Ryan McKesson

Enterprise Sales Executive

Championing business growth at Presidio, my journey in technology sales has been marked by fostering client relationships and consultative selling. 

My passion is connecting with clients and understanding their unique challenges, enabling tailored solutions ranging from Microsoft technologies to mobile enterprise applications. Beyond just transactions, it's about creating lasting value and empowering clients in Minneapolis and beyond with strategic consulting and innovative IT solutions.

Account Executive

Founded in 1989, Solution Design Group (SDG) in one of the top local IT consulting firms in the Twin Cities area. Our value proposition is simple: OUR PEOPLE and our commitment to building LONG-TERM relationships. SDG has a gold-standard for employing the best and the brightest technical talent available. This allows us to grow our business by being innovative partners to our clients.

 Our culture and business plan is structured around fostering long term relationships with our clients, our great team, and a commitment to responding to the perpetual trends and changes in the information technology industry. It is on this genuine model that SDG has been recognized by The Business Journal as a "Best Places to Work" and "Fast 50" multiple times.

 SDG provides IT Consulting Services and Staff Augmentation in Project Delivery, Microsoft Solutions and Open Source/JAVA application development in the Twin Cities market.


 Specialties: Java, Groovy, .Net, SQL Server Developers (SSIS, SSAS, SSRS) and DBA's, SharePoint, IT Consulting, Staff Augmentation, Project Managers and Business Analysts, Project Management, Business Analysis, Database development, Application Development, and Product Implementation.

I have been a part of a few events over the years, but last night was everything! 


The first annual American Cancer Society Taste for Hope event was a smashing success. 

Putting on an event is hard. 

Creating one from scratch and hosting the inagural version of it is insane.  

Congratulations to Danielle Ottman for having the courage to dream this event into reality. 

And to Sarah O'Brien for leading this into the magical evening it turned out to be. 

Thank you to everyone who was there and/or played a role in making it happen. It was incredible.

IT Ambassador, People Connector, Lifelong Learner and Purveyor of all things Positive.

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Congratulations CIOs Against Cancer - Minnesota  on an incredible TechSHEroes event! 

It was a day filled with joy, inspiration, and at times the sobering realization of just how much cancer affects all of our lives. 

One of the themes of the day was the importance of community. And I couldn’t be more proud of what we are building here in MN. 

Together, you all raised over $142k to fund cancer research that WILL save lives in the future. 

It was an honor for us at Presidio to sponsor lunch with our friends at Wiz. 

We are now gearing up for the CIO Auction Party taking place on May 7th. 

Hope to see many of you there too!

I did the most terrifying thing this morning. I went to the gym without my cell phone...


Well, I didnt GO to the gym without it, I got there and realized I'd forgotten it. 

I instantly thought about turning around. I didn't. 
But I was surprised by how difficult it was to carry on without my precious device.  

My first reaction was, what's even the point if I can track my workout in an app? Or listen to something "productive"? Heck, I couldn't even take a picture to prove I was there. 

I'm obviously poking fun at the situation, but this is not satire. 

I'm embarrassed by how afraid I was to be without my phone for an hour. And while my distraction-free workout wasn't life-changing. It was freeing enough to make me want to try it again. 

Soon.

Seven years ago, I published my first article on LinkedIn.


Looking back, the writing makes me cringe a little… but the message still makes me proud.

It was about the importance of networking events for women. Especially in technology.

Seven years later, that conversation feels more important than ever.

The impact of women coming together to learn, share, and grow with one another is undeniable.

Today, it’s an absolute honor to attend the 2nd Annual CIOs Against Cancer - Minnesota TechSHEroes event.

I’m proud of the community being built here in Minnesota, and incredibly grateful to be even a small part of it.

I’ve always felt that my writing on LinkedIn is incredibly selfish. Here’s why.


First and foremost, my target audience is me. I’m always writing to myself. Any advice I’ve shared here about networking, discipline, or habit formation has been aimed squarely at the person who needed to hear it most: me.

Second, I write about things that interest me, not what I think will interest everyone else. Some of the worst advice I’ve ever received was to only write about things I already know. That always felt limiting.

