The Head of Product Support will lead the Product Support organization, defining support strategies, building scalable systems, and enhancing customer experience while managing a team of support professionals.
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!
Top Skills
Ai-Enabled Workflows
APIs
Cloud Platforms
Support Tooling
Similar Jobs
.png){kind=logo}
AdTech • Cloud • Digital Media • Information Technology • News + Entertainment • App development
The Product Manager will oversee data product strategy, ensuring alignment with business objectives, and work closely with stakeholders to enhance data quality and analytics solutions.
Top Skills:
AIBi ToolsCloud Data WarehousesConfluenceData EngineeringJIRASQL
AdTech • Cloud • Digital Media • Information Technology • News + Entertainment • App development
The Senior Cyber Security Engineer will conduct security analysis for technology deployments, ensuring secure integration of Cyber Security best practices and guidelines.
Top Skills:
Application SecurityCis ControlsCloud SecurityCyber SecurityEdrMitre Att&CkNetwork SecurityNist GuidelinesOwasp
Fintech • Machine Learning • Payments • Software • Financial Services
As a Unit Manager, you will lead and develop a team, ensuring high customer service standards and managing performance metrics.
Top Skills:
Google SuiteMS Office
What you need to know about the Calgary Tech Scene
Employees can spend up to one-third of their life at work, so choosing the right company is crucial, not just for the job itself but for the company culture as well. While startups often offer dynamic culture and growth opportunities, large corporations provide benefits like career development and networking, especially appealing to recent graduates. Fortunately, Calgary stands out as a hub for both, recognized as one of Startup Genome's Top 100 Emerging Ecosystems, while also playing host to a number of multinational enterprises. In Calgary, job seekers can find a wide range of opportunities.
