The Community-Oriented Event Series for Tech Execs · Hosted by VSP

Actual Intelligence

A community for tech leaders who want to level up, connect, and have a little fun.

We built the event we’d actually want to attend: an ongoing monthly series and community for CTOs, engineering leads, and technical founders. And if you’re going to come out for the evening with us, you might as well have a good time. That’s why we start with an icebreaker or game, then we’ll hear from a real practitioner for 30 minutes, followed by plenty of time for networking, drinks, and apps (the kind you can eat). We look forward to seeing you.

Register via Meetup
Audience engaged at Actual Intelligence Speaker presenting to the room Executives networking at the event
How does the evening work?
Part murder mystery, part real talk, part open networking – in that order.
When & Where
Held the last Tuesday of each month · Starting in the Capitol region and expanding to new cities
How long will it run?
Doors open at 6:00 PM. The game begins at 6:45 PM. You’re done by 9:00 PM.
Who should come?
CTOs, engineering leads, and technical founders – and the people who work alongside them.
Why We Built This

Most “AI events” are vendor
catalogs in a ballroom.

We’ve all been in a great room – the kind where the conversation keeps going well past when it was supposed to end, and you leave with two or three connections that actually mean something. Those rooms don’t happen by accident. They happen because someone put the right people together and gave them something real to talk about from the minute they walked in.

“Everybody’s got a chatbot on their roadmap. They’re not seeing the whole picture because they can’t see it.”

– CTO & AI advisor, 26-portfolio growth equity firm

The panels aren’t working. The sponsored thought leadership isn’t working. What actually works is putting sharp people in a room, giving them something to talk about – something that isn’t a business card exchange – and then getting out of the way. That’s what Actual Intelligence is built to do.

So we start every session with a game. Not a trust fall. A murder mystery – where talking to strangers is literally the only way to solve it. Suspects are planted in the audience before doors open. Paul sets the scene, announces the crime, and gives the room 30 minutes to find the culprit. You have to introduce yourself to do it – that’s the whole point. By the time the speaker takes the floor, everyone’s already laughed together. That’s not an accident. That’s the whole design.

The Format

Every session, the same three things.

The mystery scenario changes. The speaker changes. The topics change. But the structure stays the same – because it works. Short enough to respect your evening, open enough to let the real conversations happen.

Part One 30 min
The Mystery

Every session opens with a tech murder mystery. Paul sets the scene and plants suspects in the room. You have 30 minutes to find the criminal – which means introducing yourself to everyone. The crime scenario changes each time. The game is always the same.

Part Two 30 min
A Real Conversation

One practitioner. One topic they’ve actually lived. No slides, no vendor pitch – just an honest account of what happened, what they learned, and what they’d do differently. The topic rotates every session based on what the room needs to hear.

Part Three 60+ min
Genuine Connections

Open networking with the speaker, the host, and the room. The energy is already there from the first two parts. These conversations tend to keep going long after the venue closes.

Who Runs the Room

Hosted by practitioners,
not promoters.

The people on stage have actual receipts. They’ve hired the engineers, made the calls under pressure, and lived with the outcomes. No talking heads. No sponsored speakers. The keynote slot is programmed when the right person and the right topic align – not when the calendar says it’s time.

Paul Doman
Host & Convener
Paul Doman
Co-Founder & CEO, Victory Square Partners

Army veteran, DC entrepreneur, and technology services executive. Co-founded Victory Square Partners in 2019 and has grown it to 200 team members and back-to-back Inc. 5000 rankings. Member of Mindshare (class of 2024).

LinkedIn
Matt Walnock
Speaker
Matt Walnock
Head of AI & Advisory Services, Victory Square Partners

Started as a software engineer, rose to architect, served as CTO of Parature through its acquisition by Microsoft. Now leads advisory engagements helping growth-stage companies build AI roadmaps and ship faster without sacrificing judgment.

LinkedIn
Keynote Speaker
Coming Soon

We program the speaker when the right person and the right topic align. The keynote for the next session is in final confirmation. Get on the invite list to be notified when it’s announced.

Get notified
What Gets Talked About

A Menu, Not a Calendar

We don’t lock the topic in advance. Every subject here came directly from CTOs, engineering leads, and technical founders on calls we run every week – in their own words, describing their actual problems. We pick the topic that matches the room we can convene and the speaker who lived it. No theme quarter. No content committee. Just what the room actually needs to talk about.

