Head of AI Transformation

Description

Who We Are Looking For

The Head of AI Transformation, Engineering & SaaS Operations reports directly to the CTO and serves as a cross-functional transformation leader responsible for accelerating AI adoption across Engineering and SaaS Operations.

This leader will drive the adoption of artificial intelligence across product development and SaaS operations to improve engineering productivity, product quality, operational resilience, customer experience, and cost efficiency.

They will define and execute the strategy for an AI-enabled Product Development Lifecycle (PDLC), embedding AI throughout software engineering, quality assurance, security remediation, incident management, and SaaS support. Working closely with Engineering, Product, SaaS Operations, Security, Finance, and HR leaders, they will establish the roadmap, operating model, governance processes, and workforce capabilities required to realize measurable business value from AI investments.

Success in this role requires a hands-on transformation leader who combines strong engineering credibility with the ability to drive organizational change. The ideal candidate will help Charles River Development evolve its software delivery and SaaS operating model by leveraging AI to increase productivity, accelerate delivery, improve quality, reduce operational effort, and enhance service reliability.

Why this role is important to us

As AI fundamentally reshapes software engineering and operational support, CRD is committed to building an AI-enabled organization that delivers better outcomes for clients while improving efficiency and scalability.

This role will:

Accelerate feature delivery and engineering throughput through AI-assisted development and automation.

Improve product quality through AI-enabled testing, validation, and quality engineering practices.

Reduce engineering effort associated with defects, technical debt, and vulnerability remediation.

Transform SaaS operations through intelligent automation, proactive monitoring, and AI-assisted support workflows.

Reduce operational costs while improving service quality and customer experience.

Establish a measurable roadmap for AI adoption across the software delivery lifecycle.

Enable workforce evolution through new skills, roles, and operating models.

Deliver transparent reporting on adoption, efficiency gains, quality improvements, and business outcomes.

Ensure AI investments deliver measurable return on investment.

What you will be responsible for

AI Strategy & Transformation

Define and execute the enterprise roadmap for AI adoption across Engineering and SaaS Operations.

Assess organizational AI maturity and identify gaps in processes, tooling, governance, skills, and operating models.

Establish adoption goals, success metrics, and transformation plans aligned to business objectives.

Identify emerging AI technologies and evaluate strategic opportunities for adoption.

Engineering Productivity & Software Delivery

Drive adoption of AI-powered software development practices across the entire product development lifecycle.

Apply AI across requirements generation, backlog refinement, architecture, design, development, testing, release management, support, and operations.

Deploy and scale coding copilots, engineering agents, and software delivery automation capabilities.

Improve engineering productivity through automation of repetitive development and maintenance activities.

Accelerate modernization initiatives, including technical debt reduction and code migration programs.

Apply AI-driven approaches to vulnerability management, defect resolution, and security remediation.

Partner with architects and engineering leaders to improve architecture design, governance, and technical decision-making through AI-enabled capabilities.

Quality Engineering Transformation

Establish AI-enabled quality engineering practices across all product teams.

Implement AI-powered test generation, regression testing, quality analysis, release validation, and defect prediction capabilities.

Improve automated test coverage and reduce defect escape rates.

Increase confidence in software releases through AI-assisted quality controls.

SaaS Operations & Support Transformation

Transform SaaS operations through AI-powered observability, anomaly detection, incident prediction, root cause analysis, and automated remediation.

Implement AI-assisted support workflows that improve case triage, knowledge retrieval, investigation, and resolution.

Automate Customer Health Check process after weekend maintenance periods.

Reduce customer-impacting incidents and accelerate issue resolution.

Increase the percentage of issues resolved without engineering intervention.

Establish enterprise knowledge management capabilities that improve engineer and support productivity.

Organizational Change & Workforce Transformation

Define the future operating model for AI-enabled engineering and SaaS operations.

Recommend and lead implementation of organizational, process, and workforce changes required to operate effectively in an AI-enabled organization.

Develop training, enablement, and adoption programs that accelerate AI proficiency across the organization.

Partner with HR and business leaders to support workforce evolution and long-term capability development.

Governance, FinOps & Business Value Realization

Establish governance, risk management, and responsible AI practices.

Manage AI-related budgets, tooling investments, token consumption, infrastructure costs, and vendor relationships.

Develop ROI frameworks that measure productivity, quality, operational efficiency, and cost benefits.

