Chelle O’Keefe, CHRO at Associa

Show Notes

Integrating at Scale: Associa’s CHRO on Culture, Identity, and Bottom‑Up AI

Summary

How do you integrate 16 acquisitions at once without losing the soul of each local business?

Chelle O’Keefe, Executive Vice President and Chief Human Resources Officer at Associa—the largest property and community management company in North America—shares a practical playbook for scaling culture while honoring local identity.

With 30,000+ communities and 4 million homeowners across the U.S., Canada, and Mexico, Associa grows primarily through M&A. Chelle explains how her team balances standardization with autonomy, why new acquisitions with seller-owners need a different glide path, and how reframing “loss of control” as “evolving identity” changes resistance into buy-in.

She details a bottom‑up approach to AI—automating painful, repetitive work first—and a real-world example of using AI to model 401(k) scenarios that saved significant cost.

Chelle also breaks down Associa’s succession strategy in a niche industry, including a new tool pushing frontline leaders to develop their replacements and maintain high internal promotion rates.

Expect candid insights on titles, urgency traps, and building leaders who can thrive through constant change.

Timestamps

[00:45] – Associa overview: largest in community management, acquisitive growth, scale across North America

[01:23] – Integrating 16 companies at once: standard platforms vs. local differentiation in employee experience

[03:13] – Managing “branch presidents”: core branches vs. new acquisitions with seller-owners

[05:46] – From control to identity: why titles matter and creating space during integration

[09:28] – Escaping the urgency trap: learning, networking, and the realities of HR’s “lonely” role

[12:02] – Bottom‑up AI: start with painful, repetitive work instead of forcing AI into processes

[14:58] – AI case study: modeling 401(k) scenarios, validating with providers, and saving money

[17:42] – Succession at scale: promoting from within, frontline ownership, and a new succession tool

Takeaways

- Lead integrations through identity alignment—don’t erase local culture; evolve it.

- Define two playbooks: one for core branches and one for newly acquired, seller-led teams.

- Slow down where it matters—acknowledge title changes and create space for employees to be heard.

- Apply AI from the bottom up: automate repetitive, low‑value tasks before redesigning everything.

- Pilot AI on real business problems, then validate with experts to ensure accuracy and trust.

- Push succession planning to the frontline—develop replacements to enable upward mobility and retention.

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Rebecca Taylor (00:00)
Hello and welcome to HR Voices. I'm your host, Rebecca Taylor, and I'm here with Shelly O'Keefe. She's the Executive Vice President and Chief Human Resources Officer at Asocia. Welcome, Shelly. Thank you for being here.

Chelle O'Keefe (00:11)
Thank you, Rebecca. Thanks for having me.

Rebecca Taylor (00:14)
Yeah, I'm so excited to chat with you because I think I've been chatting with some others that are sort of in the real estate space. So rather than me kind of try to explain what I think and I've heard that's sort of common between them, can you tell us a little bit about Asocia, about your role and about sort of the various types of employees that you support?

Chelle O'Keefe (00:32)
Sure. So Asocia is the largest company in the property and community management space. So we operate throughout North America. We oversee over 30,000 communities, which is roughly four million homeowners across those countries across Canada, the U.S. and Mexico. We are highly acquisitive, which means we acquire multiple businesses ⁓ during the year, which will translate, I think, really well into some of the challenges that we face from an HR perspective.

Rebecca Taylor (01:04)
was just going to start to get into that and ask that too. Because whenever I hear acquisition, I come from HR myself. I've done a very fair share of &A work and integration and kind of trying to put those pieces together. But can you talk about some of the challenges that that brings and how you're kind of looking at them, facing them, and if you have a playbook for them?

Chelle O'Keefe (01:23)
Yeah, of course. So like I said, we grow primarily through acquisition. We joke internally, both in my HR team, but also as an executive team, that the best problems to have are growth problems. So I do understand that as we talk about the complexity that all of that acquisition brings, that it's still a good problem that we have. At the same time, we integrated 16 companies on January 1st into our HR platform and onto our benefits plans. So

You know, what's interesting about that, it was a lot of work. So what's interesting about that is I think the biggest challenge is trying to keep a global, united culture as a company, but also allow for local differentiation. So our business is neighborhoods and communities. so everything is very local. People want to connect with their neighbors and their communities in a very local way. At the same time, we're a global company. And so it's the flexibility between

Rebecca Taylor (01:51)
haha

Right.

