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.

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.

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. 

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.

Shannon is a Partner with experience as a business and IT leader for a Fortune 100 retailer and as a management consultant. She has spent her career focused on helping companies use technology to enable their businesses to grow and optimize performance.

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.

Ana is a dynamic and strategic professional boasting a successful history of aligning teams and streamlining operations. With a proven track record, she excels in translating business goals into innovative technological solutions, driving enhanced efficiency, system simplification, and increased automation.

Andres is a seasoned tech professional with over eight years of experience, specializing in fintech and ride-hailing.

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

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.

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

Carolina is an experienced product manager with a proven track record of aligning global teams and supporting organizations to use data to understand and connect with their customers and markets.

Chris has more than 20 years of experience, both as a consultant and as an operator, working at the intersection of technology products, experience design, and business operations.

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

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.

Eduardo has over 7 years of consulting experience, designing and implementing cloud driven data architecture solutions for a range of clients across industries.

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.

Esteban is passionate about all facets of data analysis, finding satisfaction in all stages of the process. He focuses on delivering client value with a high attention to detail, employing a diverse set of tools to transform raw data into operational opportunities. Esteban has skills in data visualization, ETL pipelines, and generating insights.

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.

Kyle is a creative and strategic thinker with a passion for defining data-driven digital solutions to organizations’ most top-of-mind problems. He uses quantitative and qualitative data to fully understand user needs and leverages those insights to build a customer-focused digital product strategy.

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. ​

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.

Juliana is an experienced data scientist and technology consultant with expertise in cloud deployments, data architecture, data strategy, and Artificial Intelligence.

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. 

Lauren is a pragmatic problem solver who is focused on collaborating with clients to improve their business processes and successfully implement new technology solutions.

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…

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.

Lia brings over 23 years of project and delivery management experience, including deep competencies in data and delivery.

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.

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.

Sebastian is a dedicated professional with a fervent enthusiasm for leveraging technology to drive organizational value. Currently serving as a Data Visualization Specialist at Cuesta, he is pivotal in helping organizations establish robust technological practices to deliver analytical insights within strategic domains. 

Simon is a data visualization expert with extensive experience designing and implementing impactful dashboards that drive data-driven decision-making.

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.

Zahra is passionate about holistically learning about systems and using that knowledge to bring about efficiencies and dynamic problem solving. Zahra has worked for two of the top five pharmaceutical companies in both their technical operations department.

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.

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.