Ryan McKesson

Enterprise Sales Executive

Presidio

Senior Account Manager

Solution Design Group

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.

Account Executive

ADP is consistently named one of the "Most Admired Companies" by FORTUNE® Magazine, and recognized by Forbes® as one of “The World’s Most Innovative Companies,” ADP has over a half-million clients around the globe and 60+ years of experience as a world-wide leader of business outsourcing solutions. 

My role within ADP is to connect with business owners and executives to help them focus on their core competencies and reach their business goals. I do this with strategic business consulting, including payroll, time and attendance, and back office operations development. Advising businesses in areas such as: risk mitigation, monitoring for profit leaks, and controlling their total cost of labor.


My specialties include:
- Affordable Care Act Strategies
- International Expansion
- Strategic Human Capital Deployment
- Time & Labor Management Solutions
- Tax & Compliance
- Business Process Outsourcing (BPO)

Major Accounts District Manager

AT&T Mobility

•	Responsible for profitable revenue and net add growth on a portfolio of accounts. Establish a trusted partner relationship with Executive level (CEO, CIO, Functional President or leadership equivalent).
•	Penetrate new national accounts and leverage new products to increase revenue within current accounts.
•	Develop and execute an account strategy, and sales relationships at multiple levels. Lead and manage the sales process for all product/applications.

•	Participated in extensive six months Business Markets Group sales program.
•	Acquired and sharpened comprehensive solution selling skills based upon three integrated approaches and methodologies.
•	Assisted in cold calling, prospecting, and business development activities with a field based Corporate Account Executive.
•	Compiled and internalized through understanding and knowledge of AT&amp;T Mobility systems and procedures.

Corporate Account 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.

If my OOO could be a photo, this would be it…


We are headed to Florida to soak up the sun as we take advantage of the MEA break. 

And it just dawned on me how much of a blessing it is to actually put on my out of office. 

For years I neglected doing so as a badge of honor. I took plenty of vacations, but would always stay connected and almost hide it from anyone outside of my office. 

But I now I see how valuable it is to have teammates who can back me up, and customers who know me enough to know how important this time is with my family. 

Will I be checking email this week? Of course. 

Will I respond right away? Probably. 

But I also plan to leave my phone unattended for several hours at a time over the next few days. 😎

Cheers,

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

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Our kids might not think we are “cool”…


But they’ll never have to worry about us being “too cool” for the activities they love. 

Happy Halloween!

Your LinkedIn profile is not your resume...


But it is the first place I’ll look after being introduced to you.

When I land on someone’s profile, I’m really just looking for three things:

1️⃣ Your photo
 A professional headshot is great, but mostly I just want to recognize you when we meet in person. Real > perfect.

2️⃣ Your job status
 What’s your current role, and are you still in that position?
 This is where I actually like the “Open to Work” banner. People have strong opinions about it, but I’d rather not guess if you’re in transition or have to awkwardly ask.

3️⃣ Your activity
 What are you posting, commenting on, or engaging with?
 I’m not judging how often you show up—just curious what kind of content grabs your attention.

And for context: I’m not a recruiter.

So when I look at your profile, I’m not evaluating whether you can do your job.
I’m just trying to understand who you are, what you care about, and how you show up.

Because the truth of the matter is, most people who look at your profile aren’t recruiters either.

What do you look at first when you check out someone's LI profile?

When it comes to service and hospitality, I believe most people fall into one of two categories…


Those who can’t stand poor service, and those who love an exceptional experience.   

I have always found myself in the latter category. 

So when Kristie McKesson and I chose Travail to celebrate a recent career milestone, our expectations were pretty high. 

To say they exceeded them would be an understatement. 

I’ve been wanting to experience this restaurant for over a decade. And that is exactly what this was. An Experience. 

There is something magical about watching a team of people do something they obviously love. 

The attention to detail, the creativity, and the commitment to each and every guest was inspiring. 

