---
title: 'Principal | Technology Due Diligence & Private Equity at Cuesta Partners'
canonical: 'https://feeny.ai/job/principal-technology-due-diligence-private-equity-cuesta-partners-chicago-0p5gjcxzy9c0'
type: 'job'
last_seen: '2026-09-11'
---

# Principal | Technology Due Diligence & Private Equity at Cuesta Partners

- **Company:** Cuesta Partners
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-04-29
- **Last confirmed live:** 2026-09-11
- **Apply:** https://jobs.ashbyhq.com/cuesta-partners/98429517-c3bf-4527-a0ff-8f709776d11f

## Job description

## 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.

## About Cuesta Partners

## Company Overview
- **One-liner**: Cuesta Partners is a technology strategy consulting firm that helps mid-market organizations navigate complex transformations, from M&A and AI implementation to data strategy and core technology modernization.
- **Entity Type**: Private (bootstrapped/self-funded, no funding rounds disclosed)
- **Headquarters**: Not publicly available (remote-first organization)
- **Founded**: Not publicly available
- **Founders**: Riley Scott (quoted as founder figure on the careers page)

## Core Business
- **Primary industry**: Technology strategy consulting, M&A advisory, AI and data strategy
- **Target customers**: Mid-market companies, organizations of various sizes across industries (B2B, enterprise)
- **Mission**: To turn technology into a true catalyst for growth and competitive advantage, helping clients move from ambition to outcomes with clarity and speed.

## Products & Services
- **Technology Strategy**: Helping CIOs and CTOs define clear, actionable strategies aligned with business priorities, covering software systems, infrastructure, cybersecurity, operating models, and AI.
- **Data Strategy & Execution**: Building data infrastructure, governance, and analytics to turn raw data into trusted, business-ready intelligence. Includes master data management, margin analytics, and resource demand analytics.
- **AI Strategy & Execution**: Identifying high-impact AI use cases, prototyping, and scaling solutions with clear ROI, using proprietary methods to evaluate AI and data maturity.
- **Mergers & Acquisitions Advisory**: Full lifecycle support including product/tech diligence, cybersecurity, post-merger integration, and AI readiness to unlock hidden value in deals.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (private company)
- **Key Metric**: Not publicly available (no revenue or funding figures disclosed)
- **Notable Investors/Partners**: Not publicly available
- **Growth Signals**: Actively hiring for multiple remote roles (Data Engineer, Data Analyst, Engineering Manager, Technical Lead, etc.) with a focus on Latin America, indicating expansion. Client case studies show measurable results (e.g., $10K monthly labor cost reduction, $1M annual profit improvement for a $1.5B logistics provider).

## Competitive Advantages
- **Business-first, tech-smart approach**: Strategy grounded in business goals, not technology for its own sake.
- **Flat, non-hierarchical team structure**: Diversity of thought and experience; everyone teaches and learns, from newest hire to most senior.
- **Value-led delivery**: Co-creates with clients, stays engaged until value is realized, and focuses on measurable ROI.
- **Proprietary AI and data maturity evaluation methods**: Accelerates diligence and integration in M&A and transformation projects.

## Strategic Focus
- **AI readiness and implementation**: Helping clients define and scale AI strategies grounded in technical feasibility and high-value use cases.
- **Data foundation modernization**: Building scalable, cloud-ready data environments to enable real-time insight and innovation.
- **M&A value creation**: Turning acquisitions into platforms for scalable growth through deep technical and commercial diligence.
- **Expanding talent pool**: Hiring remote talent across Latin America to support growing client demand.

## Why Work Here
- **Remote-first culture**: "We’re Where You Work. Not Where You Live." Fully remote positions with a focus on work-life balance.
- **Generous PTO**: Encouraged up to 5 weeks of paid time off annually, with a minimum of 2 weeks; managers ensure time off is taken.
- **Competitive benefits**: Competitive salary, continuous education support, leading parental leave with flexible return options, full health care and ancillary insurance, plus 7 company holidays and 3 floating holidays.
- **Flat, learning-oriented culture**: Everyone is both teacher and student; autonomy to create your own path; emphasis on humility, entrepreneurship, speed, and diversity.
- **Growth opportunities**: Ability to lead and learn at every career stage; mentorship and exposure to diverse technologies and industries.

## Sources
1. [cuestapartners.com](https://www.cuestapartners.com/) – Main site overview of services and approach
2. [cuestapartners.com/about](https://www.cuestapartners.com/about-2/) – About page with mission and team structure
3. [cuestapartners.com/careers](https://www.cuestapartners.com/careers-2/) – Careers page with benefits, culture, and founder quote
4. [jobs.ashbyhq.com/cuesta-partners](https://jobs.ashbyhq.com/cuesta-partners) – Current job listings
5. [cuestapartners.rippling-ats.com](https://cuestapartners.rippling-ats.com/jobs) – Additional job listings showing remote roles in Latin America

## Other roles at Cuesta Partners

- [Senior Data Analyst | Latam](https://feeny.ai/job/senior-data-analyst-latam-cuesta-partners-latin-america-colombia-2x9hgj0ja02g) — Latin America / Colombia
- [Associate Recruiter](https://feeny.ai/job/associate-recruiter-cuesta-partners-latin-america-colombia-yp520y1wj713) — Latin America / Colombia
- [Machine Learning Engineer](https://feeny.ai/job/machine-learning-engineer-cuesta-partners-latin-america-colombia-7tvkrv6f3dsg) — Latin America / Colombia
- [Databricks Architect | Canada](https://feeny.ai/job/databricks-architect-canada-cuesta-partners-canada-w9tk248evcgt) — Canada
- [Databricks Architect | Latam](https://feeny.ai/job/databricks-architect-latam-cuesta-partners-latin-america-colombia-p0xg8k16rh3e) — Latin America / Colombia
- [Databricks Architect | US](https://feeny.ai/job/databricks-architect-us-cuesta-partners-united-states-r0y42sav3530) — United States
- [Data Architect | Canada](https://feeny.ai/job/data-architect-canada-cuesta-partners-canada-pjnzhczkgjj0) — Canada
- [Manager/Sr. Manager - M&A Technical Due Diligence](https://feeny.ai/job/manager-sr-manager-m-a-technical-due-diligence-cuesta-partners-united-states-jmph7ht0zgnj) — United States
- [Analytics Engineer | CA](https://feeny.ai/job/analytics-engineer-ca-cuesta-partners-canada-9d972twww6bn) — Canada
- [AI Solutions Architect | US](https://feeny.ai/job/ai-solutions-architect-us-cuesta-partners-united-states-asdc157t165k) — United States