Head of Professional Services

Klass; Toronto; On-site; CAD 120,000 - 160,000; Full time

Job summary

A technology services company is seeking a Head of Professional Services to lead their team in delivering high-quality engagements. The ideal candidate will have over 10 years of experience in enterprise professional services, with a proven record in leadership and stakeholder management. This hybrid role is based in Toronto and requires strategic alignment with customer success. Competitive salary and performance bonuses offered.

Benefits

Competitive annual base salary

Performance bonus

Extended health/dental benefits

Learning budget for professional development

Flexible/Hybrid work model

Qualifications

• 10+ years in enterprise professional services or consulting services required.
• 5+ years in a leadership role essential.
• Experience in developing proposals and SOWs during pre-sales.

Responsibilities

• Deliver engagements with on-time and on-budget metrics.
• Manage and grow the Professional Services team effectively.
• Align with Customer Success for client renewals and follow-on work.

Skills

Enterprise professional services experience

Leadership in technical delivery teams

Executive presence with c-level customers

Stakeholder management

Strong communication skills

Job description

Job Description

Job Description

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 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

Requirements

• 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

Benefits

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 developmentFlexible / Hybrid work model