And it this morning it has me wondering how I can bring the same level of dedication to my career. 

Because it’s rarely just about what we do. It’s about how we make people feel while we do it. 

What is the best dining experience you’ve ever had? And did it motivate you as well?

Never underestimate the power of sending someone a "This made me think of you" message... 


A few days ago, a friend of mine sent me a note here on LI with a link to an article. Her message said, " This made me think of you. It reminded me of your writing, and I thought you might enjoy it too."

And I don't remember the last time I felt that seen or heard. 

Because here is what I've learned. Anything worth doing also comes with an inherent insecurity about whether or not it is worth doing.

So when someone sends you a note to tell you that you matter. It matters. 

Here is my challenge to all of you. 

When (not if) you find yourself thinking of someone this week who has had an impact on you, regardless of how long it has been since you told them, take 3 minutes to write them a message and send it.  

You will feel an instant boost just from sharing your appreciation. But the best part of all is that you never know when a well-timed note of validation can be the spark that person has been waiting for.

Positivity is a choice, and so is who you follow... 


There's a lot of noise out there. Negativity, outrage, and cynicism seem easier to find than ever right now. 

But the reality is, there are also incredible people using this platform to share hope, gratitude, and optimism.  You just have to look for them. 

And that's exactly what I have been doing over the past few years. Curating a list of people who consistently lift me up with their stories, vulnerability, and perspective. 

People who make me pause, reflect, and smile 😃 

So today, I am sharing this list to show appreciation for those who brighten up my feed on a regular basis.

Laura King
jason player
Jeni Cleveland, MBA
Tom Priebe
Heather Boschke
Chris Cathers
Colleen Kranz💡
Nick Hernandez
Anne Pryor, M.A.
Jane Ryan

And I know there are many more. So, if you have people in your feed who bring the same energy, please tag them below. And let's kick start this week with some positivity!

Winter is coming…



I used to hate fall in Minnesota.

No matter how beautiful the leaves got, all I could think about was what came next. The snow, the cold, the months of scraping windshields and layering up just to take the trash out.

I let my dread of winter steal the joy of the best season we have.

These days, I’m trying to live a little differently.

To appreciate the season I’m in instead of fearing the one that’s coming.

Because when you stop worrying about what’s next,
you start noticing how good right now actually is.

And that’s a beautiful thing.

The problem is not that we all face times of overwhelming stress and anxiety... 


It's that when we do, we often trick ourselves into believing we are the only ones going through it. 

Today is World Mental Health Day. And while I don't have any grandiose advice, I feel compelled to share what has helped me the most in the past several years. 

Talking about it. 

Not in front of large groups of people or on social media, but with friends, family, and when necessary, with a professional.

Being vulnerable with others has given me a gift that I never realized I needed. 

Proof that I am wonderfully normal. 

That my fears, anxieties, and insecurities are not unique to me. They are part of the human experience. 

Life is hard. And beautiful. And messy. and amazing. 

But I truly believe that in order to experience all of those emotions fully, we need to do so with others. 

Harvard conducted a famous study that determined the number one predictor of long term happiness is the strength of your personal relationships. That is all well and good, but i'm also convinced that what determines your ability to be happy today, is whether or not you have someone to call when you need to. 

Thank you for letting me share. And for anyone who sees this and wants to talk, I am here for you.

My greatest fear isn’t failure, it’s standing still...


I’ve always considered myself a lifelong learner. 
The idea of reaching a point where I’m no longer growing, or stretching, or worse, no longer curious… it quite frankly terrifies me.

Because growth isn’t supposed to be smooth. It dips. It wobbles. It tests you.

 And every setback I’ve ever experienced, personally or professionally, has ultimately turned out to be a setup for something better later on.

So when I see the dips, I no longer fear them. Because they’re usually a sign that I’m in motion. And motion is always a good sign of growth. 

