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 up-to-date 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!

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📌 Head of Product Support (Manitoba)
🏢 Mechanical Orchard
📍 Manitoba