BetterWorld Technology

Co-Founder & Chief Operating Officer

General Manager

Vice President of Operations

Director of Customer Operations & Training

Forbes Technology Council

Official Member

Working Excellence

Senior Director

Robert Morris University, Chicago, IL

Adjunct Professor Of Business

Staffing Network LLC

 Vice President , Information Systems

V&V Supremo Foods Inc

Senior Manager, Information Systems

Easter Seals Inc.

Senior Director Information Technology

Director IT Operations

IT Operations Manager

Recall

Regional IT Operations Analyst 

Knightsbridge Solutions LLC

IT Operations Analyst

Baker and McKenzie

Team Lead Desktop Support Analyst

Transforming IT Landscapes as Co-Founder & COO | Certified VCISO | Thought Leader in Cybersecurity & Managed IT

As the COO of BetterWorld Technology, I leverage extensive experience in the nonprofit sector and a proven track record as a VP of Technology to deliver operational excellence. As a certified VCISO, I specialize in providing strategic cybersecurity solutions alongside Managed IT and IT Consulting, helping organizations of all sizes stay secure, efficient, and innovative.

BetterWorld Technology is a nationwide, 24/7 Managed IT, Cybersecurity, and IT Consulting provider, delivering enterprise-grade solutions for organizations of all sizes. We’re big enough to offer robust, scalable technology and security services, yet small enough to provide personalized care and attention, ensuring tailored support that drives success.

John Jordan

The vCISO role is evolving faster than most boardrooms can keep up with.

Not long ago, cybersecurity was a line item, a compliance box to check. Now, it’s a board-level conversation—sometimes a heated one. I’ve sat in those meetings where the question isn’t "Do we have a policy?" but "Are we actually safe?"

Here’s the uncomfortable truth: AI and machine learning are rewriting the rules. Autonomous agents can spot threats in milliseconds, but they can also be used to launch attacks that move just as fast. The same tools that protect us can be turned against us. It’s a chess match, and the board keeps changing.

For executives, this isn’t just about tech. It’s about risk, reputation, and resilience. Are you asking the right questions? Do you know what your AI is doing—and what it could do if it went rogue? Are you ready for the next regulatory curveball, like the EU AI Act?

At BetterWorld Technology, we’re seeing clients rethink their entire approach. Not just patching holes, but building security into the DNA of their business strategy. It’s messy, sometimes frustrating, but it’s the only way forward.

So, what’s your next move? Are you leading the conversation, or waiting for the next breach to force your hand?

#vCISO #cybersecurity #AI #governance #compliance #TechStrategy #betterworldtech

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Trusted Leader in IT & Cybersecurity | Co-Founder & COO | Certified VCISO | MBA | Proven Leader in IT, Cybersecurity 🛡 & Business Transformation | One of Newsweek’s Most Reliable Companies for 2025 | Let’s Connect

AI is the new intern. 

Except this intern never sleeps, learns at warp speed, and sometimes makes decisions you didn’t ask for. 

I’ve watched organizations rush to deploy AI tools, hoping for a silver bullet. But here’s the catch: every new capability is a new attack surface. 

Autonomous agents can optimize workflows, sure. But they can also be hijacked, manipulated, or simply go rogue. (If you’ve ever seen an AI write a 3 a.m. email, you know what I mean.) 

The real opportunity? Leaders who ask, "How do we govern this?" not just "How do we use this?" 

At BetterWorld Technology, we’re helping clients build AI governance frameworks that align with business goals and risk tolerance. It’s not glamorous, but it’s what keeps innovation from turning into chaos. 

If you’re not already mapping out your AI risks, you’re behind. But it’s not too late to catch up. 

What’s your biggest AI headache right now? Let’s swap stories—maybe we’ll find a solution together. 

#AI #cybersecurity #TechStrategy #governance #vCISO #betterworldtech

Quantum computing used to sound like something out of a Marvel movie. Now, it is a real threat to the encryption we all rely on. 

I have had more than one conversation lately where someone says, "We will worry about quantum when it gets here." But by then, it is too late. The data you are protecting today could be vulnerable tomorrow. 

The smart move? Start planning for post-quantum security now. Inventory your critical assets. Understand which systems rely on vulnerable encryption. Build a roadmap for migration, even if it feels early. 

At BetterWorld Technology, we are helping clients future-proof their security strategies. It is not about panic—it is about preparation. 