How about you? Do you ever catch yourself mistaking comfort for progress?

What is the most essential trait for successful IT leaders to possess in this ever-changing landscape? 𝘊𝘶𝘳𝘪𝘰𝘴𝘪𝘵𝘺


Yesterday, I attended my first HMG Strategy conference as part of my membership with Society for Information Management (SIM)- Minnesota Chapter. 

It was a brilliant day of learning, growing, and connecting with some of the brightest technology leaders in town. 

My biggest takeaway from it all: The importance of being a lifelong learner.

And it has long been my belief that the best way to learn is from our peers. That is why events like this one are so special. They are not designed to collect business cards. They are created to foster connections. 

Congratulations to all of the Global Leader Award winners, and thank you again, HMG Strategy, for including the SIM membership in the event. It really is a tremendous time to be in technology!

A great conversation should never feel like a tug-of-war...


Your topic vs. my topic.
My experience vs. your experience.
“Cool story… but wait until you hear mine!”

Sociologist Charles Derber once described two types of conversational responses:

The Shift Response — when we redirect the focus back to ourselves.

The Support Response — when we stay with the other person and invite them to go deeper.

It’s the shift response that creates that tug-of-war feeling — where both sides keep pulling for control of the dialogue.

We often do this to be relatable (I’m guilty of it too). But every time we shift instead of support, we miss a chance to actually learn something new about the person in front of us.

One simple way to catch it in real time:
 👉 A shift response usually sounds like a statement.
 👉 A support response usually sounds like a question.

In the end, being interested in others is still the best way to be interesting to others.

Is it possible to lose a game, but still walk away feeling victorious? I believe so…


And the Toronto Blue Jays may have proven exactly that this week. 

On Monday night, the Blue Jays lost one of the most grueling games in World Series history — an 18-inning marathon that ended with a walk-off home run by Dodgers’ Freddie Freeman.

It would’ve been easy for the Jays to crumble after that kind of loss.

Eighteen innings of effort. A heartbreak finish. On the road.

But instead of folding, they rallied.

They came back to win the next two games at Dodger Stadium, proving something far more important than a single victory could ever show.

When asked about that 18-inning loss, players shrugged it off as “just another game.”

But I think it was something bigger.

That was the night the Blue Jays realized they belonged.

They proved to themselves and to the world that they could go toe-to-toe with the defending champions, that they had earned their place on that stage.

And that’s the part that resonates beyond baseball.

Because sometimes, even when the scoreboard isn’t in your favor, you still walk away with a deeper kind of victory. The confidence, the belief, and the lessons that carry you further than any single win ever could.

“The time you enjoy wasting is not wasted time” - Bertrand Russell 



The clarity that comes from stepping away may be hard to quantify, but it’s easy to measure. And that unit of measurement is energy. 

The amount of energy you bring back to your work after taking a break. 

So, while I am feeling particularly energized after an extended break, i’m also reminded of the importance of incorporating smaller acts of “recovery” into my week. 

And giving yourself permission to waste time, is what seems to make that time wasted so valuable.

One of the most underrated traits in leadership may also be one of the hardest to maintain in the age of AI transformation... 

Negative Capability. 

It's a term coined by the poet John Keats, and one that was recently brought to my attention in Brene Brown's new book, "Strong Ground."

Keats used the term to describe the ability to remain "in uncertainties, mysteries, and doubts, without any irritable reaching after fact and reason" 

In other words, being comfortable with uncertainty. 

And it may perfectly describe why GenAi is making many people leery of its implications. 

You see, technology has always been used to eliminate uncertainty.  

From telling time to predicting the weather to knowing exactly when your pizza will be delivered to your home.  

And while GenAI is unequivocally the most powerful technology we have ever experienced, it has also created far more uncertainty than any other tool we have encountered before. 

However, the leaders who can embrace this uncertainty will also be the ones who move forward with cautious optimism, seeking ways to leverage these tools for the benefit of their organizations and their customers.

