Delivery & Transformation

Because the right plan deserves flawless execution

Delivery & Transformation

Turn strategic visions into measurable, lasting results

From Concept to Reality – Accelerate Your Transformation

 

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Architect with Confidence, Execute with Clarity

Cuesta brings the structure and foresight needed to guide high-stakes programs from concept to execution. Leveraging AI-powered research and analysis, we accelerate planning and surface better options, faster. Our seasoned experts define the blueprint, align cross-functional priorities, and set a trajectory for long-term success – ensuring you move forward with confidence and control.

Delivery & Transformation

Trusted Navigators Through Complexity

Complex transformations demand more than coordination – they require clarity. We cut through the noise to align stakeholders, simplify decisions, and manage dependencies, helping you deliver business-critical programs on time, on budget, and with minimal disruption.

“Cuesta’s work consistently delivered unique, high value outcomes”

 

— John Dailey
COOFlinn Scientific (PE Owner Distribution Company)

Where Tech Meets Operational Know-How

We bridge the gap between technology and operations. With experience as both builders and business leaders, we know how to deliver strategies that not only look good on paper, but actually work in practice – across systems, teams, and timelines.

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Momentum Without the Missteps

Speed matters – but not at the cost of sustainability. Cuesta uses AI to enhance visibility into risks and dependencies, helping your team move faster without sacrificing quality. We provide just enough process and just-in-time insights to keep momentum strong and missteps few.

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Change That Actually Sticks Over Time

We don’t just launch new systems – we help your people embrace and sustain them. With a pragmatic approach to organizational change management, we make sure your teams are engaged, enabled, and equipped to succeed in the new reality.

Our Capabilities

Program Health Check

Quickly diagnose your program’s trajectory with an unbiased view of scope, schedule, financials, and largest areas of risk

We evaluate critical elements such as schedule adherence, milestone achievability, and the capability of key team members to deliver on program goals. Additionally, we assess organizational enablement processes, ensuring that the right structures and participants are in place to support smooth transitions and fortify adoption.

By identifying critical risks and pinpointing root causes of stagnation, our Program Health Check delivers actionable insights to improve program stability and help guide successful outcomes.

Complex Program Delivery

Mastering complex program delivery: precision, alignment, success

At Cuesta Partners, we excel in navigating the intricacies of large-scale, multifaceted initiatives. Our seasoned team of technologists and operators orchestrate multiple workstreams, ensuring seamless execution and strategic alignment. We establish robust governance structures, manage vendor relationships, and provide data-driven insights for informed decision-making. Our approach combines best practices in program and product management with delivery methodologies, tailored to your unique needs. We embed ourselves within your team, fostering transparency and accountability at every level.

With Cuesta, complex programs transform into measurable, sustained success stories.

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Solution Blueprint

Bridge the gap between strategy and execution with a clear, actionable plan

Cuesta’s Solution Blueprint sets the foundation for successful execution – whether deploying a packaged system or building a custom digital solution. We define business processes and requirements, assess solution fit, and for custom builds, align on a product vision, roadmap, and agile delivery model backed by scalable architecture. We evaluate stakeholder impacts, rationalize applications, and map out key components like custom development, data migration, and reporting. Each blueprint ends with a pragmatic rollout strategy and interim architecture to guide delivery.

With Cuesta, execution begins with clarity, alignment, and a plan built for real-world success.

Software Selection & Implementation Planning

Navigating software selection: from vision to implementation

At Cuesta Partners, we guide you through the complex journey of selecting and implementing the right software solutions for your business. Our comprehensive approach begins with a thorough assessment of your current landscape and future needs—including considerations for AI-enablement and long-term data compatibility. We craft tailored RFPs, facilitate vendor evaluations, and create detailed scorecards that balance functional requirements with strategic objectives. Our team expertly navigates stakeholder perspectives, weighing quantitative and qualitative criteria to ensure the best fit. We don’t stop at selection – we prepare you for successful implementation with structured guidance on requirements, process mapping, and deployment planning. 

With Cuesta, you’ll confidently choose and implement solutions that drive operational efficiency and long-term growth. 

