There's a particular kind of credibility that comes from having sat on both sides of the table, and Jacob Kosior has earned it the long way. Before he became VP of Client Strategy at EliseAI, Jacob spent more than a decade inside property management, most recently leading centralized services at Cardinal Group, where he was building centralized teams and using EliseAI as a customer himself. So when he talks about what AI can do for an onsite team, he's speaking from the leasing office as much as from the product roadmap.

That dual perspective is exactly why I wanted to sit down with him. Our industry has spent the last couple of years swinging between breathless excitement and quiet skepticism about AI, and most of us are living somewhere in the middle, trying to sort out what's real, what's ready, and what it all means for the people who do this work every day. Jacob brings a refreshingly practical take, grounded in workflows that actually get finished, residents who mostly want a fast and accurate answer, and teams who deserve tools that make their jobs better. 

Chelsea Kneeland: Well, hello, I want to thank everyone for joining us and watching this amazing little interview we have going on today with one of my favorite people, Jacob Kosior, who is our VP of Client Strategy for EliseAI. Hi, Jacob.

Jacob Kosior: Hi, Chelsea. Thank you for having me again coming off of Demo Day here.

Good to see your face so many times here in a given week, doesn't happen often enough.

Chelsea Kneeland: That is a lot of Chelsea, so I apologize in advance, but you know, we are so excited because we get so excited about EliseAI and what you guys do every day, and just the story of your company is always fascinating to me.

The way that you figured out how to solve for some problems that were there, some solutions that you've decided on and how you guys use tech so well and you're so brilliant.

I always joke that only the smartest people work at EliseAI.

Jacob Kosior: We try, it is all kudos to our CEO Minna who very much leads by example from her time going and working on site at a real estate admin office to up to getting to hire folks from the industry like myself, which I bet we're going to talk about today.

Chelsea Kneeland: That is actually my very first question because I know that I knew you back, way back when, when you were on the other side of things, and I'm so curious, you went from on-site operations to a supplier partner and running client strategy here at one of the fastest growing tech companies that I think we see in our space.

What really made you feel like, hey, I want to make that transition?

I want to go from not just experiencing the problem, but being part of the solution like, how do you decide to do that and why did you decide to do that?

Jacob Kosior: Yeah, a little bit personal, a little bit professional, I think. Well, I guess they're all professional, but you know, professionally, I thought I was given a great opportunity by Elise.

I had been a client of theirs at both BH Management and Cardinal Group Management, especially during my time at Cardinal doing centralized operations.

They were just really hungry to learn, like how are you doing this? What type of work are you moving off site? What are those team members doing?

So, I got to work closely with them to co-develop a couple tools just as they were looking at a new way of working, and I got to be a really great case study for that.

So professionally, I knew great, I get to help kind of this juggernaut of a technology company, Elise, kind of fine tune their approach.

But personally, I got really inspired by a quote from the CEO of Salesforce who said, this is a couple years ago at this point, but he said today's executives are going to be the last that lead an entirely human workforce.

The executives of the future are going to have to manage a human workforce and an AI workforce.

And I thought, well, what I love about property management is the people. That's what kept me in it for over a decade.

I had that experience, but if I was going to be a successful leader in the future, I needed that technology experience.

So, you know, I was motivated as a great partner of theirs to come and make the jump, but personally, I was inspired to say I feel like I've checked the boxes on a couple areas of experience, and this is one working at a technology company.

As operations and technology become more and more intertwined, I need that technology experience, and I was lucky enough that EliseAI gave me that opportunity.

Chelsea Kneeland: What a great opportunity also, I mean, that's just an incredible thing, and I love that it was inspired by something you read, as a fellow reader.

Jacob Kosior: Yeah!

Chelsea Kneeland: I love that.

Jacob Kosior: Being a news junkie pays off.

Chelsea Kneeland: Let me tell you, you never know where your next inspiration may come from.

Jacob Kosior: Absolutely.

Chelsea Kneeland: In this role, Jacob, your role is VP of Client Strategy, I'm so curious, what does client strategy actually mean, like day-to-day at EliseAI?

Like what are you in your team, what do you spend time on and why is it important?

Jacob Kosior: Yeah, so my team, we're all former operators.

We all have slightly different backgrounds to make sure that we can speak to different segments of the industry, different roles that are in the industry, and now we're a cross functional team that supports sales, marketing, product and customer success.

So obviously we're there, you know, to talk about the tools from not just from an operator's lens, but folks who've actually used the technology.