In reality, one of the best ways I’ve found to learn something is to write about it.

Writing isn’t just a way to share ideas. It’s one of the best ways I’ve found to understand them.

And finally, writing ideas out of my head has been incredibly freeing. My brain has never been great at turning itself off. Writing feels like opening a valve and letting the mental clutter flow somewhere useful.

I suspect a lot of people feel that same pull to write, share, or create something.

If that’s you, do it for yourself first.

The rest tends to take care of itself.

This is one of the coolest things I’ve ever seen an MLB manager do...


And that’s saying something, because this same manager once brought my kids onto Target Field and gave them a moment they’ll never forget.

But what Skip Schumaker did this week will go down in baseball lore forever. 

In the middle of their final spring training game, he walked out to the mound not to pull his pitcher, but to tell him he made the big leagues.

Carter Baumler thought his night was over. Instead, he got the call every player dreams about, and found out his career is just beginning. 

If you haven’t seen it, it’s worth watching.

My older brother played high school ball with Skip, and this is exactly who he’s always been. Thoughtful. Genuine. The kind of leader who understands moments matter. But people matter more. 

And this week, he created a moment that Baumler will remember for the rest of his life.

Can you imagine how many times Rory dreamt of curating this menu? 


The champions dinner at the Masters is one of the greatest traditions in sports. 

If you are not familiar, on Tuesday night of the tournament week, the past year’s champion hosts a dinner for all previous champions. 

The winner not only selects the menu, they actually have to pick up the tab as well. 

Truly happy Rory gets to finally  have this moment. And personally love the sticky toffee pudding choice for dessert 😀

What if I told you that In-N-Out makes the best cheeseburger on the planet? Would you agree?


Now, what if I also shared that growing up in California, my dad would take me there almost every Saturday after baseball, and that the nostalgia plays a big part in how I feel about it?

Would that at least help you understand my opinion?

I read this line in a book recently: Everything makes sense when you have all the information.

And I can’t stop thinking about it.

Where else am I too quick to judge or disagree, simply because I don’t have the full picture?

Because the truth is, most of the time… we probably don’t.

The biggest misconception about networking...

Is that your network is YOUR net worth? It is not. 

The value of your network isn't measured by how many people can help you. 

It's measured by how many people you can positively impact. 

The most meaningful connections I've made in my career were for other people. Not for me. 

When you approach it this way, networking starts to feel less like collecting contacts and more like connecting dots.

Less like a Rolodex… and more like putting together a puzzle.

And besides, it’s a heck of a lot more fun, too.

As Zig Ziglar famously put it, “You can have everything in life you want, if you will just help enough other people get what they want.”

Your time and attention are the greatest gifts you can give another person…

And most of the time, they’re enough.

For years, I held myself back from growing my network because I second guessed how I could possibly help someone, instead of simply finding out how.

Networking is rarely about bringing something to the table you can offer. It’s about showing up at that table to find out how you can help.

Let the Madness begin!!


For the past 23 years, no one close to me has ever asked me for advice when filling out their NCAA tournament bracket. 

Because every single year, I have the same team winning it all. My alma mater, the University of Arizona.

In many of those years, I was hoping for the Cinderella story, but a handful of times, it also looked like I knew what I was talking about. Or at least the basketball pundits agreed with my assessment of their chances. 

This year's tournament looks to be one of those times. 

My affection for UofA Basketball is well documented. But what I've rarely shared is the unexpected joy I've gotten from bringing my family along for this ride every March. 

My children refer to Arizona as "our" team. With comments such as "We have a real chance this year!" 

So while my hopes for this March Madness are both exceptionally high AND well justified. Win or lose, the real victory for me will be sharing it with my family. 

BEAR DOWN!

When an event sells out, there’s usually not much you can do about it...


But we were able to open up a small number of additional tickets for Taste of Hope Twin Cities next week.

So if you were hoping to attend, you have one more shot.

