Working in Microsoft Digital, the company’s internal IT organization, means being part of a group that operates at massive scale, deploying and managing the technology solutions that enable the company to collaborate, achieve, and fully embrace its shift to a Frontier Firm.

“Being successful in today’s fast-paced environment requires more than technical expertise. Success comes from embracing change, adapting quickly, and continuously learning alongside others. The most impactful teams combine technical capability with curiosity, collaboration, and a mindset of continuous evolution.”

Miguel Uribe, principal PM manager, Microsoft Digital

Our work touches on nearly every aspect of the business, from the network our employees rely on to safely connect to corporate resources, to the productivity apps they rely on every day, to the devices that power our global enterprise. We’re also key to the internal deployment and adoption of agentic AI tools for a global workforce of over 200,000 people.

Microsoft Digital employees have the daily opportunity to tackle complex, real‑world challenges while shaping how Microsoft develops new technologies, serving as Customer Zero for the company’s use of its own products and services.

“Being successful in today’s fast-paced environment requires more than technical expertise,” says Miguel Uribe, a principal PM manager in Microsoft Digital. “Success comes from embracing change, adapting quickly, and continuously learning alongside others. The most impactful teams combine technical capability with curiosity, collaboration, and a mindset of continuous evolution.”

The path to Microsoft Digital

Managing the full breadth of IT responsibilities at an organization the size of Microsoft requires a workforce with a diverse range of perspectives and lived experiences. Accordingly, the people who work here possess a wide variety of backgrounds and skill sets, and hail from around the world.

Networking and relationship-building are often helpful in finding your way into the organization. Mykhailo Sydorchuk, a principal product manager in Microsoft Digital, started his career in Ukraine at a SharePoint solution startup with some prominent global customers. After a successful implementation with one of them, he built a strong relationship with a manager there.

When that person’s company later opened up a SharePoint role, Sydorchuk applied, was hired, and relocated to Los Angeles. He wore many hats in the job, serving as a SharePoint administrator, Microsoft 365 tenant administrator, developer, and project manager for internal IT rollouts and large-scale change management efforts.

Eventually, he was ready for a change.

“My colleague eventually joined Microsoft,” Sydorchuk says. “She felt I would be a good fit and suggested I apply. I went through the interview process and landed the role here about six years ago. So, I got the job very much through networking.”

Some employees at Microsoft Digital have an extensive work history, while others are just getting started in their careers.

“The internship structure is very supportive. Interns are given broad, open‑ended problems rather than tightly scoped tasks, which allows for deeper exploration.”

Jeni Huang, product designer, Microsoft Digital

Internships offer a great opportunity for many candidates who are new to the job market, giving them a way to get a foothold at the company. Microsoft hires thousands of interns each year globally, with year-to-year fluctuations based on hiring conditions and program scope. Within that broader program, design interns are part of a smaller, close-knit cohort, making mentorship and studio connections especially meaningful.

“The internship structure is very supportive,” says Jeni Huang, a product designer in Microsoft Digital who started with the company as an intern in 2022. “Interns are given broad, open‑ended problems rather than tightly scoped tasks, which allows for deeper exploration.”

In Huang’s early work as an intern at the company, she was encouraged to explore more forward-thinking design concepts rather than incremental improvements. That freedom helped her build strong relationships with her manager and others working in the design studio.

“Even though I’m now on a different team, many of the same people remain,” Huang says. “Those connections played a big role in my return as a full‑time Microsoft employee.”

Interesting, impactful work

The people who work at Microsoft Digital routinely tackle ambitious, forward‑thinking projects, with an eye toward reimagining how IT operates at a global scale. Our teams focus on building intelligent, AI‑powered employee experiences, using cloud-native platforms and data-driven insights to simplify work, boost productivity, reduce friction, and help everyone at the company do their best work.

“Microsoft, even after a long and storied history, remains one of the best places for employees to thrive professionally and personally. Experimenting and innovating are at our core—managers are encouraged to provide the time and space for innovation, and to celebrate both successes and learnings.”

Andrew Osten, general manager, business operations and programs, Microsoft Digital

Many of our projects involve large-scale automation, modernizing legacy systems, and embedding responsible AI into everyday workflows, including personalized self‑service technologies, adaptive productivity tools, and predictive insights for decision making. This environment creates a feeling of autonomy for employees and allows them to make significant impact.

“Microsoft, even after a long and storied history, remains one of the best places for employees to thrive professionally and personally,” says Andrew Osten, general manager for business operations and programs in Microsoft Digital. “Experimenting and innovating are at our core—managers are encouraged to provide the time and space for innovation, and to celebrate both successes and learnings.”

Microsoft Digital employees work on front-line technologies that matter. Their efforts serve as living case studies for Microsoft products, testing them in real-world conditions before they reach our customers. The result is a portfolio of work that combines innovation, pragmatism, and long-term thinking.

“We run hackathons sessions like ‘Fix, Hack, Learn,’ where we train ourselves on new technologies and then actively experiment,” Osten says. “That’s one of the most exciting parts of working here: We’re always pushed to explore the latest and greatest technologies and find real value in them.”

The pace can be fast and intense, but it offers the opportunity to work at the cutting edge and be part of transformative software releases. Innovative products result from being given the time and trust to invest and iterate.

“Open-mindedness and flexibility are critical here,” Sydorchuk says. “Technology evolves too quickly to get attached to specific ideas or scopes. Constant change is the norm, and learning to live with uncertainty is essential.”

Customer Zero: Our defining mission

A central component to working in Microsoft Digital is our role as Customer Zero. This concept describes how we use our own products and services internally before releasing them to customers, subjecting them to security, compliance, and productivity demands at an enterprise-level organization.

