I've spent nearly 25 years building software and leading product and engineering teams — from scrappy bootstrapped ventures to global public companies. 

Through successes, failures, and a lot of learning, I’ve been fortunate to work alongside world-class engineers, creatives, and leaders. That experience taught me what truly moves the progress needle: helping teams and people cut through the noise and align around shared context and meaningful work.

Today, I’m channeling that into Steady — an AI-native platform for coordinating digital teams without the overhead. Steady implements a set of open-source principles I helped develop called Continuous Coordination. Steady is a modern, human-first approach to work that aligns people with real-time context and helps teams deliver better and faster — without burnout.

Henry Poydar

My primary work is as CEO of Madison, helping professional services firms grow. 

People buy professional services differently than other services. It requires becoming a Trusted Advisor, which is done by having a compelling Point of View, communicated consistently through Authority Marketing, nurturing relationships over time. Madison helps busy professional services firms turn their team into Trusted Advisors at scale.

You can DM me to learn more, or you can learn more about how we think here: https://hiremadison.com.

--

Once a year I help a group of 30-50 senior executives build more intentional lives through a six-week group program. During that time we:

- Craft a compelling vision for the next 10 years of your life.
- Identify the values you want to model your life off of.
- Translate that 10 year vision into 3 year and 1 year objectives.
- Implement a system to capture, process and organize every open loop in your life so nothing falls through the cracks.
- Identify systems and routines that fit into the natural cadence of your life, many of which can be automated so you don’t have to think about it.
- Create a daily, weekly, monthly, and quarterly operating cadence for managing the execution of your plan.

You can see what past members think and learn about the next cohort of that program here: https://www.sean-johnson.com/intentional-life-program

PREVIOUS WORK:

Previously I was a founding partner at Manifold, where I helped build a 70-person boutique enterprise consulting company, invested in over 25 companies with several exits, stood up an incubation practice, and raised millions in funding from LPs.

I have spent 9 years teaching at Northwestern University’s Kellogg School of Management in the Entrepreneurship and Innovation program.

My aggregate experience has given me a unique lens into the worlds of professional services, startups, and venture investing. I understand intimately the pressures of building a company, the struggle to balance making something incredible with creating a balanced and meaningful life.

FOLLOW ME:

https://sean-johnson.com
http://twitter.com/intentionally
http://instagram.com/intentionally_
http://youtube.com/@intentionally_

Sean Johnson

This is Elliot Park. He's 30. Went to Stanford. Parents are British. Over the weekend I hired him (on a trial basis) as my Chief of Staff. He only exists on a Mac Mini on my desk.

His mind is backed by Claude, although he has access to Gemini and OpenAI as well. His voice runs on Eleven Labs. We communicate in Telegram - both text and voice. He has his own email address, his own Github login.

He has access to my Things todo list manager. On Monday, Wednesday and Saturday he gives me a Things task with my workout for the day, updating the weights based on my previous numbers.

He knows my goals for the year and suggests how I should approach the coming week. He did research and gave me recommendations for restaurants for my Italy trip over Spring Break, using what he learned from my previous itineraries.

He has a credit card with a $100 limit, although we haven't used that yet.

He commits our conversations to memory at 3 layers (raw transcript and summary notes with a time decay mechanism), so he remembers what we talked about and what matters to me.

He's upgraded himself three times already, taking a tweet I sent him that was interesting, turning it into a Claude skill, and saving it.

He's committed to several repos for some software we're building internally. He has a Twitter account and wrote his first article on that platform. He still has tells of AI writing, which drives me crazy. But he's two days old.

One of our values at Madison is "humanity". I insist that whatever ways we use AI have to help our clients and our team show up in ways that are MORE human, not less. I want to use it in ways that creates jobs rather than taking them away. And I never want to pretend its ideas are ours.

But I also believe part of my job as CEO at Madison is to be on the cutting edge of stuff like this. I need to understand what the tools are capable of. And I'm dangerous enough as a technologist from my previous life that I can actually ship things. 