And let’s be honest, if you are still using "password123," quantum is the least of your worries. 

What steps are you taking to get ready for the next wave of tech disruption? Share your thoughts. #cybersecurity #quantumcomputing #TechStrategy #vCISO #betterworldtech

Sometimes I wonder if we’re all just one compliance update away from a collective meltdown.

Regulations are coming at us from every direction—GDPR, CCPA, the EU AI Act, and who knows what’s next. It’s enough to make even the most seasoned execs want to hide under their desks. But here’s the thing: compliance isn’t just about avoiding fines. It’s about building trust, protecting your reputation, and keeping your business in the game.

I’ve seen organizations treat compliance like a fire drill—scramble, check the boxes, breathe a sigh of relief, and move on. But the real leaders? They use compliance as a catalyst for better governance and smarter risk management. They ask tough questions: Are we ready for the next wave of regulation? Do we have a plan for when—not if—something goes wrong?

At BetterWorld Technology, we help clients turn compliance from a headache into a competitive advantage. It’s not always pretty, but it works.

What’s your biggest compliance challenge right now? Let’s swap stories and maybe even a few survival tips.

#compliance #governance #riskmanagement #cybersecurity #vCISO #betterworldtech

AI is the shiny new toy in every boardroom, but let’s not kid ourselves—most organizations are still figuring out how to use it without breaking something.

I’ve seen leaders get excited about autonomous AI agents, only to realize their data is a mess and their security controls are stuck in 2015. The opportunity is massive, but so is the risk. AI can spot anomalies faster than any human, but it can also amplify mistakes at the speed of light.

Here’s my advice: before you chase the next big thing, get your fundamentals right. Do you know where your sensitive data lives? Are your teams trained to spot AI-driven phishing attacks? Are you tracking the right metrics, or just the ones that look good in a report?

At BetterWorld Technology, we help clients cut through the noise. It’s not about having the fanciest tech—it’s about building a culture that can adapt, learn, and recover when things go sideways. Because, let’s face it, they will.

How are you balancing innovation with security? What’s the biggest AI headache you’ve faced so far?

#AI #cybersecurity #TechStrategy #vCISO #betterworldtech

Here’s a hard truth: most security incidents don’t start with a zero-day exploit. They start with a missed patch, a reused password, or a well-meaning employee clicking the wrong link. 

It’s not glamorous, but operational excellence in cybersecurity is about sweating the small stuff. 

I’ve seen organizations invest in the latest tech, only to be undone by basic hygiene failures. It’s like buying a state-of-the-art alarm system and leaving the front door wide open. 

At BetterWorld Technology, we focus on fundamentals: regular risk assessments, clear incident response plans, and relentless user education. 

If you want to build a security culture that lasts, start with the basics—and never stop. 

What’s the most overlooked security habit in your organization? I’m curious to hear what slips through the cracks. 

#cybersecurity #operationalexcellence #riskmanagement #vCISO #betterworldtech

The vCISO role is not what it was five years ago. 

Honestly, it barely resembles what it was last year. 

AI is rewriting the rules, and not always in ways that make life easier. Autonomous agents, deepfake phishing, quantum threats on the horizon... it feels like the plot of a sci-fi movie, except the budget is your reputation and the stakes are your business. 

Boards and executives ask me, "What should we be worried about?" I tell them: worry less about the next shiny tool, and more about the questions you’re not asking. 

Are we mapping our risk appetite to our actual business goals? Do we have a plan for when—not if—AI-generated attacks slip past our defenses? Are we tracking the right metrics, or just the ones that look good in a report? 

It’s not about fear. It’s about readiness. 

At BetterWorld Technology, we see organizations that treat cybersecurity as a living, breathing part of their strategy—not a box to check—are the ones who adapt fastest. 

Truth is, the future will always outpace our playbooks. But the leaders who build cultures of curiosity, transparency, and resilience? They’re the ones who sleep at night. 

What’s the one question you wish your board would ask about cybersecurity? I’d love to hear the ones that keep you up—or help you rest easy. 

#vCISO #cybersecurity #AI #governance #compliance #TechStrategy #betterworldtech

Let’s talk about the elephant in the server room: aligning IT and business goals is harder than it looks.

I’ve seen too many tech projects stall because the business side and IT are speaking different languages. One’s talking about ROI, the other about zero trust architectures. Somewhere in the middle, the real priorities get lost.

