CTO Engagements

On-demand technology leadership for startups or strategic large-enterprise projects. I guide early and growth-stage teams to smart technical decisions that accelerate time-to-market, reduce risk, and support scalable growth. I also help large enterprises modernize legacy applications, rationalize technology portfolios, and successfully navigate complex, high-stakes technical projects.

  • This retainer-based service provides flexible, executive-level technology guidance to help CEOs, product owners, and technology leadership navigate complex technical decisions. This service delivers rapid feedback, strategic direction, or input on urgent or high-impact topics – ideal for companies who only need executive technology experience on an ad-hoc basis. It’s also valuable for larger companies who want to augment their strategic thinking with outside expert perspective. Every session is focused on moving the business forward — helping leadership teams make better technology decisions, faster.

  • A fractional executive technology leadership engagement for startups and larger enterprises organizations that need CTO-level guidance without the time, cost, and risks of hiring a permanent executive.  I bring strategic value within the technology organization and across other business functions. As Interim CTO, I support existing technology teams, guide technology direction, interface with the board and investors, engage strategic customers on high-level issues, and ensure technology roadmaps support business growth, and scale, and future financings. Key to my interim CTO engagements is using my experience with your organization to help you find, recruit, and integrate a permanent CTO - but only when your company is ready.

  • A focused, high-impact engagement designed to ensure that product and technology roadmaps are aligned and able to support broader business objectives. By evaluating the relationship between revenue goals, customer scale, feature evolution, and technical architecture, this service identifies gaps, inefficiencies, and opportunities — and ensures your technology roadmap can support the business you’re building. This isn’t a code review or a roadmap workshop – it’s a strategic process that connects your product vision and business targets with the technical foundation required to deliver both.

  • A structured engagement that identifies opportunities to improve a product's underlying technical architecture. These efforts are undertaken at pivotal moments in a product's lifecycle such as post-prototype, in preparation for business scaling, or during a critical refactoring effort. This service establishes a new technical baseline capable of supporting rapid business growth, improved gross margins, and minimized future technical challenges.

  • A technical advisory or leadership engagement designed to help organizations confidently navigate cloud transformation. It’s not just about choosing the right cloud providers — it’s about designing the right path to get business, product, and engineering teams aligned on what cloud adoption really means and how to do it well. Whether you’re lifting-and-shifting legacy servers, migrating applications to SaaS, or modernizing proprietary applications, this engagement delivers the clarity, strategy, and technical insight to move forward with confidence.

  • Create, troubleshoot, or expand DevOps / DevSecOps capabilities that align with your engineering culture and technology profile. This service delivers an assessment of current state, recommended future state, and a DevOps roadmap to start moving forward. Areas of focus typically include current staffing, skills & practices; alignment of tools to processes; and implementation of tooling like version control, CI/CD pipelines, test automation, IaC tooling, configuration management, monitoring & observability, and secrets management.

  • An in-depth, cross-functional analysis of how your technology, product, and security organizations are structured, how they operate, and how effectively they support the business today and ongoing.  It’s not about seeking change for the sake of change – it’s about ensuring the right people, processes, and structures are in place to support your business model, velocity, and ambition. This service provides a clear, executive-level understanding of organizational health, identifies structural strengths and weaknesses, and offers actionable recommendations to align teams with growth, innovation, and delivery goals.

  • A strategic engagement designed to help mid-sized and large enterprises assess, streamline, and modernize their technology application portfolios. As organizations grow, their technology portfolios often become bloated, fragmented, and difficult to manage. This is especially true when companies grow via acquisition or encounter frequent unsanctioned technology purchases (shadow IT). This service provides a clear path to reduce redundancy, cut costs, and improve operational efficiency across the enterprise. It’s a top-down analysis that connects business goals with real-world portfolio strategy, helping you optimize without chaos.

The descriptions below help clarify how companies most often leverage my experience. If you’d like more specifics, contact me with your requirements and I’ll share relevant engagement plans as a starting point.

Common Engagement Scopes