The most intelligent answers often come from the simplest questions…


“Why do we do it that way?”
“What if we didn’t?”
“Can you explain that again?”

After 10 months at Presidio, I’ve realized that my lack of knowledge in certain areas has created one of my greatest assets. Curiosity. 

Because curiosity opens doors. It invites collaboration. It helps you understand not just what something does, but why it matters.

I joined Presidio to be an even greater resource for my customers. But I wasn’t sure what that meant until I got the courage to ask the simple questions. 

What I’ve found since has given me a deeper appreciation for just how challenging IT leadership is today.

Leaders are constantly asked to:

Innovate — but only if costs stay down.

Transform — but please don’t disrupt the status quo.

Modernize — but don’t compromise security.

And while I am confident we can help in all of these areas, i’m also certain that it doesn’t matter until we understand the why behind them. 

Curiosity led me here.
And it continues to shape how I show up every day, not with all the answers, but with better questions.

"The opposite of a good idea can also be a good idea" - Rory Sutherland


It's been a while since I shared a book recommendation, but Alchemy by Rory Sutherland might be the most impactful book I've read in over a decade. 

I saw Rory speak at the Welcome conference last month and was blown away. He is an advertising executive, and while his message is geared toward his marketing expertise, at its core, this is a book about human psychology. 

My favorite part, though, is that it has restored my faith that AI is still a long way from accurately predicting human behavior, especially when we realize that we can't even predict it ourselves.

Is the AI hype train finally pulling into the station?


I don’t know. But I do feel like it’s shifting directions. 

Because while technology changes quickly, people change slowly. 

And this isn’t about adoption. It’s about intention. 

People and organizations are moving away from asking, “What can this tool do FOR me?” to “What can this technology do WITH me?” 

And the latter is the far better question. Because it focuses on enhancement, not replacement. 

What will you accomplish WITH AI in the future?

When it comes to AI, interest is no longer the issue; execution is... 


I finally made it to my first Applied AI conference yesterday, and one thing was clear: enthusiasm for AI is at an all-time high. 

Congratulations to Justin Grammens, Shannon Seaver NBCT, Molly Doyle, and the entire team who hosted the sell-out crowd yesterday. 

People are eager to drive real value from AI. And this conference was a great place to learn. Every session I attended was valuable, insightful, and actionable. 

But one theme seemed to resonate throughout the entire day. 

The challenge isn't curiosity, or even desire. Its execution.  

Turning ideas into measurable impact requires strategy, data readiness, and cultural alignment. Not just tools and talent. 

The energy in the room yesterday was undeniable. But now comes the hard part, turning that excitement into execution.

AI is reshaping how we approach traditional infrastructure... 


We’re past the point of asking if AI will impact IT. The real question now is how and where AI will make a difference. 

And it's not just on the application side anymore. Organizations are now using AI to redefine the infrastructure beneath their digital assets.  

Compute, storage, networking. Every layer is being forced to evolve for scale, latency, and security in ways we haven’t seen before.

It's one of the surprise developments that I've noticed with my customers lately. Moving the conversation from "What do you hope to gain from AI? to “Is your foundation even ready for it?”

And it's why Presidio is in such a great position to help our customers bridge the gap between foundational IT and digital transformation. 

Because the organizations that win in this next chapter won’t be the ones chasing AI features.

They’ll be the ones modernizing their foundational infrastructure so they can move at the speed of AI. 

Is your organization preparing its infrastructure to keep pace with AI?

