Head of Product & Engineering

Role Overview: The Head of Product & Engineering will lead our AI-driven transformation efforts across acquired portfolio companies - owning the end-to-end strategy and execution roadmap to transition legacy platforms into modern, scalable cloud-native infrastructures. This senior role encompasses technical due diligence, the creation of AI transformation blueprints, and the orchestration of strategic execution. The ideal candidate combines deep technical expertise with a bias for execution, and a strong understanding of operational scale, compliance, and product leadership in regulated sectors. We are seeking a hands-on leader with a proven track record of driving successful enterprise transformations—who thrives on leading execution from the front and continues to be energized by rolling up their sleeves to deliver outcomes.

Responsibilities:

• Technical Due Diligence: Lead technical assessments during acquisition phases, evaluating target software platforms for modernization potential, AI readiness, and identifying technical debt, transformation levers, and modernization risks.
• Transformation Blueprint Development: Design, develop, and drive detailed architecture transformation plans, outlining the roadmap for transitioning from legacy systems to cloud-native, AI-enhanced platforms. Translate architectural assessments into execution-ready blueprints that evolve legacy software into modern platforms. Establish milestones that can be measured against once the blueprint is rolled out. Leverage AI driven productivity gains.
• Strategic Execution: Drive and manage the execution of AI-enabled modernization, including cloud migration, AI model deployment, feature integration, workflow automation, and advanced analytics deployment. Coordinate with internal transformation teams, strategic hyperscaler partners, and specialized consultancies to ensure rigorous, scalable, and compliant AI implementation.
• Stakeholder Alignment and Change Management: Lead structured, cross-functional engagement to align technical and business leaders around roadmap execution—translating complex transformation plans into shared operating narratives, driving sustained buy-in, managing change adoption, and anchoring delivery to measurable milestones. Champion organizational and technical change management across people, process, and platform to rally teams and executives around a shared modernization vision.
• AI Integration at two levels: (a) user-facing features (LLM agents, predictive analytics, dynamic workflows), and (b) engineering acceleration (codegen, test automation, AI copilots).
• AI Innovation and Thought Leadership: Continuously identify and evaluate emerging AI technologies, methodologies, and best practices that enhance our competitive advantage and operational efficiency. Provide thought leadership internally and externally on AI-driven value creation.
• Talent Leadership: Build, mentor, and lead high-performing AI and data teams,responsible for executing complex modernization initiatives, instilling technical rigor, delivery discipline, and a culture of AI-driven innovation, quality, and continuous improvement. Ensure alignment with our strategic objectives, while serving as a visible champion of transformation across senior leadership, engineering, and operations. Drive change within the teams to leverage productivity gains by using AI enabled tools.
• Execution Accountability: Operate with clear ownership over transformation delivery, holding both internal teams and external partners accountable to milestones, quality, and outcomes.
  

Qualifications:

• Extensive experience in leading modernization in vertical software, ideally within Financial Services, Payments, Insurance, or other regulated sectors.
• Proven ability to architect and lead modernization strategies, aligning executive, product, and technical stakeholders around a shared transformation roadmap.
• Proven ability to lead multi-phase transformation programs from blueprint to scaled adoption, maintaining momentum through complexity.
• Proven track record in conducting technical due diligence, AI readiness assessments,and translating findings into actionable transformation blueprints.
• Deep technical knowledge of cloud-native AI architectures, AI model integration, ML operations, and data-driven workflow design.
• Track record of mobilizing cross-functional teams and individuals and managing strategic partnerships to deliver complex transformation programs.
• Demonstrated ability to deliver outcomes that enhance product differentiation, accelerate time-to-market, or unlock new revenue opportunities.
• Excellent strategic, analytical, and communication skills with a proven ability to deliver impactful business outcomes.
• Experience establishing and leading governance forums (e.g., transformation steering committees, Data and AI Centers of Excellence) to ensure consistent alignment, visibility, and accountability.
• Consistently applying and advancing leading-edge AI practices, with a demonstrated ability to adapt to emerging technologies and translate innovation into operational impact.
• Exceptional strategic, analytical, and communication skills, with a focus on delivering measurable business outcomes.