Product Management

Elevating product management: from vision to market success 

We transform your product management practices to drive innovation and business growth. Our approach spans the entire product lifecycle, from market research and customer discovery to go-to-market strategies and product analytics. We help you define clear product visions, set measurable goals, and align them with broader business objectives. Our expert product managers streamline backlogs, prioritize initiatives, and synchronize capabilities across programs. Increasingly, we integrate AI-powered insights into backlog refinement, roadmap planning, and product analytics – enhancing speed, accuracy, and differentiation. We emphasize user-centric solutions, continuous improvement, and data-driven decision-making to elevate product quality and customer satisfaction. 

Whether you’re scaling through high growth or revitalizing established products, we work alongside your team to build robust product organizations that deliver tangible business value and market success. 

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Operating Model Design

Translate strategic goals into action with a fit-for-purpose operating model aligned to your organization’s ambition and scale.

We assess core components of your operating model – including structure, roles, decision-making, governance, and ways of working – to ensure they’re aligned to your strategy and built to scale. Our approach bridges the gap between vision and execution by grounding recommendations in your real-world constraints and cultural context. 

Whether you’re undergoing transformation, integrating after a deal, or simply outgrowing your current model, our Operating Model Design delivers pragmatic, actionable recommendations that unlock speed, clarity, and performance. 

Impact Enablement (OCM) 

Making transformation stick—from vision to true enablement  

At Cuesta, we turn change into momentum by embedding organizational change management into every stage of your transformation. We partner with clients to define a compelling vision, align leadership, and build stakeholder-driven roadmaps that focus on outcomes, not just activity. Through structured assessments, we identify where change will matter most – and tailor plans to maximize adoption and impact. Our approach includes interim state planning, targeted communications, change champion development, and engagement strategies that prepare your organization to operate differently and better. 

Whether it’s a complex system rollout or a post-merger integration, we help ensure your teams are ready, supported, and equipped to turn transformation into measurable business value. 

Agile Transformation

Accelerating value delivery in a complex world

We guide organizations through comprehensive agile transformations, aligning technology delivery with business strategy. Our approach breaks down complex initiatives into manageable increments, fostering rapid response to market changes and continuous improvement. We establish cross-functional teams that work in short cycles, prioritizing customer-centric solutions and data-driven outcomes. By blurring traditional boundaries between business, data, and technology, we create a fluid, transparent network that values individuals and interactions.

Our services encompass team alignment, program increment planning, and agile metrics implementation, ensuring your organization can deliver instant, frictionless value at scale while navigating technological and organizational complexities.

Rapid Technology Assessment

Gain clarity and control: rapid evaluation of your technology landscape

Our comprehensive rapid technology assessment answers key questions about your technology landscape in as little as 4 weeks. We assess key areas including applications, data posture, integrations, cybersecurity, infrastructure, and team effectiveness. Through a customized, agile discovery period, we analyze your current technology landscape against industry best practices and deliver actionable insights.

This process equips decision-makers with the knowledge they need to optimize technology investments, prepare for potential company sale, or support significant strategic shifts.

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Technology Strategy & Roadmap

Chart your path: strategic technology roadmaps for success

We specialize in creating technology roadmaps that define a clear, actionable path toward your organization’s broader goals. Our approach ensures that every technology investment supports growth, innovation, and operational resilience. Through stakeholder interviews, detailed technical assessment, trade-off analyses, and creative problem-solving, we develop tailored strategies that balance long-term vision with near-term execution.

With AI transforming what’s possible across industries, we help you understand where and how these capabilities fit – ensuring your roadmap reflects both foundational technology needs and future opportunities. The result is a grounded, forward-looking strategy built for today’s complexity and tomorrow’s potential.

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Post-Merger Integration

Maximizing value: seamless post-merger integration

Cuesta’s Post-Merger Integration expertise ensures a smooth transition and accelerated value realization for your M&A investments. Our seasoned team of technologists and operators delves deep into critical areas, including technology assessment, data integration, cybersecurity, cultural alignment, and early identification of AI enablement opportunities. We establish a robust Integration Management Office, develop tailored integration playbooks, and provide data and AI strategy and execution services to streamline operations. From strategic roadmap definition to execution of complex workstreams Cuesta acts as the glue binding all aspects of your integration. 

