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

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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.

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.

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…

If we only took on challenges with a high probability of success, they would not be called challenges.


Now that we have made it to February, which is usually about the time I have abandoned my resolutions in the past, I am reminded why I still like them.

There have been years I tried too many, and years where I swore them off altogether. In my experience, though, starting a year by challenging myself has almost always led to something positive.

What I have learned is that motivation is a fleeting emotion. Or at best, it is a limited resource.

Relying on motivation alone is where we tend to “fail” at creating lasting change. It might get you out of bed a few times, in January, but the real shift happens when that motivation fades.

Because that is when you realize it was YOU who made it happen.

How are you feeling about your resolutions right now?

Illustration by Liz Fosslien

Bethany Global University

As a strategic leader at Bethany, I drive growth, leadership development, and donor engagement through high-impact initiatives. I chair Bethany’s largest fundraising event (that has over 200 leaders attend), and co-founded the Excellence in Leadership event that introduces 70+ new leaders to our mission every quarter.

I manage over 300 donor accounts, and report directly to the President. Additionally, I’ve spearheaded critical software negotiations, hired and managed multiple contractor relationships, and optimized business-critical systems. This role serves my passion for business as missions, I’m committed to equipping leaders and driving lasting impact.

Advancement Officer

Servant Leaders in Training

As the Founder of Servant Leaders in Training, I equip men to lead with purpose through service, mentorship, and intentional growth. Our monthly volunteer group mobilizes 35+ people to serve nonprofits, fostering a welcoming community of impact.

I also lead an annual Men’s Retreat, guiding 20+ men in defining their values and creating action plans for lasting transformation. Additionally, I co-lead a Personal Executive Board, where 35+ men align their mission, time, and finances with what truly matters.

At the heart of it all, I am passionate about equipping leaders to serve with purpose, build authentic community, and live out their values with intentionality.

Founder

Trissential

At Trissential, the Twin Cities’ largest technology consulting firm, I drove business growth by managing the entire sales process, from prospecting to closing, while building strong client relationships.

I developed account plans for our top three major clients, leveraged LinkedIn to identify key consulting buyers, and successfully secured high-value meetings. I also played a key role in inviting over half the attendees to our largest event, strengthening engagement with industry leaders.

Through strategic outreach and collaboration, I consistently contributed to Trissential’s reputation for excellence in consulting.

Business Development Manager

Minnesota Chamber of Commerce

At the Minnesota Chamber, representing 6,300+ organizations and 11,000+ business peers, the nation’s #1 Chamber in 2021, I helped drive economic growth by connecting businesses to key resources, advocacy, and strategic opportunities. I met weekly with 7+ business owners and C-suite leaders, implementing the Go-Giver philosophy to provide real value—offering connections, waste/energy reduction solutions, employee benefits, and economic growth strategies.

During my tenure, I exceeded financial goals, served on the Diversity Committee, led a Bible study, encouraged team volunteerism, and contributed to the growth of the Chambers leadership programs. I was also honored to be selected and participate in Leaders Lab, the Chamber’s exclusive leadership program.

Infor

As an Account Executive on Infor’s Major Accounts Team, I managed and sold to Infor’s largest enterprise clients, specializing in the manufacturing industry. I drove ERP software sales by identifying and qualifying new opportunities, executing strategic sales plans, and building lasting relationships with key decision-makers.

I worked closely with C-suite leaders and stakeholders to deliver tailored enterprise solutions, ensuring seamless account management, renewals, and revenue growth. By leveraging deep industry expertise, I helped manufacturers optimize operations, increase efficiency, and drive digital transformation.

Account Executive – Major Accounts

Macy's

As a Sales & Customer Service Manager at Macy’s, I led sales growth, team performance, and customer satisfaction in a fast-paced retail environment. I managed and coached sales teams, set and achieved revenue targets, and implemented strategies to enhance the customer experience.

I analyzed sales metrics, optimized team performance, and resolved escalated customer concerns, ensuring a seamless shopping experience. By fostering a collaborative, customer-focused culture, I contributed to increased sales, retention, and overall store success.

Sales Leader / Sales Manager

Tiffany & Co.

As an Operations and Assistant Store Manager at Tiffany & Co., I played a key role in delivering the Tiffany Experience, ensuring seamless store operations, inventory management, and client service while upholding the brand’s commitment to excellence.

Beyond operations, I partnered with the leadership team to coach sales professionals, enhancing their ability to engage and sell to Tiffany’s top-tier clients—those spending $100,000+ annually. Additionally, I acted as Manager on Duty, overseeing store performance, client interactions, and team leadership to ensure an elevated luxury experience.

With a focus on operational excellence, sales leadership, and client engagement, I contributed to achieving sales targets, process improvements, and unforgettable in-store experiences that reflected Tiffany’s heritage of craftsmanship and timeless design.

Assistant Store & Operations Leader

Target

As an Executive Team Leader at Target, I led guest experience, sales growth, and team development in a high-volume retail environment. I managed and coached teams, optimized staffing for peak traffic, and ensured seamless operations across checkout, self-checkout, order pickup, and drive-up services.

I drove sales, service efficiency, and guest loyalty through strategic planning, performance management, and real-time problem-solving. As a key carrier, I upheld safety, compliance, and operational excellence, creating a smooth, customer-focused shopping experience.

Executive Team Leader

The Nicholas Collections Mall

As Assistant Store Manager at The Nicholas Collections Mall, I played a key role in operations, sales, and customer engagement for our family business. I assisted with hiring, product ordering, and team training, ensuring strong product knowledge and customer service excellence.

I managed CRM systems to track top customers’ special events, led email marketing campaigns, and optimized store displays to enhance the shopping experience. Additionally, I handled deposits and financial transactions, ensuring smooth day-to-day operations.

By combining strategic merchandising, personalized customer outreach, and operational efficiency, I helped drive sales growth and customer loyalty.

Account Executive / Assistant Store Leader

Servant Leader dedicated to making a positive impact in the lives of others | Technology Enthusiast | Strategic Partner | Community Builder

Passionate about servant leadership, mentoring, and building meaningful relationships, with a mission to empower others and create a lasting impact. My purpose is to be a man of God who leads with an entrepreneurial spirit, a youthful mindset, and a love for family and friends.

Throughout my career—spanning roles in business development, sales, leadership coaching, and non-profit—I’ve embraced the power of connecting people, fostering growth, and serving with integrity. Whether cultivating partnerships at Bethany, mentoring emerging leaders through Servant Leaders in Training, or working in corporate leadership, my mission remains the same: to develop and equip others to thrive in their calling.

I'm guided by five core values:
1️⃣ Faith – Follow Jesus daily 🙏
2️⃣ Integrity – Always do what’s right, even when it’s hard
3️⃣ Health – Your body is a temple; take care of it
4️⃣ Growth – Always have a growth mindset
5️⃣ Travel – Exploring the world is important ✈️🌍

Myers Briggs: Extraversion | Intuition | Feeling | Perceiving

Ennegram: Type 7

I believe true leadership is serving first, leading second—while staying grounded in faith, wisdom, and a commitment to lifelong learning.

Let’s connect and create opportunities to inspire, grow, and serve together. You can book a virtual coffee with me or email me at Benjamin.nicholas2007@gmail.com or Ben@servantleadersintraining.com

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The Battle

Ryan McKesson

Ben Nicholas

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