Mechanical Orchard

• Work as part of small, cross functional XP teams building advanced technology for customers or for Mechanical Orchard using a variety of modern programming languages • Pair program with other engineers and collaborate closely with other roles such as product managers and designers • Learn and apply XP engineering practices such pair programming, test-driven development, refactoring, continuous integration and continuous delivery • Operate and support production applications as a team in the context of the agile DevSecOps model • Collaborate on technical discovery efforts for existing customer systems including legacy applications • Continuously learn about relevant emerging technologies or practices and foster the growth of the organization through mentorship, tech talks, and other means • Contribute to research efforts using the latest technologies in generative AI and data engineering

• Own the end-to-end deployment model — from reference architectures and installation workflows to hardening, upgrades, and ongoing environment support across customer environments • Enable Delivery teams and SI partners to use Imogen effectively, and draw a clear boundary between Mechanical Orchard's infrastructure ownership and partner-led modernization execution • Partner with Platform to influence roadmap and architecture decisions, serving as the voice of real-world deployment complexity in platform prioritization • Engage with Sales and Delivery during pursuits to define infrastructure scope, set readiness criteria, and reduce downstream delivery risk before engagements begin • Build, hire, and develop a high-performing infrastructure engineering team through consistent coaching, career development, and a culture of ownership • Define the processes, playbooks, and metrics that move infrastructure delivery and support from heroics to a repeatable, scalable operating model

• Own the end-to-end deployment model — from reference architectures and installation workflows to hardening, upgrades, and ongoing environment support across customer environments • Enable Delivery teams and SI partners to use Imogen effectively, and draw a clear boundary between Mechanical Orchard's infrastructure ownership and partner-led modernization execution • Partner with Platform to influence roadmap and architecture decisions, serving as the voice of real-world deployment complexity in platform prioritization • Engage with Sales and Delivery during pursuits to define infrastructure scope, set readiness criteria, and reduce downstream delivery risk before engagements begin • Build, hire, and develop a high-performing infrastructure engineering team through consistent coaching, career development, and a culture of ownership • Define the processes, playbooks, and metrics that move infrastructure delivery and support from heroics to a repeatable, scalable operating model

• Work as part of a small, cross functional XP team installing Imogen into client cloud environments partnering with client infosec, infrastructure, and IT teams. • Pair program with other engineers and collaborate closely with other roles such as product managers and designers • Work with client infrastructure, security, and network teams to deploy Imogen to their cloud infrastructure • Lead and collaborate on technical discovery efforts for existing customer systems cloud infrastructure and adapt Imogen to their public cloud estate • Apply and evolve XP engineering practices such as pair programming, test-driven development, refactoring, continuous integration and continuous delivery • Adapt XP practices for working with AI—whether co-writing code, managing agents and their context, or knowing when to push back and trust your own instincts • Help onboard client developers and/or new Mechanical Orchard team members with practices and techniques • Continuously learn about relevant emerging technologies or practices and foster the growth of the organization through mentorship, tech talks, and other means

• Report to the VP of Engineering, providing strategic direction, product thinking, and cross-functional alignment across Platform, Forward-deployed Engineering, Sales, Security, and Product Management • Manage the Product Infrastructure and Release Engineering teams • Ensure that the Imogen Platform is designed as a scalable, repeatable, and evolving product surface that accelerates customer adoption and long-term platform success • Ensure all of Imogen's components are released and deployable into a diverse set of customer environments, meeting the needs of enterprise customers • Turn infrastructure into a first-class product capability, opinionated where possible, flexible where necessary, and aligned with Mechanical Orchard’s modernization strategy and GTM motion

