From Hesitation to High-Impact: How Holly Novak Navigated the Leap to CPO with Grace at Jack Henry

 Why CHROs Need This
Becoming a CHRO isn’t just a promotion—it’s a pivot into uncharted territory. In this candid conversation, Holly Novak shares how she went from hesitating to apply for the CPO role to leading transformation and developing AI chatbots at a 7,000-employee fintech company. You'll learn what she wishes she knew earlier, how she built deep alignment with her C-suite peers, and why HR can—and should—own the future of AI adoption.

What You’ll Learn:

• How Holly made the leap from HR Ops to CPO, including the decision-making process with her family 
• What she did in the first year to build trust with the CEO, CFO, CLO, and COO 
• How her team built an internal HR chatbot—and why they scrapped the out-of-the-box solution 
• A candid look at how AI is reshaping recruiting, onboarding, and instructional design
• Practical tips for building resilience in one of the most emotionally demanding roles in business Best For:

CHROs who are considering a promotion into the top role, navigating their early years as a CPO, or leading HR innovation in the age of AI.

Enjoyed this conversation? Join 150+ to the 10th Annual Big CHRO Event in Dallas area for an AI and HR Workshop.

Apply* to receive an invite: https://www.chropartners.com/bighr

*Exclusively for sitting CHROs and Chief People Officers at companies with 500 or more employees.

Transcript generated with the help of AI

Cindy Lu: [00:00:00] Hey everyone, it's Cindy Lu with CHRO Partners. I'm joining you from Dallas, Texas today, and I've got Holly Novak. Where are you joining us from? Holly? I am joining also, north of Dallas, so north of Dallas, little 

Holly Novak: Elm area. Okay. 

Cindy Lu: Awesome. Welcome. We're gonna have Holly tell you a little bit about herself.

Before we get started, I just wanted to let everyone know that the comments that are made today will be those of Holly not yhat personally not of her organization, Jack Henry. And she has a wealth of knowledge that she's gonna bring in. Today we're gonna talk about the pivotal moments, either leading up to the CHR or CPO role as well as.

Some of the big moments that are coming up for us, including this whole AI revolution that we're living in. So if you're joining us as Holly's introducing herself, can you pop into the chat and just let us know where you're joining us from today. Holly, over to you. 

Holly Novak: Alright. Hi, I am Holly Novak.

I am the current Chief People Officer for [00:01:00] Jack Henry. We are financial technology, so we provide technology for banks and credit unions, usually mid-size. I've been in the HR space for a long time, about 25 years, starting in staffing actually. And then I was in nonprofit for about 12 years and then in consulting for a little bit, and then I started at Jack Henry almost seven years ago.

As an HR business partner leader, and then moved my way up the ladder to head up our HR operations team. And then I've been in my role as CPO for about three years. So yeah, it's been a ride. 

Cindy Lu: So understand for you that one of the big, pivotal moments and was just deciding. Whether or not you wanted to be the CPO?

Holly Novak: Yeah, absolutely. I was a little surprised when my my boss the chief people officer decided to move on to a different role within inside the company. And they suggested that I apply and it took me a while. We had to have a little family meeting to really decide, and that it was a big jump for me.

[00:02:00] Going from. A lower level position, even thinking about applying for the CPO role you have a lot of pressure at it. There's a lot of scrutiny, there's a lot of travel a lot of hours. And so we had a little family meeting to talk that through and decide do we as a family. Are interested in that, do we wanna do that?

And yeah. And I made the decision to apply and it was a few months of very stress, very stressful interviewing process and all of that before, before I got the job. But yeah, I'm glad I did now. But it was a big, it was a big decision. Yeah, 

Cindy Lu: we are too. You brought it lot to this. This world of chief HR and people officers.

I had the privilege of watching Holly go from that, her previous role in HR operations to the chief people officer role. And I must say that you did it with such grace, so often. I see, people step into that top role and you're never fully prepared. I've never heard a single person say, oh, I was perfectly developed, to [00:03:00] take over that role. And just because I think there's so many confidential conversations, so I'd love for you to comment on that, but I wanna say hello to some folks here today. Yeah, I see Mike Summer. Aiden. Looks like we've got Chicago in the house with Terry and then another. Terry from Dallas.

