Meet Our Operators

Chris helps clients solve thorny problems using technology. He brings a knack for matching pieces of business value chain with technologies that can enhance and simplify operations.

Riley is a Partner at Cuesta who excels at helping private equity firms assess the technology posture of potential deal targets and execute technology initiatives throughout the deal lifecycle.

John has developed a unique skillset that leverages his deep technology expertise combined with pragmatic views on business that allow him to design creative technology solutions to business challenges. 

Tom is a Partner with a software background focused on using technology to transform organizations. At Cuesta, he is responsible for both client sales and delivery.

Amy is a thoughtful and curious leader who can take highly complex problems, simplify, and clearly communicate strategies to diverse teams.

Andrea helps clients navigate product strategy and delivery execution. She is passionate about enabling people to do their best work, equipped with cutting-edge digital capabilities and pragmatic operating models.

Brandon is a dynamic senior leader with a proven track record of building high functioning PMO organizations, delivering projects, and optimizing business processes.

Brendan is a driven and empathetic problem solver with a track record of enabling organizations of all sizes to become more effective in carrying out their missions.

Brett partners with individuals and organizations to co-create solutions in their quest to become more efficient and effective operators.

Chris is a seasoned CIO with a focus on identifying and implementing value creating initiatives.

Danielle is a specialist at translating business objectives into technological solutions that result in more efficient processes, simplified systems, and increased automation.

Danny brings an enthusiasm for breaking down complex business problems by applying his experience in data analytics, project management, and visualization techniques.

Darren has a 20+ year track record of partnering with enterprises to drive strategic advantage from their use of data. In the last 14 years Darren leveraged that insight to focus on leading customer-driven product organizations, in the enterprise data management software market.

David is an experienced senior executive who enjoys working with clients to tackle their most difficult problems by leveraging technology to drive sound business outcomes.

Dylan is a senior leader with 15+ years of diverse experience across a variety of tech industries including e-commerce, healthcare/wellness, and ed benefits.

Holt is a technology leader with a passion for setting up agile development teams, an obsession with good analytics and visualization, and a penchant for successful change management.

Jack excels at using technology and process to transform manufacturing organizations.

Jamie is a leader in Cuesta’s Private Equity practice.

At Cuesta Partners, Jim is a senior associate on the private equity and venture capital team. Jim participates in technology and commercial due diligences.

Joy is a passionate leader who enjoys helping organizations build scalable processes, leverage talent and technology while achieving profitable, sustainable growth.

Justin has a passion for helping organizations use technology to capture value. He leads Cuesta’s Software Systems and Platforms practice, where he helps organizations define and deliver technology strategies that enable growth and drive efficiencies.

Kristi is an enthusiastic collaborator and creative strategist with a broad background in helping businesses start, grow, transition and innovate. 

Leonard is passionate about helping organizations build a data-driven culture that empowers people with the right information at the right time.

Russ is an executive level cybersecurity engineer who loves partnering with clients to build and scale cyber architecture solutions in order to conduct enterprise and enclave cyber operations to keep critical data secure. 

William is a servant leader who is passionate about implementing innovative technologies and helping organizations unlock their potential through both digital and agile transformations.

Zach is a data-driven associate with expertise in analytical problem-solving, market research & competitive analysis, marketing operations, and B2B marketing strategy. He has extensive experience with VC-backed software startups and SMBs in the hyper-growth phase.

Zach enjoys finding new opportunities to apply his data enablement capabilities across enterprise data architectures.

Joel has more than 20 years of experience in the intelligence and information assurance fields.

Kevin is a three time public and private company Chief Information Officer (CIO), including being recognized as the 2019 CIO Innovator of the Year in Chicago.

Nate is a resourceful and strategic-minded senior technology leader with 20+ years of experience in enterprise solutions, program and project life cycle management, vendor management, and IT process optimization.

Nosh has a deep background in application development, having served as director of product strategy at MongoDB during that firm’s primary growth phase.

Peter has over thirty years of experience in information systems consulting and training with a focus on data warehousing, master data management and analysis and planning systems. He has been the primary architect on multiple large, cross functional implementations. He has also worked to support implementation teams from system integrators, providing coaching and filling a…

Vicki advises technology clients on team effectiveness and organizational health – as key differentiators of successful companies. She coaches client leaders to be the best version of themselves.