Chelle O'Keefe (02:21)
bringing everybody in to standardized platforms, whether that's on the client side or on the employee side, but also recognizing that your employee experience is influenced most directly by your leader and the colleagues that you have around you. And so how do we recognize and...

Rebecca Taylor (02:40)
That's a really, really interesting point that's sort of, know, HR can centralize, HR kind of, you know, is sort of orchestrating a lot at the top to create unity either in tools that you're using or even just sort of, you know, cultural values, mission statements, things like that. ⁓ But I'd love to kind of dig a little bit into the, I guess, the on-site manager that the person will be sort of working more closely with. And how does your team relate to the on-site managers and how does that

What are those dynamics in those relationships like?

Chelle O'Keefe (03:13)
Great question. So we call those managers branch presidents. So we have over 150 of those across our network and we really treat them in two different ways. So I will say one way is more on the broader large organization side and we call those our core branches. And so they're the companies that have been with us five or more years. They're a little more into our established rhythms.

And we work with those leaders to really talk through the core competencies, the core values, and how do you create an associate culture within your local environment. That's one group. The other group is our newer acquisitions, and a lot of them have seller owners. So those individuals are used to running their own shop.

They're used to kind of being the master of their domain. And so we do actually treat them differently and allow them more freedom and flexibility, even in keeping some of their things that are core to them. So if they founded their company on some specific core values, instead of taking those and putting the associate values in place, we talk about alignment. So what about that company? What about those values?

align with the broader associate platform and over time the goal is to bring them more broadly into the fold.

Rebecca Taylor (04:39)
I love how you're describing that, that you're kind of letting them work at their own pace to an extent, right? And, you know, because that was always the hardest part for me in acquisitions, to be honest. Yes, there's the integration of the platforms, there's the technology, there's that stuff. But I always found that the most complicated and hard part was sort of helping people to navigate identity in a way and overcoming that sort of us versus them mentality, especially when you're looking at someone who may have been.

at the company that was acquired for a long time. Maybe they even founded it. They've built it. It's their pride and joy. And now it is sort of this identity shift to kind of be part of a bigger organization. And I've seen companies sort of say, your last company is dead. It's dead now. It no longer exists. You're us now. And that's the fastest way to just erode trust, any kind of trust that might be there. So I love that you're kind of letting people sort of work at their own pace and get there when they need to get there. Because in the meantime, they're still taking care of the people who are

you know, in the community, they're still doing that important work. And I just think that's really cool how you're doing that.

Chelle O'Keefe (05:46)
you said about identity, think that's really important. And actually, that's going to be one of my takeaways even from this conversation. Sometimes in the acquisition integration process, we focus on control. And as we as we integrated all of these companies that I mentioned for January 1st, there is a real loss of control from those local leaders as local HR team members of now you're going to do it a different way where you're going to do it our way. But I love to flip that you just provided around

Rebecca Taylor (05:56)
Mm-hmm.

Chelle O'Keefe (06:14)
Maybe instead of focusing on the lack of control, we understand it on a more human level as the loss of identity or the change of identity. And how do we then help all of these leaders and the HR counterparts that sit next to them in their local branches really think through that evolution of identity instead of a loss? So it's just as you and I change, you know, regularly.

Rebecca Taylor (06:38)
Yeah.

Chelle O'Keefe (06:42)
How do we allow for those different companies to experience their identity is evolving as they're part of this broader company?

Rebecca Taylor (06:42)
Yeah.

Yeah, think it maybe that could be a takeaway for anyone listening to this too is that that's, I think that we can tend to over process change sometimes and change does need a lot of process and most change initiatives fail because of the lack of process we've done, we know this, right? ⁓ But I really think that when you think about how much time we spend at work, especially in the US, our identities are very much wrapped up in work. So even something as simple as, I remember I was doing an acquisition once and

the acquiring company called sales reps, sales representatives, but the company that was acquired called them account executives. And so even just, I'm no longer an account executive. I'm now considered sales representative too, or whatever that was. That was, that there was, you can't, I guess you can't skip that part because that's the part that it's in those little tiny interactions that might seem like not a big deal at the top when you're trying to juggle a lot of things at the same time. But that's where you really have the chance to kind of

hear an employee out and help someone to kind of build that trust, feel heard, feel seen, which is mostly what people just want. They just want to be heard. And I think it's cool that you're doing that too.