The future belongs to organizations that bridge that gap. With AI, automation, and quantum computing on the horizon, the stakes are only getting higher. It’s not enough to have a great tech stack—you need a strategy that ties every IT decision back to business outcomes.

At BetterWorld Technology, we push for conversations that connect the dots. What’s the business problem we’re actually trying to solve? How does this technology move the needle?

If you’re not asking those questions, you’re just collecting shiny objects.

How do you keep your IT and business teams rowing in the same direction? Any tips or war stories to share?

#TechStrategy #cybersecurity #AI #vCISO #betterworldtech

Every time I hear someone say, "We’re too small to be a target," I have to resist the urge to hand them a stack of breach reports.

Cyber threats don’t care about your company size. In fact, smaller organizations are often the low-hanging fruit—less budget, fewer resources, and sometimes, a false sense of security. I’ve seen startups and mid-sized businesses blindsided by attacks they never saw coming.

The good news? You don’t need a Fortune 500 budget to build real resilience. Start with the basics: strong passwords, regular training, and a clear incident response plan. Layer in the right technology, and suddenly you’re not such an easy target.

At BetterWorld Technology, we work with organizations of all sizes to build practical, scalable security strategies. No scare tactics, just honest conversations about what works.

What’s one simple step you’ve taken to boost your security posture? Let’s help each other raise the bar.

#cybersecurity #vCISO #operationalexcellence #riskmanagement #betterworldtech

Let’s talk about the elephant in the boardroom: aligning IT and business strategy. 

Too often, I see tech teams and business leaders speaking different languages. One side talks about uptime and firewalls, the other about growth and market share. 

The magic happens when both sides realize they’re after the same thing: resilience, agility, and trust. 

At BetterWorld Technology, we help bridge that gap. It’s not about translating jargon—it’s about connecting priorities. 

Ask yourself: Are your IT investments driving business outcomes, or just adding complexity? Are you measuring what matters, or what’s easy to count? 

The best strategies are the ones everyone understands—and believes in. 

What’s your biggest challenge in aligning IT and business goals? Let’s get real about what works (and what doesn’t). 

#TechStrategy #cybersecurity #leadership #vCISO #betterworldtech

There is a myth that only big companies need a vCISO. 

I have lost count of the number of small and mid-sized businesses who call us after a breach, wishing they had asked for help sooner. 

Cyber threats do not care about your revenue or headcount. Ransomware, phishing, supply chain attacks—they hit everyone. The difference is, smaller organizations often have fewer resources to bounce back. 

A vCISO is not just a luxury for the Fortune 500. It is a lifeline for any business that wants to survive and grow. We bring strategy, structure, and a little bit of sanity to the chaos. 

At BetterWorld Technology, we have seen firsthand how a tailored security roadmap can turn panic into confidence. It is not about fear—it is about being ready. 

If you think you are too small to be a target, think again. 

What is holding your organization back from investing in cybersecurity leadership? I am all ears. #vCISO #cybersecurity #leadership #betterworldtech #TechStrategy

Here’s a hard truth: most security strategies look great on paper, but reality is messier.

I’ve lost count of how many times I’ve seen beautifully crafted policies that never make it past the boardroom. The real world is full of distractions, shifting priorities, and, let’s be honest, a little bit of wishful thinking.

The best strategies are the ones that actually get used. That means building security into daily workflows, not just annual audits. It means empowering teams to speak up when something feels off, even if it’s inconvenient. And it means tracking metrics that matter—like time to detect and respond, not just how many boxes you’ve checked.

At BetterWorld Technology, we focus on practical, actionable steps. No silver bullets, no magic wands. Just real progress, one decision at a time.

What’s one small change you’ve made that had a big impact on your security culture? I’d love to hear what’s working (and what’s not).

#cybersecurity #TechStrategy #vCISO #operationalexcellence #betterworldtech

Quantum computing used to sound like science fiction. Now, it’s the elephant in every cybersecurity room. 

We’re not there yet, but the clock is ticking. Encryption standards that feel rock-solid today could be obsolete tomorrow. 

I get it—most executives have enough on their plates without worrying about quantum threats. But here’s the uncomfortable truth: waiting until it’s urgent is a recipe for regret. 

Forward-thinking leaders are already asking, "What’s our post-quantum plan?" They’re mapping out migration paths, evaluating vendors, and building flexibility into their tech stacks. 