Good to see you guys from Dallas from. For live in Fort Lauderdale, but Dallas is home. Okay. Awesome. Great. Thanks to everybody for joining us and really appreciate you saying hello. 'cause we actually can't tell if anybody's on this call at all, unless we, so we just having a conversation by ourselves or what, but yeah.

Holly, tell us a little bit about that entry into that role was like, and just. How you handled that with such grace? 

Holly Novak: Oh gosh. I like, as you mentioned, there's no way that you can fully prepare for stepping into a rollout like this before you get into it. I think as much as anybody [00:04:00] can do to prep you for it, you don't really understand the full scope and the full just pressure and all those things until you step into it. And so I really appreciate that you said that I have Grace. I did not feel prepared. It took me a lot of research and learning and I still, daily I, I learn things and I still don't feel prepared fully at times to do the role, and I'm still surprised.

A lot of times that I even am in this role. It's a big role and so it's nice of you to say that, but Yeah. Yeah, I think just a lot of learning, a lot of listening, a lot of being curious, learning the business, all those things is super important. 

Cindy Lu: Yeah. So we, when we were talking before you said something about you've gotta build those relationships, right?

Not just with the CEO. Give us a little bit of context as to Jack Henryfor the people joining today.

Holly Novak: Yeah Jack Henry, as I mentioned, we're financial technology. We have about 7,000 employees all throughout the us so we're only US based, we're not international. And we, like I said, we [00:05:00] provide all kinds of technology for banks and credit unions, mid-size banks and credit unions.

And I think, one of the biggest things, I had some good relationships with some of our senior leaders before, of course being HRVP and all that stuff, but, it surprised me, the just how deep your relationship has to be, not only with your CEO of course, but also with your CFO and with your chief legal officer and your COO and really making sure that.

As you're working through, like I, I mentioned before, we I got into my role actually during COVID, right? And so I was in HR operations. We were walking through all of that. And then that continued on after I got my role. And I think as we make, super hard decisions work through.

Stuff that we never thought in a million years would happen in our world. You have to have that tight alignment and that tight relationship and that trust built with those, especially those people to really be successful in the role. So that takes some time, obviously, to build that trust and [00:06:00] comradery and collaboration and all of that, but it's super important.

Cindy Lu: I was laughing before when you told me that you stepped into the role and then the pandemic happened. I know your predecessor, she's the one who recommended you to join our mastermind groups. And I was laughing. I'm like nice going there, Tiffany. Yeah. Like bye-bye. Okay.

Holly Novak: And actually she, she was in the role a little bit through COVID.

And but yeah. 

Good times. Good times. Yeah. 

Cindy Lu: Alright, welcome David from Dallas. Somebody from Dallas that I can't see their name for some reason. Paige and, Hey Eric. Tracy. Good to see you guys. We've got Sean Huurman,

Holly Novak:  Some other people not from Dallas. That's fair. Alright.

Cindy Lu: Yep. Having some people at maybe their lunch hour. Okay. These relationships. Everybody talks about these relationships like, and you mentioned getting to know the business better even more in this role than you did as a business partner or in your HR operations role. Tell me specifically, what were some of the things that you did that really helped you leapfrog and get to know the business more?[00:07:00] 

Holly Novak: Yeah, I think just being involved in, budget meetings and strategy meetings, all of that is super helpful. But one of the biggest things I focused on early on, and I still do it is just really trying to figure out like, how do we make money as an organization? Where does our revenue come from?

How, what's our biggest expenses? Of course that's people, right? Because we don't have equipment, but what does that look like? And just truly understanding. What are we interested in the future for innovation? What does that look like? And then how do we support that from a people perspective to make sure that we have the right people in place to be successful?

And so really just focusing as much as possible on the business acumen. I had a little bit of it 'cause I was an HRBP before, right? But I only was in, certain pockets of the organization. And so as a big picture organization, like what is it that is most important to us? How do we make money? How do we lose money?

What does that all mean? And then really focusing on how to support our leaders through that has been my biggest focus, and it still is every day. 