“Because we deploy these products internally at scale, we learn a tremendous amount, especially since many of these capabilities are early-stage or newly released.”

Andrew Osten, general manager, business operations and programs, Microsoft Digital

This approach surfaces functionality gaps, risks, and usability issues early, turning internal teams into live stress tests for new technologies before they are released to customers. Customer Zero helps ensure our products are resilient, fit for purpose, trustworthy, and grounded in real-world needs, not idealized scenarios. Just as importantly, these practices help create repeatable governance, adoption, and change strategies that customers can reuse, translating internal learning directly into external value.

“Because we deploy these products internally at scale, we learn a tremendous amount, especially since many of these capabilities are early-stage or newly released,” Osten says. “Our role is to generate energy and interest, help teams adopt the tools in ways that deliver real value, and then capture those learnings.”

Customer Zero means that Microsoft Digital functions differently from a typical IT organization, even though we’re still on point for the fundamentals, like keeping the network and its related infrastructure running safely and securely, managing the tenant, providing IT support, driving deployment and adoption, and ensuring our employees have the right tools, devices, and AI-powered services to succeed in a complex global enterprise.

What makes us unique is that we get access to ground-breaking new Microsoft products, features, and capabilities first. We provide early feedback, are the first to try out new experiences, and validate them at enterprise scale.

“We’re often operating at the edge,” Osten says. “For example, I’m currently using early-stage hardware and agentic technologies that haven’t been released yet for general availability, to both provide product feedback and drive value realization as soon as possible. Years ago, through our internal dogfooding program called Elite, I was using a next‑generation Xbox before it launched publicly. Those experiences are part of how we learn about and improve our products.”

Growing AI-based skills

A good example of something truly transformative to emerge from Microsoft Digital recently was our enterprise‑wide deployment and operationalization of Microsoft 365 Copilot—acting as Customer Zero for generative AI technology at scale.

Rather than treating Copilot as a productivity add‑on, we led a full reinvention of how knowledge work happens at the enterprise level. Building everything from governance and data-hygiene standards to role‑based adoption models and change management playbooks, we went all out to change employee habits and safely embed AI into daily workflows across the company.

“AI is behavioral,” Osten says. “To get real value, we work closely with business units to understand the problems they’re trying to solve, map those processes, identify where people can focus on higher-value work, and then build and drive adoption of agents to support that shift.”

In essence, Microsoft Digital is engaged in building an entire business model with AI serving as a governed, trusted, role-aware layer of intelligence. The company refers to this as the Frontier Firm concept, combining human judgment with AI agents—tools that can reason, plan, and execute tasks across systems.

“Building agents just because we can isn’t the goal. The goal is value. Microsoft Digital plays a key role in identifying the right problems, ensuring the right tools are available, and scaling solutions responsibly, so we’re solving problems while not creating new ones.”

Aisha Hasan, principal product manager, Microsoft Digital

The work Microsoft Digital does to conceive, build, and incorporate agents falls under a company-wide initiative known as Microsoft Agent 365. It focuses on three broad questions:

• What problems are we trying to solve?
• How can we build AI agents and workflows to solve them?
• How do we manage and scale this work without creating sprawl or duplicative solutions?

“Building agents just because we can isn’t the goal,” says Aisha Hasan, a principal product manager in Microsoft Digital. “The goal is value. Microsoft Digital plays a key role in identifying the right problems, ensuring the right tools are available, and scaling solutions responsibly, so we’re solving problems while not creating new ones.”

Prospering in Microsoft Digital

In addition to the central role they play as Customer Zero and the opportunity to engage closely with agentic AI, Microsoft Digital employees also benefit from a wide range of opportunities that go beyond technical skills. Rather than limiting our roles within narrow job definitions, we focus on a more holistic career experience that supports pursuing growth opportunities across Microsoft.

“We invest in growth, exposure, innovation, and collaboration in a way that makes the work both challenging and fulfilling,” Osten says.

Employees at Microsoft Digital use traits like curiosity, empathy, and adaptability to thrive within a fast-moving technical landscape. Being curious leads to learning, learning enables adaptation, and empathy pulls it all together, helping people grow as they collectively manage challenges.

“Technology is evolving so fast that keeping up with everything is a challenge in itself,” Hasan says. “Empathy, for yourself and others, matters when everyone is navigating constant change.”

It’s common for employees to leverage a range of responsibilities both within and between different jobs. Open-mindedness and flexibility are critical. Technology evolves too quickly to get attached to specific ideas or job scopes.

“I began in engineering and operations, moved into network engineering, and then gradually ‘peeled back the onion’ by stepping into technical program management,” Hasan says. “That allowed me to see the end-to-end picture: business value, technology, end users, adoption, and long-term maintenance.”

To be successful at Microsoft Digital, technical skills are important, but what really matters is the ability to innovate and work through uncertainty.

“I look for people who thrive in ambiguity, who enjoy taking on new challenges rather than waiting for perfect clarity,” Osten says. “Collaboration is equally important. In an environment this dynamic, you may be accountable for an outcome, but your success depends on the work of many other teams.”

How Microsoft values drive our work

No description of what it’s like to work at Microsoft Digital is complete without a discussion of the principles that fuel us, both at the department level and for the company as a whole.

“It often feels like drinking from a firehose, in terms of the volume of information one needs to process. It’s high-intensity, but being able to work at the cutting edge and be a part of major technological transformation that empowers everyone on the planet to achieve more makes it totally worth it.”