This year’s event will feature tasting stations from some of the Twin Cities’ most incredible culinary partners:

Borough • Bradstreet Crafthouse • Diane's Place • Krewe • Liliana • Mallards • Mirabelle • Molly’s • Nadia Cakes • O’Donovan’s Irish Pub • Pajarito • Pau Hana • Performance Foodservice – Twin Cities • Pimento Kitchen • Starling • Tequila Butcher

All are coming together for one evening at Orchestra Hall to support the American Cancer Society.

📍 March 12 | Orchestra Hall, Minneapolis
 🎟️ Tickets: tohtwincities.acsgala.org/

Hope to see a few more of you there.

#TasteOfHopeTwinCities #AmericanCancerSociety #TwinCitiesFood #EndCancer

The best time to start networking was 20 years ago. The next best time...



is today. 

Here’s the good news: you probably already know how.

If you’ve ever helped someone inside your company succeed and built alliances along the way, you know how to network.

If you’ve spent weekends on the sidelines of youth sports and built friendships with other parents, you know how to network.

If you’ve sat in a book club discussing ideas and listening to different perspectives, you know how to network.

We tend to overcomplicate networking when our need to receive is highest. When we’re looking for a job, making a sale, or trying to open a door.

But when you focus on giving first, the pressure fades.

And that is when you start to show up as your real self. Which is the only way to make real and genuine connections.

This year's CIOs Against Cancer - Minnesota Auction is going to be amazing! And we are making one final push to secure sponsors and make this the biggest event we've ever had. 

This is my favorite event of the year because it shows just how incredible this community of IT leaders truly is. 

Do not miss out on your opportunity to put yourself and your company in front of the most influential leaders here in town. 

Before you head out on spring break, add one more item to your to-do list and check out the remaining sponsorships we have available. 

Details in the comments section, or reach out to me directly for how to get involved!

If Mel Brooks could feel like a fraud while writing some of the greatest comedies of all time, it’s no surprise the rest of us wrestle with the same doubts.


This past weekend, I watched a new documentary about Brooks’ life and career. The film is full of famous actors describing the influence he had across Hollywood.

But what stuck with me most was how openly he wrestled with imposter syndrome along the way.

One line in particular stayed with me:

“You always agree with the most negative reviews because you know you’re a fake.”

We tend to assume the most successful people are also the most confident. 
That they believed in their genius long before anyone else did.

But in my experience, self-doubt seems to attach itself to almost any worthwhile pursuit.

Which is why it’s always inspiring to hear someone admit it out loud.

For context, Brooks shared that line shortly after releasing The Producers, more than a decade before the term “imposter syndrome” even existed.

Maybe his self-deprecation was part of his comedic genius. But it’s also honest. And wildly relatable. 

It must have been exhausting to second-guess himself so often.

But the real tragedy would have been if he had let that doubt stop him.

Because then, my friends…

We might never have gotten Spaceballs.

Jay Olson

Hi, I’m Jay Olson—a seasoned People Leader passionate about driving organizational change and continuous improvement. With deep expertise in HR transformation, I lead large-scale initiatives that optimize top-talent recruitment, retention, AI and technology enablement, and overall organizational effectiveness.

Please note: I primarily use LinkedIn for networking, engaging with content, and connecting with people, **not** as a messaging inbox. With multiple work and personal emails to manage, responses may be delayed or not sent at all. Thanks for understanding! 

Sr. Director of Talent Acquisition

AI can write emails, screen resumes, and summarize meetings. But it still can’t read the room.


That’s why emotional intelligence might be one of the most important leadership skills in an AI-driven workplace.

On the newest episode of What the HR!, Lena Scullard and I sat down with emotional intelligence expert and author Amy Jacobson to talk about the human skills that technology still can’t replace.

Amy has spent years helping leaders understand how emotional intelligence shapes performance, engagement, and how teams actually function. In a world that is rapidly adding more technology into the workplace, that perspective matters more than ever.

In this conversation we explore:
• Why emotional intelligence becomes more valuable as AI becomes more common
 • How EI changes the way leaders approach difficult conversations
 • Practical ways to strengthen emotional intelligence in everyday interactions
 • The role HR can play in helping teams build trust, ownership, and purpose

Technology is evolving fast.

