What Does an AI-Driven Client Management Operating System Look Like?

AI Knowhow: Episode

83

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AI Knowhow Episode 83 Overview

Professional services firms live and die by client retention and growth, yet many still rely on scattered CRM data, tracking client satisfaction in spreadsheets or with quarterly surveys, and individual heroics to ensure client success. In this episode of AI Knowhow, Courtney Baker sits down with Pete Buer to map out a repeatable client management operating system—and the role AI plays in turning relationship chaos into insight you can act on in minutes. This episode previews an upcoming client management operating system webinar that Courtney and Pete will host on Thursday, May 22nd.

What is a client management operating system?

We kick the episode off by defining what we mean when we talk about a client management operating system. As Pete says, it is the combined set of processes and objectives that have dependencies on one another that, ultimately, power your business. Whether you think of them as an interconnected OS or not, every business has them. The five active ingredients of a high-performing operating system are:

  1. Cascaded goals and objectives
  2. Clear roles and responsibilities
  3. Aligned incentives
  4. Purpose-built meeting cadence
  5. Data-driven decision making

Why does this matter for services leaders?

Taking a scientific approach to how you manage clients may sound “academic.” In reality, however, the fate of any professional services company relies on continually honing and perfecting its operating system. Here’s why now is such a vital time for any professional services leader to consider how they deliver value to their clients and where AI can plug in:

  • Retention fuels growth. A 5-point lift in client retention can increase profits 25–95 percent.

  • Data is there—but disconnected. CRMs, ticketing tools, email threads, invoices, and Slack DMs rarely line up in one view.

  • AI is ready. Modern LLMs can now ingest unstructured touch-points, infer sentiment and risk, and surface next-best actions—no army of analysts required.

“AI makes everyone on the team some degree of expert,” Pete says. “No more context hunting, only decision-making.”

Be sure to tune in to the full episode below for more, and register for our May 22nd webinar to take a deeper dive into what an AI-powered client management operating system can do for you.

AI in the News: OpenAI is keeping its non-profit roots after all…

While Courtney, David, and Mohan were recording footage for upcoming episodes, the news broke that OpenAI won’t pursue converting to for-profit status after all. The move comes after pressure from Elon Musk, among others, to retain the non-profit status and posture the company has had since being founded in 2015. It also harkened back to our Hot Takes episode from earlier this year, when David predicted just such a move.

On that episode, David looked into his crystal ball and said, “I just think we are going to look up in two years, and OpenAI isn’t going to be the clear leader anymore, and the assets will still exist somewhere, but they won’t be seen as the leader. The assets will be somewhere distributed. I don’t know if they’ll get acquired. I don’t know if they’ll merge somewhere. I don’t know if they’ll go back to being a pure not-for-profit, and the profit engine will be spun off somewhere…”

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Show notes

What if every client touch point in your business was being digested by an AI assistant that never forgets and never sleeps?

And what if you could pull a full client snapshot in minutes before that big account review instead of digging for hours just to get half truths?

Hi, I’m Courtney Baker, and this is AI Knowhow from Knownwell, helping you reimagine your business in the AI era.

As always, I’m joined by Knownwell CEO David DeWolf, Chief Product and Technology Officer Mohan Rao, and NordLight CEO Pete Buer.

But first, some breaking news happened this week when David, Mohan, and I were in the recording studio for a few roundtable interviews.

David, Mohan, today, while we’ve been in the studio, some real life breaking news dropped.

I wanna get your reaction because, legit, everybody listening, we’ve been in the studio for a long time.

Our producer said, hey, I want you, I’ve got something for you.

So, David and Mohan, totally in the dark, I think.

So I wanna get your reaction to this.

Via New York Times, OpenAI backtracks on plans to drop non-profit control.

The company will become a public benefit corporation and the non-profit that has controlled it will be its largest shareholder.

So, one more headline for you.

I’m gonna give you one more second while your jaw is on the ground.

Washington Post, OpenAI scraps the plan to transition into a for-profit company.

The chat GBT maker has sought to separate from its non-profit board but reverse course after pressure from former employees and a lawsuit from Elon Musk.

David, Mohan, thoughts here?

Well, I think we predicted this in our hot takes, didn’t we?

And I think we specifically called out that something had to change and that Elon Musk and if he got together with Satya, I think is what we said, something altogether different would happen.

So I don’t know that we predicted this outcome that they would just totally backtrack, but there’s been something going on for a while.

It’ll be interesting how this plays out.

I don’t think this story is done.

