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 used to hate going to the gym in January. Until I realized that I was the problem...


For years, I would complain about going to the gym in January. 

Too crowded.
Too many New Year's resolutioners. 
Too many people who "won't be here in February."

Then it hit me. I was the problem. 

Not the people showing up nervous. 
Not the ones trying to create new positive habits.
Not the folks choosing to get out of their comfort zones. 

I'd confused consistency with entitlement. 

The gym in January is not filled with people getting in my way. It's filled with people trying to get out of their own way to accomplish their goals. 
Choosing hope.
Choosing to start. 

And it reminded me of something I've known for many years. 

Life is better when you cheer people on. 

So, if you’re beginning something new this year, I’m rooting for you.

And if you’re already one of the regulars, be the reason someone else feels welcome to start.

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

Growing up in Southern California, I had a very different picture of how my career would look...


Yesterday, I spent the entire afternoon on a frozen lake with some of my favorite people in our industry. Colleagues, friends, partners, and even competitors. All coming together to raise money for the fight against cancer.

And today, my children are home from school because it's literally too cold for them to be there. 

None of that would have made my vision board coming out of college. 

But moments like this make me incredibly grateful for how it all turned out. The community we have here in Minnesota is special. And yesterday was a reminder of just how lucky I am to be part of it.

Growing up playing competitive golf has been an asset in my professional career, just not in the ways I ever expected.


The greatest gift golf ever gave me was how I view my competition.

Far less business gets done on a golf course than most people think. Sure, it is a great way to build trust and strengthen relationships. You learn a lot about someone by watching how they handle the frustration that comes with the game.

But in the 20+ years of my sales career, no one has ever bought anything from me because I could hit a 2-iron.

The real gift golf gave me was perspective.

In golf, your competition has zero ability to affect your game.
They cannot tackle you when you are about to hit a shot.

At most, they can only hope that you mess up. And in my experience, the more you wish for your competitors to falter, the better they seem to play.

It took me a long time to realize how valuable these lessons have been to my career.

In sales, cheering against your competition rarely helps. Over time, I have learned far more from respecting and admiring my competition than I ever gained from fearing them.

PS: What lessons from sports or competition have shaped how you show up in your career?

PSS: This embarrassing photo is proof that my love for the game came before my fashion sense.

One of the coolest things I've seen in golf in a long time... 


Tommy "Two Gloves" Gainey earned a spot in this weekend's Korn Ferry tournament in the Bahamas. And then he gave it up. 

Not because he couldn't make it. But so that a tour rookie could take his spot and chase their own dreams. 

But what I love most about this is how he withdrew from the event. 

He picked up the phone and called the tournament director himself, specifically to say how much he appreciated the invite, but that he thought it would be more important for a younger guy to get the opportunity instead.

This wasn't about sacrifice. 
It was about stewardship for the next generation. 

In a sport where just getting a chance to compete can be the hardest part, this was an incredible gesture. 

We’re only a week into the new year, and this might already be my favorite sports story of 2026.

I finally broke down and bought my first pair of reading glasses...


It wasn’t that I couldn’t read without them — it’s just far easier with them on.

That’s when I realized I’ve been doing this most of my life.

Making things slightly more difficult so that it felt more earned.

Like making sure my first car had a manual transmission, or waiting until the last minute to finish a college paper.

I’m not afraid of getting older; I’m worried that I’m losing my grit.

The best networking technique in the world isn’t a technique at all.


It’s simply being interested in people.

That’s why the best networkers never make you feel like they are networking.
Because they aren't. They are making connections. 

And real connection starts with curiosity. 

Because those people know that the best way to help you is to get to know you first.

Getting ready to head down to one of my favorite events of the year! Phishapalooza! 

This event is always a great exercise in remembering people's names and identifying them in their winter gear. This one is shaping up to be an even greater challenge on that front. 

But remember folks, there's no such thing as bad weather, only bad gear!

For anyone challenging themselves with change this New Year…


Remember this quote from Robin Sharma, “All change is hard at first, messy in the middle, and georgous at the end” 

So if it feels difficult right now, good. You are right on schedule. 

But it’s even more important to know that the next phase is no cake walk either. 

Let this be the year you run into the mess, instead of back into comfort. 

Illustration by VisualHustles

No alternative text description for this image

If you have been following me for a while now, or know me outside of linkedinland, you are probably aware of my love for hospitality. 


But it's not just the industry I'm obsessed with, it's the experience. 

So when Danielle Ottman told me she was going to bring to life an event she had been dreaming about for years. One centered around food, spirits, and the amazing people here in MN who make it magical for all of us. AND it would be raising funds for the ACS Hope Lodge. I had to be a part of it! 

The 1st Annual Taste of Hope event is happening at Orchestra Hall on March 12th. And we cordially invite all of you to experience it with us. 

Tickets are on sale now: https://lnkd.in/gJRyqUcF

We have all heard the saying, “Be kind. Everyone is going through something you know nothing about.”


But here’s the part we don’t talk about enough.

We usually reach for that reminder when someone is struggling, when they’re short, distracted, or clearly having a hard time.

Some of the most positive, supportive, and generous people in your life are also going through things you know nothing about.

They still show up.
They still encourage.
They still make space for others.

Not because life is easy for them, but because they choose to be that person anyway.

Those are the people who are truly special. And the ones worth appreciating out loud.

Know someone in your life that fits this description? 

Do not tag them here. 

Reach out to them directly. 

And then the next time you see them, ask them how they are doing…

As an engineering team, how do you balance responsiveness AND responsibility? 


That was one of the many thought-provoking ideas that Angie Schulke, Matt Lego, Matt Sonnek, and Drew Tabing shared with the Society for Information Management (SIM)- Minnesota Chapter last night. 