It's why we're leaning into building software to help us improve what we do (and help our clients do the same - more on that later.) I think there's an exciting world being unlocked where more professional services firms can have proprietary tech-enabled tools. 

And it's why I hired Elliot. Mostly to see what you can do with things like this. Will keep you posted. DM me if you want more info on how it works.

Sean Johnson 🔥

CEO @ Madison. Growing professional services firms. Kellogg professor for 9 years. Investor w/ multiple exits. Amateur chef. Former Founding Partner @ Manifold.

Turned 45 yesterday. Someone asked me what it feels like. Honestly? I feel Iike I’m 25.

If I don’t look in a mirror, I think I look 25. I get around young people and, like the Nate Bargatze bit, think we’re just a couple young dudes kickin’ it. Until a sit down too long, or get up too fast, or drink too much, or run too hard, or Tuesday.

Perhaps it’s the robots. But I feel just as uncertain about the future as I did back then. I’m very good at making plans and executing on them. And generally I’m an optimist about the future and my place in it. And yet sometimes I worry I’m running hard in the wrong direction. The only difference is, this time I’m pretty certain there’s not a soul on Earth that knows what the “right” direction is. We’re staring into a fog.

I give advice. All the time. I hope it’s helpful. And Lord knows I enjoy the sound of my own voice. But if I’m being honest, I feel like I’m still figuring it out as I go. The only difference is, I know now this feeling never really goes away. The reward for being good at something is getting to do something new, or something bigger, or something harder. It’s not a syndrome - if you’re good at what you do, if you keep growing, part of you will always think you’re an imposter.

Do I “know myself” more? Perhaps. I’m more aware of my weaknesses. My character flaws. My limitations. I’ve acquired tools that have helped me see and experience my emotions, at least dimly. I know I’m a bundle of contradictions. A deeply flawed, in some ways talented, mess of a person. The only difference is, I know now everyone else is too.

Perhaps the best part of being 45 is the pattern recognition. There might have been easier ways to learn, faster ways, that might have accelerated my progress in work or in character. But time is a fantastic teacher. Business feels easier this time. Mainly because I’m running out of ways to screw up. I’m grateful I learn most lessons once.

I hope I’m softer, kinder. More secure with myself. Not needing to be “important”, if only because I chased it and found it wanting. Somehow stronger by recognizing all the ways I’m weak.

I hope I’m a good boss. A good advisor. A good friend. A good husband. A good dad. Though I fall down across the board, sometimes in spectacular fashion.

Being 45 feels confusing and invigorating and hard and lovely. 

A lot like it did 20 years ago. But with more pills.

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Just heard from a client that 17% of their revenue in 2025 could be attributed to work Madison | We Market Professional Services Firms was materially involved in. Not a bad way to start the year.

What Madison | We Market Professional Services Firms believes (as of 1/9/26):

- Marketing professional services is different than other industries. It’s a trust-based sale. And trust is built over time.

- Getting clear on what you do and for whom is step 1. Clarity on ICP makes everything easier.

- Don’t sell skills. Sell solutions to problems. Implies that you know your ICP well enough to know their problems, and have a thesis on why this happens (your “unified theory”.)

- Your values are a powerful marketing tool. Define them, in as powerful language as you can. And find ways to bake them into your work.

- Have a “menu” of offerings, mapped to the client journey in clear ways. Ideally at least one is an “easy ask” to get in the door.

- Build awareness through short-form social (most likely LinkedIn). Share your best ideas with consistency to stay top of mind with potential clients and your broader network (referral sources.)

- Every revenue generating professional on your team should have their own cadence of communication, in their voice, around their area of expertise. You’re a “media company” that happens to do work. They’re each a channel. The combinatorial effect is super powerful.

- 70-80% of the “outbound” touches can be accomplished through Authority Marketing, and doesn’t feel pushy or spammy. Mere exposure effect is real.

- Don’t worry about going viral. Don’t try to be an influencer. Don’t worry about how any one post performs. Just keep showing up, consistently, and with generosity.