I'm myself, I've, I've used it myself. I was a user.

I gave lots of feedback in the past, but as users of the product, we try to kind of speak to that for operators. On the marketing side, we get to go to all the industry conferences.

That's why I get to see, see you all the time.

We host our own events because we realize, you know, I was on that operator side leading webinars and trainings with my team virtually and we always heard the need to come on site.

And so, my team does a lot of traveling across the country. We're hitting ten cities this fall. Just bring the same show to 10 cities to talk with operators in person.

On the customer success side, we are there to again, I've been in your seats. I've submitted those tickets before too.

So, as we're looking at new performance data that are pulling in things like speed of responses, not just conversions, but how quickly are customers moving through the journey now, we support customer success and having those conversations help elevate the conversations around KPI's.

Then lastly, on the product side, which is my favorite part of my role, we get to do the sniff tests on all the new things that are coming out.

So, case in point, I used to do a lot of new developments in the past, and we just launched some new LeasingAI settings for new developments. And so, I got to sit down with the product manager to say, "Yep, here's what a new development schedule looks like."

"And here's what LeasingAI is going to need to do when that, you know, banner goes up announcing the splash page just to generate inquiries," versus, you know, the AI needs to communicate, "Hey, Chelsea, this is a hard hat tour. So, you need to wear closed toed shoes on your tour."

Those operational insights are what I really like to bring to our product team.

Chelsea Kneeland: I love this so much because I used to judge.

Jacob Kosior: Isn't it fun?

Chelsea Kneeland: My dream job would be a "commonsense consultant."

That's literally what I used to say all the time when I was on the operator side is I'm like, let me just go talk to these companies and say, "Hey, here's all the other stuff you need to know, or here's how we're going to use your product or our developers," and you get to do that.

Jacob Kosior: We get to do that. Yeah.

Chelsea Kneeland: I love it, and what an incredible company too that allows for that position because I think so often it that's not how it works, right. There is a problem and then they say, "Oh, we have a solution for that and whether it fits perfectly or not, that's OK.

We're just going to kind of make it fit."

And for you guys to be so in tune with the industry to say no, we need to know exactly what it's like at a lease up. We know exactly what it's like at a new development.

I, kudos to everybody, I think that's what sets you apart.

Jacob Kosior: Here's hoping and again, I'll give kudos to our CEO Minna, because all of that, you know, staying in touch with the customers, talking to the clients every day.

That is still part of our culture. It gets harder as the organization grows and grows.

I joined Elise two years ago as, I think I was like employee 125, 130 maybe? And now we're over 600.

So, with that many people joining all the time, like we one of the things we do is we just host live training sessions for new hires to say, "This is the multifamily housing industry. This is what an operator is versus owner, but this is what a REIT is versus an owner upper."

Just explaining to them kind of the industry, so that as part of their onboarding, they are set to serve our client base in addition to kind of all of our internal processes.

Chelsea Kneeland: I love that. I often think our industry is unique, in that there's so much knowledge that you really need to have to be successful. And not that that's not the same in other industries, but I think that it's just, I once had someone tell me, "Sales is sales."

I did it over there, I could do it over here.

And I was like, "OK, that's cute." Yeah, hold on, let me help you because it's different.

Our industry has a lot of little nuances and niches and things that you just don't know until you've been in it and don't fully understand.

So, I love that.

Jacob Kosior: Yeah,

Chelsea Kneeland: Yeah, very cool. So, speaking of our industry and knowing all the little things, what is a misconception you feel like most operators still have around AI and multifamily?

Like, what is the misconception that you find yourself correcting the most?

And then I can't wait to tell you what I think about this.

Jacob Kosior: OK, love it.

The number one thing: fear that the AI is going to say the wrong thing because, and this is, you know, I mentioned kind of traveling around the country.

This is one of the things we focus on a lot is explaining the different types of AI that yes, you might go to Gemini or you might go to ChatGPT and you're chatting with it, and it gives you an incorrect answer or it gives you an answer that's not fully accurate or it leaves out a part of information.

That's the last thing we want to happen when we're talking with our customers.

But and we do, you know, we do warn against that for some tools that we would say are more of like a ChatGPT wrapper, you're putting your brand on an agent that you're just pulling directly from ChatGPT.

But what's different today with agentic AI, the technology that we use is, you know, it's not pulling from the Internet. It's not pulling from, you know, data that you're not familiar with.

It's pulling with what you trained it on.