Mykhailo Sydorchuk, principal product manager, Microsoft Digital

Here are four core Microsoft Digital value pillars, as Osten describes them:

1. People development and skilling. This includes technical skills—including around emerging technologies like agentic AI—as well as people skills. We focus on stakeholder management, storytelling, and career development skills that support long‑term employee growth.
2. Leadership and manager development. We continually build leadership capability through a growth mindset, reinforcing principles like creating clarity, generating positive energy, and driving success. We invest heavily in helping both current and future leaders build “model‑coach‑care” skills.

3. Connection and collaboration. We intentionally create opportunities for teams to understand one another’s dependencies, whether through global meetings or structured collaboration initiatives. It’s easy to become siloed in a large enterprise, and these connections are critical, especially as AI continues to blur traditional boundaries.
4. Inclusion. This means being inclusive across communities, geographies, languages, cultures, and work environments. We focus on how we meet, how remote participation works, and how to ensure everyone can contribute effectively, regardless of location or role.

Following our pillars, and being benchmark examples of Microsoft’s value model, contributes to the success of Microsoft Digital and enables our employees to thrive  working at one of the world’s most prominent tech companies.

“Microsoft is a fast-paced environment, primarily due to scale and constant innovation,” Sydorchuk says. “It often feels like drinking from a firehose, in terms of the volume of information one needs to process. It’s high-intensity, but being able to work at the cutting edge and be a part of major technological transformation that empowers everyone on the planet to achieve more makes it totally worth it.”

Key takeaways

Here are five keys to employee success at Microsoft Digital, which can be applied to any IT organization:

• To get a foot in the door, be resourceful. Microsoft Digital employees find their way into the company through a variety of channels, including personal networking, internships, vendor relationships, and Microsoft external and internal career sites.
• Embracing Customer Zero is crucial. The concept of using Microsoft employees as early adopters of new products and services is a strategic cornerstone and an essential aspect of how the company operates.
• Understand what it means to be a Frontier Firm. Orienting your approach to work in a way that corresponds with the benefits of agentic AI can help you align with Microsoft Digital’s journey, as we become a lighthouse example of a Frontier Firm for other IT organizations.
• Develop your curiosity, empathy, and versatility. Technical skills are valuable, but continuous learning and softer skills are foundational to professional and personal growth and success.
• Know your organization’s core values. Collaboration, connection, and inclusion are vital tenets for succeeding at Microsoft Digital, as reflected in the organization’s values.

Try it out

Empower your future with an IT career at Microsoft.

Related links

• Learn more about our company’s mission, values, and products.
• Check out the main Microsoft Careers page.
• Read about Olutunde Makinde’s journey to Microsoft.
• Learn about Anahit Hovhannisyan’s impact on IT at Microsoft.
• See how Microsoft Digital is transforming IT at the company.
• Discover how Microsoft Digital leverages Customer Zero to drive AI innovation.
• Understand more about how agentic AI is core to becoming a Frontier Firm with this deployment readiness guide.

The post IT on the cutting edge: Working in Microsoft Digital in the era of AI appeared first on Inside Track Blog.

With agent usage growing rapidly, our team here in Microsoft Digital, the company’s IT organization, has invested in events and learning sessions to help employees adopt agentic approaches and get more value from Microsoft 365 Copilot.

One example was Camp Copilot, a peer‑led virtual training event dedicated to building employee Copilot skills. We also offered a Copilot Expo, which delivered a more formal, large‑scale learning program focused on role‑specific skills and deeper daily usage.

Now, we’ve consolidated learnings from those programs into Agent Launchpad, an accessible, multifaceted six‑module curriculum. Our instructional program is designed to develop our employees’ agentic AI skills, empowering them to take advantage of existing agents in their day-to-day work and build their knowledge and confidence to create new agents.

Why we built Agent Launchpad

Companies that fail to grasp the growing role of AI and agents in the workplace risk falling behind teams and organizations that are already redesigning their work around hybrid human-agent teams. We created Agent Launchpad to acknowledge this shift, demonstrate the power of agents, and show how they can be integrated into everyone’s daily work.

Unlike basic assistants that only respond to direct prompts, agents can plan, carry out actions, monitor progress, and iterate until they meet a goal. They can perform tasks like drafting content, analyzing data, automating workflows, scheduling meetings, triggering processes, and coordinating across multiple apps and services.

“Think of an agent as like hiring a really intelligent, enthusiastic university graduate. They may not have deep business experience yet, but they bring a high level of intelligence, energy, and scalability to the tasks you give them.”

Kevin Wooldridge, senior director of business programs, Microsoft Digital

At a higher level, agents can act as proactive collaborators, taking on routine tasks so human workers can focus on higher‑value thinking. Employees who aren’t engineers can create agentic tools, which becomes a cultural differentiator.

“Think of an agent as like hiring a really intelligent, enthusiastic university graduate,” says Kevin Wooldridge, a senior director of business programs in Microsoft Digital. “They may not have deep business experience yet, but they bring a high level of intelligence, energy, and scalability to the tasks you give them.”

Understanding how agents work is the new baseline for staying competitive. It’s the defining trait of the emerging Frontier Firm: A human‑led, agent‑operated organization designed for the AI era. Workers become agent bosses who define outcomes, while autonomous agents plan, reason, and run the workflows to deliver them.

How Agent Launchpad enables agent adoption

Integrating agents into existing workflows and processes can feel overwhelming. Our Agent Launchpad curriculum can help our employees get the most out of the technology.

“Our employees told us they didn’t want someone lecturing over slides. They wanted peer‑to‑peer learning, storytelling, showcases, and hands‑on experiences.”

Tom Heath, senior business program manager, Microsoft Digital

To build our curriculum, our team incorporated input from a variety of stakeholders across Microsoft representing a range of backgrounds and technical expertise. They also included feedback from the Copilot Champs Community.