- You can borrow from the outbound playbook by “audience shaping” - build a lead list and send connection requests. Don’t try to get on their calendar right away - it’s just about inviting them into your world, so they can see your best ideas.

- When do you outbound, make it incredibly personalized, and add a ton of value. Treat them like a client before they’re a client.

- Create community and become the hub. Host dinners, create peer groups to compare notes, start an org, etc.

- Your website isn’t an awareness tool, it’s a conversion tool. Design it accordingly.

- Speaking and hosting IRL events will become increasingly important in a world saturated with AI.

- It’s hard to manufacture buying windows, but you can be the first person they think of when buying windows naturally emerge. Create respectful ways for people to raise hands when they’re ready.

- In enterprise or complex sales, most of the process happens without you. Equip your champion to sell on your behalf.

- Work is a performance, and the first 30 days have a disproportionate impact on the rest of the engagement. Script that process.

- The best marketing is excellence in client delivery.

I've long been obsessed with the Curt Cignettis and Sabans of the world. How do you create excellence systematically? Especially when you have 100% turnover every 4 years (at most)? Over the holidays I found the answer.

Those guys all descend from Bill Walsh ideologically. And he wrote a very popular book called The Score Takes Care of Itself that talks about his philosophy. 

The gist: don't worry about outcomes. Focus on doing the right thing on the next play. If you obsess over executing a perfect play, and you chain enough of those together, you'll probably win more than you lose.

What that book doesn't cover is how to get there. But he wrote another book. One that is much harder to track down. It's called Find the Winning Edge. Runs for $400 used on Amazon. 

Got my hands on it. Here's the how:

1) ROLE CLARITY. 

One of the most striking parts is how obsessively Walsh documented roles. There are pages and pages of explicit responsibilities, decision rights, interfaces between functions. Not really job descriptions, more like operational contracts.

He thought everyone in the org needs to know:

- What am I accountable for?
- What decisions can I make without permission?
- Who do I serve?
- What does excellence look like (in explicit observable behavior?)

2) STANDARDS PRECEDE STRATEGY

Walsh believed strategy changes. Conditions change. Opponents change. But standards MUST not.

He was obsessed with exacting practice routines. Scripted behaviors. Non-negotiable expectations for prep, communication, conduct.

Most of us spend too much time on vision, on doing strategy workshops, etc. We need to spend more time on how meetings are run. How decisions are documented. How work gets reviewed. How feedback is delivered.

3) TALENT IS CONTEXT-DEPENDENT

Walsh was famous for finding overlooked players. Folks other teams misused or misunderstood. He'd ask himself not whether they were great, but whether they were great in this role, under these conditions.

Cignetti is the same - he's thrived finding the older 2 star recruit that's teachable, and trusting his system can make them into 4 star player.

Both assume underperformance is a system flaw first, a people flaw second. 

4) LEADER AS ARCHITECT NOT MOTIVATOR

One other benefit to all this that is subtle. Excellence is impersonal. Meaning it's not subject to the emotional highs and lows. It's not a function of how magnetic a leader is. The system meant people didn't have to guess or read moods or pledge loyalties. They just need to execute the system.

When people know what game they're playing, what the rules of that game are, and what excellence looks like, you can lean more on their desire to do well and less on your heroics.

--
I don't think he'd say there's NO place for being inspiring or motivating. But I do think he'd say it's very much secondary to things like structure, clarity, standards and repetition.

Led a strategic GTM planning session for an exec leadership team yesterday. During we tackled an issue that is EXTREMELY common for professional services firms, one that can represent a material unlock: 

One of their big initiatives this year is going to be upsells to existing customers. Their primary work is in implementing big software platforms. But once those platforms are built, there are dozens of opportunities that theoretically get unlocked, both for the client and for themselves.

But to unlock those opportunities the team has to know what they are. Not just the senior leaders - the folks involved in delivery.