I think that this is probably just a step back in their plans.

I think the DNA of the company is very much turning into a for-profit company.

So what does that mean?

And how does this governance reality start to impact that?

And I don’t know.

I think this is just kind of an interesting milestone.

Okay, Mohan, before you respond, I’ve got David’s hot take in front of me, actually.

Nice!

What did I say?

Yes, you said, I just think we’re going to look up in two years and OpenAI isn’t going to be the clear leader anymore.

The assets will still exist somewhere, but they won’t be seen as the leader.

The assets will be somewhat distributed.

I don’t know if they’ll get acquired.

I don’t know if they’ll merge somewhere.

I don’t know if they’ll go back to being a pure not-for-profit and the profit engine will be spun off somewhere.

Got to say!

That’s pretty good.

I hope Will recorded that so we can publish it.

Yeah, maybe we can just insert that.

You actually giving that part of the hot take.

Mohan, what do you think of this news?

My God, this is actually big news.

It’s very surprising to me that that’s where they’ve ended up because there’s been massive internal tension.

But I think this is a good balanced compromise, right?

So just because they’re a non-profit, it doesn’t mean that they’ve had any dearth of capital investment going in, right?

So if anything, it’s been so massive, right?

So it’s probably gives a good balance between capital investment and, you know, oversight of their mission.

And this hybrid structure could be, you know, could probably be the best short-term compromise for the dynamics within the company.

But I suspect, like David said, this is not the last chapter.

I think there is going to be a new chapter in this tension.

Where do you think this came from, Mohan?

Do you think this was forced by Elon in the lawsuit?

Do you think it was Microsoft?

Do you think it was really the employees, as the article says, just the culmination of all of it together?

What do you think?

I think it’s definitely outside pressure, right?

So there’s no question about it, because if left to Sam, I think it would have gone the other way.

I think this is a lot of outside pressure and his recognition of this is the best chess move in the short to intermediate term, to just keep things clean.

Projecting is clean, huh?

Exactly.

I mean, you know, and also it might be something to do around, let’s not rock the boat.

I mean, just to think of it, that OpenAI is a legit company, right?

So with billions of dollars in revenues, and we all know the stats.

No company has grown as fast as it has in the last three, four years.

So I think they’ll keep going for market share.

And one of the things about nonprofits that always sort of, I have to remind myself is, yes, a nonprofit is zero profits, but on the other hand, they can have infinite revenues.

That’s right.

There’s no limit on making on revenues.

Yeah.

So let me ask David and Courtney, why do you think this move was taken?

I think it’s just a pragmatic window dressing thing.

I think the reality that it’s going to be a nonprofit holding company with a for-profit entity underneath it.

I think Sam’s going to run the for-profit as a for-profit.

I think it says in there that they’re going to continue to take in outside investment.

SoftBank, I think, just invested $40 billion, if I’m not mistaken, or committed $40 billion.

I think what’s going to happen is the nonprofit is going to continually get diluted more and more as more outside capital is brought in.

So how that shakes out will be really fascinating.

I mean, that could be the strategic play here is just for Sam to raise so much capital that he dilutes control away from the non-profit.

What does it mean for a non-profit to own a for-profit business?

It basically, so it happens a lot, and it basically means that the profits of the subsidiary accrue up to the not-for-profit.

Those profits basically are for the disposal of the non-profit to further its mission, right?

Which is what the for-profit is all about.

In a lot of examples, for-profit entities cancel out the losses of other entities under the umbrella.

I don’t know what would happen here in the case of OpenAI, and I can’t imagine that the subsidiary is going to be distributing any sort of dividends or anything back to the not-for-profit.

It’s an interesting question to think about.

It’s not like there are operating costs that I know of that sit in the not-for-profit entity, right?

It sounds like they’ve probably pushed as much as they can down to the for-profit entity.

So practically speaking, it’s almost like having a holding company, if I’m imagining it correctly.

Yeah, and it’s really interesting for everybody listening.

You can go read Sam Altman’s letter that corresponds with this.

It’s quite a little bit of a lengthy letter, but it gives a little more insight into some of the decision and kind of some of the impetus to it.

But all in all, very interesting new development, and I’m sure there will be more coming out in the weeks ahead.

But David, Mohan, big news, and really great to get it here live with you today.

What does an AI-driven commercial management system look like?

Well, Pete and I dig into a topic.

We’ll be covering more in depth in an upcoming webinar.

Pete, thanks for being with us today.

This is a really, this is exciting, because usually when I’m talking with you, it’s to dive into some of the latest AI news.