“Our employees told us they didn’t want someone lecturing over slides,” says Tom Heath, a senior business program manager in Microsoft Digital. “They wanted peer‑to‑peer learning, storytelling, showcases, and hands‑on experiences.”

Baked into our Agent Launchpad program are:

• Detailed, approachable explanations of the existing agents available in the Copilot ecosystem
• Practical guidance for how to use the agents
• Step-by-step, hands-on labs for building new agents—regardless of the employee’s level of technical expertise

“People were being bombarded with information about agents, many of which were already live,” says Stephan Kerametlian, a senior director of business program management in Microsoft Digital. “Launchpad became a way to bring clarity and help them discover what already exists.”

Our curriculum explains how to get the most out of available agents, like our Employee Self-Service Agent. It also supports employees who want to build their own agents, whether by using Agent Builder for no‑code development or utilizing Copilot Studio for light coding (otherwise known as pro‑coding).

“Launchpad covers that full end‑to‑end journey at a time when information feels scattered and overwhelming,” Kerametlian says. “It gives people a structured, guided, modular path from the fundamentals all the way to developing agents, if that aligns with their skills and needs.”

Built for flexibility: Our Agent Launchpad curriculum

Given the broad range of skills and goals that our employees bring to the learning process, our six-module curriculum format was designed around two different tracks: The Explorer path and the Builder path.

“We talk about ‘buffet‑style learning’ a lot at Microsoft, and that applies here—but with AI and agents, many people don’t even know what they need. That’s why we built two learning paths.”

Cadie Kneip, senior business program manager, Microsoft Digital

Participants can sign up for live sessions or, if they prefer a self-guided approach, they can move through our modules on their own schedule. Learners have the option to earn participation badges by finishing modules, completing paths, or achieving other milestones within the curriculum.

“We talk about ‘buffet‑style learning’ a lot at Microsoft, and that applies here—but with AI and agents, many people don’t even know what they need,” says Cadie Kneip, a senior business program manager in Microsoft Digital. “That’s why we built two learning paths. We don’t believe everyone needs to be a builder, but everyone benefits from using agents to do their best work. Our goal is high‑quality agents and great usage experiences.”

Each path aligns with specific parts of our curriculum:

• Explorer path, Modules 1-3: Offering both context-setting information as well as examples and usage guidance for existing Copilot agents, our first three modules are for those who want to understand broader agentic context and enhance their day‑to‑day work with available agentic options.
• Builder path, Modules 1-6: For those who want to build their own agents, our full curriculum includes not only the first three modules but also no‑code agent development in Agent Builder (Module 4), agents that involve pro-coding via Copilot Studio (Module 5), and a showcase for new agents with recorded demos and use cases (Module 6).

As an enterprise-level company, Microsoft employs people with a wide variety of skills and backgrounds. That’s part of why Agent Launchpad works: People can choose their own agentic adventure.

“Launchpad provides a centralized starting point, with clear signposting to other assets and a sense of community. It lets us scale across the company and meet people where they are,” Wooldridge says. “If someone is deeply technical, there’s a path for them. If someone isn’t technical but wants to understand the hype and experiment, there’s a path for them too.”

The Frontier Firm mindset: A new way to think about work

While our Agent Launchpad curriculum includes detailed technical guidance for using and building agents, it’s also vital to emphasize the Frontier Firm mindset that employees need as we collectively approach a new era of AI-based work.

“When our core team was designing what Agent Launchpad would look like, we wanted to make sure we weren’t just tackling the technology, but also the mindset and behavioral changes that come with it.”

Alexandra Jones, director of business programs, Microsoft Digital

In the near future, a human‑led, agent‑operated organization built for the AI era—one in which humans define the outcomes they want, but agents decide how to achieve them—will become the new norm. The first module in our curriculum is designed to make sure that concept lands with learners, and it could be the most important part of the training.

“When our core team was designing what Agent Launchpad would look like, we wanted to make sure we weren’t just tackling the technology, but also the mindset and behavioral changes that come with it,” says Alexandra Jones, a director of business programs in Microsoft Digital. “That’s why we decided to cover the concept of the Frontier Firm—why people’s mindsets need to shift, and how we can address common concerns about AI.”

Agentic AI: A shifting landscape

Given the pace of innovation in the AI landscape, our Agent Launchpad program needed to be resilient, flexible, and minimally dependent on product documentation that might soon be outdated.

“It’s challenging to anticipate people’s needs in such a fast‑moving environment,” Wooldridge says. “We’re only slightly ahead of our employees on this journey ourselves, so we’re learning what’s valuable at the same time they are. That means we’re constantly recreating or updating content—it’s a hamster wheel of creation, delivery, revision, and more delivery.”

The pace of change is an ongoing challenge.

“All of this is part of our evolution. Our first immersive learning experience was Camp Copilot. We learned from that and evolved it into Copilot Expo. Now we’ve iterated again and built Agent Launchpad. It’s essentially version 3.0—the best of what we learned from the earlier programs, retooled around agents.”

Stephan Kerametlian, senior director of business program management, Microsoft Digital

New agents ship constantly. The tools evolve every day, and the technology moves at lightning speed. Keeping Agent Launchpad current remains a priority, and our curriculum is continuously adapting.

“All of this is part of our evolution,” Kerametlian says. “Our first immersive learning experience was Camp Copilot. We learned from that and evolved it into Copilot Expo. Now we’ve iterated again and built Agent Launchpad. It’s essentially version 3.0—the best of what we learned from the earlier programs, retooled around agents.”