Deliver executive dashboards that provide transparent reporting on adoption, outcomes, risks, and realized value.

Success metrics

Success in this role will be measured through improvements in:

Engineering Productivity: Engineering throughput, Feature cycle time, Deployment frequency, Lead time for change, AI-assisted work percentage, AI-generated code acceptance rate, Pull request review cycle time, Developer onboarding time

Quality & Security: Defect escape rate, Automated test coverage, Vulnerability remediation cycle time, Release quality metrics, Technical debt reduction

SaaS Operations: Mean Time to Detect (MTTD), Mean Time to Resolution (MTTR), Customer-impacting incident rate, Proactive issue detection rate, Automated remediation rate, Incident recurrence rate, Support cases resolved without engineering intervention

Adoption & Workforce Enablement: AI adoption and maturity by team, Percentage of lifecycle activities supported by AI, Employee proficiency and adoption metrics

Financial Outcomes: Productivity gains realized, Engineering capacity created through automation, Capacity released or staffing demand avoided, Cost per resolved incident, AI expenditure by team and use case, Return on AI investment

What we value

These skills and leadership characteristics will help you succeed in this role:

Proven success leading large-scale engineering, technology, or operational transformation initiatives.

Strong program leadership skills with the ability to drive change across multiple organizations simultaneously.

Experience influencing senior technology and business leaders and building alignment across competing priorities.

Demonstrated ability to translate emerging technologies into measurable business outcomes.

Strong understanding of modern software engineering practices, including cloud-native architectures, CI/CD, DevSecOps, observability, platform engineering, and site reliability engineering.

Experience implementing AI-enabled software development, testing, operational support, or automation capabilities.

Strong commercial mindset with experience establishing business cases, KPI frameworks, and ROI models.

Experience leading Engineering Productivity, Developer Experience (DevEx), Platform Engineering, DevOps, or SRE initiatives.

Excellent communication and executive presentation skills, with the ability to translate technical concepts into business value.

Consultative and collaborative leadership style, with the ability to influence without direct authority.

Strong people leadership, coaching, and talent development experience.

Hands-on technical background with the ability to engage credibly with engineers, architects, and operational teams.

Ability to operate comfortably at both strategic and tactical levels.

Education & Preferred Qualifications

Bachelor's degree in Computer Science, Engineering, or a related technical field.

Advanced degree preferred.

15+ years of experience in software engineering, platform engineering, SaaS operations, engineering productivity, DevOps, SRE, or related technology leadership roles.

5+ years leading engineering organizations or enterprise transformation initiatives.

Experience in investment management, capital markets, fintech, enterprise SaaS, or other highly regulated industries preferred.

Experience leading enterprise-wide adoption of AI-enabled software development, quality engineering, or operational support practices.

Familiarity with modern AI technologies, including GenAI platforms, engineering copilots, agent frameworks, MCP ecosystems, and AI orchestration platforms.

Understanding of LLMs, vector databases, AI infrastructure, and modern AI architectures sufficient to guide technology strategy, platform selection, and adoption decisions.

Experience evaluating AI platforms, vendors, and strategic technology partnerships.

Experience managing cloud cost optimization, FinOps initiatives, or large-scale technology investment programs.

Proven experience delivering large-scale software platforms and operating technology environments with demanding availability, scalability, and performance requirements.

Conditions

$170,000 - $282,500 Annual

The range quoted above applies to the role in the primary location specified. If the candidate would ultimately work outside of the primary location above, the applicable range could differ.

Employees are eligible to participate in the company’s comprehensive benefits program, which includes: our retirement savings plan (401K) with company match; insurance coverage including basic life, medical, dental, vision, long-term disability, and other optional additional coverages; paid-time off including vacation, sick leave, short term disability, and family care responsibilities; access to our Employee Assistance Program; incentive compensation including eligibility for annual performance-based awards (excluding certain sales roles subject to sales incentive plans); and, eligibility for certain tax advantaged savings plans.

For a full overview, visit the company's site .

About the company

We keep our clients at the heart of everything we do, and smart, engaged employees are essential to our continued success.

We are committed to fostering an environment where every employee feels valued and empowered to reach their full potential. As an essential partner in our shared success, you’ll benefit from inclusive development opportunities, flexible work-life support, paid volunteer days, and vibrant employee networks that keep you connected to what matters most. Join us in shaping the future.

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Job Application Disclosure:

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.