But that is not what we’re doing today.

Today, we’re here for something a little different.

We wanted to give listeners a preview of an upcoming webinar about how professional services leaders can incorporate AI into their client success or commercial success operating system.

And so first of all, what should our audience know when it comes to thinking about their operating system?

Where do they begin?

First, we should probably begin by explaining what we mean by operating system.

There’s deliberate choice of language there suggesting that client management or account management, we sort of use them interchangeably, isn’t just a thing in a vacuum, it’s a combined set of processes that have dependencies on one another.

When they’re working well together, you achieve amazing outcomes.

And when they’re working poorly together, you don’t.

Kind of like the way Apple’s operating system connects you to your hardware, to hundreds of apps, seamlessly when you need it, together and all toward a good end.

So when we talk about the client management operating system in professional services, the idea is a connected set of processes and objectives, and the componentry of which when working together drives customer retention and growth outcomes.

I think you’re probably already going to go there, but I’m just curious, what exactly is the componentry that you’re talking about?

Yep.

So for our purposes, we’ve narrowed down to the five active ingredients, and let me just buzz through them.

So a cascaded set of goals and objectives.

So what are we doing?

Why are we doing it?

And how does what we’re doing day in and day out relate to the direction and strategy of the firm?

Second, clear roles and responsibilities.

Who’s in charge of what?

How do we work well together?

How do we not bump into each other?

Aligned incentives.

So making sure we’re motivating the right goal-oriented and collaborative behavior within these working systems.

Fourth, is a purpose-built meeting cadence.

So orchestrating the work to ensure we’re maintaining momentum and driving a focus on outcomes and intervening as necessary.

And then lastly, the fifth, data-driven decision-making.

Do we have all the information we need to really understand portfolio and client health in order to diagnose and make really good decisions about how to drive to retention and growth outcomes?

There’s all kinds of evidence out there to suggest that you get any of these right on its own and it drives a performance increment.

You get any of them wrong on their own and it destroys not just company performance, but customer value and employee value and getting them right altogether kind of puts you in the stratosphere from a performance perspective.

The good news is a lot of it’s within your control.

So, understanding how the pieces work and how to get them right from a best practice perspective is something that you can do day in and day out.

In fact, the processes surrounding the goals, the roles, the incentives and the meetings is all within your control to manage.

In focusing on continuous improvement and each one of them drives continuous improvements across the business.

The bad news though is that fifth one, having great up-to-date information about clients, has been the Achilles heel of professional services for all of time because of the business model, because of how delivery works.

Very little transactional data available as compared to, for instance, a product or a platform company.

What little data we do have is unconnected and sits in a bunch of different source systems in the tech stack.

And any insights we have into day-to-day relationships with clients sit in the heads of the expert humans who are doing the work.

And at many times, there are lots of them and lots of folks on the other side of the fence in the customer organization that they’re interacting with.

All of it at some level unmanageable and unattainable.

This is where AI comes in.

Now, before you go there, Pete, because I know this is like what everybody’s probably really excited about is hearing, oh my goodness, okay, yeah, how do we run this?

How does the AI help us?

I mean, first, everybody has an operating system, whether they recognize it or not.

Something is fueling things, rhythms within the organizations.

If it’s just some of the components, maybe not all of them, but there are things happening.

But are there some things that you can think of or help advise people?

I think in general, most people are like, yeah, yeah, we got that, we got that.

But there are symptoms that kind of come to play that maybe you just need to rethink some things or there is a level up from where you are.

Are there some real quick hitters that you can help the audience think about?

To know like, yeah, if you’ve run into any of these, it might be time to just take a refresher on what your commercial operating system is, how are you really looking at what is driving your client’s success?

Great question, Courtney, thanks.

As it happens for each of the five dimensions that we’ve mentioned, there’s a level of maturity that you typically observe across commercial organizations.

And by the way, we have a checklist where you can sort of test your level of maturity if you’re so inclined.

But so for each one of them, there’s kind of a definition of what best practice looks like.

If you just take goaling as a starting point, are we working backwards from company strategy?

Do people see day in and day out how the work that they’re doing matters and how it matters to strategy?

Have we broken down the company revenue goal to all of the commercial functional goals, to all the segment goals, to all the way to the level of client by client goals?

And for each of those client by client goals, do we have a plan in place to get after them?

So yeah, and the way you know it’s not working typically is you’re missing goals.

Or people can’t answer on the elevator, what we’re trying to accomplish across the next three years.

