Dmitry Yun, Founder and CEO of Skyward IT Solutions – Interview Series

Founded in 2013, Skyward IT Solutions is a Maryland-based digital services company and federal contractor specializing in Artificial Intelligence and Machine Learning, Agile DevSecOps, Data Science, and Customer Experience. The company delivers secure, scalable, and user-focused technology solutions aimed at supporting federal initiatives.

Over the past decade, Skyward IT Solutions has collaborated with various U.S. federal agencies to modernize mission-critical systems and enhance public service delivery. Its clients include the Centers for Medicare & Medicaid Services (CMS), the U.S. Small Business Administration, the Department of Transportation, and the Department of Homeland Security.

The company emphasizes outcomes, transparency, and agile methodologies in its approach, aiming to support the federal government in adopting next-generation technologies for improved efficiency and effectiveness.

Can you share the inspiration behind founding Skyward in 2013 and what motivated you to focus on serving U.S. federal agencies?

Unlike many other startups, the main motivation and inspiration behind founding Skyward wasn’t having a perfect business plan with a multi-million exit on the horizon. At the time, I had been working for federal agencies for quite some time already and I saw it all: inefficiency, waste, outdated tech, slow processes, and proprietary solutions and technology that lock in government processes, limiting flexibility and inflating the prices. At some point, I knew that there must be a better way to serve American taxpayers using transparent, modern technology and innovation. I wanted to unify the best of 2 worlds: the agility and speed of a startup, and the people-first approach of the governmental agencies. As a result, I came up with Skyward, with a mission to revolutionize and change the way the government works.

In the early stages of building Skyward, what were some of the most significant challenges you faced, and how did you navigate them?

Working with the federal government and competing for contracts is a very niche market – there are a lot of nuances and intricacies when it comes to building relationships and actually delivering results. When I founded Skyward I only had experience working inside the government, not with it, so there was a big learning curve. I would say that the first 4 years were the hardest – it was just me in the company, so I grinded a lot. I was very lucky to have great mentors who really helped me along the way. Eventually, we got our first major governmental contract with CMS, which accelerated the growth of the company.

What has been the most transformative moment for Skyward since its founding, and how has your vision for the company evolved over the years?

The people who joined us along the way have been instrumental in transforming our company. Hiring deeply curious, experienced, and talented team members is a huge priority for us. When you’re innovating and creating a whole new market, the team that you have is the most important thing. We want our team members to actually partner with stakeholders to create new solutions and help shape our strategic vision. What I’m most proud of is that we’ve built more than just a IT services company. We’re a mission-driven team of skilled builders united by one goal: serving America’s taxpayers. Every person who chooses to walk this path with us transforms not only our company, but our collective impact.

Skyward recently launched SkyAI Hub, a modular AI agent framework designed to help federal agencies deploy mission-ready AI tools. What was the initial inspiration behind this technology, and how did you identify the need for such a solution?

The idea came from the pain points we are saw repeatedly with our federal partners. Practically every federal agency needs a solution that is tailored to their specific needs. 6 months into developing AI solutions, we started to see a need to scale and create an environment in which the agents would be deployed. With the rise of Model Context Protocol and open-source agents, we saw an opportunity to standardize how the government adopts agentic AI. SkyAI Hub was born out of necessity — to give federal agencies more control, visibility, and efficiency when deploying AI.

SkyAI Hub aims to close the gap between AI innovation and institutional implementation within federal agencies. Can you explain how this technology works and how it addresses the challenges of adopting AI at the federal level?

SkyAI Hub is a centralized control center for all workflows that include Agentic AI – analysis, computation, administrative processes and any other tasks. It’s built on Anthropic’s MCP protocol that enables federal agencies and enterprises to securely implement multiple AI agents and tools through one unified framework, eliminating the build-versus-buy decision. The platform automatically routes user requests to the best model or agent for each task, processing everything through a single interface that streamlines usability and user onboarding. Functioning as a cockpit for all AI agents, SkyAI Hub makes it easier to audit operations, authorize users, and maintain compliance while providing clean, organized backend security that enables safer monitoring and scaling of AI in federal environments.

