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Entrepreneur · Technology Leader · Chicago, IL

Hernan
Silva

Co-Owner, CIO Landing · MSP Founder · EO Chicago Member

From Buenos Aires to Chicago. I build things that work — businesses, teams, systems. I've been running a managed IT services company in the Chicago area for over a decade, and I'm still learning something new every week.

1992
In IT Since
Chicago
Home Base
My Story

From Buenos Aires
to Chicago

Growing Up in Argentina

I grew up in Buenos Aires, Argentina — a city that teaches you to be resourceful early. Life there shaped how I think: you solve problems with what you have, you move fast, and you don't wait for perfect conditions.

My family was central to everything. My brother and I were close growing up, and that relationship — the hustle, the conversations, the shared ambition — planted the seed for my entrepreneurial path. We both understood early on that if you wanted something, you had to go build it.

"You don't wait for perfect conditions. You build with what you have, and you improve as you go."

First Steps in Business

Before I ever landed in the United States, I was already running a business in Argentina. That experience taught me the fundamentals that still guide me today: margins matter, clients remember how you make them feel, and the only way to grow is to hire people smarter than you in specific areas.

My first venture wasn't in IT — it was the kind of business you start when opportunity meets necessity. It didn't scale forever, but it gave me the confidence that I could figure things out. That confidence was the real asset I carried into the next chapter.

The Move to the USA

Moving to the United States was the biggest decision I've made. New country, new language, new rules. I arrived in the Chicago area and quickly understood that adapting wasn't optional — it was the only way forward.

English was and still is something I work on deliberately. I record my meetings with Krisp, I run transcripts through AI analysis, I work with a speech therapist, and I track my fluency scores over time. I don't pretend to be further along than I am. I treat my own English improvement the same way I treat any business problem: measure it, find the highest-leverage weakness, and drill that one thing.

The early years in Chicago included different jobs and roles — always in technology-adjacent spaces, always learning the market, always building relationships. Each step was a brick in the foundation for what became CIO Landing.

Building in Chicago

The Chicago area became home in every sense. Northbrook is where my family lives, where my daughters go to school, where I sit on the HOA board at our building on West Hutchinson, where I'm active in the Entrepreneurs' Organization. The city gave me my business and my community. I gave it back by showing up.

I'm a member of EO Chicago — Entrepreneurs' Organization — where I've given and listened to talks, participated in the 5% Reflection practice, and built relationships with other founders who understand what it means to carry a business on your back while also trying to be a good parent and partner.

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Photo coming soon
Buenos Aires, Argentina
1980s
Buenos Aires, Argentina
Grew up in Argentina; early entrepreneurial mindset shaped by family and environment
1990s
First Business Venture
Started first business in Argentina; learned fundamentals of running a company
2000s
Move to the United States
Relocated to Chicago area; started building in the US technology market
2012
CIO Landing Founded
Launched the MSP that would become CIO Landing; early days of building recurring revenue
2013
Strategic Merger
Merged with JC; CIO Landing's lineage formalized
2023
Acquired BSSI2
CIO Landing acquires BSSI2, expanding capabilities and client base
Today
Northbrook, IL
EO Chicago member, HOA board, family in the Chicago metro
The Business

CIO Landing —
How We Built It

CIO Landing started in 2012 out of a simple belief: small and mid-sized businesses in the Chicago area deserved enterprise-level IT support without the enterprise price tag. I'd seen the gap. I knew I could close it.

The company merged in 2013 with JC, which gave us additional depth, processes, and clients. That early history shaped the operational DNA of what CIO Landing is today: a team that takes client relationships seriously and runs on recurring managed-service contracts.

Over more than a decade, we grew from a startup into a stable, growing business with a diversified client base, tight operating margins, and a technical team built to deliver. In 2023 we acquired BSSI2, expanding our capabilities and client base further. We serve small and mid-sized businesses across the Chicago metro — handling everything from day-to-day IT support to cybersecurity advisory, cloud infrastructure, and compliance work.

"We built CIO Landing to be what a small business's internal IT department would be — if they could afford a great one."

What I'm most proud of is the team. Running an MSP means being on call when something breaks at 10pm on a Friday — and our people show up. That culture of reliability is not an accident. It's built through hiring carefully, communicating clearly, and setting expectations that we then consistently meet.

Today I'm also exploring what the next chapter looks like — whether that's continued organic growth, strategic partnerships, or evaluating acquisition opportunities. The MSP market is consolidating fast. We intend to be deliberate about how we move in that environment.

