DIGITAL

Reimagine the future of your
business

Enhance innovation across your product suite

Create actionable, data-driven insights

Modernize operations and achieve scalability

Build technology that drives customer behavior

Elevate your engineering efforts

Drive operational excellence

Deliver exceptional product performance

Focus on growth and outsource your digital backbone

Our solutions and services are stronger together

Discover how our integrated approach delivers greater value and drives better results for your business.

Expertise across key industries

Aerospace and Defense

Create sustainable strategies to address complex regulatory compliance, achieve cost efficiencies, and optimize processes and technology.

Consumer Goods
and Retail

Tackle challenges with rapid, sustainable strategies that address rising costs, demand shifts, and evolving customer preferences.

Financial Services

Adapt to market shifts, encourage innovation, and evolve for sustained growth. Gain insights drawn from deep expertise across fintech, banking, capital markets, and insurance.

Healthcare

Delivering holistic solutions that make healthcare more effective by integrating strategy, technology, and leadership.

Manufacturing

Address challenges such as supply chain disruptions, demand variability, and capacity constraints through strategic, practical solutions that drive growth and network resiliency.

Private Equity

Leverage our expertise to maximize value, accelerate growth, and strengthen your leadership teams, processes, and operations at every stage of the deal lifecycle.

Technology

Scale systems, processes, and teams to excel during pivotal moments like expansion periods, regulatory shifts, and transactions.

Our Digital leaders

Jake Shepherd

Senior Managing Partner

Jake Shepherd is the Senior Managing Partner for Highspring’s Digital Services and Labs, leading AI innovation, software engineering, and enterprise transformation.

With over 15 years in venture funding, innovation strategy, platform modernization, and business transformation, Jake advises C‑level executives across financial services, health‑tech, SaaS, non‑profits, and manufacturing. His expertise aligning technology with strategic goals helps enterprises navigate disruption, unlock growth, build digital capabilities, and achieve measurable results.

Through Highspring Labs, he accelerates AI‑driven engineering and next‑gen solutions that help clients modernize at scale and achieve success.

Jake’s people‑centric leadership empowers bold ideas with cutting‑edge technology at the speed of thought. He believes that when human potential meets innovation, extraordinary outcomes follow—a mindset that fuels Highspring’s culture and shapes the future of business.

Kurt Dowswell

Principal Delivery Lead, AI Accelerated Engineering

Kurt Dowswell is a seasoned Software Architect and technology leader with over 13 years of experience delivering secure, scalable enterprise solutions. As Principal Delivery Lead for AI Accelerated Engineering at HighSpring, he drives AI-powered engineering practices that enhance productivity and solution quality. 

A published author of Programming with GitHub Copilot (Wiley, 2024), Kurt is recognized for his expertise in AI-assisted development, responsible AI practices, and security considerations. His deep technical knowledge spans cloud platforms, modern development frameworks, and AI tools, enabling clients to navigate digital transformation with cutting-edge solutions. Kurt holds a BS in Computer Science from James Madison University. 

Ben Mickey

Managing Partner

Ben Mickey is a technology executive with deep expertise in building and scaling managed services that accelerate digital transformation for enterprise organizations. With a background in software product development and leadership roles across various technology companies, Ben has helped organizations productize their delivery models and modernize operations through cloud, data, and AI-driven solutions. At Highspring, he focuses on delivering outcome-based managed services that combine technical excellence with business impact. His approach emphasizes agility, continuous improvement, and long-term value for organizations navigating complex technology landscapes. 

Greg Leonardo

Principal Solutions Architect

Greg is a seasoned Cloud Architect and Microsoft MVP, helping organizations navigate the complexities of cloud adoption, innovation, and digital transformation. With a deep passion for cutting-edge technology, he specializes in architecting scalable, secure, and high-performing cloud solutions, particularly within the Azure ecosystem. 

Greg’s journey in IT began in the military, where he developed a strong foundation in leadership, strategy, and technical execution. Over the years, he has held diverse roles across the industry, providing him with a well-rounded perspective on cloud engineering, automation, and AI-driven optimization. 

Beyond architecture, Greg is a Microsoft Certified Trainer and a Certified Solutions Architecture Expert, dedicated to mentoring the next generation of cloud professionals. As an early adopter, speaker, and thought leader, he thrives on exploring emerging technologies and driving innovation. Whether optimizing multi-cloud environments, enabling FinOps strategies, or spearheading AI-powered cloud efficiencies, his mission is to empower businesses with future-ready cloud solutions. 

Outside of his professional work, Greg is a proud father, veteran, and lifelong educator—always eager to share knowledge, challenge the status quo, and push the boundaries of what’s possible in the ever-evolving cloud landscape. 

Kevin Baynes

Head of Technical Delivery

Brant Elliot

Principal Delivery Lead, IT and Infrastructure

Brant Elliot, Principal Engagement Lead in Solutions Architecture, specializes in guiding small and medium-sized businesses through complex technology challenges. With a focus on aligning technological solutions with business objectives, he ensures clients achieve optimal outcomes. Brant’s expertise enables organizations to navigate the evolving tech landscape effectively. Outside of work, Brant is a passionate mentor of early-stage startup cofounders, enjoys playing baseball, and staying curious about emerging tech trends.