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.

Amari, a Senior Associate at Cuesta, brings extensive experience in product development, management consultant, business strategy, predictive analysis, and change management. ​

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.

Brian is a passionate and curious career technologist, focusing on enterprise infrastructure and strategic platform alignment. After 25 years of architecting application hosting solutions and evangelizing the benefits and pitfalls of cloud computing, Brian has the experience to help organizations make the right platform decisions and to improve and streamline these deployments. ​

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

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.

Estefany is a passionate and driven Data Engineer with a solid educational background and a burning desire to make data work for businesses. She is on a mission to turn raw data into valuable insights while being a true problem solver who thrives on challenges and excels in turning complex data into meaningful patterns.

Greg, a Senior Associate on the Data Strategy team at Cuesta, is motivated by unlocking novel business insights using creative data analytics and visualization.​

Heather is a transformation expert with a focus on delivering measurable results through innovative solutions. She is passionate about value delivery and systems thinking and has a track record of formulating strategic solutions for teams, processes, strategy, and technology.​

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.

Jeff is a seasoned consulting and industry leader focused on delivering impactful business​ results underpinned by practical technology solutions. Jeff has developed a unique skillset​ blending deep operational expertise with broad technology exposure enabling him to help clients​ solve an array of complex challenges ranging from technology strategy and product management to large-scale transformation. ​

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

Kristi Pihl is a go-to-market and product strategy expert with over 15 years of experience in management consulting, entrepreneurship, and startup COO roles. She is an accomplished professional with a collaborative approach, listening to clients and colleagues to develop effective solutions that drive growth. She is passionate about helping clients use data and technology to…

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.

Jordan possesses over 11 years of applications development experience in healthcare, finance, and insurance industries. His technical background in solutions architecture and data management led him to the digital product development space. He excels in translating complex technical processes to stakeholder groups and breaking down data to inform their decision making.

Leo is a curious and determined individual who has over 6 years of experience in the data space focusing on modern data architecture, design and engineering. He calls himself a data magician who has the ability to translate business problems/requirements into data analytics empowering stakeholders to drive strategic actions via insights.​

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

Accountant turned Data Analytics Engineering Leader, consultant to growth startups and Fortune 500 companies, with 10+ years experience in finance and analytics. ​Contributed to the successful design and implementation of enterprise data models to enable analytics, internal operations, and customer-facing product features across 30 organizations within Fintech, SaaS, Consulting Services, Restaurants, Sports Entertainment, and more.

Meredith is an enthusiastic problem solver who excels in strategic thinking and process creation. She thrives in dynamic environments where she can make and leverage partnerships between a multitude of players to drive profitable and streamlined business outcomes.

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. 

Sarah is passionate about empowering her clients and their teams to take ownership of the tools, processes, and systems they need to achieve their goals. Sarah is a member of the Software Systems and Applications practice, where she supports clients in identifying and implementing technology strategies to unlock next-level growth and efficiency.

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.

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…

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.

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.