When I joined SIM a few years ago, it was to be in these rooms, hearing firsthand how IT leaders solve problems and create positive outcomes for their customers. 

Thank you, Angie and team, for sharing so candidly with all of us. 

Congratulations to Brian Johnson, MBA, for the excellent programming we have lined up for 2026! If last night was any indication of what's to come, we are in for a transformational year with this group. 

PS - If you are interested in getting involved with SIM, please let me know!

A colleague once asked me, "When does imposter syndrome go away?"


My response. "If you're lucky, never."  

By definition, imposter syndrome is the feeling that you somehow snuck through the cracks to end up where you are. That you fooled people, and eventually someone's going to notice. 

But in my experience, success rarely happens by accident.
It happens through action. Through showing up. Through reps, discomfort, mistakes, and consistency over time.

So what's the solution when that voice inevitably shows back up? 
Giving credit where credit is due. To yourself. 

Acknowledge the work you put in. The sacrifices you made. The growth you earned. 

And then reframe the feeling altogether. 

Because imposter syndrome isn’t proof that you don’t belong.
It’s a sign that you’re outside of your comfort zone, and that's where the real growth happens. 

What helps you keep going when imposter syndrome creeps in?

Tim Ferris used to ask the same final question to each and every guest on his podcast…


"If you could have a gigantic billboard with anything on it - what would it say and why?”

Well, this is what mine would say because it perfectly describes my philosophy on business, and on life. (For the record it’s a quote by Harry S. Truman, not my own)

It is also exactly what we are building in our Minneapolis office here with Presidio. 

Between all of the customers, vendors, partners, and yes, even the occasional competitor we work with, it is not about who wins. 

It’s about the outcomes we deliver. 

And while we don’t have a billboard just yet, we put this decal up in our office as our North Star for 2026. 

So, what would your billboard say?

One of the foundational rules of investing also applies to networking: you can’t time the market...


The best relationships don’t come from perfectly timed actions. They come from consistently investing in the people around you. 

A quick check-in.
A coffee with no agenda.
An intro that simply feels helpful.

Most of it doesn’t feel like networking at all, and that’s why it works.
Because just like financial investing, relationships compound. 

Small, consistent interactions build trust and context over time.

It’s far more meaningful to connect with one person a month than to reach out to twelve in January when you need something.

And over time, those small moments turn into something bigger.

So, how are you investing in your network today?

Did you ever dream of being a rockstar, then end up in IT? 


Ok, that one may just be relevant to me. 

But either way, you can join us on stage as we take the CIOs Against Cancer - Minnesota Auction event to The Fillmore this May 7th, 2026!

Thank you to all of the returning sponsors who continue to support this event and make it successful. I can't wait for you to see how this venue will put a spotlight on your brand! 

For any other organizations looking to get involved this year, we have a few sponsorship opportunities left and would love to have you join us. 

For more information, please reach out to Bryce Dominick , Charlie Hieb , or me, and we can fill you in.

Last night's College Football Championship wasn't a comeback story. 
It was a finding-the-right-environment story...


Two different quarterbacks with two very different paths. 
Both given a chance to shine on the biggest stage in their sport. 

Fernando Mendoza was overlooked coming out of high school. He developed quietly, earned his way, and kept improving without the spotlight. Indiana didn't make him a star; it gave him the stage for the rest of us to see it.

Carson Beck had already competed at the highest level. Having dealt with the pressure of expectations and the microscope that comes with a top-tier program. Then came injury and uncertainty.  Miami wasnt a shortcut. It was a second chance. 

The transfer portal isn't perfect, and college sports are far from it right now. But last night wasnt about the portal or the state of college sports. 

It was about two programs that gave everything they had to their teams, communities, and to their sport. And we, the fans, benefited from all of it.

Never ask a question you don't know the answer to...


This may be terrific advice for a trial lawyer, but it's terrible for making connections in the real world. 

Curiosity will get you much farther than leading a witness ever will. 

But make no mistake, it takes  courage to allow a discussion to go in any direction. To abandon your next brilliant response in order to learn more about the person sitting across from you. 

And for the record, I fail at this realization every day. 

But being interested in others is still the best way to make you interesting to them.

Do you have any idea how old you will be by the time you accomplish your goals?


The same age you will be if you don’t. 

So let’s get started…

Today is the first of the month, and it’s good luck to say “Rabbit, Rabbit” before you say anything else.


I’ve known of this superstition for at least 20 years, and I can count on one hand how many times I’ve actually started a month by saying it.

Not because I believe in it (I don’t). I’m not prone to superstitions — and I usually forget.

But this morning I nailed it.

So cheers to a little extra good fortune this month. And wishing you some as well.

Is this the year AI finally bridges the gap between IT and the business?


For decades, we’ve acted like these were opposing sides.

Technology vs. outcomes.
Speed vs. stability.
Innovation vs. risk.

AI changes that.

Not because it’s another tool for IT to manage, but because it forces a different conversation altogether. One that starts with business outcomes and works backward to technology, data, and execution.

In 2026, the winners won’t be the organizations “doing the most AI.”
They’ll be the ones using AI to get aligned with their counterparts and closer to their customers. 

No more “that’s a business problem” or “that’s an IT problem.”
Just shared accountability for results.

When AI is approached this way, it doesn’t take sides. It removes them.

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! 

taplio

The Battle

Ryan McKesson

Jay Olson

Followers

Posts

Engagements

Likes

Performance ScoreRyan McKesson's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Ryan McKesson

Jay Olson

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Ryan McKesson's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreRyan McKesson's LinkedIn Performance