Managed IT ServicesDay-to-day support, monitoring, and helpdesk for SMBs across Chicago metro
Cybersecurity AdvisoryRisk assessments, cyber insurance prep, and ongoing security posture management
Cloud InfrastructureMicrosoft 365, Azure, and hybrid cloud environments built and managed
AI & AutomationHelping clients understand and adopt AI tools that actually move their business forward
🏢
CIO Landing HQ
Chicago Area
2023
Acquired BSSI2
1992
In IT Since
2012
Year Founded
100%
Recurring Revenue

Recognized by

Entrepreneurs' Organization (EO) Chicago member · Active in the Chicago MSP and technology community · HubSpot partner for sales & marketing automation

Family

The People
Who Matter Most

Family isn't a balance I try to achieve against work. It's the reason the work matters. Every decision — business, financial, personal — runs through the lens of what's best for them.

💛
Andrea
My wife and partner in everything. She holds the family together with a warmth and steadiness I genuinely admire. Fourteen-plus years of business, two kids, one immigrant adventure, and she's still the first person I want to talk to.
Tina
Rising 6th grader at Wood Oaks, sharp and curious. Watching her navigate school, friends, and the world with the same energy I remember having at that age — it's one of the best things I get to witness.
🌟
Viky
Working on her English through programs like Kodland — and taking it seriously. She's got focus beyond her years. I see a lot of myself in her approach to learning: methodical, determined, not afraid to ask questions.

"Every business decision eventually comes back to this: what does this mean for the family? That's not a constraint — it's a compass."

Outside the Office

How I
Recharge

🤖
AI & Technology
Staying ahead of AI tools isn't just work — I genuinely find it fascinating. Claude, Krisp, Google Cloud, automation workflows. I experiment constantly.
🏡
Home Projects
DIY work around the house — window caulking, electrical, whatever needs doing. I like solving problems with my hands as much as with a spreadsheet.
✈️
Family Travel
Exploring the world with Andrea and the girls. We fly out of O'Hare and try to make at least one big family trip a year. The planning is half the fun.
📣
EO Chicago
Entrepreneurs' Organization keeps me connected to people building real things. I give talks, listen to others, and practice the 5% Reflection. It's one of the best investments of time I make.
🏘️
Community
HOA board member at our 24-unit building on West Hutchinson. I show up to the things that matter in my community, even when they're unglamorous.
🗣️
English Improvement
I treat my own language learning like a project: speech therapy, ELSA Speak, AI transcript analysis, fluency tracking. Spanish is home, English is the mission.
Writing

The
Blog

I write about three things: artificial intelligence and where it's going, IT and managed services, and personal reflections on business, family, and growth. Pick your topic.

🤖
How I Built a Ten-Agent AI Marketing Team for My MSP
Most small businesses think AI is something Fortune 500 companies use. I built a ten-agent marketing system for a Chicago-area MSP. Here's how — and what I learned.
💬
Using Claude and Krisp to Improve My English — A Real Workflow
I record every meeting, run transcripts through AI, track fluency scores over time, and drill specific weaknesses. This is the exact system I use.
🔍
GEO: Getting Your MSP Cited by ChatGPT and Claude
SEO is about ranking on Google. GEO is about being recommended by AI. The tactics are different, and most MSPs are ignoring this entirely.
🔐
Cyber Insurance Is Changing — What Your MSP Needs to Know
I recently reviewed cyber insurance quotes for a law firm client. The requirements have tightened significantly. Here's what insurers are actually looking for now.
📊
The MSP M&A Wave: What Owners Need to Understand Before It Hits Them
Private equity is buying MSPs at a pace most owners haven't seen before. If you're not thinking about your options, someone else is already thinking about yours.
🖥️
IT for Small Businesses: What You're Probably Paying For That You Don't Need
After a decade running an MSP, I've seen the same mistakes over and over. Here's a no-jargon breakdown of what actually matters versus what vendors upsell you on.
🇦🇷
What Buenos Aires Taught Me About Running a Business in America
Growing up in Argentina in the 80s and 90s meant learning resourcefulness by necessity. That same muscle is what I rely on every week running CIO Landing.
🌱
Learning English at 40-Something: How I'm Treating Myself as a Case Study
I'm a non-native English speaker running a US business. I don't hide that — I track it, measure it, and improve it systematically. Here's the approach.
👨‍👩‍👧‍👧
Family First Is Not a Cliché — It's an Operating System
Every time I've let "family first" become a slogan rather than a filter, I've made worse decisions. Here's how I actually apply it when things get complicated.
Get in Touch

Let's Have
a Conversation

Whether it's a business conversation, a collaboration, or just a question about IT, AI, or the MSP world — I'm happy to talk. I respond to every genuine message.

Send a message