Head of Professional Services

Role: Head of Professional Services (DevOps & AI Tools/Platforms)

Company: iTmethods,

Location: GTA (hybrid - approx. 1 day per week)

Reports to: Chief Revenue Officer (CRO) 

Type: Full-time / Permanent

Travel: Up to 30%

About iTmethods

iTmethods is a profitable, founder-led company, helping large enterprises run DevOps toolchains and AI workspaces securely in their own clouds. Our iTmethodsONE platform standardizes tools on AWS/Azure with a focus on security, compliance, and AI-native delivery. We partner with leading ISVs and hyperscalers to accelerate time to value.

iTmethods enables enterprises to excel in their digital transformation journeys through expert professional services and cutting-edge managed platforms. Our offerings include strategic consultation, expert implementation, toolchain integration, and extensive ongoing support options. Our solutions address key challenges in DevOps and AI/ML deployments and ongoing operations, security, and compliance, ensuring maximum return on technology investments.

Opportunity

We are hiring a hands-on Professional Services leader to scale the services department, deliver high-quality engagements, and tie services to client retention and growth. This position will be the the head of the professional services department. Success in the role will include on-time/on-budget delivery, strong utilization and gross margin, and development of new offerings. If you are interested in owning the professional services practice, leading and growing a client delivery team, building out services offerings and playbooks, and working on pre-sales initiatives with the CRO, then this opportunity is for you.

Responsibilities

• Deliver engagements predictably: ensure scope, acceptance criteria, and change-order discipline; target on-time/on-budget at 90% or better.
• Productize services: keep custom work to at most 15%; harvest deliverables into reusable products, playbooks, and adapters.
• Lead the Professional Services business: forecast accurately; manage utilization and billable realization; improve gross margin; reduce bench and revenue leakage.
• Lead, manage and grow the team: build an on/offshore staffing model; coach p/s consultants and managers; set quality bars and delivery standards.
• Drive sales and expansion: co-sell with the CRO; align with Customer Success on client QBRs and renewals; translate business outcomes into follow-on work.
• Partner alignment: shape offers with AWS/Azure and key ISVs; co-present on pursuits; support joint wins and accelerators.
• AI-native efficiency: use AI-assisted proposals and SOWs; codify delivery templates

First 90-day Outcomes

• Development of a services catalog (v1) with clear pricing/estimation guardrails
• Forecasting hygiene in place (weekly cadence); utilization and realization dashboards live
• SOW templates and change-order process standardized; proposal turnaround time reduced
• Customer activations delivered on time and on budget; referenceable outcomes documented

• A minimum of 10+ years of experience working in enterprise professional services or consulting services 
• Experience working for a software/platform company or a 3rd party integrator/consulting company
• A minimum of 5+ years of prior experience in a leadership role
• Proven ownership of resource planning, utilization, forecasting, gross margin, and delivery quality
• Executive presence with c-level / enterprise customers; stakeholder management skills and strong negotiation and escalation management skills
• Proven success managing technical delivery teams, implementation consultants and client facing engagements
• Strong leadership and people management capabilities with prior experience growing teams
• Prior experience developing proposals and SOWs during the pre-sales stage
• Track record of productizing services and reducing custom work while improving outcomes is an asset
• Clear, concise written communication skills; strong cross-functional alignment with Sales, Product, and Engineering departments

Nice to have

• DevOps toolchains and platform engineering exposure
• Familiarity with regulated enterprise environments
• Experience with Professional Services automation: proposal tooling, SOW hygiene, delivery playbooks, accelerators
• Comfort with AI-assisted workflows for proposals and delivery documentation
• Background in single-tenant or air-gapped deployments

The company offers team members multiple benefits, including the following:

• Competitive annual base salary plus an annual performance bonus
• Extended health/dental benefits plan
• Learning budget for professional development
• Flexible/Hybrid work model