At BetterWorld Technology, we’re helping clients future-proof their security strategies, even if the future feels a little fuzzy. 

If you’re not talking about quantum yet, you will be. Might as well get ahead of the curve. 

What’s your take—are we overhyping quantum, or not worried enough? Let’s hear your predictions. 

#cybersecurity #quantumcomputing #TechStrategy #vCISO #betterworldtech

Building a security culture is not about posters in the break room or annual trainings everyone clicks through half-asleep. 

It is about making security part of the daily conversation, from the C-suite to the front desk. I have seen organizations where people are afraid to speak up about mistakes. That is a recipe for disaster. 

The best leaders I know create space for honesty. They reward curiosity, not just compliance. They ask, "What did we learn from this incident?" instead of, "Who is to blame?" 

At BetterWorld Technology, we work with teams to turn security from a checklist into a mindset. It is not easy, and it is never finished. But it is the only way to stay ahead. 

If you want to know how strong your security culture is, ask your newest employee what they would do if they spotted something suspicious. The answer will tell you everything. 

How are you building a culture of security in your organization? Let’s swap ideas. #cybersecurity #leadership #vCISO #betterworldtech #operationalexcellence

The vCISO role is not what it was five years ago. 

Back then, you could get away with a solid risk assessment, a few policies, and a quarterly board update. Now? The job description might as well read: part strategist, part therapist, part fortune teller. 

AI is rewriting the rules faster than most organizations can keep up. Autonomous agents, deepfakes, quantum threats on the horizon... it sounds like science fiction, but it is already knocking on the boardroom door. 

I have conversations with executives who want certainty. They want a checklist, a guarantee. But the truth is, cybersecurity is a moving target. The best leaders I know are the ones who ask uncomfortable questions: Are we ready for the next regulatory curveball? How are we measuring resilience, not just compliance? 

At BetterWorld Technology, we see the shift every day. The vCISO is no longer just a technical advisor. We are business partners, translators, and sometimes, the only ones in the room willing to say, "This risk is bigger than you think."

If you are still treating cybersecurity as an IT problem, you are already behind. 

What is the one question you wish your board would ask about security? I am genuinely curious. #vCISO #cybersecurity #AI #governance #compliance #TechStrategy #betterworldtech

Here is a hard truth: most security incidents are not caused by zero-day exploits or nation-state hackers. They are caused by missed basics. 

Unpatched systems. Weak passwords. Forgotten backups. The stuff everyone knows, but not everyone does. 

I have seen organizations spend big on the latest tech, only to get tripped up by a simple oversight. It is frustrating, but it is fixable. 

Start with a clear inventory. Know what you have, where it lives, and who has access. Set up alerts for the things that matter. Review your incident response plan like it is a fire drill, not a formality. 

At BetterWorld Technology, we help clients focus on what works. Fancy tools are great, but discipline wins every time. 

What is the one basic security practice you wish every company would take seriously? Let’s talk about the fundamentals. #cybersecurity #vCISO #TechStrategy #betterworldtech

Let’s be honest, most executives would rather get a root canal than talk about compliance frameworks. 

But here’s the thing: ignoring governance is like skipping oil changes and hoping your car makes it across the country. 

With the EU AI Act and new U.S. regulations rolling out, the stakes are higher than ever. It is not just about ticking boxes. It is about building trust—with customers, partners, and your own team. 

I have seen organizations scramble to retrofit controls after a close call. It is expensive, stressful, and usually avoidable. The smart move? Start with the basics: map your data, know your risks, and make sure someone is actually accountable. 

Metrics matter, but so does culture. If your people are afraid to report a mistake, you have a bigger problem than any audit can reveal. 

At BetterWorld Technology, we help leaders turn compliance from a burden into a business advantage. It is not glamorous, but it works. 

What is the most surprising lesson you have learned from a compliance project? I would love to hear your war stories. #compliance #governance #cybersecurity #leadership #betterworldtech #vCISO

Cybersecurity is not a spectator sport. 

I’ve lost count of how many times I’ve heard, "We have a great IT team, so we’re covered." If only it were that simple. 

The reality? Security is everyone’s job, from the boardroom to the break room. Culture eats policy for breakfast. 

At BetterWorld Technology, we see the most resilient organizations are the ones where leaders model good security habits, ask tough questions, and make it safe to speak up about risks. 