M & D Consulting

Consultant/Advisor/Program Manager for multiple industries
- Financial Services
- Municipal
- Digital Products

Principal Consultant/Owner

Tactile Medical

•	Responsible for PMO, IT governance, request intake/prioritization, process improvement, IT/business relationship management, IT strategic planning

•	Re-launched PMO and Portfolio Management – Built the PMO team, led construction/rollout of Project Delivery Framework SDLC for waterfall and agile approaches, established Priority Project reporting and dashboards, created/drove business functional outreach and platform update reporting to promote IT transparency, also served as POC/IT relationship leaders for Sales team 

•	Built/defined IT Governance, established official policies and procedures for change management, enterprise request intake, PPM, etc., led IT work with internal and external auditors, drove PI work for official Company accreditation

•	Major business solution implementations – Directly led or oversaw project managers for the following:
- Flexitouch Lower Extremity ComfortEase Launch – First major product improvement in four years (national rollout, 350 field sales reps, 10,000+ providers)
- CRM Pilot launch – First CRM in Company history (pilot Q4 2022; full rollout targeted for 1H 2023)
•	Major business solution implementations – Directly led or oversaw leaders for the following:
- Flexitouch Lower Extremity ComfortEase Launch – First major product improvement in four years (national rollout, 350 field sales reps, 10,000+ providers)
- CRM Pilot launch – First CRM in Company history (pilot Q4 2022; full rollout 2023)
- NetSuite ERP launch – First external ERP in Company history (financials, manufacturing and commercial operations) 
- Patient Trainer and Patient Support Portals

- Patient Trainer and Patient Support Portals

•	Established Process Improvement capability, built team and established methodology, mapped/improved 70+ processes across seven business areas, transitioned responsibility and team to business

IT Director – PMO, Governance, Analysis, and Strategy

•	Consultant/Adviser/Program Manager for the Financial Services industry

•	Recruited to run loan servicing platform transformation for Cascade Financial (Phoenix, AZ)
- Converted entire book of loans to new servicing (LoanServ) and document management (Nautilus) platforms with no loss in servicing performance or investor reporting ($3.4B UPB, 5.5MM documents, 100+ total users, 38K customers)
- Led first ever servicing transfers to both the old system and the new system
- Drove improvements to the new servicing system and data warehouse/reporting platforms
- Stabilized, coached, and transitioned IT servicing team for long-term support and growth

Ditech Financial LLC

•	Owned operational and project responsibilities for MSP/Black Knight Loan Servicing products, Servicing-side Originations, Bankruptcy, Loan Servicing Product Management, Customer-facing Technologies, and Divisional CIO for Recovery Collections business

•	Major business solution implementations -- Directly responsible for the following:
- Fannie Mae to MSP Loan Servicing platform – Largest IT program in Ditech’s history ($30MM+, 300+ team members, 40 workstreams, 18 months, $230B in UPB impacted, 1.3MM customers)
- MSP launch enabling Freddie Mac and government loan servicing 
($70B UPB added, $10MM savings)
- Omnichannel customer website and IVR redesign and replatform (enhanced experience, 1-year ROI)
- Investor Portal improvements (established best-in-class functionality)
- Call Recording (video and audio) replatform (compliance requirement)
- Ditech New Loan and Co-Issue Boarding (23 new brokers, $60B UPB) 
- Landmark Collections business launch (additional charge-off Recovery company)

•	Drove re-launch of the ePMO and Portfolio Management – Built the ePMO team, oversaw portfolio of all projects, led construction/rollout of the Project Delivery Framework SDLC

•	Led IT work for the Business Process Outsourcing ($20MM+ savings), MetLife acquisition, EverBank acquisition, Marix division closure, Originations launch, BKFS contract negotiation ($150MM), and Cypress due diligence ($500MM) among other initiatives

Vice President Information Technology/Divisional CIO

GE Capital

IT Solution Delivery Leader: Installment and Revolving Products & Canada	              12/2008 –10/2011 

•	Expanded responsibilities: 1) revolving products (store brand and for-purpose cards) and 2) IT leadership of GE Capital–Canada ($4B additional sales, 35 new clients, $25M savings)

•	Among solutions completed was the launch of the Unsecured Installment product (new product to market, personally received the GE Capital President’s Award for this initiative)