Chelle O'Keefe (08:00)
That's a fantastic example because that title, while it might seem little to the company that is making the change, meaning we're the ones imposing the change on all of those employees, that can be really impacting on that individual level because there is a difference in the way I think about my job as an account executive versus as a sales representative. Those are very different. And I think sometimes our tendency as the bigger company that comes in and making the change is to just

do it and move on because we have all of these other things to get to. And so I think it's about how do you intentionally create space and create some acknowledgement of these are changes. Obviously people take pay and benefits and those things very personally. But to your exact point, things like job titles that have to change because they align to the titles that we have in our HRAS and our compensation models and all of the things.

Rebecca Taylor (08:54)
Yep, the levels, yeah.

Chelle O'Keefe (08:57)
those are still big changes for people and we have to make space. And I'm not saying we are good at that. So I want to put that out there. We have a process that we have to go through and we're all packing boxes to a certain extent because it's very complicated work. But to your point, people want to hear her feel heard and seen. And how do we create space within the process, within all of the

Rebecca Taylor (09:05)
I don't think anyone is very good at it, to be fair, because it's hard, right? But yeah. Right.

Chelle O'Keefe (09:24)
checklist items that we have to accomplish for exactly that.

Rebecca Taylor (09:28)
Yeah, I found that it's kind of, it has a lot to do with urgency, because we feel an urgency usually to go through our processes and say, come on, let's go, let's get this done. There are so many other things ahead of us. And, you know, it makes sense in businesses, you know, move fast and break things and all of that stuff. But I know that now, thankfully, I think people are, you know, pivoting from that a little bit. But there is still always the sense of urgency to kind of just get things done fast.

Chelle O'Keefe (09:49)
Sorry.

Rebecca Taylor (09:55)
It's, you know, I've been doing this work myself. We talk about this a lot, even at All Voices, is sort of let's put things in perspective of, you know, is this really something that we need to rush through or is this something that can take a little bit more time? And is it really, you know, what are the things that truly are urgent and important and what are the things that can happen, you know, more slowly and evolving over time? Because there will always be work for us to do. There's never going to be a lack of work.

Chelle O'Keefe (10:21)
There is never a lack of work. That's so true. I mean, I would say that's why it's important to listen to things like this or to meet with colleagues and to network because otherwise we do get stuck in our own urgency trap and everything, you know, and moving everything towards the specific goal. But like I said, I've even benefited already from this conversation and hopefully the audience benefits from listening to it because

Rebecca Taylor (10:43)
You

Chelle O'Keefe (10:47)
It's where you get new ideas and you can stop and think, but we as leaders have to pause and we have to make time intentionally for our own growth and development so that we can learn these new things and think a little bit differently about all of the work that never ends.

Rebecca Taylor (11:03)
No.

Yeah. Yeah. And it's funny because I think that there's, ⁓ there are a lot of people that are kind of starting to balance that out a little bit now, especially when it comes to learning. We're, sort of in this time where we're all trying to learn AI at the same time, broadly speaking, right? So that's the, that's the example that always just sort of comes up. It's like, regardless of the size of your company, most HR folks are grappling with what do I do about AI? And so that's another one where I'll advocate for just like,

You don't have to move so fast that you're just putting AI on everything without really knowing what's going on. But you do have to start to take some steps and learn. And talking to other people, listening to stuff like this, especially because HR can be a really lonely role, right? Because there are things that we can't share with other members of the organization just because of the way that the role is. So other HR communities talking to other HR people, it's just a good way to kind of get that perspective, I think.

Chelle O'Keefe (12:02)
You know, my example on that, and it helped me flip my perspective on AI. was a couple years ago and I was at a conference, so was listening to someone and I think we are all, you had a great point, we're all thinking about this. And I think the question we're asking ourselves is how do we incorporate AI into our processes? How do we help our workforce learn AI and all of those things? I think that's the wrong question. And when I heard this in a conference, I loved it because the real question is,

What is the painful work? What is the work at that bottom level of the pyramid that is painful and repetitive and my team doesn't love to do it? And those are the things that you can start to automate and think about the use of AI for, as opposed to thinking at the top level, how do I insert AI into my processes? It's thinking bottom up and saying, what are the processes that our routine wrote?

Rebecca Taylor (12:55)
Mm-hmm.

Chelle O'Keefe (13:00)
somewhat painful that my team would love to get rid of. How can I use AI at that level and then progress it through my other operating system?

