Head of Product Support

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