GenAI Implementation Lead

Company Overview

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.
Our seasoned professionals deliver services based on Milestone’s best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Job Overview

Milestone’s Data & AI Practice is seeking an experienced Principal Consultant to champion GitHub Copilot and other DevAI initiatives—whether driving a full end-to-end implementation, leading a targeted POC, or conducting a course correction assessment on an existing deployment. You’ll provide hands-on leadership to a dedicated, cross-functional team while partnering closely with clients to tailor and execute change management and technical strategies. Through strategic refinement of our proven, risk-aware methodology, you’ll uncover adoption gaps, drive experimentation, and surface data driven insights that deliver lasting, measurable transformation.

Key Responsibilities

In this role, you’ll lead our dual-track adoption model - empowering developers with frictionless onboarding, prompt fluency, champion networks, and habit building, while equipping leaders with governance frameworks, manager coaching, vendor alignment, and KPI visibility. Collaborating closely with client stakeholders and your dedicated project team, driving a data-driven, iterative approach to secure lasting transformation.

• Lead Phased Implementations & Assessments
• Drive full end-to-end Copilot rollouts, targeted POCs, or course-correction assessments using our risk-aware, iterative methodology.
• Lead each phase: Preparation, Pilot, Scale, Hypercare, and Risk Mitigation ensuring tailored enablement, telemetry setup, and continuous refinement.
• Design and facilitate workshops and pilots tailored to diverse, geographically dispersed developer personas.
• Facilitate analysis sessions to surface blockers, validate assumptions, and adjust the rollout plan.
• Provide Hands On, White Glove Client Partnership
• Customize and iterate surveys, enablement materials, and pilot designs to fit the client’s environment.
• Lead and facilitate workshops, office hours with both managers and developers to drive alignment, share best practices, and build momentum.
• Maintain high-touch engagement with executive sponsors, core teams, and vendor partners to align on goals and remove blockers.
• Orchestrate & Execute Organizational Change Management
• Design and execute a holistic OCM strategy: sponsorship alignment, communications, role-based training, and community of practice establishment.
• Prepare for and facilitate workshops, office hours, champion network meetups, hackathons and community of practice engagements.
• Ensure knowledge transfer through playbooks, training kits, and CoE enablement to embed sustainable, self-service capabilities.
• Lead Change Control Board sessions, risk-register reviews, and lessons-learned workshops to sustain momentum and guardrails.
• Define & Manage Metrics, Reporting & Financial Models
• Architect telemetry and survey frameworks, build executive dashboards, and translate data into adoption, productivity, and compliance insights.
• Lead reporting-results reviews with client stakeholders, translating data into actionable insights.
• Co-develop business cases and outcome-based contract milestones, linking behavior change to cost savings and ROI targets.
• Enable Governance & Vendor Alignment
  • Serve as the primary consultant liaison for client sponsors, procurement, security, and IT leadership.
  • Provide guidance on embedding GitHub Copilot performance and governance KPIs into vendor SLAs/SOWs; manage escalations and risk mitigation.
• Drive Innovation & Experimentation
• Stay abreast of emerging DevAI features and technologies.
• Guide POCs on emerging DevAI tools and expanded use cases, balancing stability with forward-looking pilots.
• Maintain an Innovation Roadmap to integrate new features and best practices into the enterprise DevAI program.
• Mentorship & Practice Evolution
• Guide and coach project managers, business analysts, and data/reporting leads on agile delivery, DevAI best practices, and stakeholder engagement.
• Contribute lessons learned and insights back to Milestone’s Data & AI Practice to help refine our DevAI methodology, templates, and playbooks for continuous improvement.

Qualifications

• 8+ years of consulting or in-house delivery leadership in software engineering, DevOps, or AI/analytics (consulting experience highly desirable)
• Hands-on expertise with GitHub Copilot and AI-assisted development—IDE integration, prompt engineering, and SDLC/DevSecOps pipelines
• Experience managing developer ecosystems—toolchains, CI/CD pipelines, and governance—in highly regulated industries (e.g. insurance, financial services, healthcare)
• Proven success in organizational change management: stakeholder alignment, community-of-practice formation, and workshop facilitation
• Experience engaging diverse, geographically dispersed developer personas
• Proven track record leading targeted POCs and course-correction assessments
• Strong change-management and community of practice facilitation skills
• Deep experience in designing telemetry architectures and translating data into strategic insights
• Demonstrated success in diagnostic assessments—surveys, telemetry, gap analysis, and best-practice benchmarking
• Proven ability to lead POCs and experimentation on emerging DevAI tools and frameworks
• Excellent stakeholder management, communication, and presentation skills at executive levels
• Comfort with vendor engagement, contractual frameworks, and outcome-based delivery models
• Track record of contributing to and refining consulting methodologies and best practices within a Data & AI practice
• Bachelor’s in Computer Science, Engineering, or related field

Compensation

Estimated Pay Range:
Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.

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