes across multiple engagements

• The role includes regular domestic travel to client sites, up to approximately twice per month, to support customer relationships, delivery oversight, and key engagement moments

• You will work closely with executive-level client stakeholders and internal leaders, often navigating high-stakes conversations and tradeoffs

• Much of the work involves complex legacy systems and long-running modernization efforts, where progress is incremental and risk must be actively managed

• The work often spans ambiguity across customer needs, partner capabilities, and platform maturity

• Collaboration across time zones is part of the role, particularly with partners based in the US and India

The Ideal Candidate

• The ideal candidate brings significant experience leading complex, client-facing delivery efforts in technology environments and is motivated by owning outcomes rather than simply managing process. They are comfortable operating at the intersection of product strategy, delivery execution, and partnership, and take pride in guiding teams through ambiguity while maintaining quality, momentum, and trust.

• They have a strong track record of working with executive-level stakeholders, navigating high-stakes conversations, and aligning diverse groups around shared goals. They understand the realities of enterprise systems and long-running modernization efforts, and can balance customer needs, partner capabilities, and platform maturity when making decisions.

• They are strong people leaders who can mentor and support cross-functional teams, foster collaboration, and create clarity in complex environments. Experience with enterprise software, platforms, or large-scale modernization initiatives is highly valuable, especially when paired with a product-led mindset and a systems-oriented view of delivery.

Mechanical Orchard, Inc. is an Equal Opportunity Employer and Prohibits Discrimination and Harassment of Any Kind. Mechanical Orchard, Inc. is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at Mechanical Orchard, Inc. are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. Mechanical Orchard, Inc. will not tolerate discrimination or harassment based on any of these characteristics. Mechanical Orchard, Inc. encourages applicants of all ages. Mechanical Orchard, Inc. will provide reasonable accommodation to employees who have protected disabilities consistent with local law.

We look forward to reviewing your application. Thanks!