So, if it's got access to your pricing, if it's got access to your fees, if you built out the knowledge bank with your SOP's, well, now it's as if you have an agent that's just referencing all of your internal documents to give you the approved answer.

And so, I love that because it, it shows operators that there's a lot more control that you have with agentic AI, something that's working off of your knowledge, your systems, your SOP's, than just a chatbot that you're interacting with, you know, on an AI platform.

Big, I think, you know, we're slowly getting there, and just as the technology just is moving too fast.

And you know, those are terms that your average operator who is knee deep in renewals and rate strategies and marketing plans, they're not expected to know that!

In fact, that's what gets me motivated to talk about it because when I was at Cardinal, you know, my training team didn't have the resources, they didn't have the knowledge of the time yet.

I was the AI guy!

And so, now I take it as kind of my personal responsibility when we're going out and talking to the industry to just do some education like this on as the technologies evolved, that means there's more and more control in your hands to work at scale like never before.

Chelsea Kneeland: I love that, and I think you are so right, you really hit the nail on the head of one thing is that our teams, our operations teams are now expected to be experts in so much, right?

So now we need to know how to be an expert at the buildings, the leasing of the buildings, the marketing of them, the running of them, the financial part.

Plus, now, all of this tech that really, we had the Internet before a little bit, so it's wild to think of how much knowledge is needed now to successfully run a portfolio or run a company, a multifamily company that's dealing with operations.

And I can't imagine trying to keep up with it all unless you look to a partner who this is your specialty and this is what you know and you're able to tell them better.

Jacob Kosior: Yeah, and it's, it's fun when we get to unlock stuff and it clicks with operators when I tell them things like, you know, OK, you're exactly right.

Our team members, they're being asked to do more than ever.

They've got, you know, more things that they have to log into, but inevitably, probably sometime this week, that team member on site is going to get a phone call and someone's going to say, "I've got a Section 8 housing voucher."

And you're just going to have to cross your fingers that that team member on the phone is going to remember exactly what you trained them on that, you know, online platform eight months ago when they first started, right.

Theres things like that to say, OK, well, let's just take that SOP. How do you respond to that question?

Let's put it in the knowledge bank. Let's tag it as legal.

That tells the AI, "Communicate this verbatim."

And now when that customer asks that questions to AI, they get your company approved response and that it's communicated the same way to every customer every time.

So, we can think about little things like that, it's not that we don't see the value that your team member is bringing.

It's you just inundated them with so many things, but then they have to be on their toes, especially the like a compliance related question comes in and that's just too much and it leads to burnout and then people leave and then, you know, we just recycle the same problems over and over again in our industry, unfortunately.

Chelsea Kneeland: That is so, so incredibly true.

Jacob Kosior: Thank you for letting me get on my soapbox there for a second, Chelsea.

Chelsea Kneeland: I'm always saying that, I'm like, where are our mental health professionals for our industry specifically? There's a lot going on here.

Jacob Kosior: Yeah.

Chelsea Kneeland: So I love that you talk about how your agentic AI is a lot different than maybe what people might be more familiar with.

We also talked about some of the challenges for the teams and how they learn to use it and, you know, trusting that it's easier to use or it's easier to have this knowledge at their fingertips.

So now that you've seen from supplier side and operator side, what does a successful AI rollout actually look like versus like a rollout that stalls or even if it's not AI, if it's a tech rollout, how can we help our operator teams to be more successful in their rollout?

Jacob Kosior: Yeah, everyone could be more successful in their rollout if they just had one, two-hour meeting with cross departmental leaders to talk about, what all is this going to change.

Because we often see it, you know, maybe it's just the marketing team that's rolling it out or maybe it's just the operations leaders or maybe you do like a project management innovation strategy team that's rolling it out.

But inevitably we see it too often.

And you know, that's every industry, right.

We have our silos and we talk about our silos, but this is… AI we find is really exposing how high are those walls of your silos?

Because if you were going to make, you know, let's say you piloted, you were happy with the results and you wanted to roll it out full portfolio.

OK, well, great.

That means we need to update the training materials to now say this is our leasing process before this is our leasing process with AI. We need to update job descriptions, because I bet some of the job descriptions on your leasing consultant is what the AI is going to do now.

What do you want to replace on those job descriptions, so that leasing consultant knows I'm focusing on more on tours and experiences and you know, in market marketing that my marketing team is going to direct me to do.

So, great. We've already had to update the training materials, and we've got to update the job descriptions.

Chances are those people probably weren't involved with the pilot.

Then do we need to look at what new KPI's are we going to track for bonusing or things like that?