How does SkyAI Hub ensure that federal agencies can deploy AI agents without the costly ramp-ups or custom builds typically associated with AI implementations?.

We describe SkyAI Hub as the “UberEats of AI.” The main idea for the Hub initiative is that in the future agencies won’t need to develop their own agents anymore, or pay millions to the tech contractors. Instead, you can just implement the SkyAI Hub, search for the right agent, tailor it to your needs and use cases, deploy it right in the Hub environment, and control it there. It also helps automate compliance and testing workflows, so adoption becomes faster, safer, and significantly cheaper than legacy builds. Moreover, the Hub framework is owned by the Agency, avoiding “vendor and infrastructure lock-in”.

Skyward emphasizes compliance, explainability, and security in its AI solutions. How does SkyAI Hub meet these stringent requirements, and why are they critical for public-sector AI adoption?

Having worked in the public service industry for many years, I understand that security and compliance are the key principles when it comes to public sector work. SkyAI Hub is designed with modular compliance baked in. We run agency-specific validation workflows, prioritize explainability, and ensure every agent is transparent in how it operates.

SkyAI Hub is built on open-source principles to avoid vendor lock-in. How important is open-source to your mission, and what benefits does it provide to federal agencies using your technology?

We believe that closed source technology can often hold the customer hostage. If you’re locked in a certain ecosystem without open source capabilities, you are limited in terms of available tools, audit the code, or develop new functionality crucial for your work processes. Open source is central to our philosophy. It gives agencies real ownership — they’re not locked into expensive, proprietary ecosystems. It’s more ethical, more transparent, and ultimately, more sustainable for government innovation and modernization.

Looking ahead, what role do you see Skyward playing in the future of AI within the public sector, and what excites you most about the potential impact of technologies like SkyAI Hub in the coming years?

Right now, the focus is on enterprise efficiency, mostly for federal agencies. We are currently working on speeding up procurement, document review, audits, knowledge management, and other features. One of the things about the future that excites us the most is processing and auditing claims with the help of AI Agents. Even though we’re still working on practical implementation, I firmly believe it’s going to be one of the highest-impact areas. At CMS, for example, AI Agents could ensure that Medicare Advantage claims are properly audited and processed to ensure that the patients are receiving proper care and treatment. The mission is to prove that Agentic AI can be used ethically and effectively to improve government’s most basic and on-the-field functions.

What advice would you give to entrepreneurs looking to enter the GovTech or AI/ML space, especially when navigating the complexities of working with federal agencies?

As I mentioned before, the main unique trait of the GovTech industry is the level of compliance and transparency that you’re expected to provide. I can’t stress enough how big this is a priority for us here at Skyward. When you manage taxpayer money, you should go beyond the rules and do as much as you can, not just meet the set minimum. Be clear and on point when it comes to your edge, you need to understand what makes you different from everyone else, and believe me, there’s going to be a lot of competition. Another important thing is to learn the programs and systems of the field that you’re planning on working in. There’s a lot of intricacies in the governmental management space, so you need to understand the environment you’re in. Build the right relationships, make the right pitches, use the right words and amplify the right messages when presenting your project. The federal space is complex, but the impact is worth i

Reflecting on your 12 years at Skyward, what is one key leadership lesson you’ve learned about driving innovation while managing the regulatory and compliance challenges of the public sector?

Always keep moving, no matter what’s going on out there. Progress doesn’t always come fast, and to be honest, the setbacks can feel personal at times. I’m a firm believer in learning from your mistakes, so I see all failures and rejections as an improvement opportunity for myself, leadership, and the whole company. Figure out what went wrong, try to fix it, and test the solution. Little wins stack up over time, and that’s how real change happens – one informed step at a time.

Thank you for the great interview, readers who wish to learn more should visit Skyward IT Solutions.