Fractional Director, Enterprise Technology Transformation

Director, Enterprise
Technology Transformation
Company: Brainyyack
Location: Remote – North America (Canada or US preferred)
Employment Type: 6-month contract may lead to permanent
Reports To: CTO
Travel: Occasional travel to client locations in the United States
About Brainyyack. Brainyyack is a technology and AI engineering consultancy helping
organizations modernize enterprise systems, improve operational eGiciency, and
implement technology-driven transformation.
We work directly with executive teams to translate complex business challenges into
practical technology solutions, combining enterprise architecture, software engineering,
cloud infrastructure, AI, automation, and managed services.
About the Role
We are seeking an experienced Director, Enterprise Technology Transformation to lead
complex enterprise modernization and IT transformation programs.
Our immediate priority is a large-scale transformation engagement with a US-based
enterprise organization. The program involves modernizing legacy applications and
infrastructure, improving operational eGiciency, introducing AI and automation, and
transitioning selected internal IT functions into a managed-services delivery model.
We are looking for someone who has successfully led similar transformations from
planning through execution.
This is not a traditional project management or advisory role. We need a hands-on
transformation leader who understands enterprise technology environments, can
coordinate multidisciplinary technical teams, manage complex migrations, and deliver
measurable business outcomes.
Key Responsibilities

• Enterprise Technology Modernization
• Lead the execution of enterprise-wide technology modernization programs.
• Oversee legacy application modernization, platform migrations, cloud

transformation, and systems integration.

• Work with enterprise architects and engineering teams to translate target-state

architecture into executable delivery plans.

• Identify opportunities to consolidate, retire, replace, or modernize existing

applications.

• Manage dependencies across applications, infrastructure, cybersecurity, data, and

operations.

• IT Transformation & Managed Services Transition
• Lead the transition of selected internal IT functions into externally managed service

models.

• Assess existing IT operations, staGing, responsibilities, service levels, and operating

costs.

• Develop transition plans covering knowledge transfer, service continuity,

governance, and operational readiness.

• Support the redesign of IT operating models to improve eGiciency and

accountability.

• Ensure transitions are executed with minimal business disruption.
• Program Leadership & Execution
• Own integrated transformation roadmaps, including 30/60/90-day execution plans

and longer-term modernization initiatives.

• Coordinate multiple delivery workstreams involving engineering, cloud,

infrastructure, data, security, AI, and IT operations.

• Manage project budgets, resources, timelines, risks, dependencies, and delivery

commitments.

• Establish governance, reporting, and escalation processes.
• Ensure technical initiatives move from assessment into implementation and

measurable results.

• Operational EOiciency & Automation
• Identify opportunities to reduce manual work, simplify processes, and improve IT

productivity.

• Collaborate with AI and automation specialists to prioritize and implement high-

value opportunities.

• Establish baseline operating costs and measure realized eGiciency gains.
• Translate modernization initiatives into quantifiable business benefits and cost

savings.

• Executive & Stakeholder Leadership
• Serve as a senior point of contact for client executives and IT leadership.
• Communicate transformation progress, risks, decisions, and financial impact.
• Navigate complex organizational environments and competing stakeholder

priorities.

• Work collaboratively with Brainyyack's Chief Architect, CTO, and delivery

leadership.

• Lead cross-functional teams without requiring direct authority over every

participating resource.
Required Qualifications

• 10–15+ years of experience in enterprise technology delivery, IT transformation, or

modernization.

• Demonstrated leadership of large, complex enterprise migrations or modernization

programs.

• Experience transitioning internal IT functions to managed-services or outsourced

delivery models.

• Strong understanding of enterprise applications, cloud infrastructure, systems

integration, cybersecurity, and data platforms.

• Proven experience managing multiple concurrent technical workstreams.
• Experience overseeing significant transformation budgets and distributed teams.
• Strong commercial awareness, including resource planning, vendor management,

cost optimization, and ROI.

• Excellent executive communication and stakeholder management skills.
• Ability to translate technical complexity into actionable business decisions.

Preferred Experience

• Insurance, financial services, or other regulated enterprise environments.
• Application portfolio rationalization and legacy platform modernization.
• IT operating model redesign and managed-services transitions.
• AWS, Azure, hybrid cloud, and enterprise integration environments.
• AI-enabled operational transformation and intelligent automation.
• Experience working with both internal enterprise IT organizations and external

technology delivery partners.
What Success Looks Like
First 30 Days

• Establish an integrated modernization and IT transition delivery plan.
• Validate priorities, resource requirements, dependencies, and risks.
• Establish baseline costs, service performance, and measurable outcomes.

First 60 Days

• Lead initial modernization initiatives and prioritized operational transitions.
• Establish eGective governance across all delivery workstreams.
• Demonstrate measurable progress on eGiciency and service improvements.

First 90 Days

• Deliver initial modernization milestones and operational improvements.
• Establish stable managed-services operations for approved transitioned functions.
• Demonstrate progress against cost, capacity, service quality, and eGiciency targets.
• Present an executable roadmap for subsequent transformation phases.

Ideal Candidate
You have led complex enterprise technology transformations and understand what it takes
to move from strategy to execution.
You are comfortable working directly with executive leadership while remaining close
enough to the technology to challenge assumptions, resolve delivery obstacles, and
coordinate technical teams.
You bring the discipline of enterprise consulting with the practical execution experience of
a technology services organization