Derek Iannelli-Smith

Be patient and get around folks who are generous, accountable, vulnerable and have candor.


Derek R. Iannelli-Smith is a graduate of Columbia International University with an M.Div Pastoral Counseling concentration and has been ACBC Certified and PeaceMaker (Legacy) coach/mentor since 2005. He has taught evangelism to bible college and seminary students at Columbia International University and is passionate about discipleship evangelism. He was on staff with Campus Crusade for Christ Military Ministry, Setting Captives Free, and is a tent maker minister (actually just an IT dork with a bunch of certifications), and now the owner of Outsourced CIO LLC with the official title of vCIO & Trusted Advisor, and author of MSP or Fail.

No stranger to discipleship (counseling), He has discipled since 1999 in all areas of the Christian life. Was the Biblical Counselor, Small Groups Director and Technical Director for a PCA Church while going through ordination (did not complete – took an exception), and his last sermon before he resigned is down below. Assessed for Acts 29 Church planting (not approved), planted a successful reformed house church, and participated in a Sovereign Grace Church Plant. Prior to his current position(s), he owned a couple of technology companies, served in the military, and was/is published, writer.

Raised in Western Massachusetts, Derek now lives with his grace and kindness from God, Connie in Summerville, SC. He is blessed with two daughters, Samantha and Brie who remind him of the love of the Father. He is actively coaching, discipling, evangelizing, and consulting. An active member of Oakbrook PCA. A ferocious reader and book reviewer (previously for Harper Collins, Crown Publishing Group, and

In between reading, writing, discipleship-evangelism, keeping up with technology, studying for the Project+ and dating his wife, he tries to find time to get on the elliptical or do the 7-minute workout, listen to trance/dance/techno/80’s/90’s music, fish and play with his Siamese cat Niko. Part of his family serving on a mission has been to found the King’s Grant Nextdoor Neighborhood.

Where did the idea for your company come from?

As a fan of the Table Group (Patrick Lencioni) for many years, and after reading each of his 11-books, our discontent grew with how businesses were run in the IT sector. We love IT and it seemed that it was a different beast to tame, and yet, so simple that we found ourselves perplexed on how many businesses just did not seem to get it. You have to admit that watching customer service levels and customer experience a downward spiral in the IT business has been going on for many years.

We have seen corporate wastes, abuse of clients, lack of follow up, over-charging, unprofessionalism, lying, stealing, training on the client’s dime, beta testing with the client, nickel-and-diming to death, and just bad unethical behavior. We attempted to change and influence these companies from the inside by 360-Degree Leadership. At times there was a glimmer of hope but for the most part, disappointment. Part of providing the best service did not make us popular and even affected our employment status at times. So we decided to do something about it after reading a great article on ways to improve customer service. Thus Outsourced CIO, LLC.

We found that most companies think they take care of clients well, and even understand their client’s businesses, but the truth of the matter is, that over time, the “newness” wears off and customer service levels drop and respect and thankfulness for clients wanes. Today many companies offer vCIO services as an “add-on” while not really understanding what a CIO is, much less offering one to their clients in the capacity that is needed. What many companies offer as vCIO services really should be called account management or business development. As far as we know, we are the only company who offers these types of services from an experienced, disciplined, lessons learned, future-proofing, best practices, industry standards and systematic approach. Outsourced CIO, LLC is a company solely focused on providing vCIO services. We call it Competitive Edge as a Service (CEaaS).

What does your typical day look like and how do you make it productive?

A typical day is scheduled and filled with many interruptions. This varies from outside appointments scheduled by others, to client engagement scheduled engagements. I spend much time on client sites, engaging C-Suites by coaching and mentoring through digital transformation and IT strategy.

How do you bring ideas to life?

Ideas are based on reading, networking, and lifeline relationships. Reading contains blogs, books, podcasts, and videos. Networking contains everything from attending 1 Million Cups, TechAfter5, Friday’s @ The Corridor, Startup Grind, Bunker Labs Launch Lab Online, and social media. Lifeline relationships are industry leaders in my verticals. I have done business plans in the past, now I a strategyzer fan, meaning Business Model Canvas, Value Proposition, and Customer Profiles.

What’s one trend that excites you?


What is one habit of yours that makes you more productive as an entrepreneur?

Continual learner (books, podcasts, RSS feeds, networking).

What advice would you give your younger self?

Be patient and get around folks who are generous, accountable, vulnerable and have candor.

Tell us something that’s true that almost nobody agrees with you on.

Don’t climb a mountain when there is an elevator next door.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Read, listen, network, find some lifeline relationships and a support squad.

What is one strategy that has helped you grow your business?

I graduated from Bunker Labs Launch Lab Online, as a member of the Winter 2018 Cohort. I was all in, did all the lessons, did all the reading, did all the work and it paid off.

What is one failure you had as an entrepreneur, and how did you overcome it?

One of the mistakes I made early on was not vetting a strategic partner/vendor better which resulted in clients unsatisfied with their services and reflected on me and my reputation. It was repairable, in that when I started to see the “writing on the wall” I started a 3-month process to come up with a 5-subject area, 35+ questionnaire that all MSP/IT Companies must answer before they are 1) added to my referral network and 2) given access to my contacts. This has weeded out quite a few big and small companies who for varying reasons (could not answer the questions sufficiently, did not respond in the required format, were lazy and sent me documents versus answering the questions etc). The recommendation, vet your strategic partners/vendors before beta-testing on your customers regardless of where they come from.

Because of this lesson and result, I now have a small list of viable MSP/IT companies that I work with and customer satisfaction is back to what I want the OCIO reputation to be. The problem was “blindly” trusting some of those resources because they presented well (had a good website, contained a good footprint online, etc). I now realize that if customer service and customer experience are core personal values for OCIO, then it was worth learning this lesson to have the caliber of partners to offer my clients.

What is one business idea that you’re willing to give away to our readers?

I think a great business idea would be to create disruptive innovation in the healthcare industry by fining vendors/providers for over-charging for health care products and services.

What is the best $100 you recently spent? What and why?

I bought a friend of mine a Gospel Transformation Bible (out of print) and XL Bible Cover as he was recently regenerated and received Jesus Christ as his Lord and Savior.

What is one piece of software or a web service that helps you be productive? How do you use it?

Calendly has given me my time back in that the usual back and forth emails about scheduling meetings used to really tick me off. Now I send a link, and they choose and done

What is the one book that you recommend our community should read and why?

Never Eat Alone by Keith Ferrazzi. It will remind that people have feelings, are made in the image of God and deserve respect, generosity, and reciprocity. Especially in a business where many have an agenda to relationships.

What is your favorite quote?

“Don’t climb a mountain when there is an elevator next door.” Robin Robins (in an audio on Technology Marketing Toolkit, 2006)

Key learnings:

• I don’t want to connect with everyone, I only want to connect with “connectors” meaning folks who are also like-minded with generosity and reciprocity.
• Everyone does not need to be your friend on Social Media. Never Eat Alone taught me to prune/trim my social media for a few variables: important relationships that I want to keep up on vs “send this to 6 of your friends – dog video) for opportunities to serve them and stay connected, as well as direct my feeds to provide industry/thought leader information that is important to me and my business.
• There is enough business to go around and no one can outwork me.
• Always be on the lookout for people with the 4-mindsets (accountability, vulnerability, generosity, and candor) while remembering that everyone is made in the image of God and deserves respect.
• God is our Father, and we are His family. Jesus is our Lord, and we are His servants. The Holy Spirit is our Guide and Sender, and we are His missionaries.