Like, it starts to touch so many things that I've just found, if we could do a two-hour strategy session to say, "OK, here's what our leasing consultant does for, you know, managing leads or here's what our assistant manager does for collecting rent."

You'll start to see all the various teams that are involved and okay here's how we do a comprehensive rollout as opposed to just, "Here's the point solution we're rolled out.

Hope you enjoy it teams."

What's really going to make it stick is that cross to mental across departmental approach.

Chelsea Kneeland: I think that is so true and so incredibly important.

I have one of my close friends helps with project management for a large management company and they are always telling me that when someone comes to them and says, "Hey, we just decided on whomever, right, we're going to have this roll out."

And that that person often has to be the one who says, "Yeah, so I wish you had called me because here's the reason", right?

"That that's not going to work. We can't do it until this day," or whatever we thought.

And if they had had that two-hour meeting like you're talking about at the beginning, we would have figured that out earlier.

Jacob Kosior: We would have figured out so many things, yeah.

Chelsea Kneeland: Yeah, it would make it better for everybody.

Jacob Kosior: Everybody, and I genuinely feel, I know and I got to see this firsthand at Cardinal Group—I can't speak highly enough about the team and the innovation at Cardinal--is that's the stuff, that cross departments, the leaders like to get involved with is like forward-looking strategy.

How is this technology going to impact our processes and our people?

Every department touches that.
And so I've yet to find an executive who would say, "Nope, I don't want to sit at that table."

"I don't want to be a part of that conversation."

It's just very few leaders are bringing it all together to say we can do this faster, we can do this more comprehensively and with a stronger communication to our teams around the why, the what, and the how.

If we just have one two-hour kind of cross department leadership meeting in advance.

Chelsea Kneeland: I love it, and we'd let our leaders be leaders. That'd be amazing.

Jacob Kosior: Yeah, love that. Love that.

Chelsea Kneeland: Yeah! So, we went over that part of things, which I think is really fascinating for both sides of the fence.

For you, I know you're passionate about this, so if you had to distill all of this down to one piece of advice that you would give an operator who's about to start their centralization journey or their big like AI push.

In that two-hour meeting, what is your one piece of advice that you would give them that, "This is what I wish you knew. This is what I want you to do."

Jacob Kosior: Think about it like an assembly line.

I think about centralization today like, I'll quote Marc Benioff, CEO at Salesforce, I looked to him for the quote on managing AI.

I look to the Ford assembly line to think about centralization, to say if you've got, you know, a portfolio of fifty properties, all fifty of your properties are building a car individually, that's one way to do it.

There is a more efficient way.

That's what we did in manufacturing. We did an assembly line. Thank you Henry Ford for that.

And so, that's how I started to think about centralization was okay, we've got our team over here doing rent collection.

We've got our team over here doing renewal offers.

We've got a team over here doing application reviews.

We've got a team over here managing work order responses, and when we can build those teams along the customer journey, then we see what's leftover and that is often the stuff that can only be done on site, and that's what our site teams get charged with.

Then we can start to build teams that are hospitality focused at the site level, that our system and process focused at the central level, and then now the leadership level becomes change management training, visionary strategy.

Maybe that was a long answer for you, Chelsea.

Chelsea Kneeland: No, I love it!

Jacob Kosior: But I'd say like, don't, don't get scared of it.

I can tell you it is absolutely possible.

There are enough organizations out there doing right now to show that whether you're an owner operator or a third-party manager, whether you're small or large, it can be done.

I found that that's just a good mind shift to say, let's take ourselves outside of property management for just a second and see other industries have tackled this and they found a more efficient way to do things.

So let's just think if that assembly line was servicing our customer, what are the stages that we could better do at scale with a focus team, just like we have at the corporate level, a focus team at the central level of our operations.

Chelsea Kneeland: I love that so much too because, I think so often there's some hesitancy because we are a people business and we care about our team members, and there's some concern like, oh, if we centralized, what does that mean for our teams?

But so often it might mean that your teams are happier because listen, when I was hired to do sales as a leasing consultant, I should not have been in charge of a budget.

I shouldn't, I should not have done it, right? That is not my skill set.

And so whoever put me in charge of doing S.O.D.A.'s and move out balances and all of that, like this is a terrible idea.
I would have been much happier if I could have focused in on the thing I was going to excel the most at and really grew my strengths, and I think that's the same for all of our teams.

As we're looking at centralization, maybe that means that the people who are really great at numbers get to do more numbers and the people who are really great at people get to, you know, advance that part of their career.

