Fractional Director, Enterprise Technology Transformation

Job not on LinkedIn

🕒 October 23

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

⏳ Contract/Temporary

🔴 Lead

👔 Director

👻 Ghost score 17%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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BrainyYack

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2006

🤖 Artificial Intelligence

💼 Consulting

🏢 Enterprise

Artificial Intelligence • Consulting • Enterprise

BrainyYack is an AI-focused digital transformation and engineering consultancy that helps organizations move AI from strategy to production. They design and deploy purpose-built AI agents and intelligent assistants, build automation pipelines and enterprise integrations (including custom LLM integrations), and provide AI data compliance, governance, and legacy modernization services. Their offerings include AI workforce assessment, workflow automation, change management, and custom software/enterprise platform engineering to embed AI into existing workflows and systems for measurable operational impact.

📋 Description

• Lead the execution of enterprise-wide technology modernization programs • Oversee legacy application modernization, platform migrations, cloud transformation, and systems integration • Translate target-state architecture into executable delivery plans with enterprise architects and engineering teams • Identify opportunities to consolidate, retire, replace, or modernize existing applications • Manage dependencies across applications, infrastructure, cybersecurity, data, and operations • Lead transitions of selected internal IT functions into externally managed service models • Assess IT operations, staffing, responsibilities, service levels, and operating costs • Develop transition plans covering knowledge transfer, service continuity, governance, and operational readiness • Support IT operating model redesign and execute transitions with minimal business disruption • Own integrated transformation roadmaps, 30/60/90-day execution plans, and longer-term initiatives • Coordinate delivery workstreams across engineering, cloud, infrastructure, data, security, AI, and IT operations • Manage budgets, resources, timelines, risks, dependencies, and delivery commitments • Establish governance, reporting, and escalation processes • Identify opportunities to reduce manual work, simplify processes, and improve IT productivity • Collaborate with AI and automation specialists to implement high-value opportunities • Establish baseline operating costs and measure efficiency gains, business benefits, and cost savings • Serve as senior point of contact for client executives and IT leadership • Communicate transformation progress, risks, decisions, and financial impact • Navigate competing stakeholder priorities and lead cross-functional teams without direct authority over every resource • Work collaboratively with Brainyyack's Chief Architect, CTO, and delivery leadership

🎯 Requirements

• 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 in insurance, financial services, or other regulated enterprise environments • Preferred experience with application portfolio rationalization and legacy platform modernization • Preferred experience with IT operating model redesign and managed-services transitions • Preferred experience with AWS, Azure, hybrid cloud, and enterprise integration environments • Preferred experience with AI-enabled operational transformation and intelligent automation • Experience working with both internal enterprise IT organizations and external technology delivery partners

🏖️ Benefits

• 6-month contract may lead to permanent • Occasional travel to client locations in the United States

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