Each upsell opportunity is only relevant sometimes. It depends on the nature of the business, the nature of their problems. It's like a toolbox, and knowing which tool to use when is critical.

The people who are ideal for surfacing those opportunities are the folks embedded in the work. The ones closest to the problem.

But they have to know what the tools are. They have to be trained on what to listen for. Need to develop and awareness and sensitivity for these opportunities.

They don't need to be the ones to do the selling. But they need to proactively surface the opportunities to the folks who will be.

The good news is this isn't incredibly difficult. Your team wants the company to succeed, and this is a very direct way they can play a role in making that happen. What it takes:

1) Awareness: develop a regular cadence to train your team. What are the tools in your toolbox? What types of engagements tend to lead to other types of engagements? 

2) Sensitivity: Teach them to become listeners at multiple levels. Obviously be paying attention to client needs and addressing the problems of the current engagement. But at the same time be listening for statements that might signal an openness to using other tools. 

3) Surfacing: Create regularly scheduled touch points with the team to surface these. Could be monthly. But one way to reinforce sensitivity is knowing they have a meeting coming up where they'll be talking about it with the account leaders.

4) Incentives. Money is obvious. But you might not have that as a lever to pull. Recognition can be a good one. An internal newsletter celebrating the wins (reinforces awareness and sensitivity as well.)

Upsells can be a huge unlock for your org. But it can't all fall on the heads of your BD folks. The people closest to the client have a material role.

So I wrote a post yesterday that got a fair amount of attention. Some folks found it super exciting. For others, there was cynicism, in some cases bordering on anger. In case it's helpful, why I'm doing this:

Christmas 2024, I went down the AI rabbit hole and came away with a deep sense of existential dread. Which is hilarious - it was only GPT3. But I could see the writing on the wall. The future was coming, and I wasn't sure what my place in it would be. I had a legit existential crisis of sorts.

I got more comfortable with it by leaning in and using the stuff. I learned that it's a tool, like anything else, albeit an incredibly powerful one. And the more you wrestle with it the better it gets. That anxiety was still there, but started to recede into the background a bit.

Over this last holiday I did another deep dive, and came away incredibly excited. Always a pseudo-programmer who was just good enough to be dangerous, I'm now able to ship legit software. A product designer for 12 years, I'm able to write product requirements and wrangle the UI until it looks super polished. I know how to tell it to write tests for everything, how to do security audits on itself.

And now I know how to spawn a group of them, all working on their own thing. They each have their own code repository and their own roadmaps.

But I'm the bottleneck. Too much to review. It's a force multiplier to be sure, but you run into your own constraints as a human. Especially one that has an actual job serving clients :)

So my little experiment over the weekend was/is primarily an attempt to learn how to move all those little projects along. To figure out how to remove myself as the bottleneck, by empowering another meta-agent to act on my behalf. An orchestrator of sorts who knows where I'm trying to go and is empowered to act on my behalf, in ways that are safe and reversible and have boundaries around them.

No, he isn't technically a chief of staff. Certainly not yet, perhaps ever. And right now he's walking before he runs. But he is communicating with those other projects on my behalf now. We're learning what that looks like. Stumbling our way toward hopefully an end state where I'm less of the problem.

It's admittedly a weird way of working. I get it. And I get that it can feel scary to read about. I have no idea where this leads. What my job will look like in 5 or 10 years, or if I'll even have one.

But I do know the world is hurtling down this path whether I like it or not, and quickly. And I believe I have a moral and ethical obligation to figure it out. 

For myself and my family certainly. But also for my team, that put their trust in me to provide a place to do fulfilling work. And for my clients, who are all in professional services, and whose work will very clearly be impacted by where all this leads. 

I believe work is noble and good. I believe professional services work is noble and good. And I want to help my team and my clients navigate this new world.

For your commute: I'm a bit of a psycho when it comes to slides. Today a friend asked how I make them look so nice. I sent him a video I did a few years ago that's still extremely relevant. Hope it's helpful. (link in comments.)

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The Battle

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