Metrics matter, but so does mindset. Are you tracking how quickly your team reports phishing attempts? Are you rewarding curiosity, or punishing mistakes? 

The best security cultures are built on trust, not fear. And they start at the top. 

What’s one thing you wish your leadership team understood about cybersecurity? I’m all ears. 

#cybersecurity #leadership #vCISO #operationalexcellence #betterworldtech #TechStrategy

Sometimes I wonder if the term vCISO is already outdated. Not because the role is going away, but because the job keeps mutating faster than the language can keep up. One week I’m talking to a board about quantum risk, the next I’m fielding questions about AI agents that can write code (and, apparently, phishing emails that sound like your favorite uncle).

It’s a strange feeling, being both the translator and the alarm bell. I’ve learned that most executives don’t want a technical deep dive—they want to know what keeps them out of the headlines, and what keeps their business running when the unexpected hits. Fair enough.

But here’s the catch: the threats are getting weirder, and the regulations are getting stricter. The EU AI Act, for example, is a wake-up call for anyone who thinks compliance is just a checkbox. It’s not. It’s a moving target, and it’s coming for all of us, whether we’re ready or not.

So, what do you actually do? You start with questions, not answers. What data matters most? Who has access? How fast can we recover if something goes sideways? The best security cultures I’ve seen are the ones where people aren’t afraid to ask the uncomfortable questions.

Honestly, I still get surprised by what I don’t know. That’s probably a good thing.

What’s the one risk you wish your team would talk about more openly? I’d love to hear the ones that keep you up at night.

#vCISO #cybersecurity #AI #governance #compliance #TechStrategy #betterworldtech

Corner Alliance

Founder

Working with government and non-profit leaders to innovate, communicate, and build better programs, including the Department of Homeland Security, National Institutes of Health, National Institute of Standards and Technology, and Department of Commerce.

OwnerRx.com

Building the always on AI-enabled strategic copilot for SMB owners.

Owner

Entrepreneurly

Board Member

OwnerInstitute

Owner Institute helps owners grow their businesses while achieving independence.

Entrepreneurs'​ Organization

James Lee Witt Associates

Director

SRA Touchstone Consulting Group

Principal

The Touchstone Consulting Group, SRA International, Inc.

extreme blue intern

US Senator Max Baucus

Speechwriter

CEO @ Corner Alliance | Author @ The Small Business Mentor

I spent 17 years and $200K+ hunting through every business course, mastermind, and guru to find the nuggets that actually work.

EOS? Implemented it. Scaling Up? Read it. EO/YPO? Joined both.

The result? 10,000+ hours distilled into OwnerRx - the AI coach that knows every framework, every playbook, every shortcut.

What it took me years and big dollars to learn, OwnerRx delivers in seconds for a fraction of the cost.

Alan Pentz

A consulting firm came to me at 15% margins.

Target: 20%.

Five years ago, I had a playbook for this:

Old playbook:

- Better hiring → get 1-2% back (maybe)
- Global talent → squeeze out 3-5% (with cultural pain)
- Cut overhead → another 1-2% (one-time gain)

We'd grind our way to 20% over 18-24 months.

Today? That playbook is obsolete.

Here's what I'm seeing with AI agents:

Get 10% margin expansion by holding back office costs constant and growing topline.

Not cutting. Not offshoring. Not grinding.

Growing revenue without scaling headcount.

The new math:

Professional services firm:

- Revenue: $5M
- Back office: 8 people
- Margin: 15%

Deploy AI agents for:

-Financial Analysis
-Client Reporting
-Marketing
-Proposals and Quoting
-Quality Control
-Meeting analysis and follow ups
-Employee onboarding and HR 
-Client research (80% faster)
-Hiring

Result:

- Same 8 back office people
- Revenue grows to $7M (+40%)
- Margin: 25%

Owner @ OwnerRx.com | OwnerRx uses battle-tested playbooks from decades of building and coaching SMBs to create AI agents that run your business for you. | Read my newsletter: newsletter.ownerrx.com

I spent 10 hours a day for 4 days in a row re-building all my AI workflows last week.

3 months ago, I was building OwnerRx, the newsletter, and my Linkedin. I had 4 vendors helping with each aspect. Spend was out of control at $30k a month.

Now I've replaced them all with AI agents. That saves $360k a year.

First came the client tracker agent - every interaction, deadline, and renewal date monitored automatically. 

Then the meeting analyzer that turns Zoom recordings into 5 different artifacts to track and follow up on the meeting content.