We focus on minimizing disruption, optimizing synergies, and aligning integration efforts with your overall business strategy, ensuring long-term success beyond the initial merger. 

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Cuesta Partners offers a comprehensive suite of complementary services

From Mergers & Acquisitions and Technology Strategy to Delivery & Transformation and Data & AI, we’ve designed our services to support you through every stage of your technology journey. Our team has the expertise and experience to get you from where you are to where you want to be.

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Mergers & Acquisitions

Navigate the full deal lifecycle with deep tech, product, and operational diligence.

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Execution & Orchestration

Technology Strategy

Build forward-looking tech strategies that balance innovation and practical execution to drive measurable results.

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Data Strategy & Execution

Ground your strategy with trusted, scalable data foundations that power reliable analytics.

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AI Strategy & Execution

Rapidly identify, validate, and deploy high-impact AI use cases to drive measurable business value.

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SOME Of The Brands that Trust Us

“As the CIO at three different global organizations, I’ve partnered with Cuesta at each of them, and they have consistently delivered unbiased, strategic technology advice. Their ability to align IT initiatives with business goals has helped me transform my business.”

— Benn Reynolds
Global CIOAerospace Company

Success Stories

Explore our Success Stories to see how we help complex programs deliver real results – on time, on budget, and on scope. These case studies highlight how Cuesta’s hands-on approach to delivery and transformation drives clarity, accelerates execution, and turns ambitious initiatives into measurable business outcomes.

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How We Work

Your Path to Seamless Execution

At Cuesta, we’re more than consultants—we’re your co-pilots in turning challenges into opportunities. Whether you’re navigating complex program delivery, implementing new software, or orchestrating organizational change, we bring deep expertise and a collaborative approach to every engagement. We roll up our sleeves, dive into the details, and tailor solutions that fit your unique needs. Our process is designed to streamline operations, align teams, and deliver tangible outcomes, all while keeping the journey as smooth as the destination.

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Clarity that Drives Action

We kick off by understanding your world – evaluating program health, technology gaps, and operational readiness. Using AI to accelerate research and pattern recognition, we surface critical insights faster and more deeply. This clarity allows us to align strategies with what matters most to you, ensuring every initiative is grounded in real-world, data-backed understanding.

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Precision in Every Detail

From agile transformations to post-merger integrations, we manage the moving parts with precision. Our team uses AI to analyze risk factors, model scenarios, and anticipate blockers – enhancing decision quality and delivery speed. We design robust roadmaps, coordinate cross-functional efforts, and tackle obstacles head-on to ensure seamless execution every step of the way.

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Results that Speak for Themselves

Our success is your success. We use AI to elevate deliverables, quantify impact, and enhance how value is realized and communicated. With a focus on measurable success, we deliver solutions that not only meet immediate needs but also set the stage for long-term growth. It’s about elevating your capabilities and empowering your team to thrive.

Insights

Explore our blogs, informed by cutting-edge research, real-world project experience, and the latest industry trends, to gain valuable insights and stay ahead in your field. Discover expert perspectives and actionable advice that can enhance your knowledge and skills.

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Our Team

Technology is our backbone. Engineers. Operators. Owners. Entrepreneurs. We come from the same backgrounds as our clients — and use that perspective to understand your goals. This experience and flexibility means that we’re a team full of leaders who work differently. There’s no hierarchy. We teach each other, and we learn lessons from every project and each client.

Meet Our Team

Tom Derhake
Partner
Tom Derhake

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.

Shannon Warner​
Partner
Shannon Warner​

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.

Justin Sheridan
Principal
Justin Sheridan

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.

Erin Markowski
Principal
Erin Markowski

Erin has a passion for guiding and supporting organizations that seek to change their trajectory by utilizing technology in new ways. She is an authentic and empathetic leader that prioritized people and process alongside the technology for sustained impact.

Jeff Jbara
Principal
Jeff Jbara

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.

Heather Wilson
Principal
Heather Wilson

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.​

Brett Ellison
Senior Manager
Brett Ellison

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

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Let’s Chat – Your Technology Can’t Wait.

Deliver complex programs with confidence. Start your transformation today.