The Power Of Community
What We Learned from Three Days at IT Nation Connect – Powered by ConnectWise

I’m an extrovert but even conferences get me a little antsy.  There is a lot of loitering and networking and hand shaking and surface conversations.  It sometimes drains my energy before I even go.  This is what I was feeling in early November 2021 before heading to the ConnectWise IT Nation conference.  It was going to be my first time there.  You know what it’s like to dive into a category for the first time.  Confidence is a little shaky.  Okay, it’s just a little scary.    We were still in COVID times as well and I was heading across the United States.   My good friend, Jamison West, the co-founder of Connectstrat and a long-time MSP operator, was encouraging me to go and I knew he was right.  This was a conference of outsourced IT services professionals, a community of collaborators coming together for 3 days of learning, experience, fun, and growth.  How could I not go if this was the deep end where Stride was staking its future?

Of course, I was going to go.  We’re building a great business at Stride and our target customer segment is swarming at this conference.  I knew I needed to change my headspace to get in the game.  I had to get out of my head that this is about sales or any pressure around that.  It’s not like we had a booth or were on stage (next year maybe 😉).  What I needed and wanted to embrace was connection.  It is about curiosity.  It is about developing awareness and building rapport.  Oh yes, I can totally get into that.  Energy re-ignited!  

And from the minute I got into the conference, my energy level soared.  ConnectWise did a great job orchestrating the event.  I was so impressed with how well ConnectWise pulled together an ecosystem of collaborative individuals.    Here are some key takeaways from the experience.

Why did Stride go to IT Nation?

Stride is an outsourced bookkeeping and accounting firm for over 100 professional service companies around the United States.  We have built our business to support companies with day/day bookkeeping services for those clients that not only want to get their financial data well organized but actually use it to make better decisions by drilling down into things like customer level profitability.  We have a handful of MSP’s in our client base and we want to focus on it and grow it.  We have been investing in PSA training and the stack of technologies to facilitate cross application syncing, client payments, and process efficiency.  We’re energized and excited to become an integral partner in the community.

Who did we meet at IT Nation?

Here are some of my highlights from the introductions and experiences I had:

1. Pax8 University:  Rex Frank welcomed me warmly after a mutual friend introduced us.  I had known Sea-Level by reputation and was excited to meet Rex.  We have since had a follow-up call.  What impressed me about Frank was not only his deep operating experience, but how he sees himself as a coach, not a consultant.  
2. Ed Viesturs (Keynote Speaker):  It is a gift to hear from a man who has scaled the 14 highest peaks in the world.  His grit and perseverance are inspiring.  I also appreciated that he accepted a copy of my new book, One Life to Lead.  Thanks Ed.
   
3. Service Leadership and SLIQ:  Lots to acknowledge here. Paul Cissel was kind enough to spend time with me showing me the assessments that help guide clients on where to prioritize action based on their operating leadership model.  Super powerful insights and impressive.  I can see why ConnectWise welcomed SLI into its fold.
4. Char-Tec:  Nick Points did a great job presenting on how to structure incentive sales agreements with your sales team.  Excellent information and great value add in follow-up.  
5. ConnectWise:  I’ll first start with Paul Dippel.  I can’t say enough about his presence and message.  Paul does a great job communicating data in a way that is very digestible for aspiring to mature MSP’s.  With years of data assembled on what makes a strong performer, it is no surprise that Paul commands and audience and turns information to action.  I also really appreciated the time I spent with Andrea Barrow who heads up program management for their Invent program.  Invent is a great way for partners to integrate into the ecosystem with the support of ConnectWise.
6. TimeZest:  It was such a pleasure to meet Gerwai Todd, the CEO of TimeZest, an application that integrates with the PSA for meeting scheduling.  A slick application that is solving a real pain point.  We’re also excited to be supporting TimeZest as a Stride client.
7. ConnectStrat:  Jamison West and the cofounding team at ConnectStrat of Brett Jaffe and Jason Knight put on some strong sessions talking about the 5p’s of business operational maturity:  People, Performance, Process, Priorities and Perspective.  These are strong operators that have built a consulting firm to support MSP’s that are motivated to build equity value.  Jamison recently launched a new book, The Emotional Side of Selling a Small Business, so we did a little book swap (I just published One Life to Lead)
   
8. Wise Sync:  Freddy Flis and I tried to get together about 4 times before we landed a time on the last day.  I’m glad we did.  I had a chance to learn about their ConnectWise Manage to QBO sync application and their client payment portal.  They have created a very elegant way for MSP’s to transition their financial ledger to the cloud (QB Online or Xero) which allows companies like us to serve efficiently.
9. Insperity:  One of my first introductions was with Dannie Diego  who is the Strategic Alliances Manager at this national HR organization.  They had a booth and she was super cool in helping me get a lay of the land quickly.  
10. FocusPlanit:  I sat next to Calvin Johnson on the returning bus from Universal Studios.  You never know when you’re going to meet great people.  We have subsequently had a call with Bill Black, FocusPlanit’s CEO, and are talking about ways to get them involved when we are evaluating taking over a client’s back-office books.
11. MSPCFO:  I had brief conversation with Larry Cobrin and just remain so impressed with what he has built to help MSP’s focus on labor efficiency and customer level profitability.  

What did I appreciate about IT Nation?

Here are the top 5 takeaways that impressed me about this community:

1. 1. Built for curiosity:  This was a conference chock full of learning sessions and an openness to being curious.  So many MSP’s are there trying to figure out how to grow and scale their business. 
   2. Low ego factor:  I didn’t meet anyone who was aloof or unwilling to get to know me, the problem we are trying to solve and how they could help.  I don’t think I sat down for one conversation where there wasn’t a genuine interest in our work.
   3. Business builders abound:  I couldn’t think of any other conference with such a commitment to helping business owners build their organizations.  From culture to tools to financial management, all the content was designed to help entrepreneurs succeed.  
   4. An environment of learning:  The great thing about building a business is that no one pretends to have all the answers.  Every business is dealing with its own circumstances, and everyone has enough battle stripes to acknowledge that it can be hard going.  There was this really nice balance in the culture of empathy and accountability, a powerful duality when supporting business leaders.  

• Welcome to the fold.  When I exchanged cards (yes, there were business cards exchanged – what a concept), there was a genuine desire to have a follow-up call to learn more.  I felt welcomed into the community.  Outsourced IT services is a massively growing industry and there is a heartfelt desire to welcome those that want to enter it to make a mark.

I am unfortunately (or fortunately) leaving out the details from the Harry Potter immersive 3d rollercoaster at Universal Studios that ConnectWise organized one evening.  Why? Well, my eyes were closed for about 85% of it and I broke into a cold sweat about 20 seconds in.  There is only one piece of learning there which is you’ll never find me on that ride again!  But it was a small price to pay for an evening with new friends.

If you have an opportunity to join me next year at IT Nation, please consider doing so.  Big shoutout to the ConnectWise team for creating such a welcoming experience.  These types of events that bring people together at scale but with a family feel is how industries accelerate.  

We’re excited to be a part of it at Stride.  If you want to learn more about what we’re doing to support the back offices for MSP’s, please reach out to me at russell.benaroya@stride.services.