Principal | Technology Due Diligence & Private Equity

About Cuesta Partners Cuesta Partners is a boutique technology consulting firm supporting private equity firms and their portfolio companies in creating lasting technological advantage. We deliver pragmatic, tech-focused strategy and execution across the entire deal lifecycle, from pre-close diligence through post-close transformation. Job Overview We are seeking an experienced and results-driven Technology Due Diligence & Private Equity Practice Principal to lead and drive high-impact, fast-paced engagements in the technology and M&A advisory space. This role is designed for a dynamic professional with a strong background in technology due diligence, mergers and acquisitions, and private equity consulting. The ideal candidate will have experience managing buy-side and sell-side due diligence processes, providing critical insights into technology assets, IT systems, cybersecurity, and overall digital value creation for our private equity clients. This position requires deep expertise in evaluating technology risks and opportunities, combined with strong leadership skills and a client-centric mindset. Key Responsibilities Lead Technology Due Diligence : Manage and execute comprehensive technology due diligence assessments for M&A transactions, evaluating IT systems, software architecture, cloud infrastructure, cybersecurity, data management, and overall scalability for private equity and corporate clients. Oversee day-to-day work of the Cuesta deal team to ensure high-quality and timely client deliverables. Client Advisory : Serve as the primary point of contact for private equity clients and deal teams, delivering strategic recommendations based on detailed technical assessments. Provide insights into technology risks and opportunities to support informed investment decisions. Private Equity Support : Work closely with private equity partners to evaluate technology's role in post-transaction integration, value creation, and growth strategies, ensuring technology assets align with overall investment objectives. Technology Risk Management : Identify potential risks, including cybersecurity vulnerabilities, technical debt, software scalability issues, and integration challenges, and propose actionable mitigation strategies for clients. Industry Expertise : Stay up to date on the latest trends and advancements in enterprise technology, artificial intelligence, digital transformation, cybersecurity, and cloud computing to deliver relevant and insightful guidance to clients. Business Development : Support business development initiatives by contributing to thought leadership, engaging in client pitches, and helping expand the firm’s footprint in the technology due diligence and M&A advisory space. Practice Development: Continually identify and implement improvements to the delivery process and artifacts. Identify ways to make delivery of the service more efficient. Ideate on new, incremental add-on offerings and design how to take them to market. Mentorship and Team Development : Coach and mentor junior team members, fostering a culture of continuous learning, collaboration, and excellence in project execution. Key Qualifications Experience : 7+ years of experience in technology due diligence, M&A advisory, private equity consulting, or related roles, with a strong focus on technology evaluations for transactions. Technical Knowledge : Deep understanding of enterprise IT systems, software architecture, cloud infrastructure, cybersecurity, and digital transformation strategies, particularly in the context of M&A. Critical Thinking: Ability to quickly analyze complex, multi-faceted technology topics and distill the meaning and implications for non-technical audiences. Communications: Excellent written and verbal communications skills and proven ability to interact with senior level private equity stakeholders. Experience with the following Technology Paradigms Strongly Preferred : Infrastructure – On-Premises/Co-location & Cloud Custom Software – Prior background in an organization that develops custom software solutions. Familiarly with a variety of code platforms, frameworks and architecture. Cybersecurity – Experience implementing and/or advising on cybersecurity tools and solutions Data – Familiarity with data warehouse paradigms and technologies M&A Expertise : Proven track record of conducting buy-side and sell-side technology due diligence, including identifying technology risks, assessing scalability, and developing actionable recommendations to improve deal outcomes. Client-focused : Excellent client relationship management skills, with the ability to communicate complex technical concepts in a clear and actionable manner. Education : Bachelor's degree in Information Technology, Computer Science, Engineering, or a related field (MBA or equivalent advanced degree preferred). Preferred Qualifications Experience in private equity transactions, particularly with middle-market or large-cap funds. Industry certifications in IT systems, cybersecurity, or cloud platforms (e.g., CISSP, AWS Solutions Architect). Exposure to technology transformation initiatives, including cloud migrations, ERP implementations, or advanced data analytics. Salary & Benefits Competitive salary commensurate with experience. Performance-based bonus structure. Comprehensive benefits package, including health insurance, retirement plans, and professional development opportunities. Chicago or New York metros preferred, Central and Eastern time zones strongly preferred.