Understanding people still takes work.

🎧 Listen now: https://lnkd.in/gZ_CqxBX

#TCSHRM #WhattheHR #EmotionalIntelligence #HRLeadership #FutureOfWork #LeadershipDevelopment #HumanSkills Twin Cities SHRM (TCSHRM)

Director, Global Talent Acquisition | Medtronic

🚨 Episode 116: Bringing Emotional Intelligence to Every Conversation – Even in an AI World 🚨

As AI continues to reshape the workplace, one human skill is becoming more valuable than ever: emotional intelligence.

🎙️ In this episode of What the HR!, cohosts Jay Olson and Lena Scullard are joined by Amy Jacobson, an emotional intelligence and human behavior specialist who delivers EI programs, keynotes, and workshops across Australia and internationally.

Amy is a twice Wiley-published author of Emotional Intelligence: A Simple and Actionable Guide to Increasing Performance, Engagement and Ownership and her newest book, The Emotional Intelligence Advantage: Mastering Change and Difficult Conversations. As a sought-after media commentator, Amy’s mission is to break down misconceptions around emotional intelligence and help leaders build purpose-driven teams that deliver results. 

Together, they explore:
✅ Why emotional intelligence is more critical than ever in an AI-driven world
✅ How EI shapes difficult conversations and workplace relationships
✅ Practical ways leaders can strengthen emotional intelligence in everyday interactions
✅ How HR can help create purpose-driven teams that perform and thrive

If you’re navigating change, technology, and the human side of leadership, this conversation will give you practical insights you can use right away.

🎧 Listen now: https://buff.ly/AKJNNo9 

#TCSHRM #WhattheHR #Episode116 #EmotionalIntelligence #HRLeadership #FutureOfWork #LeadershipDevelopment #HumanSkills

We talk a lot about engagement. Let’s talk about wealth.


Nobody likes a bad manager. Not your team. Not your culture. Not your bank accounts.

In this episode of What the HR!, I sat down with Jeffery Robinson and Eric Howell, GCDF, ORDM from BUILD WEALTH INC to unpack the real cost of poor leadership.

Spoiler: it is not just frustration and stress. It is financial stability. Career mobility. Confidence.

We dive into:
• How ineffective management impacts financial security
• The link between leadership and upward mobility
• Why financial wellness belongs in HR strategy

Bad management is expensive. This conversation helps explain why.

🎧 Listen now! https://buff.ly/KRNcSAX

#TCSHRM #WhattheHR! #LeadershipMatters #FinancialWellness #WorkforceDevelopment #HRLeadership #EconomicEmpowerment Twin Cities SHRM (TCSHRM)

🚨 Episode 115: Nobody Likes a Bad Manager — Not Even Your Money 🚨
 
What does poor management really cost?
 
It’s more than engagement scores and exit interviews — it’s financial stability, career mobility, and long-term wealth building.
 
🎙️ In this episode of What the HR!, host Jay Olson is joined by @Jeffery Robinson and Eric Howell, GCDF, ORDM of Build Wealth MN for a powerful conversation on the financial ripple effects of leadership — and why bad management doesn’t just hurt people, it hurts their money.
 
Jeffery, Senior Program Director, shares how his journey from client to leader fuels his mission to help families build generational wealth through financial education, workforce development, and housing counseling.
 
Eric, Senior Innovation & Expansion Director, brings his expertise in workforce strategy and innovation, connecting the dots between leadership, economic empowerment, and expanding career pathways.
 
Together, they explore:
✅ How ineffective management impacts financial stability and upward mobility
✅ The connection between workplace leadership and generational wealth
✅ Why workforce development and financial wellness belong in HR strategy
✅ What organizations can do to create lasting, measurable change
 
If you care about leadership, accountability, and the true cost of disengagement — this episode is for you.
 
🎧 Listen now! https://buff.ly/KRNcSAX
 
#TCSHRM #WhattheHR! #Episode115 #LeadershipMatters #FinancialWellness #WorkforceDevelopment #HRLeadership #EconomicEmpowerment

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Jay Olson

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The Battle

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Jay Olson

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Engagements

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