The content pipeline was the game-changer. What took 2 hours to write now takes 3 minutes to generate and 15 minutes to polish.

Total investment: 100+ hours of my nights and weekends. 
ROI: 20 hours a week saved and $360k

But there's a downside: the exhaustion is real.

Every improvement reveals 10 more possibilities. Fix the client tracker? Now you see how broken your invoicing is. Automate content? Your distribution system looks ancient.

Last week's 4-day marathon started as "quick workflow optimization." 

The shift from doing work to building tools that do work isn't optional anymore. Teams still manually tracking clients in spreadsheets are losing 15-20 hours weekly that automated teams invest in growth.

My clients now run smoother with zero employees than they would with 5. 

But the pace is picking up. Some people spend all day building tools to make their tools work more effectively.

I'm not sure how many of us can handle it but the productivity increases are real and some people are achieving breakout.

One of biggest PE firms just allocated $1.5B to buy businesses like yours at traditional multiples, deploy AI, and watch margins expand.

Their thesis? You won't adapt fast enough.

I keep having the same conversation. Four owners last month asked me: "Should I sell before AI disrupts my business?"

Meanwhile, I invested in a metal fabrication company. The owner was spending 20-30 hours per week processing purchase orders. Not sustainable when you're trying to grow.

We built an AI system in two weeks. PO processing now takes 5 minutes. He got 25 hours of his week back.

We're closing on our second acquisition next month. Same playbook: build the AI capability once, plug each new company into the same operating system.

That's exactly what the PE firms are doing. At scale.

Here's the data that matters:

95% of AI pilots fail. But the 5% who break through? 91% see revenue boost. 86% improve margins.

This isn't a technology problem. It's a commitment problem. Pilots are experiments nobody owns. The winners pick one process, assign ownership, and measure results until it works.

The rinse and repeat.

The gap between "wanting to use AI" and "actually transforming your business" is where most owners get stuck.

That's exactly the gap PE firms are exploiting.

I'm not going to pretend I'm not doing the same thing PE firms are. The difference: I'm showing you exactly how it works so you can do it yourself.

Build the capability yourself, or become someone else's margin expansion play.

What's the one process eating 20+ hours of your week that you keep saying you'll fix "next quarter"?

$300K.

That's what each failed sales hire costs when you add: salary + lost deals + operational chaos + owner time back in the weeds.

The owner I talked with last week had just gone through his third failed sales hire. 

The pattern?

"We hired for product knowledge... failed to look at character."

But here's the deeper mistake:

They were trying to hire ONE person who could do everything the founder does.

Product expertise + all the relationships + sales nuance + operations + strategy.

That's not a job description. That's a unicorn.

And unicorns don't exist.

Here's what happens when you track your sales process with AI and ask: "What am I actually doing?"

AI breaks it down:

- Marketing: 9 hours/week (lead gen and qualification)
- Admin: 5 hours/week (Writing and sending followups, updating the CRM and dashboards)
- Selling: 7 hours/week (actual conversations with buyers)
- Meetings and Reporting: 5 hours/week (in internal meetings and preparing for those meetings)
-Customer Service: 10 hours/week (Talking recent sales through onboarding issues)

You're not hiring for one role. You're trying to get one person to do a bunch of different stuff.

The AI insight:

Don't hire 1 "unicorn" at $150K who'll fail in 18 months.

Engineer it into 3 achievable roles:

- Sales Rep ($75K) - hire for relationship skills and ability to close
- Operations Coordinator ($55K) - hire for ability to track actions, update the CRM, and do follow ups.
- Customer Service Rep ($60K) - hire for deep product knowledge and ability to answer customer questions 

Then AI generates hiring scorecards for each:

- 5 character traits (integrity, ownership, learning ability, culture fit, resilience)
- 5 technical competencies (specific to THAT role, not "do everything")
- Interview questions revealing both dimensions
- Red flags from your past failed hires

The real problem:

You're not bad at hiring.

You're trying to hire another version of yourself.

The solution:

Stop looking for unicorns.

Start engineering roles AI can help you fill.

Drop your calendar export in ChatGPT and ask:

"What am I actually doing, and should this be 1 role or 3?"

OpenAI just launched ChatGPT Shopping 3 days before Black Friday. It's built for products.

But if you run a professional services firm, the behavior change matters more than the feature.