Or you’ve got employee engagement problems, because people don’t feel what they’re doing matters to the outcome and to the plans of the firm.

So there’s lots of ways to notice that it’s going wrong, and then lots of ways to get it right.

Pete, as we’ve talked to hundreds of professional service firms, so many times, they’re not able to really articulate, like, what’s the meeting cadence that drives these things?

Of course, everybody has a meetings, but you just don’t think about how that’s so core to your commercial management system.

And it’s really important that you know what that cadence is and what the components of those meetings are to really fuel the outcomes.

It rolls all the way back up to the goals that you were just talking about, but that’s a really easy checkpoint.

If you or your team aren’t easy, able to actually articulate that might be a time to sit down and think about it more clearly and how you roll that out.

Many more, but I just think that that’s one that I’ve seen over and over again.

The best indicator that meetings aren’t working is when you find yourself looking for reasons to reschedule it or not attend this week.

I would revisit.

Okay, so we know what a management system is.

We know why it’s important.

Okay, let’s get into the good stuff about AI and really how we start to think about utilizing AI to power our client management operating system.

Now, real quick, Pete, before we do, I just got to say one more thing.

When you look at professional service firms over and over again, what I’ve experienced is on the revenue side of things, very detailed operating systems.

Going back to what I just said about meeting cadences or processes really dialed in, but sometimes not so much on the client side.

And so I think this is actually an opportunity for the client management side to skip ahead of the revenue section by utilizing AI to drive this.

So thank you, Pete, for helping us get ahead here.

Okay.

Okay.

So Pete, I know you already talked about kind of the struggle for professional service firms.

Because it is a relationship business, not a transactional business.

It’s been hard.

It’s kind of at a disadvantage, like you said.

So how does powering the system with AI help?

It’s kind of like one by one, all those bullets that I laid out that make information, data-driven decision-making difficult and professional services.

AI is kind of there to help solve for each one of them.

So you can get around a lot of the information problem.

Crawling through all our transactional systems in the first place to pull an integrated view of the customer, enrich that view with insights taken from natural information flows.

So the stuff that’s not in our systems, like email exchanges and video meets and call logs and the ticketing system outcomes and you name it.

You can scan external resources.

You should have the ability to get to on a timely basis.

So news and investor reporting, for instance, to get a feel for the outside in factors affecting customer relationship health and bring all that together in one place.

Up to the minute, easy to access and best of all, using inference capabilities to help make fast decisions and to drive intelligent action steps.

This feels to me like, and we’ve said it in other settings, but this feels to me like the moment for professional services.

If this vision of an AI-powered commercial management system sounds intriguing to you, I hope you can join Pete and me for our webinar on May 22nd at Moon Eastern.

We’ll be doing a deep dive into this topic that we’re both really passionate about so you can keep and grow those clients you worked so hard to win.

Register today at knownwell.com/masterclientsuccess.

We’ll save you a front row seat, and if you can’t make it, make sure you register anyway so you get the on-demand recording afterwards.

We look forward to seeing you there.

Okay, so Pete, I know we’ll get into a lot more use cases during the webinar, but paint as a picture of how this actually plays out to really make it tangible.

Imagine that I’m a client partner, an account manager preparing for a key call.

So how does AI improve that experience?

Well, I think the best way to lay it out is to talk about it as a before and after picture.

So you’re prepping for an important call.

This is one that’s going to matter to your outcomes this quarter, and you need the story, right?

So let’s begin with the before picture.

You send a Slack note or an email note out to the entire team, everyone you can think of, and I’m sure you’ve missed a few, to try to gather up your best sense of the recent interactions and status updates.

So basically what’s in folks’ heads, which will therefore be heavily recency and primacy biased, what happened most recently, what’s the most important thing that they remember.

It’s only as good as what you get back if they bother to get it back to you.

Often it’s got a bit of a positive orientation, because why would I choose today to be the day to let Courtney know who I screwed up with in a customer call last week.

All that probably takes a couple of days, maybe, or maybe a couple of hours if you’re lucky and you’ve got strong SLA established between yourself and the rest of the company.

But in parallel, while you’re waiting for all that to come in, you take a journey through your various systems in the tech stack to gather additional information.

So, reviewing any records that hopefully people made in the CRM, opening up the ticketing system to look for complaints and whether or not they were resolved.

Maybe check the finance system to see where payments stand.

Of course, you have to pull out your personal spreadsheet because everyone’s got a personal spreadsheet on the customers in their portfolio.

