Full-Time

Director of Engineering

Product Infrastructure and Release Engineering

Mechanical Orchard

Mechanical Orchard

51-200 employees

Custom app development and cloud operations

No salary listed

Remote in Canada

Remote

Remote-first; no in-office requirement. Travel to meetings/customers 1–2 times per quarter (up to ~20%).

Category
Engineering Management (1)
Requirements
  • Ten or more years of experience in infrastructure engineering, platform engineering, or developer tooling.
Responsibilities
  • Own the end-to-end infrastructure product vision, including installers, deployment tooling, reference architectures, and operational patterns.
  • Define and evolve a cohesive infrastructure roadmap aligned with Platform architecture, customer needs, and go-to-market strategy.
  • Partner closely with Product Leadership to balance near-term customer needs with long-term platform scalability and repeatability.
  • Establish infrastructure as a product with clear value propositions, constraints, supported configurations, and lifecycle expectations.
  • Drive standardization where possible while enabling extensibility for complex enterprise environments.
  • Define platform architecture and roadmap decisions to ensure deployability, operability, and customer-environment compatibility are first-class concerns.
  • Ensure infrastructure requirements are surfaced early in platform design discussions.
  • Champion architectural patterns that reduce installation complexity, operational burden, and long-term support cost.
  • Partner with Security and Compliance to ensure infrastructure designs meet enterprise and regulatory expectations.
  • Partner with Infra Delivery Leadership to define installation and deployment strategy across customer and Mechanical Orchard environments.
  • Ensure installation processes are repeatable, measurable, and continuously improving, leveraging the latest advancements in AI to support execution.
  • Build Mechanical Orchard’s system for reliable software releases, by defining standards, providing tools, and establishing clear boundaries between the release engineering team and platform product teams.
  • Define and refine success metrics for infrastructure delivery into customer environments (for example, time-to-install, failure rates, support load).
  • Ensure feedback from real-world deployments is systematically incorporated into infrastructure product evolution.
  • Partner with Sales, Infra Delivery Leadership, and Product to ensure infrastructure capabilities are accurately represented in pre-sales and go-to-market motions.
  • Partner with Infra Delivery Leadership to define and maintain sales-enablement assets (reference architectures, deployment options, constraints, and expectations).
  • Serve as a senior technical partner during complex or high-risk sales pursuits.
  • Ensure infrastructure offerings align with pricing, packaging, and customer expectations.
  • Help shape go-to-market strategy around standard vs. custom infrastructure deployments.

A consultancy that blends custom application development with managed cloud operations to help Global 2000 and other scale-focused clients build secure, reliable, and scalable software. It offers end-to-end support from design and development to ongoing cloud management, integrating development and operations to deliver cloud-ready solutions. Building on the Pivotal Labs lineage, it emphasizes risk reduction, predictable outcomes, and experience with legacy modernization and large-scale deployments. The goal is to let clients focus on their core business by removing the risks of building and running software in the cloud, delivering predictable results.

Company Size

51-200

Company Stage

Series B

Total Funding

$81M

Headquarters

San Francisco, California

Founded

2022

Simplify Jobs

Simplify's Take

What believers are saying

  • $50M Series B from GV fuels Imogen scaling after $10M revenue profitability.
  • Thoughtworks partnership accelerates Imogen adoption in enterprise IT transformation.
  • Carahsoft GSA contract opens federal sales for Imogen on April 9, 2026.

What critics are saying

  • Thoughtworks partnership delivers no joint projects, eroding Imogen credibility in 12-18 months.
  • GV pressures dilute Global 2000 focus, burning cash without revenue growth in 6-12 months.
  • AWS and IBM tools commoditize Imogen, slashing pricing power in 18-24 months.

What makes Mechanical Orchard unique

  • Imogen platform enables end-to-end mainframe modernization for Global 2000 clients.
  • Applies Pivotal Labs' Agile and XP practices to cloud operations and legacy migration.
  • AI-native tooling ensures iterative, low-risk transitions from mainframes to cloud.

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Benefits

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

0%

2 year growth

0%
Thoughtworks
Apr 3rd, 2025
Mechanical Orchard ignites major shift in enterprise IT transformation with launch of end-to-end mainframe modernization platform "Imogen" and announces first partnership with Thoughtworks

Applied AI pioneer Mechanical Orchard is today announcing the launch of Imogen, an end-to-end mainframe modernization platform, and its first partnership with global technology consultancy Thoughtworks.

Pulse 2.0
Aug 13th, 2024
Mechanical Orchard Raises $50M for Modernization

Mechanical Orchard raised $50 million in a Series B funding round led by GV to help companies transition from legacy IT systems to modern, cloud-based applications. The company uses AI-enhanced tooling and an iterative approach to ensure continuous proof of successful migration. Founded in October 2022 and based in San Francisco, the team includes notable leaders like Rob Mee and Matthew Work, with an international presence. The investment highlights the urgent need for IT modernization.

PR Newswire
Jul 30th, 2024
Exiger Acquires aDolus for Cybersecurity Boost

Exiger has acquired aDolus Technology Inc. to enhance its software supply chain visibility. This acquisition integrates aDolus' ability to generate software bills of material (SBOMs) and analyze binary software provenance, extending Exiger's Ion Channel platform to binaries without SBOMs, device firmware, OT, and IoT. This move addresses the urgent need to secure operational and legacy technologies, with software supply chain attacks expected to triple from 2021 to 2025, affecting 45% of organizations.

The Business Journals
May 2nd, 2024
Fast-growing AI startup moves headquarters to 1 Post St. in S.F.

Generative AI firm Mechanical Orchard is moving its San Francisco headquarters to 1 Post St. as it continues to hire employees.

Forbes
Feb 7th, 2024
Pivotal Founder Rob Mee's New Startup Is Using AI To Drag Ancient Mainframes Into The Cloud

Mechanical Orchard has raised $24 million from Emergence Capital at a $95 million valuation after reaching $10 million in revenue and profitability in just over a year.