People are getting trained to ask AI for recommendations instead of searching Google. "What do I need?" "Who can help me?" "Who's best for my situation?"

Right now, that's mostly products. But the habit is forming.

So I ran an experiment.

I asked ChatGPT: "Who are the best fractional CFOs in Austin for manufacturing companies doing $5-10M?" (Congrats to vcfo Austin, you won)

What showed up varied each time I asked with a slightly different query (AI results aren't consistent like Google). But patterns emerged in what seemed to influence recommendations:

- Firms with clear website positioning about who they serve
- Those with substantial Google reviews
- People mentioned in industry publications
- Content that directly answered the type of question I asked

The firms with vague "we serve everyone" messaging? Didn't appear.

Here's my hypothesis for professional services:

Your next client might never Google you. They might ask AI. And AI appears to synthesize everything it finds about you into a recommendation. Or not.

This isn't proven science yet. But it's worth investigating.

Three things worth trying this week:

1. Ask ChatGPT who the best [your profession] in [your city] are for [your ideal client type]. Run it 3-4 times. See patterns in who shows up and what signals seem to matter.

2. Look at your Google reviews. Not just the star rating. The actual words clients use. AI reads those.

3. Check if your website clearly states who you serve and what problems you solve. Specificity seems to beat vagueness.

The shopping feature is for products. The behavior shift affects all of us.

What patterns did you notice when you ran the search for your profession?

Last month I had the same conversation with four different owners. All professional services - consulting, marketing, accounting. All asking the same question: "Should I sell before AI disrupts my business?"

Not one of them is failing. They're all profitable. But they see what's coming.

I asked each of them the same questions: 

-Are you willing to learn this yourself - not delegate it? 
-Can you force organizational change even when your team resists? 
-Will you commit 2-3 years to rebuilding how work gets done?

One went quiet. Then honest: "I'm 5 years from retirement. I don't want to spend them becoming a technologist."

That's not weakness. That's clarity.

Here's what's interesting: these are all knowledge work businesses. The consulting firm owner is more worried than the metal fabrication company I invested in. 

Professional services feels the threat more acutely because their product IS knowledge work - exactly what AI does well.

Here's what I'm seeing: Owners who built great businesses over 20 years are struggling because they can't make themselves learn new systems. 

PE-backed competitors are acquiring AI capability through rollups. Multiples that look reasonable today won't in 18 months.

So I've started having a different conversation. Three paths:

BUILD: Learn deeply, force change, create proprietary AI workflows that competitors can't copy. 2-3 year commitment minimum.

PARTNER: Bring in PE or an operator who already has AI capability. Trade some equity for transformation capacity.

EXIT: Sell while you can get 5-8x EBITDA instead of waiting until AI-enabled competitors compress your margins to 2-3x.

No wrong answer. The only wrong choice is "wait and see."

This isn't pessimism. It's strategic honesty.

Do you have an AI strategy yet ?

For the last year, I've been watching a founder I coach hold onto a toxic performer. 

He wasn't great to work with and grumbled about how he could run the business better. 

So fire him? Problem was he was bringing in $1m in revenue.

But he cost the company too. They lost 2 good employees because of Mr. Toxic.

The founder didn't want to pull the trigger and risk the revenue.

So he waited. And waited. His behavior would improve for a few months, then get worse again.

Until he started actively undermining the owner with other employees.

That finally made it unbearable.

He got fired and guess what happened?

They didn't lose any revenue. In fact, they just kept growing.

The real cost of KEEPING him? Two good people gone. $50k in recruiting and rehiring costs. And 3-4 years of stunted growth because nobody wanted to work on his team.

the founder thought he was making a business decision by keeping the million-dollar producer.

He was actually making an emotional decision driven by fear.

What I learned: Track your performance conversations.

If you're using AI to transcribe meetings, run those transcripts through an LLM to track relationship health and accountability patterns.

It will highlight the problems earlier—before you lose good people, before someone poisons the culture, before you waste years tolerating what you know needs to change.

My founder waited 3 years and racked up $50k plus in costs.

AI would have shown me the pattern in month 3.

What high performer are you tolerating because you're afraid of the revenue loss?

Talked with an owner last week who runs a $10M compliance consulting firm for large construction projects.

$3M EBITDA. Niche expertise. Regulatory moat.

But AI is coming for the core deliverable. The environmental studies his team spends weeks researching and writing? AI can now draft those in hours. Not perfectly—but good enough to commoditize the work.