Driving interest: Enthusiastic responses to Agent Launchpad

Employees are seeing the value of our curriculum, as strong usage data indicates broad interest in the program. In addition to online engagement with our coursework, thousands of our employees have attended in-person sessions. It’s a level of participation that helps drive the goals of both agentic adoption and the Frontier Firm mindset at Microsoft.

Feedback has been overwhelmingly positive, with employees reporting high satisfaction along with a demonstrable uplift in weekly active agent usage across Microsoft. Many thoughtful recommendations have been captured and turned into insights that will inform our next phase of Agent Launchpad.

“Launchpad unexpectedly became extremely popular—it was supposed to be our pilot, and we didn’t promote it heavily,” Kneip says. “Because of that huge engagement, we want to find more ways to lean into rewards and celebrate people who submit their work, so people feel recognized and come back to learn with us again.”

Key takeaways

Here are some things to keep in mind as you develop your own training programs around the new agentic way of working:

• Understanding how agents work is the new baseline for staying competitive. This is the defining trait of the emerging Frontier Firm: A human‑led, agent‑operated organization built for the AI era.
• Agent Launchpad delivers insights to employees about the fast moving agentic AI landscape. By building on our experiences with Camp Copilot and Copilot Expo, the program gives learners a structured, approachable way to understand, use, and build AI agents in their daily work.
• The curriculum is designed to meet employees where they are. With Explorer and Builder paths, Agent Launchpad supports both agent adoption and agent creation—regardless of technical background or learning style.
• The program helps employees develop a Frontier Firm mindset. The curriculum emphasizes not just how agents work, but how human led, agent operated teams are reshaping the future of work and the new habits we all need to build to leverage them.
• Strong engagement and Copilot usage shows that our participants are benefiting from the program. High participation rates and increased agent usage across Microsoft signal growing confidence, capability, and enthusiasm for agentic AI among employees.

Try it out

Learn more about AI agent adoption at Microsoft Learn.

Related links

• Discover how to build your own agents with Copilot Studio.
• Try our 7 tips for driving Microsoft 365 Copilot adoption with Camp Copilot.
• Explore how Microsoft enables meaningful AI adoption with the Microsoft 365 Copilot Expo.
• Learn how the Copilot Champs Community drives AI tool adoption.
• The Frontier Firm: Discover how knowledge workers are forging their own AI tools at Microsoft.

The post Skilling up for the future of work at Microsoft with Agent Launchpad appeared first on Inside Track Blog.

To accomplish these huge tasks, it’s essential to cultivate a range of perspectives, expertise, and lived experiences.

Olutunde Makinde is an example of this.

“A friend once laughed at me back in college when I said I wanted to work at Microsoft, like it was impossible. But I knew I could achieve the impossible if I could just be focused. I never gave up.”

Olutunde Makinde, senior service engineer, Microsoft Digital

Makinde, a senior service engineer in Microsoft Digital, came to the company the long way around—roughly 7,000 miles away from the Redmond, Washington, headquarters, in fact. He’s originally from Lagos, Nigeria.

As a global organization, Microsoft builds teams where people with different experiences and life journeys actively influence how products, services, and internal platforms are designed. Makinde, commonly known around the office as “Tunde” (“rhymes with Sunday,” he notes), embodies that diverse approach, bringing his unique insights and experiences to critical work at the company.

“A friend once laughed at me back in college when I said I wanted to work at Microsoft, like it was impossible,” Makinde says. “But I knew I could achieve the impossible if I could just be focused. I never gave up.”

Launching an IT career in Nigeria

Makinde’s journey to Microsoft began with earning a degree in computer engineering in Lagos, after which he found work as a network engineer. He spent the next several years developing his skills through certifications and other learning opportunities.

“I did a lot of self-paced training, learning how to configure Cisco routers. Eventually I became a Cisco-certified network professional (CCNP),” Makinde says. “Around that time, I had a friend who was preparing for Windows Server 2008 certifications, and through his study materials I started learning more about Microsoft and its products.”

Makinde’s first direct encounter with Microsoft came in 2014, when the company he worked for received a contract to deploy the first Microsoft Azure cloud installation in Nigeria.  

“I spent the last day of 2014 and the first day of 2015 at the customer site, figuring out how to connect their on-premises network to Azure,” Makinde says. “It had never been done before in Nigeria, and taking up that challenge really propelled me into the world of Microsoft-specific technology.”

From there, Makinde set his sights on a career at Microsoft. He parlayed his initial exposure to cloud architecture into a focus on Azure, as well as Amazon Web Services. After spending some time in the United Kingdom, he achieved his goal when he was hired by the Microsoft Digital team in 2022. He moved to the United States in 2025.

He credits support from his family, especially his wife, with helping him achieve his dreams.

“My wife was a pillar of support through every career transition, from Nigeria to the UK to the United States,” Makinde says. “She believed in me when I faced rejections, celebrated with me when I finally got the offer, and now keeps me grounded whenever work gets intense. I couldn’t have made this journey without her.”

Making an impact from day one

Kathren Korsky, a principal technical program manager in Microsoft Digital and Makinde’s hiring manager, remembers the impression he made right away. It was clear that Makinde’s experience and technical background were major assets.

“What caught my attention was how well-prepared he was for the conversation and how well he communicated,” Korsky says. “The stories he shared about his work with Azure deployment in Nigeria really drew my interest. But I was also intrigued by how he was able to bridge technology with the business world, working with different banks across the continent to gather requirements, understand them, and build solutions.”

Upon being hired at Microsoft, he initially worked remotely from the UK on a Redmond-based device and application management team. The team was looking to deploy Cloud PC internally and needed a system in which employees could request access and get approvals to use Cloud PCs.