Mechanical Orchard is reinventing how the world’s most critical software gets modernized. We’re an applied AI company focused on one of the hardest problems in enterprise technology: rewriting complex legacy systems in a way that is provably correct, low risk, and fast enough to matter. By focusing on system behavior rather than code alone, we turn modernization from a high-stakes, failure-prone effort into a repeatable, confidence-building process that unlocks ongoing innovation. Joining Mechanical Orchard means working on problems that truly matter—to our customers, their businesses, and the people who rely on these systems every day. We’re building technology and methodology that challenge long-standing industry assumptions, prioritizing proof over promises and progress over theatrics. If you care deeply about quality, rigor, and doing the right thing—even when it’s hard—you’ll find your people here. Position Overview The Director of Product Infrastructure and Release Engineering is a senior leadership role responsible for the strategy, coherence, and execution of Mechanical Orchard’s infrastructure and release capabilities—spanning infrastructure products, installation and deployment workflows, and operational enablement for customers and forward-deployed engineering teams. In this role you will: - Report to the VP of Engineering, providing strategic direction, product thinking, and cross-functional alignment across Platform, Forward-deployed Engineering, Sales, Security, and Product Management. - Manage the Product Infrastructure and Release Engineering teams. - Ensure that the Imogen Platform is not merely “delivered,” but designed as a scalable, repeatable, and evolving product surface that accelerates customer adoption and long-term platform success. - Ensure all of Imogen's components are released and deployable into a diverse set of customer environments, meeting the needs of enterprise customers (quality, software supply chain audits, and more). - Turn infrastructure into a first-class product capability: opinionated where possible, flexible where necessary, and aligned with Mechanical Orchard’s modernization strategy and GTM motion. Key Responsibilities Infrastructure Product Strategy & Ownership - 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 GTM 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 Platform & Architecture Alignment - 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. Execution & Operational Excellence - 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 (e.g., time-to-install, failure rates, support load). - Ensure feedback from real-world deployments is systematically incorporated into infrastructure product evolution. GTM, Sales & Customer Enablement - Partner with Sales, Infra Delivery Leadership, and Product to ensure infrastructure capabilities are accurately represented in pre-sales and GTM 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 GTM strategy around standard vs. custom infrastructure deployments. Ideal Candidate Profile - 10+ years of experience in infrastructure engineering, platform engineering, or developer tooling. - Proven track record building infrastructure as a product, incl. deep expertise with deployments in complex enterprise environments (cloud, hybrid, regulated). - Strong architectural instincts paired with pragmatic delivery experience. - Hands-on experience with latest AI coding tools, model capabilities, and industry trends - Demonstrated ability to operate cross-functionally across Product Engineering, Product, Forward-deployed Engineering Teams, Sales, and Security. - Excellent written and verbal communication skills, particularly around architecture, strategy, and executive alignment. - The ability to navigate ambiguity and deliver high-quality product experiences on tight timelines and in line with our business aspirations. - A bias for action - you’re not afraid to roll up your sleeves, to talk to a customer or to figure out a new way to use AI tools to your advantage. Mechanical Orchard is a remote-first company, with employees working across time zones and locations. This role does not have a requirement for in-office attendance, but is expected to work hours that maximize collaboration with their team (specifics can be discussed during the interview process). There will be travel to company and team meetings, as well as customer visits (1-2 times per quarter, up to ~20% of the time). 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!

• Own the vision and roadmap for AI-driven code generation, defining how our platform accelerates large-scale legacy modernization • Collaborate closely with our forward-deployed engineering teams as well as technical partners to turn real-world modernization challenges into scalable product capabilities • Translate rapidly evolving foundation model capabilities into reliable, enterprise-grade developer experiences • Ensure cross-team alignment of roadmap and technical strategy within the product organization and across Mechanical Orchard • Measure impact, track adoption, code quality, and modernization velocity to guide product decisions • Define quality, reliability, and evaluation standards for AI-generated code • Represent your product internally and externally with executive stakeholders, technical partners and customers • Articulate customer value and benefits of your team’s offering and help position it within an evolving market landscape

• Build, scale, and lead a world-class Product Support organization • Define the support vision and strategy aligned with company and product strategies • Build and mentor a high-performing team of Product Support Specialists, Technical Support Engineers, and Support Operations professionals • Represent Product Support at the leadership level and drive cross-functional initiatives • Establish a customer-obsessed, data-driven, and technically rigorous culture • Design scalable support workflows, escalation paths, and quality standards • Define and manage SLAs/SLOs aligned with customer and partner expectations • Implement support tooling (ticketing, knowledge base, monitoring, automation) • Own support analytics: volume, root causes, trends, friction points, and performance metrics • Partner with Engineering to build automation that reduces repetitive work • Build tight feedback loops between customers and Product • Influence roadmap decisions and collaborate with other teams to improve onboarding and self-serve pathways