His question: When do I sell?

He's the sixth owner in two months who's asked me some version of this.

The trap: Actual disruption might be 3-5 years out. But buyers see the writing on the wall earlier. By the time your industry is visibly changing, your multiple has already dropped.

You're not racing disruption. You're racing the perception of disruption.

His business trades at 5-6x EBITDA today. If buyers start pricing in AI risk, that becomes 3-4x. That's a $6M swing on the same business.

My advice to most owners: Go BE the AI change. Use AI to produce studies faster and cheaper. Become the consolidator, not the consolidated.

But that's not everyone's game. Some owners are 5 years from retirement. Some don't want to bet a 20-year business on a tech transition.

Both paths are valid. What's not valid is deciding without understanding what AI can actually do today.

I've watched owners dismiss AI while competitors train it on exactly their workflows.

I've also watched owners panic-sell businesses with 10+ years of runway.

The only way to know which camp you're in? Get your hands dirty. Not reading headlines. Actually testing AI against your deliverables.

Then you can decide instead of guess.

Are you building toward disruption or planning your exit?

How to win as a business onwer:

Just focus on the most important thing.

I know owners who spend 10 hours getting the best pricing on a service or product that makes up 5% of their cost.

You know what they’re not doing during that 10 hours? 

Selling a service or product that’s worth 100x that cost savings to them.

I see owners who read a book or hear a podcast about some new marketing technique then try to pivot their whole company to it.

What aren’t they doing? Doubling down on a tactic that is already bringing in leads.

Stop what you are doing and think about this one question: what single thing will guarantee that I won’t reach my goal? 

Then go solve that thing. Rinse and repeat and ignore everything else.

24,000 hours.

That's how much client interaction one consulting company records per year.

Most would say: "That's expensive storage."

They're thinking: "This is our competitive moat."

Here's what they discovered:

AI analyzed those recordings and found something competitors can never replicate:

Their methods deliver outcomes 1.5 standard deviations better than industry average.

Not "we think we're better."

Data-proven superiority from analyzing thousands of real sessions.

Now they can:

- Prove results to justify premium pricing
- Train new staff 3x faster using what actually works
- Continuously improve by spotting patterns in top performer sessions
- Show clients exactly why their approach works

*his is happening across industries:

A coaching business recording sales calls:

- AI identified: Top closer uses these 3 questions, bottom performers don't
- Automated quality coaching for entire sales team
- Conversion rate: 30% → 40% in 90 days

The dark data problem:

Right now, every meeting in your company contains:

- What actually works (buried in someone's memory and an unprocessed transcript)
- What clients really care about (mentioned once, forgotten)
- Patterns that predict success/failure (invisible without AI)
- Your team's best moves (can't scale what you can't see)

It evaporates the moment the meeting ends.

What AI can do with recordings:

1. Pattern recognition: What do top performers do that others don't?
2. Outcome correlation: Which approaches actually drive results?
3. Training acceleration: New hires learn from 100s of real scenarios
4. Competitive proof: Data-backed claims vs. competitor marketing fluff
5. Continuous improvement: Spot quality drift before it costs you clients

The 10x value play:

Companies recording systematically are building:

- Proprietary methodology (competitors can't copy)
- Pricing power (proven better outcomes)
- Faster onboarding (new hires effective in weeks vs. months)
- Quality consistency (AI catches drift)
- Category leadership (your data becomes industry benchmark)

First-movers are building 2-3 year leads.

The objections I hear:

"Storage is expensive" → Storage is $50/month. Lost knowledge costs $50K+
"No one will review it" → AI reviews it. Humans get the insights.
"Compliance nightmare" → SOC 2 + consent frameworks exist. Not harder than current QA.
"Clients won't consent" → Position as "quality improvement" + show benefit. 95%+ consent.

Most SMB owners think:
"We're too small for this."

Reality:
You're the perfect size. Big enough to have volume. Small enough to move fast.

The companies doing this wrong:

Recording but not analyzing. Terabytes of dark data, zero insights.

The companies doing this right:

Every recording becomes training data. AI finds patterns. Insights improve delivery. Better results justify premium pricing. Category domination.

Do you really want to share good content during Thanksgiving week?

I've got some gems saved up but kind of feel like everyone's still talking to their family at this point.

Maybe by Friday they are back on linkedin trying to do anything but talk with their family?

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