“He was able to stand up a full Power Automate workflow within a short period, and with a very high degree of quality,” Korsky says. “Rarely did anyone find any defects or bugs in his system.”

Makinde’s designs drove value moving forward as well, as the team made updates to his initial workflows.

“His design was so strong that we were basically able to follow exactly what he had created in Power Platform and build that exact same design in ServiceNow. It really expedited that whole process.”

Kathren Korsky, principal technical program manager, Microsoft Digital

ServiceNow was more commonly used for systems that involved access requests and approvals, but when a platform update from Power Automate was initiated the team found Makinde’s original design was durable enough to weather the shift.

“His design was so strong that we were basically able to follow exactly what he had created in Power Platform and build that exact same design in ServiceNow,” Korsky says. “It really expedited that whole process.”

Driving efficiency and managing change

Since moving to the United States to work at company headquarters, Makinde has continued to push important projects forward—working with different stakeholders to deploy policy changes across Microsoft, managing the Change Advisory Board (CAB) intake process, and driving configuration updates for security and first-party product deployments.

“There’s a lot of diligence required to see the edge cases happening, to pay attention to them, and to watch out for potential problems. Tunde stops rollouts regularly to flag potential defects or risks, which prevents issues from interrupting our work and reducing productivity.”

Jeff Duncan, principal service engineering manager, Microsoft Digital

Makinde learned how to assess change requests and understand risk profiles, as well as enforce best practices for managing change within the security environment. Within about a year, he was able to take the lead in the space and own the deployment process.

A single misconfigured policy can cause major disruption. Makinde’s role puts him in position to be the checkpoint that prevents incidents before they happen.

“There’s a lot of diligence required to see the edge cases happening, to pay attention to them, and to watch out for potential problems,” says Jeff Duncan, principal service engineering manager in Microsoft Digital and Makinde’s manager. “Tunde stops rollouts regularly to flag potential defects or risks, which prevents issues from interrupting our work and reducing productivity.”

Softer skills like transparency, collaboration, and clear communication across levels and teams are key aspects of Makinde’s work as well.

“Tunde is thoughtful and detail-oriented, and he’s very good at explaining the decision-making process when he provides overviews for leadership,” Duncan says. “There’s rational, logical reasoning behind the decisions he makes.”

Makinde has implemented new efficiencies in how he manages the CAB and deployment service using AI. This includes CABBIE—an AI-powered agent that automates CAB communications. For Intune deployments, he uses AI to streamline deployment coordination and package reviews. These innovations reflect our Customer Zero approach to AI adoption here in Microsoft Digital.

“We run weekly CAB meetings to review change requests. That comes with a lot of communication work — status updates, follow-ups, coordination with stakeholders. It was all manual,” Makinde says. “CABBIE pulls the data from Azure DevOps, generates the emails, updates requests, and logs approvals automatically. It saves time and reduces errors.”

Success at Microsoft Digital: Aptitude and curiosity

As the organization at the center of the company’s own digital transformation, we in Microsoft Digital function as a living showcase of what’s possible with Microsoft technology. Our team tests new capabilities at enterprise scale as Customer Zero for Microsoft, identifying gaps and providing insights to ensure our customers benefit from what we’ve learned.

Because the impact of Microsoft Digital extends far beyond internal systems, team members have to set the standard for digital excellence. They must demonstrate what enterprise transformation looks like in practice and empower customers with the confidence to pursue their own modernization journeys.

 Hiring talented people like Makinde is essential to this mission.

“There are three core traits I look for when hiring—aptitude, attitude, and curiosity,” Korsky says. “Aptitude is not only what you currently know, but your propensity and desire to learn and grow those skills. Attitude goes hand in hand with that—are you willing to demonstrate grit and perseverance? And then curiosity, because so much of what we do from an innovation perspective requires a willingness to challenge assumptions and think of completely new ways of doing things.”

Makinde’s journey here at Microsoft Digital embodies and illustrates the company’s larger story: how technical expertise, innovative thinking, and a commitment to continuous learning combine to deliver world-class results.

“I’m now up to 25 certifications, and I continue to learn how to do more at Microsoft to positively impact the organization and protect our employees’ experience across applications and devices.”

Olutunde Makinde, senior service engineer, Microsoft Digital

That attitude of persistent curiosity and the willingness to keep learning continue to fuel Makinde’s experience at Microsoft. 

“Self-improvement is a way of life for me that has driven my career forward,” Makinde says. “At an early stage in my career, I did a lot of self-training—from learning how to configure Cisco routers and switches, to migrating on-premises workloads to Azure and managing cloud resources. I’m now up to 25 certifications, and I continue to learn how to do more at Microsoft to positively impact the organization and protect our employees’ experience across applications and devices.”

Key takeaways

Olutunde Makinde’s career experience here in Microsoft Digital offers some important insights that you can apply to your own organizational development:

• AI adoption starts with practical problems. Makinde’s use of AI to streamline CAB communications and deployment coordination shows how Customer Zero teams find real-world applications for emerging technology.
• Different experiences and perspectives contribute to business success. Achieving ambitious goals as an organization is dependent upon attracting talented people like Makinde from a range of backgrounds, disciplines, and lived experiences.
• Strong technical skills paired with innovative thinking drives value. Makinde’s contributions to flexible cloud deployment workflows are an example of how this combination pays dividends.
• Proactive risk management and attention to detail can prevent large-scale disruptions. By being willing to stop rollouts and flag risks before they become problems, Makinde’s approach to his work exemplifies how thoughtful decision-making safeguards productivity and security.
• Persistence, curiosity, and continuous learning are critical career accelerators. Having a long and successful career at a company like Microsoft goes beyond just technical aptitude; it also requires perseverance and a passion for learning. Makinde’s self-driven training efforts and his refusal to give up have enabled him to achieve what once seemed impossible.