Maybe a cursory spin through the Internet or chat CPT to see if anything’s in the news.

Oh, look, they’re going through a merger, which I knew that.

That’s a couple hours, right?

Like, it’s a fair amount of work.

What you end up at the end of all of those steps is a jumble of inputs, a lot of the story missing.

The story that you did get isn’t all that trustworthy.

Now, it’s up to you to figure out what to do and come up with a plan for the call.

And at best, it took a couple hours.

At worst, it took a couple days.

By contrast, the after picture in a click, maybe two or three clicks, you’ve got an up to the minute relationship health score that shows you how you’re doing comprehensively across all information inputs, including historical trend line, lifting out insights and recent events to draw your attention to, maybe give you an input on something to celebrate with the customer, and recommendations on concrete action steps to take to get after very specific problems or opportunities to save your retention number or drive your growth number.

You get it kind of instantaneously and you’re done in minutes, not days.

That’s kind of what the world can look like.

That does sound quite nice for me.

I love this idea.

And just to connect to this back to your operating system, obviously, this is what you would do for one certain role for one of those meetings in this operating system.

And I think really what we’re going to be talking about on the webinar is, one, helping you really think about your operating system, making sure that you’ve got the right pieces and parts, and just some really practical pieces there.

And then, how do you drive each one of those pieces with AI?

But you got to have that first thing in place, which is so important.

If you don’t know that operating system, it’s really hard to go to the next step and really leverage AI to drive it.

And so, I think this is going to be so helpful, because we always know even once you get your operating system, you know, locked and loaded, it’s never done.

You know, you’ve always got to keep refining and improving.

Good point.

We will talk through aspects of best practice in each of the five areas, kind of on our way to getting to the discussion of AI.

We’ll make sure that the steak and potatoes are cooked properly before we bring out the sundae.

Love it.

Okay.

What else, Pete, can attendees that are going to join us, because I know everybody listening is going to sign up after our discussion here today, what else can they expect for us to be talking about?

Well, you had asked me to give my best webinar pitch.

You’re the marketer, I’m not.

So let’s see how I can do here.

My thought is that the starting point is a truth.

Not every technology does amazing things for every business, but once in a while, technology comes along that can fundamentally change the game.

My view is that intelligent applications of AI and professional services, client management, can do just that.

At last, putting actionable insight into customer relationships in the hands of the people who need it, like we’ve never had it before, and making everyone on the team some amount of experts, not just the ones who wear the expert hat.

In the webinar, we will show you how it’s done.

Not only that, Pete, but let me tell you, after last week, the CEO of Shopify, I don’t know if you heard about this, but he kind of laid down the gauntlet to his team.

He was like, do not ask for head count until you have shown that you cannot do it with AI.

Which then caused, Pete, a cascade of CEOs around the world turning to their teams and saying, what are you doing?

How are you leveraging AI to do this thing?

Well, great news.

One, you can come to our webinar.

We’re going to be talking about these things.

You can tell your CEO, here’s one thing I’m doing.

I just went to this webinar talking about how to drive your commercial management system, utilizing AI.

Second, we’re going to have a ton of just truly practical ways to leverage AI that I’m sure is going to give you lots of assets to actually go execute against.

I think this is sometimes one of those things that gets all the CEOs.

We love our CEO, by the way, right?

David, close your ears here.

You know, they get so excited, but sometimes it’s hard to practically know.

I don’t know.

I don’t know how to go do this thing.

We’re really hoping with this webinar, you’re going to walk away with a ton of great tools and assets to go deploy them in your business.

So it’s going to be really exciting.

Definitely practical.

Did I say practical?

I get a lot.

How is it practical?

I know it’s going to be practical too.

Yeah, it’s going to be practical.

Okay.

Pete and everybody listening, thank you.

We can’t wait to see you there.

Thanks, Courtney.

Thanks as always for listening and watching.

Don’t forget to give us a five-star rating on your podcast Player of Choice.

We’d really appreciate it if you can leave a review and or share this episode on social media.

At the end of every episode, we’d like to ask one of our AI friends to weigh in on the topic at hand.

So, hey, Claude, you’re up.

This episode, we’re talking about what an AI-driven client management system looks like.

So what do you think?

I think an AI-driven client management system would combine automated insights on client needs with personalized outreach that feels genuinely human.

It would handle the routine stuff like scheduling and follow-ups while surfacing meaningful patterns in client behavior that humans might miss.

And now, you’re in the know.

Thanks as always for listening.

We’ll see you next week with more AI applications, discussions and experts.

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