Executive CTO Advisor, M & A Transaction Services

West Monroe•Chicago, IL

10d•$275,000 - $343,700•Hybrid

About The Position

West Monroe is seeking an M&A Transaction Services (MTS) Executive CTO Advisor to join our Technology & Experience (TechEx) practice. This executive-level technology leader partners with private equity firms, corporate development teams, and C-suite executives to evaluate software companies and technology-enabled businesses throughout the M&A lifecycle and to drive value creation in portfolio companies after close. Serving as a trusted advisor, the Advisor shapes investment decisions by assessing software products, AI capabilities, engineering organizations, enterprise architecture, and technology operating models, then translating those findings into practical roadmaps and leading teams through software and data platform transformations. This role combines deep technical expertise with commercial acumen to lead complex engagements, originate new client opportunities, and advance West Monroe's Software & AI transaction advisory and value creation capabilities.

Requirements

Bachelor's degree in Computer Science, Engineering, Information Systems, or a related field, or equivalent professional experience.
15+ years of experience in software engineering, enterprise architecture, product engineering, technology advisory, or related leadership roles, including leadership of complex client engagements, technology implementations, or internal technical teams.
Deep expertise evaluating and leading initiatives associated with software products, engineering organizations, enterprise architecture, cloud platforms, AI-enabled applications, and technology operating models.
Experience advising private equity firms, strategic acquirers, or corporate clients on software and technology due diligence, technology strategy, digital transformation, or portfolio value creation initiatives.
Demonstrated expertise in generative AI, agentic AI, large language models (LLMs), orchestration frameworks, AI governance, and emerging AI technologies.
Strong understanding of AI-enabled software engineering and agentic development across the SDLC, with experience using AI to improve engineering productivity, software quality, delivery, and developer workflows.
Proven success originating business, leading executive client relationships, shaping large pursuits, and delivering strategic technology advisory services and implementation programs.
Exceptional executive communication, facilitation, and presentation skills with the ability to influence senior business and technology leaders.
Experience integrating AI tools (e.g., ChatGPT) into day-to-day workflows to enhance productivity and insight generation, coupled with strong critical thinking to assess accuracy, mitigate bias, and ensure high-quality outputs.
Ability to travel 25 to 50%.
Hybrid role with 2+ days per week in a West Monroe office.
A commitment to inclusion and diversity, and openness to new ideas and perspectives.
Ability to work permanently in the United States without sponsorship.

Responsibilities

Serve as the executive advisor for complex software and AI technology due diligence engagements, guiding clients through acquisitions, divestitures, carve-outs, integrations, and strategic investments.
Evaluate software platforms, product architecture, AI capabilities, engineering organizations, cloud environments, and technology operating models to assess scalability, security, product maturity, and operational readiness.
Evaluate AI-enabled and agentic software development practices across the SDLC, advising clients on how coding agents, AI-assisted engineering workflows, and emerging development models can accelerate delivery, improve quality, and reshape engineering organizations.
Advise executive stakeholders on technology risk, AI strategy, engineering effectiveness, product roadmaps, and value creation opportunities that support investment theses and post-close transformation, including prioritization of implementation investments and measurable business outcomes.
Lead multidisciplinary teams across software engineering, cloud, cybersecurity, infrastructure, and data to deliver integrated technology assessments, implementation roadmaps, and strategic recommendations.
Develop executive-level presentations and board-ready deliverables that translate complex technical findings into actionable business decisions and secure alignment around implementation priorities.
Leverage AI tools to accelerate analysis, synthesize complex information, and support data-driven recommendations for clients, exercising sound judgment in evaluating outputs.
Lead or oversee technology implementation programs within portfolio companies, including software platform modernization, data platform implementation, AI enablement, and post-close transformation initiatives, from roadmap through execution, adoption, and benefits realization.
Apply AI technologies (e.g., generative AI, automation tools, data models) to enhance insights, improve delivery efficiency, and elevate the quality of client outcomes.
Originate and grow executive relationships with private equity firms, strategic investors, and corporate technology leaders, serving as a trusted advisor throughout the deal lifecycle.
Lead complex pursuits, shape solution strategies, and develop compelling proposals that position West Monroe's Technology capabilities in the marketplace.
Identify and lead follow-on opportunities in technology modernization, software and data platform implementations, AI strategy, post-merger integration, and technology separation.
Build West Monroe's market presence through thought leadership, speaking engagements, industry events, publications, and strategic alliance relationships.
Define and evolve West Monroe's Software & AI transaction advisory offerings, methodologies, and intellectual property.
Mentor and develop consultants, architects, and technical leaders while fostering a culture of innovation, collaboration, and technical excellence.
Lead the development of reusable AI assessment frameworks, software due diligence accelerators, and delivery of assets that improve quality and scalability.
Partner with practice leadership to recruit top talent, expand technical capabilities, and drive the continued growth of the Mergers & Transaction Services practice.