Try it out

Learn more about working in IT at Microsoft by reading our Inside Track blog,

Related links

• Considering a career at Microsoft? See current openings at the Microsoft Careers portal.
• Read about a day in the life of a Microsoft employee using Copilot.
• Discover how Microsoft employees use the Total Rewards Portal to understand their value.
• Learn how Microsoft HR is using Viva and Microsoft 365 Copilot to empower our employees.
• Find out how the Microsoft Power Platform at Microsoft empowers employees.
• Connect with regional employees more effectively at Microsoft with Viva Amplify.

The post Olutunde Makinde: From Lagos to Redmond, a Microsoft IT engineer’s journey appeared first on Inside Track Blog.

At an organization the size of ours—with a global workforce, massive cloud footprint, and millions of identities to protect—relying on passwords wasn’t a sustainable security posture. We needed something stronger, simpler, and more secure.

This led to the introduction of Windows Hello for Business, which was first built into Windows 10 and then Windows 11. Windows Hello for Business replaces traditional passwords with hardware‑backed keys tied to a user’s device.

So, instead of typing a “secret phrase” that can be phished or leaked, our employees authenticate with biometrics or a PIN that never leaves the device. It’s fast, intuitive, and—most importantly—resistant to the kinds of attacks that plague password‑based systems.

“This wasn’t just a technology shift—it was a structural change in how we establish trust across the organization. The lessons we learned offer a practical blueprint for any organization looking to strengthen their security while also reducing friction for their workforce.”

Abu Kabir, director of IT service management, Microsoft Digital

Rolling out passwordless authentication at a large company like ours took more than just introducing new technology. It also required that we come up with a new way to onboard our employees securely, no matter where they work.  

The first step we took toward passwordless credentials was to create Identity Pass, which included an emphasis on Day 1 authentication (on a new employee’s first day at Microsoft). By combining strong identity proofing, a Temporary Access Pass (TAP), and automated onboarding workflows, we forged an identification system where employees could unbox their device, sign in securely, and register their credentials without ever needing a password.

The result wasn’t just a smoother user experience.

“This wasn’t just a technology shift—it was a structural change in how we establish trust across the organization,” says Abu Kabir, a director of IT service management in Microsoft Digital, the company’s IT organization. “The lessons we learned offer a practical blueprint for any organization looking to strengthen their security while also reducing friction for their workforce.”

How we launched passwordless authentication

To understand how we worked through the details of passwordless authentication, it’s helpful to explain how it was implemented in the first place.

Our passwordless security system includes several components, including face or fingerprint, a PIN tied to their device, and a physical security key (like a YubiKey), but this story focuses these on two:

• Identity Pass: the internal system for secure, passwordless onboarding and recovery
• Windows Hello for Business: the phishing‑resistant credential that Identity Pass helps users register

Identity Pass

Identity Pass, which is only used internally here at Microsoft, uses several tools to “bootstrap” the user, which is the first step in establishing trust among a user, a device, and an identity system. It’s the moment when you go from “nothing trusted” to “something trusted.” Everything that happens afterward depends on getting that moment right.

Identity Pass relies on three core elements:

• Verified ID is what we use internally to establish proof of identity. It’s an initial step and is valid for 30 days.
• Temporary Access Pass (TAP) establishes authentication.
• Conditional access enforces policy.

Identity Pass is where risk signals matter most, because onboarding and recovery are the moments when identity assurance is weakest. Those risk signals include:

• Authentication behavior detection: If a user tries to redeem a TAP or Verified ID from an unusual location, device, or pattern, Authentication Behavior Detection can flag a sign in as risky. Identity Pass can then require stronger identity proofing or block the flow.
• Global high‑risk detection: If our threat intelligence determines the user is likely compromised, Identity Pass will not allow TAP issuance or passwordless registration until the risk is remediated.
• Strong fraud indicators: If the user’s session or token shows signs of fraud (token replay, hijacking, malicious infrastructure), Identity Pass will force remediation and block bootstrap flows.
• Risk‑based identity assurance: This is the decision engine that takes security signals and determines what level of assurance is required. For example:
  • Low risk = allow TAP issuance
  • Medium risk = require Verified ID reproofing
  • High risk = block and escalate

Identity Pass is essentially the front door where these signals decide whether a user can even begin the passwordless journey.

Windows Hello for Business

Windows Hello for Business is the strong, phishing‑resistant credential that Identity Pass helps users register. Once this is in place, the risk signals listed above continue to influence authentication.

• Authentication behavior detection: Windows Hello for Business sign‑ins are evaluated like any other. If the user suddenly authenticates from an impossible location or unusual device, this system flags it as a sign‑in risk.
• Global high‑risk detection: If our detects a high‑confidence compromise, Windows Hello for Business sessions can be revoked via Continuous Access Evaluation. The user then reregisters through Identity Pass.
• Strong fraud indicators: If a Windows Hello for Business token is replayed or misused, this system triggers immediate revocation and forces secure recovery.
• Risk‑based identity assurance: This determines whether Windows Hello for Business alone is sufficient, or whether the user must step up to a stronger method based on risk.

Windows Hello for Business is the credential, but the risk signals determine whether that credential is trusted at any given moment.

What we learned: Rollout and implementation

While our toolsets and protocols offer a clear path for any organization moving toward passwordless authentication, transferring users from a typical user/password security setup can have a variety of challenges—especially at the outset.

