I work with some of Microsoft’s largest partners worldwide on how they take cloud, AI, and security to market. On stage, I turn that same material into something your team can use the week after.
You leave knowing what to do next, and believing you can do it.
“The goal was never the certifications. It was always who I was becoming.”
Sly Gittens
How Sly Can Help You
Tap a card to go straight to what you came for.
Four rooms, four different problems. The through line is that people leave with something to do, not something to think about.
The Always Be Learning keynote for the University at Buffalo Class of 2026, plus a guest lecture to the senior marketing class at SUNY Brockport. The message is that a degree is the foundation and habits decide the outcome.
What changes: students leave with a concrete next step rather than general encouragement.
Our students leave his sessions uplifted and with a list of action items to follow up on.
Sessions delivered at Pax8 Beyond in Amsterdam, Ingram Micro, and inside Microsoft. This is the same ground Sly covers as a Global Cross Solution Architect, working with some of Microsoft’s largest partners on how they take cloud, AI, and security to market.
What changes: the room stops debating whether AI matters and starts shaping an offer they can put in front of a client.
A rare combination of technical excellence and charismatic leadership. His ability to connect with people, whether through training, thought leadership, or partner strategy, is second to none.
Most organizations already own the tools. The gap is that nobody connected them to the work the team does every day. Sly has spent 14+ years across Microsoft, Ingram Micro, and RSA, and holds 100+ IT certifications, so the technical detail holds up when the questions get specific.
What changes: teams leave with named places AI fits their actual workflow, not a category to explore.
A remarkable ability to break down complex concepts into digestible pieces, consistently ensuring I grasped each topic thoroughly before moving forward.
A globally top-10 ranked podcast built to interview established women in technology, alongside sessions for the WIT Network and 100 Black Men. The show exists because Sly’s daughter inspired it.
What changes: guests reach an audience that would not otherwise have found them.
Sly has a one of a kind mindset and is always trying to progress himself as well as others around him.
Sylvester “Sly” Gittens fell in love with computers at age eight. Taking old machines apart, putting them back together, and learning everything about what made them work. Routers. Switches. Packet captures. The guts of it.
That curiosity never left. At the University at Buffalo, he majored in Business Administration with a dual concentration in IT and Marketing. He bet early that the intersection would matter. Then Facebook and Google became the biggest marketing companies on Earth, and the bet paid off.
From there, the learning stacked: servers, switches, data centers, virtualization, cybersecurity, cloud, AI. Each wave was another chance to get curious. Today, as Microsoft’s Global Cross Solution Architect, he works with some of the company’s largest partners worldwide, redefining how they go to market so their teams can empower the Microsoft channel to make real impact in real communities.
He also founded Tech Simplified (103K+ YouTube subscribers), hosts the top-10 globally ranked Women in Technology podcast, and wrote two books. One for his daughter. One for anyone trying to stay ahead.
It looks like hustle. It’s actually just curiosity, still doing its job since age eight.
He keynoted the University at Buffalo Class of 2026 and guest-lectured to the senior marketing class at SUNY Brockport. He has delivered sessions at Pax8 Beyond Amsterdam, Microsoft, Ingram Micro, WIT Network, 100 Black Men, and Anclote High School. He wrote two books. One for his daughter. One for anyone trying to stay ahead. He hosts a globally top-10 ranked podcast amplifying women in tech.
Everything Sly does is designed to give someone else a shorter path to clarity. Your next step gets easier because Sly has already walked it.
Before the keynotes, before Microsoft, before Tech Simplified, there's Molly and the kids. Everything on this site exists because they do. The curiosity that started at age eight? They are the reason I keep it burning.
When I talk about building a legacy, this is what I mean. When I say my daughter inspired the Women in Technology podcast. I mean it. When I write a book called Daddy’s Little Girl. It's for her, first.
The Gittens family. Roots in Barbados and Brooklyn. Always Be Learning.
Every family tries the sticker chart. Most stop within a month, and it is usually the same three reasons. One person ends up doing all the nagging. Somebody misses a day, the streak breaks, and the whole thing quietly dies. And a list of eight checkboxes is unusable for a four-year-old.
So I built KinHuddle, a family habit tracker where the grown-ups are on the chart too. One missed day is always forgiven. Illness and holidays are skipped instead of counted against anyone. And kid view can show a single step at a time, for the children a full list overwhelms.
Built by one family. Opened to many.
Visit kinhuddleapp.com →Sly doesn’t deliver information, he shifts perspective. His keynotes are built for the moment when an audience needs to stop fearing change and start moving through it.
What your audience experiences
Social Proof
From audiences. From mentees. From people Sly has shared the stage with.
Sly is a rare combination of technical excellence and charismatic leadership. His ability to connect with people, whether through training, thought leadership, or partner strategy, is second to none. Anyone who has the chance to work with Sly will quickly see why he’s a force in the industry.
Sly possesses a remarkable ability to break down complex concepts into digestible pieces. His attentiveness to my learning needs was commendable, he consistently ensured I grasped each topic thoroughly before moving forward. His mentorship significantly contributed to my professional growth.
Sly is a remarkable alumnus. Each event he attends, he brings his passion for helping others; his enthusiasm and energy are contagious. Our students leave his sessions uplifted and with a list of action items to follow up on. Sly’s dedication to our students and school is phenomenal.
Sly has a one of a kind mindset and is always trying to progress himself as well as others around him. What I found most unique about Sly is his generosity to help others and his creativity. He has shown his capability to succeed in any project or role he takes part in.
Sly has 100+ certifications. He’s walked every one of these roads. These four roadmaps distill that experience into a clear, step-by-step path, so you stop wondering where to start and start building credentials that open real doors.
Forget certs for a second. Which of these actually sounds exciting to you?
Pick the one that sounds closest. There’s no wrong answer.
Your answer tells me how fast to go.
Based on your answers, this path fits best.
Microsoft is retiring 11 certifications in 2026 and launching new AI-focused replacements. The paths below reflect the latest roadmap, including AI-900→AI-901 and the new AI-103.
Walk away ready to build, deploy, and lead AI solutions on Azure.
View roadmap →Full Guide AvailableWalk away qualified to protect, detect, and respond at enterprise scale.
View roadmap →Full Guide AvailableWalk away able to design, manage, and extract value from enterprise data.
View roadmap →Full Guide AvailableWalk away qualified to build and architect the cloud environments companies run on.
View roadmap →Full Guide AvailableReal walkthroughs. Real labs. Zero paywalls. New content every week.
Stories From A First-Time Dad
Written for Gabriella. Felt by every parent who’s looked at their child and thought: I want to be someone worth looking up to.
Permission to be present. For the parent who wants to lead at home the same way they lead everywhere else, with intention.
The Mindset That Powers Success
The Always Be Learning mindset isn’t motivation. It’s infrastructure. This book shows you how to build it.
A repeatable system for staying ahead, in any industry, at any career stage. Built from 100+ certifications and one unshakeable belief.
Ranked top 10 globally, Women in Technology with Sly Gittens gives you direct access to the conversations, decisions, and breakthroughs of women reshaping the tech industry.
“I have a daughter who’s going to grow up in tech. I want her to see what’s possible.”, Sly
Available everywhere you listen
On leading with purpose, navigating tech as a woman, and building a legacy that outlasts any title.