So it doesn't have to be negative.

Jacob Kosior: Exactly, and you know, every time I chat about how the career trajectory is broken, leasing consultant to assistant manager, like everybody agrees that that is broken, right?

So if that's broken and we all agree we turn over too many people on site.

Okay, well, if we all agree that we're turning people over and that the promotion ladder is broken, well then let's just rewrite the model.

And so that's what, you know, we talk about, yes, in the assembly line, but for me it's, it's born out of, I stayed in property management because I love the people.

I wanted to create better roles for them.

I wanted to give them a career trajectory that made sense with their skill set, not with whatever 25 years of industry have enforced on them.

Right, and so there's a there's a great balance in there too, to say we can be more efficient while also giving better roles, more specialized roles that are preparing site level team members, not to just be the next regional manager, but to jump to the corporate accounting team or the corporate marketing team because they're developing skills, working at scale, working with new technology that they don't get when they're on site or only that, you know, traditional trajectory exists.

So it's a people story, It's a process story, but it was that assembly line that unlocked it for me to say, "Okay, other entities have solved this."

"Let's just get out of our multifamily feels for a second and look outside the box."

Chelsea Kneeland: I love that because this is one of my parenting things that I say all the time, so you'll now know that that I say this, Jacob, but whenever my girls come to me with an issue, a lot of times I'll say, "Has anyone in the world ever solved this problem before?"

Not because it's being a jerk, because I truly am like, surely someone figured out like we cannot possibly be the first person to have this problem come up and it helps them think about, "Oh, okay, let me think, has this ever been solved?"

"Is there a solution that I could easily find?" But we talk about that all the time at home.

Of course, we should talk about it at work, right?

Jacob Kosior: Love it. Exactly, yes.

Chelsea Kneeland: Has somebody had this problem before? Somebody probably has.

So I love that.

Well, Jacob, what's your any last thing that you want our audience to know about Elise, in particular about what you do at Elise so that they really have a good understanding of who your company is at its core?

Jacob Kosior: Yeah, I'd say you heard a little about what I do.

I try to work across these departments, but what I tell, I hear all the time, "I don't know what I don't know," and I really love that folks are just that vocal about it.

I think maybe that's a millennial thing in us to just say, "I'm just going to put it out there."

"I'm busy. I got to put it out there."

I always encourage folks like ask that question, because chances are a lot of the folks that were interacting with, it's not as if they have four, five, six, ten years of experience demoing AI tools, rolling out AI tools, analyzing the results of AI tools, dealing with the change management for their teams.

Most times, this is the first time that they're doing this at their org, and so ask questions.

Ask for resources.

That's something that we got really passionate about when I joined the team two years ago, and started saying there is a playbook for this and we can help.

So we developed a centralization playbook to help with centralization.

We've got a change management toolkit with example communications of what to send to your on-site team, what to send to your regional team, what an executive team could send to owners to talk about it.

Because as you said, somebody has solved this problem before.

As leaders in the space, we've been in AI for nine years now. We've got more than six and a half million units on our platform.
We see it all, we document it all.

We're using AI tools ourselves to work at scale and for our clients.

That means all of the best practices, we are compiling them, we're putting them in guides and we have them at your disposal. So I think that speaks to our culture.

We want to learn and spread that knowledge as we grow.

That's how I got approached to say, "Jacob," our CEO, Minna, said, "Jacob, I sense that you like change. Imagine this change that you could do at scale at EliseAI."

And that really inspired me, but also encouraged me to say, "Okay, we need to put all these resources together because if we're going to move the industry forward, we need to move everybody forward together," and that's really the ethos of our culture.

So for operators out there, it's ask us questions, ask for resources.

We have them because we're going to assume that you don't know what you don't know, but you got to tell us to how can we meet in the middle to be the best partner for you?

Chelsea Kneeland: I love that.

I know I personally have loved watching Elise grow and just become this powerhouse of a company, and it's been such a wonderful journey.

And I've loved watching you get to grow in your role.

Jacob Kosior: It's so fun!

Chelsea Kneeland: It's so much fun, so I just love this whole thing.

But thank you for doing this and chatting with us and thank you for being one of our Demo Day partners.

We appreciate you more than you know!

Jacob Kosior: Happy to. I told you earlier on, but I'll give kudos to the full audience.

Chelsea, you're doing a fantastic job keeping the energy high throughout.

So thank you for having us for another year here.

Looking forward to 2027 already.

Chelsea Kneeland: Thank you, Jacob.