Rebecca Taylor (13:11)
Yeah, I think it goes all the way even up to job descriptions. Like, I'm like, throw out your job description and rewrite it. It might be, it's redefining what HR is, right? And it's kind of a chance, I think, to align with the purpose and the outcomes and the intent and then back into the how. Because so many job descriptions start with like the how first. It's like process paperwork using this or whatever it might be. And it's sort of this chance to sort of, let's throw it away.

Chelle O'Keefe (13:15)
Definitely.

Rebecca Taylor (13:40)
and see how if we were to rewrite our job description from scratch, knowing what the actual work is that we have to do with helping people navigate change, driving so much change across organizations through acquisitions, all of those things are really the core of the strategic work that's there. And then the how is really what's changing. And that's kind how it's going to impact the job description. And it might be that 70 % of it is still the same, right? But it's almost like you can only really be really honest if you're willing to just throw everything away and try again.

Chelle O'Keefe (14:10)
Which is a challenge, right? Because ⁓ when you're at a certain level or when you feel a certain level of competency at your role, I mean, but things always evolve. And so I love the idea of a white piece of paper, what would it look like? and the irony is that AI can help you with all of that.

Rebecca Taylor (14:12)
Yeah.

Exactly,

exactly. It's like you could do it just for fun, right? And it is hard too because it's also identity, you know? It's also just like, this is part of my identity, this is how I'm here. So it is, it certainly isn't easy. I think if we can experiment with things in a low pressure type of situation, it might open our minds and we could decide that at the end of the day, we're not going to do anything with that change job description. It might be like, you know what, that was a fun little exercise. We're sort of going to keep plugging along, but sometimes just experimenting is, it gets you.

Chelle O'Keefe (14:29)
Exactly.

Great.

Rebecca Taylor (14:55)
It just gets you in a different headspace that could be helpful.

Chelle O'Keefe (14:58)
that tie in, you one of my favorite examples of using AI, I think we have to be early adopters ourselves, whether it's AI or other technology, that's how we move forward and help our organizations move forward is becoming that early adopter. So we ⁓ look to change our 401k plan. And we went to our current provider and we said, you know, we need some modeling done. And they gave us what I consider to somewhat outrageous quote, as far as what it was going to cost to do that.

Rebecca Taylor (15:11)
Yeah.

Chelle O'Keefe (15:26)
401k modeling and I thought, wonder if I could use AI to help me model different scenarios. And I spent a couple days actually, not solely, but a couple days thinking through and working with the AI tool to get to a model. And I learned so much in the process. And then what I did was I took that model once it was built and I took it back to the humans, right? I took it back to.

Rebecca Taylor (15:52)
Mm-hmm.

Chelle O'Keefe (15:53)
⁓ our plan providers and our broker and I said, does this look right? Because obviously we have to check all of our processes and make sure that we're doing things. And it saved the company a significant amount of money. It taught me a ton in the process. I felt like, okay, this is a great use case of how we can incorporate AI into our day to day, but also benefiting this larger project that we were undertaking as an organization.

Rebecca Taylor (16:11)
Yeah.

Chelle O'Keefe (16:22)
Again, just trying to evolve. love your tie in with identity that we also have to be changing our own identity given all of the dynamics in the broader world.

Rebecca Taylor (16:33)
Yeah, I love that story too, because you're looking at, you're trying something to, you're using a tool to solve a current problem that's right in front of you. And from what I'm hearing is almost like, you didn't know how it was going to go. You were just like, I don't know how this whole thing is going to play out. It might be that, you know, I work on it for an hour and it's like, you know what, this isn't going to help me. And, you you could scrap it and move on. I think that's like the key is sometimes.

Chelle O'Keefe (16:48)
No.

Rebecca Taylor (16:58)
It could feel like you have to have a whole plan that's like, here's exactly how it's going to go. This is kind of how I show my competence. This is how I show that I know what I'm doing. But like, we don't know what we're doing and that's okay. And it's just like, take the steps and kind of learn, you know, learn as you go. You don't have to know what the end result is going to be, but you just have to kind of like see what it, you know, see how it turns out and what it's going to do. And when you have a goal in mind, like figuring out a new 401k model, then that's, that's sort of a grounding direction. And then you just sort of figure out the path to kind of get yourself there.

Chelle O'Keefe (17:28)
Yeah, don't be afraid to experiment.

Rebecca Taylor (17:30)
Yeah, yeah. So do you have anything exciting that you're working on right now? I know after you're integrating 16 companies on January 1st, what's on the docket for exciting stuff for this year?