IT Solution Delivery Leader: Installment Products	                                                                         7/2004 –12/2008 

•	Direct report to CIO -- Leader for all technology requests, prioritization, and delivery for  installment lending P&Ls -- Powersports, Outdoor Power Equipment, Home Improvement -- across all business functions ($5.2B additional sales, 28 new clients, $38M savings)

•	Solutions implemented included new client launches, point of sale originations portal, product profitability initiatives, and collections efficiencies

IT Integration Leader	                                                                                                                                   6/2003 –7/2004 

•	Led IT integration into GE of 900+ former Conseco Finance associates in 3 different sites – scope included all applications, infrastructure, telephony, networks, datacenters, etc.

IT Director: Solution Delivery Leader

Conseco Finance

•	Responsible for special projects, including IT outsourcing, IT support of business process outsourcing, commercial division and compliance support

•	Also led certain IT aspects of the Company’s bankruptcy reorganization and sale to GE

IT Program Leader

M & D Consulting Inc.

•	Independent Consultant as well as Owner/President -- Primarily a one-person organization but also sponsored and hired 2 H1B employees

•	Engagements were all with a single Financial Services client, and included servicing system replacement/package implementation, Y2K remediation, custom servicing system enhancements, CRM package rollout, commercial division support, and IT outsourcing

Independent Consultant/Owner

SafeNet Consulting

•	Senior Consultant/Engagement Leader for the State of Minnesota Y2K Program

•	Responsibilities included project assessment, delivery, and business development

Senior Consultant/Engagement Leader

CSC Consulting

•	Program Manager and Senior Consultant on client engagements, which included business process improvement, enterprise package implementation, and enterprise custom developed solutions

•	Clients: Medical Device Manufacturing, Healthcare, Direct Mail Marketing

Senior Consultant/Program Manager

Procter & Gamble

•	Product Supply IT Leader for the Fisher Nut Company, including cross-functional duties within the division and brand representation at P&G’s Food and Beverage IT division

•	Helped lead shut down of 2 plants to execute a product supply outsourcing strategy

Product Supply Brand IT Leader – Fisher Nut Company

I drive results through Business-IT alignment and transformation.

As a Strategic IT Leader and Digital Transformer, I am primarily known as the following:

A. Enthusiastic Mentor and Coach who grows People and Organizational Capability
- Proven track record of developing and promoting associates at all levels from entry to VP
- Particular expertise enhancing High Performing/Exceeds Expectations talent
- I foster trust and build loyalty through respect, integrity, and true concern for others in the context of cultivating staff

B. Motivating Consensus Builder who inspires teams to take action
- Skilled at driving all levels of the organization through C-level, as well as customers, business partners, regulators, and third-party providers
- Proficient with on-site, multi-site, and off shore approaches
- I diplomatically engage diverse and disparate people, collaborating to produce buy-in and tangible results

C. Accountable, Clear-Thinking Problem Solver who generates innovative, actionable solutions
- Unique ability to quickly discern relevant facts, stakeholders, constraints, and organizational/political realities, oftentimes in ambiguous or new conditions
- Recognized for thoughtful identification and evaluation of alternatives, supported by decisive yet pragmatic decision-making
- I am recognized for superior ownership (direct or indirect) of solution implementation, focusing on follow-through to completion

---------------------------------

Specialty Areas: 
- Change Leadership 
- Strategic Planning and Innovation 
- Start-ups/Acquisitions/Integration
- Platform Rationalization and Consolidation
- LEAN Six Sigma and Agile Methodologies
- System Design/Development/Integration
- Portfolio, Program, and Project Leadership
- e-Commerce/Digital Solutions
- Enterprise Applications
- Product Development/Product Management
- P&L Management and Cost Reduction
- Process Re-engineering
- Customer, Third-Party, and Vendor Relationship Management



taplio

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Ryan McKesson

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The Battle

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