Mechanical Orchard is reinventing how the world’s most critical software gets modernized. We’re an applied AI company focused on one of the hardest problems in enterprise technology: rewriting complex legacy systems in a way that is provably correct, low risk, and fast enough to matter. By focusing on system behavior rather than code alone, we turn modernization from a high-stakes, failure-prone effort into a repeatable, confidence-building process that unlocks ongoing innovation. Joining Mechanical Orchard means working on problems that truly matter—to our customers, their businesses, and the people who rely on these systems every day. We’re building technology and methodology that challenge long-standing industry assumptions, prioritizing proof over promises and progress over theatrics. If you care deeply about quality, rigor, and doing the right thing—even when it’s hard—you’ll find your people here. About the Role We’re hiring a Head of Product Support to build, scale, and lead a world-class Product Support organization. This is a strategic leadership role responsible for the full support experience across our product offering. You will define our support vision, build the systems and teams that deliver it, and partner closely with Product, Engineering, Delivery, and Sales to ensure customers experience Mechanical Orchard as reliable, responsive, and deeply technical. You will operate at the intersection of customer experience, product excellence, and operational rigor — shaping how customers interact with our technology and influencing what we build next. This role may be hired at the Senior Manager or Director level, depending on the candidate’s experience, leadership scope, and demonstrated ability to operate at scale. We are open to calibrating title and level for the right person. What You’ll Do Lead and Define the Support Strategy - Own the end-to-end Product Support vision aligned to company and product strategy - Build and mentor a high-performing team of Product Support Specialists, Technical Support Engineers, and Support Operations professionals - Represent Product Support at the leadership level and drive cross-functional initiatives - Establish a culture that is customer-obsessed, data-driven, and technically rigorous Build Scalable Systems and Operations - Design scalable support workflows, escalation paths, and quality standards - Define and manage SLAs/SLOs aligned with customer and partner expectations - Select and implement support tooling (ticketing, knowledge base, monitoring, automation) - Own support analytics: volume, root causes, trends, friction points, and performance metrics - Partner with Engineering to build automation and internal tooling that reduces repetitive work Elevate the Customer Experience - Build tight feedback loops between customers and Product - Influence roadmap decisions based on recurring issues and usage patterns - Collaborate with Documentation and Developer Experience teams to improve onboarding and self-serve pathways - Partner with Sales and Delivery on high-priority accounts and escalations - Drive initiatives that proactively reduce support volume through product quality and education Raise the Technical Bar - Ensure the support organization develops deep product expertise - Build structured training programs to create authoritative technical advisors - Lead post-mortems and embed learnings into product and support systems Required Requirements - 7+ years in Support, Technical Support, Developer Support, or Customer Experience roles, 3+ years leading teams - Experience building or scaling support functions in modern tech environments (SaaS, cloud, AI, developer tooling) - Strong technical fluency (APIs, debugging, cloud platforms, logs/metrics, dev workflows) - Proven ability to operate cross-functionally and influence product direction - Experience with modern support tooling and AI-enabled workflows Preferred Requirements - Experience supporting developer-facing or highly technical products - Experience designing scalable self-serve support models - Background in support operations, quality management, or process engineering - Comfort building systems from scratch in ambiguous, high-growth environments Mechanical Orchard is a remote-first company, with employees working across time zones and locations. This role does not have a requirement for in-office attendance, but is expected to work hours that maximize collaboration with their team (specifics can be discussed during the interview process). There will be travel to company and team meetings, as well as customer visits (1-2 times per quarter, up to ~20% of the time). 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!

• Own the end-to-end Product Support vision aligned to company and product strategy • Build and mentor a high-performing team of Product Support Specialists, Technical Support Engineers, and Support Operations professionals • Represent Product Support at the leadership level and drive cross-functional initiatives • Establish a culture that is customer-obsessed, data-driven, and technically rigorous • Design scalable support workflows, escalation paths, and quality standards • Define and manage SLAs/SLOs aligned with customer and partner expectations • Select and implement support tooling (ticketing, knowledge base, monitoring, automation) • Own support analytics: volume, root causes, trends, friction points, and performance metrics • Partner with Engineering to build automation and internal tooling that reduces repetitive work • Build tight feedback loops between customers and Product • Influence roadmap decisions based on recurring issues and usage patterns • Collaborate with Documentation and Developer Experience teams to improve onboarding and self-serve pathways • Partner with Sales and Delivery on high-priority accounts and escalations • Drive initiatives that proactively reduce support volume through product quality and education • Ensure the support organization develops deep product expertise • Build structured training programs to create authoritative technical advisors • Lead post-mortems and embed learnings into product and support systems