AThe Foundation Problems
TOPIC 01
Your Stack Is Holding Your AI Hostage

Every AI initiative that stalled in the last 18 months stalled for the same reason – the system underneath it was never built to move. Stored procedures, manual release gates, untrusted internal APIs.

“The evolution of how the product grew up... interns writing stored procedures” that compound issues still plague us.– Founder/CEO, identity-security SaaS
TOPIC 02
CI/CD to the Power of a Million

If you ignored CI/CD a decade ago you survived. If you ignore AI infrastructure debt right now, you don’t. The investment is small. The compounding gap isn’t.

“For 30 years, whenever you find out a company is not using CI/CD, you’re wondering why. Except AI debt is like that to the power of a million.”– CTO & AI advisor, growth-equity firm
TOPIC 03
More Data, More Problems

Feeding AI into a broken operating model doesn’t accelerate the business – it accelerates the dysfunction. Conflicting ground truth, accountability gaps, decision latency.

“More data is creating more chaos in what’s true. That’s the part that was not obvious until absolutely neck-deep.”– Technology advisor, knowledge-graph builder
BThe Strategy Problems
TOPIC 04
Everyone Has a Chatbot. Almost Nobody Has Production AI.

The gap between “AI on the roadmap” and “AI in front of customers” is where most companies are quietly stuck – and the board doesn’t know it yet.

“Everybody’s got a chatbot on their freaking roadmap still. They’re not seeing the whole picture.”– CTO & AI advisor, growth-equity firm
TOPIC 05
The Most Expensive Decision Right Now: “We’ll Build It Ourselves”

In-house AI development sounds like control. It costs three teams, two years, and a talent market that doesn’t favor you. The founders who killed the experiment can explain why.

“They keep firing their data team because they can’t deliver. So now we’re onto the third team.”– CEO, analytics platform company
TOPIC 06
The Solo CTO Is Your Biggest AI Risk

One technically-fluent leader carrying the whole AI transformation isn’t a strength – it’s a single point of failure. What happens when they’re saturated, recruited away, or out for two weeks?

“The CTOs are time-strapped... they have to get things done the way they’ve already been doing them.”– CTO & AI advisor, growth-equity firm
TOPIC 07
The Generational AI Standoff

Junior staff want Claude turned loose on everything. Senior leadership wants guardrails. The fight inside your firm is the same fight inside every firm – and most companies are losing both sides of it.

“We got young people saying if you don’t set Claude loose on everything at all times, we’re behind. Plus compliance concerns.”– Managing Partner, venture capital firm
CThe Commercial Problems
TOPIC 08
The Contract That Doesn’t Exist Yet

The pricing models procurement knows how to evaluate were built for a world that doesn’t exist anymore. Headcount has no relationship to outcomes. T&M is breaking on both sides of the table.

“I’m so used to selling per person. I’ve never sold a pod. How do you contract it?”– CRO, technology platform company
TOPIC 09
From Services to Software

If you sell delivery hours today, the AI-era version of your pricing model is a different model – not a discount on the old one. The founders who already made the transition can tell you what broke first.

“We started to shift from being a services company that had some cool tech to a software company.”– Founder/CEO, identity-security SaaS
TOPIC 10
The Partner Problem

There is more budget for AI delivery than at any point in the last decade – and almost nobody in the buying seat trusts the vendors in front of them. The buyer-side post-mortems are damning.

“They didn’t understand identity. They didn’t understand the use case. They were developers.”– Founder/CEO, identity-security SaaS
DThe Stakes
TOPIC 11
When AI Lies in Court

Hallucinated citations in expert-witness reports. Fabricated case law in legal briefs. AI in regulated domains isn’t an efficiency tool – it’s a liability surface. What changes when the cost of being wrong is professional sanction?

“Bastion gave me output scores for these made-up data sources... I spent a long time trying to track down the author.”– Forensic psychologist, legal-tech AI startup
TOPIC 12
The Board Asked About AI. What You Actually Tell Them.

You can run the model. You can show the output. But can you explain it upward – to the board, the investors, the regulators? Most executives can’t, and it’s stalling internal AI adoption more than any technical limitation.