Devices, environments, and remote work all matter

When an organization adopts identity‑based, passwordless authentication, one of the first realities it confronts is that the onboarding experience isn’t uniform. Employees don’t all show up with the same hardware, the same operating system version, or the same security capabilities. That diversity has a direct impact on how smoothly a user can complete the initial Day 1 setup and register a strong, phishing‑resistant credential.

“It’s not one-size-fits-all. The onboarding experience can be different by platform, version, and device. The further away you get from a homogenized environment, the more complexity you introduce.”

Matt Scott, senior IT service manager, Microsoft Digital

Device and platform diversity is one of the defining factors in designing a successful passwordless onboarding experience. Any organization adopting identity‑based authentication needs an onboarding system that can adapt to a wide range of hardware, OS versions, and security capabilities while still enforcing a consistent, high‑assurance security model.

Identity proofing and credential registration don’t look the same across platforms. A laptop might support credential setup directly at the login screen, while a mobile device might require an app‑based flow, and a non‑traditional platform might rely entirely on browser‑based enrollment. The underlying model stays consistent, but the user experience varies depending on where the user begins.

“It’s not one-size-fits-all,” says Matt Scott, a senior IT service manager in Microsoft Digital. “The onboarding experience can be different by platform, version, and device. The further away you get from a homogenized environment, the more complexity you introduce.”

Support volume

With Identity Pass in place, we have seen dramatic reductions in password reset volume (80%), onboarding delays, and help desk tickets related to account access. At the initial rollout stage, however, most organizations should anticipate a temporary spike in support needs.

“We expected an increase in volume, because we had recently gotten to 99% in terms of users being identified through Phish-Resistant Multi-Factor Authentication,” Scott says. “In reality, what’s happening is you have a lot of users who are unhappy with the experience as part of the move to a passwordless environment.”

No matter how solid the argument is for a passwordless approach or how cleanly an organization implements it, our experience shows that organizations should expect initial confusion from employees and increased pressure on support teams.

“Moving into a passwordless environment is obviously good for everyone, but we needed to make it easier for users to get the information they needed,” Scott says. “It’s not just one fell swoop of moving from password to passwordless. It’s truly a journey. And it’s very important that change management is part of that journey.”

Helping employees help themselves

Another key learning during our implementation of passwordless authentication was the importance of accessible documentation. This gives users who have yet to establish their identity credentials a way to get unblocked without having to immediately call IT support.

That documentation must stay accurate over time, so it’s crucial to build a governance strategy that ensures updates are made quickly as new devices, platforms, and scenarios emerge.

“During onboarding, if there’s a problem and a user is locked out, they may not have access to the corporate network,” Kabir says. “Having a site that they could access, with actual instruction based on which device they’re using and that shows them how to get past key blockers, was very helpful.”

Maintaining a direct line to leadership in order to help unblock lingering change requests also proved to be essential. In one case, bugs lingered in the engineering queue for days, even weeks, because the escalation path was limited (by design).

“Approval requests were blocked, and so approvals needed to be accelerated to the skip-level approver,” Kabir says. “We were able to move fast to fix that, because we had a clear understanding of the pain that folks were feeling on our side and could effectively communicate that to leadership.”

Short-term pain, long-term gain

The impact has been significant. Instead of spending long cycles troubleshooting forgotten passwords or manually verifying user identities, IT teams can focus on higher‑value work: strengthening identity protection, refining automation, and improving the user experience. This shift not only reduces operational overhead, it also aligns with our Zero Trust principles by removing weak authentication steps from the identity lifecycle.

For employees, the experience is equally transformative. New hires can unbox a device, authenticate using a TAP delivered through a secure Verified ID workflow, and immediately register passwordless methods like Windows Hello for Business. Although the onboarding journey may vary across platforms and devices, the process is fast and intuitive.

For existing users who lose access—whether due to a forgotten PIN, a lost device, or a credential reset—Identity Pass provides a self‑service recovery path that avoids the delays and security risks of traditional reset processes.

Our experience demonstrates that when these processes are redesigned around strong, hardware‑backed, phishing‑resistant credentials, organizations gain both security and efficiency. The result is a more resilient identity foundation that supports the realities of modern work.

Key takeaways

Here are some suggestions for getting started with Windows Hello for Business and Day 1 onboarding:

• Passwordless authentication start with strong identity proofing. Establishing user identity up front is essential to creating a secure foundation for all future authentication.
• Day 1 onboarding is the riskiest moment. The initial bootstrap step is where trust is first established, and risk signals matter most.
• Temporary Access Pass replaces temporary passwords. TAP provides a secure, time‑bound way for users to authenticate and register passwordless credentials without exposing the network to attack.
• Device and platform diversity shapes the user experience. Different hardware, operating systems, and compute environments require flexible onboarding paths that still enforce consistent security.
• Support demand spikes before it drops. Organizations should expect short‑term confusion and increased help‑desk volume before passwordless security benefits fully materialize.
• Long‑term gains are significant. Once deployed, passwordless authentication reduces operational overhead, strengthens security, and improves the user experience across the identity lifecycle.

Try it out

• Explore Windows Hello for Business.
• Check out Microsoft identity and access management services.

Related links

• Learn more about implementing strong user authentication with Windows Hello for Business.
• Read about phishing-resistant authentication with Microsoft Entra ID.
• See how Microsoft is using AI to reinvent network security.
• Discover how we developed a Zero Trust security model at Microsoft.
• Find out how Windows Hotpatch transformed security and compliance at Microsoft.
• Learn how Microsoft hardened our defenses with Microsoft Baseline Security Mode.

The post Getting started with Windows Hello for Business and Day 1 authentication at Microsoft appeared first on Inside Track Blog.