Chelle O'Keefe (17:42)
we have more of those to do. So we integrate on January 1st cycles just to help with the disruption of our employees. We have another 10 at least to do here as we move forward into 2027. We're already thinking and planning on all of those things. I would just say probably one of the most exciting aspects of my job is all of our succession planning and our leadership development.

Rebecca Taylor (17:50)
down.

Mmm.

Chelle O'Keefe (18:07)
not

necessarily new for anyone who's listening, but such a critical piece of the organization. We love to promote from within because we have a niche industry. Most people don't even know what an HOA or in Canada, what Estrada is before they actually are a part of one from a resident perspective. So we have a very niche industry we need to develop from within. so

Rebecca Taylor (18:27)
Right.

Chelle O'Keefe (18:33)
the large majority of our promotions. one point it was up to 80 % of our promotions were internal. We're a little bit below that now. I love one of my favorite things of my job is our leadership development programs and watching leaders ⁓ at every level progress their career as they grow with Associa. So we have just implemented a new succession planning tool so that we can get our leaders.

Rebecca Taylor (18:53)
for.

Chelle O'Keefe (18:59)
closer to the frontline thinking about their own replacements and how they're developing their direct reports because obviously that's a core competency at an organizational level to make sure that you have levels of leadership ready for the next position. But I think less so at that frontline level, people thinking about specifically, how do I make sure that I can replace myself, therefore I can move up?

Rebecca Taylor (19:10)
Yeah.

Chelle O'Keefe (19:27)
And so we're in the process of implementing a new succession tool, and then we run annual leadership development programs. So those are the most exciting things to me because of how I see people progress their careers, how I see the company grow through all of that. And because we continue to grow, we just continue to have more opportunities.

Rebecca Taylor (19:27)
Yeah.

That's cool.

I love that. That's sort of the space that's very near and dear to my heart too. So I very much relate to just wanting to see, you know, people grow and find sort of a path for their career where they can form a life around the work that they do too. It's like seeing someone get promoted isn't just about, you know, they're achieving something. It's just like they're also living their life according to what their job allows them to do, right? So the money that they're making, the flexibility, the benefits.

Chelle O'Keefe (20:11)
early.

Rebecca Taylor (20:14)
And so knowing that that's something that someone can really sort of take and see and grow is really cool. And you have thousands of employees, right? So retaining people, growing people is really, really important because it would be really expensive to have to replace everybody all the time if they were leaving.

Chelle O'Keefe (20:33)
Especially, yes, especially because we can't really pull from anyone, even in our space since we're the largest. So even pulling from competitors is a challenge, not just because we're the largest, but also because we do things differently. And so we really do have to invest. It's a great have to. We have to invest and make sure that we are developing all of our employees and our leaders from.

Rebecca Taylor (20:40)
Yeah.

Yeah.

Yeah.

Yeah, that's awesome. Sounds like a really great place to be part of. So I love that. Yeah.

Chelle O'Keefe (21:01)
It is a great place. is a great place. Hopefully, I think that

hopefully every CHRO leaves that about their organization. If not, they might be in the wrong position. But I absolutely believe we have a great place to work.

Rebecca Taylor (21:10)
Yeah. Yeah.

Yeah, and you're a huge part of making that happen, like you said, too. It's just like, someone doesn't feel that about their company, then it's either change it, or maybe it's just not the right place for you, and that's okay, too, right? Yeah. Well, do you have any closing thoughts before we end?

Chelle O'Keefe (21:19)
⁓ 100%. Make a change. Yep. Absolutely.

I would just say for everyone, I loved this conversation, Rebecca, so thank you for the opportunity. I would just encourage everyone who's listening to continue to develop yourself. We talked a lot about how is your identity, how is all of our identity changing? One of my favorite things about my career is how I've grown and changed over the years. So congratulations to all the listeners who are listening and trying to learn and improve their skills given.

their own goals and given the dynamics and the environment. And so just say, keep doing that because we all can get better and we all have to evolve, which is exciting, even if it's a little challenging.

Rebecca Taylor (22:10)
Yes, could not agree more. Well, thank you, Shelly. Thank you for sharing your insights, your perspective, and for letting our audience in on a little bit more of kind of the work that you're doing too. know learning by example, hearing what other folks are doing is really a key part of why we have this podcast. So thank you for being open and sharing. And I hope everybody listening has a great day. Bye.