“The AI piece is already a box. So like – it would be a box inside of a box. How does it do it?”– CEO, B2B analytics SaaS
TOPIC 13
The Data Moat That Never Was

You own the data. You have the customers. You should be defensible. So why is a competitor with a $9.99 LLM license eating your lunch? The story of data assets that never became products.

“You’re talking to the guy who has an analytics platform in the age of a $9.99 Power BI license.”– CEO, B2B analytics SaaS
TOPIC 14
AI on a Deadline

Federal AI guidance. Extended Producer Responsibility. State-by-state compliance fragmentation. The regulatory clock is moving faster than the tooling roadmap – and “we’ll get to it” stopped being a viable answer two quarters ago.

“People see this deadline and it’s already too late. It’s six months too late.”– Sustainability lead, packaging-compliance data company
EThe Operating Model
TOPIC 15
The Software Factory

The shift from artisan AI delivery to industrialized AI delivery. Why “we use Claude for everything” is not a strategy. What the workforce, the workflow, and the leadership look like when AI work is treated like a manufacturing line.

“The offering is the seller’s personal workflow.” If that’s true about your team, it doesn’t survive that person changing roles.– Internal critique, services-firm offsite, May 2026
TOPIC 16
The Interface Role Nobody Hired Yet

The new bottleneck in AI delivery isn’t engineers – it’s the people who can translate executive intent into agentic specifications. They don’t have a job title yet. They’re carrying the whole offering on their backs.

“We have ~160 developers, very few interface-capable. A few deals in, we run out of qualified people.”– CTO, mid-market AI services firm
TOPIC 17
The Pricing Authority Vacuum

Your pricing model lives in a document. Your pricing realization happens wherever the relationship allows. Until a pricing authority exists separate from the account owner, outcomes pricing drifts back to hourly billing on every relationship-sourced deal.

“The pricing model exists in a document. The pricing realization lands wherever the relationship allows.”– Internal margin postmortem, services-firm leadership
TOPIC 18
Doctor by Doctor: How Purpose-Built AI Eats Monolithic SaaS

A $2B SaaS company watching purpose-built AI tools replace its product one workflow at a time. The pattern reshaping every SaaS market – not as a frontal assault, but as a flank.

“$2B/7K-person company whose top strategic risk is purpose-built competitors replacing their system incrementally.”– Leadership offsite, May 2026
Who’s in the Room

The people make the room.

We’re intentional about who gets in – because the quality of the room is the whole point. If you lead a technical team, own an AI roadmap, or are actively building something, you’ll find your people here. The more honest you’re willing to be about what’s actually going on in your organization, the more you’ll get out of it.

The Engineering Leaders

CTOs, VPs of Engineering, heads of product, and senior architects at growth-stage and mid-market companies. People who own a technical team, an AI roadmap, or a delivery problem they haven’t solved yet. This is the core of the room.

The Technical Founders

Founders and co-founders who came up through engineering and are now navigating the AI build-vs-buy question with real money on the line. They bring a different kind of urgency to the conversation – and a different kind of honesty.

The Operators & Investors

Fractional CTOs, technical advisors, and PE or VC partners who see the same AI implementation failures across dozens of companies. They come because the cross-pollination is the whole point – and because they need the peer network too.

Get Involved

Three ways in. Pick yours.

You won’t get a drip sequence. You’ll hear from a real person – usually within 48 hours. Whether you want a seat at the next session, a conversation before it happens, or a slot on the stage to tell your own story, there’s a path below. Interested in co-hosting or bringing your community? Reach out the same way.

Path 01
Attend an Event

Get on the invite list. When the date is locked and the lineup is confirmed, you’ll be the first to hear about it. Tell us which topics you’d want in the room and we’ll make sure the programming reflects it.

Register via Meetup
Get on the list
Path 02
Talk Before the Event

You’ve got a specific situation – an AI initiative that stalled, a team decision you’re not sure about, a build you’re about to start. A 30-minute call before the next session puts you in the room better prepared and better connected.

Path 03
Deliver the Real Talk

You’ve lived one of the topics on the menu and you’d consider telling the real version from the stage – not the polished case study, not the roadmap slide. No deck required. Just what happened, what broke, and what you’d do differently. Pitch it here.