Cindy Lu: There's only [00:08:00] so many hours in the day. How do you pick and choose where you're gonna spend your time? 

Holly Novak: Depends on what fire is happening at the moment, and so I think every day is different. But, I am never afraid to ask to be in a meeting. And so if I see something that's going on, I recently talked to my CEO about. Really talking to clients more because I feel like, we support mid-size banks and credit unions. They have people issues too.

And so really trying to understand what are their biggest pain points so that as we're thinking through from an employee's perspective, how do we support them as our clients? And really understanding that more and being in front of them more has been important to me. That's on my goal list for this year, and so I think that's super important of having that perspective of what's really important overall for our company, but also for our clients.

Cindy Lu: Yeah, no, I think that's so smart. I think retail does that so well. Like I remember years ago, I, some friends that worked in a corporate for Crate and Barrel in Chicago and i'd be like, let's go to lunch. They're like, we can't in December. 'cause all of us at corporate go and work [00:09:00] in the stores. Oh yeah.

That's, I'm like, that's so smart. For, yeah. I don't know if they still do that, but I was like, that's a really smart thing to do. So you're literally, in the trenches with the employee every day interfacing with the customer. You stay in 

Holly Novak: the pain. Yeah. Yeah, absolutely.

Cindy Lu: Speaking of innovation one of the hottest topics right now, in fact, I just sent out a survey to our whole community saying.

What are the topics you wanna hear about? And it was like. I don't know, 85% were like AI and hr, like what's happening. And so last week we had a great session with Mandy Monk around AI in hr. Tell me a little bit about how you're thinking about this next big pivotal moment that's about to happen right to your career.

To many of our careers because of ai. 

Holly Novak: Yeah, I think. In general, data is a superpower that we can utilize in HR more than any other thing, because that's what people listen to, right? They listen to data. And so making sure that. We figure out ways to utilize innovation and [00:10:00] technology so that we can provide those insights to our people.

That's always, one of my biggest focuses and we're a little behind on the technology front at Jack Henry. We're working on it. Just trying to figure out how to get there. But I think from an AI perspective. We we just launched our AI chat bot for human resources. ‘Ask Jack’ I think is what we're calling it.

And so basically it's just a frontline instead of, we have a, have our shared services where we have the frontline to all of our employees, but this is an added frontline. And we built it in-house. And so we started with maybe the out of the box option. But when our technology people were going through that, one of the biggest concerns, and I know that I've talked to a lot of people about this, but when somebody asks a question and the chat bot comes back with the wrong answer, it's a black hole.

There's no true way when you use an out of the box. Solution to go and find, hey, where did they get that answer and why is it wrong and how do we fix it? And so we experimented with that for a while and then ended up building it in-house. Of [00:11:00] course I didn't, but our amazing technology people did.

And so that way when I. Wrong answer is given. We can go back to the specific document that's uploaded in the file and what line it is and determine, oh, hey, this is where they got the wrong answer from. And then you can train the chat bot better. And so I think that's been a huge benefit for us and we test it out the first one. So now they're working on one for finance, one for legal, like all the other, different areas. And of course, AI is coming soon, hot and heavy right now. And so people developing the agents around specific things we're also working on all of that right now too.

Cindy Lu: Yeah. I wouldn't say you're behind it all. That's pretty impressive. I, the, probably the 80% of the bell curve that I'm hearing is that. The HR folks are very interested in this topic. Of course, personally, everybody like you can't go to. Dinner party or cocktail, happy hour without this topic coming up.

Yeah. But companies are behind and a lot of the executives are like, let's slow roll this. Let's see what everybody else [00:12:00] is doing. But if you start to read some of the case studies, you realize slow quickly, companies are gonna go by the way, the dinosaur, if they don't get on. Onboard, right? Oh, 

Holly Novak: yeah. Yeah. And I think, a lot of it's expense, right? And so trying to figure out like, how do we provide the resources for all of our people? We have over 7,000 employees. And so trying to figure out how do we do that and don't do something else is, is the cost of this worth not doing something else?

And I think a lot of times it is to give your people the resources to actually, build that efficiency and really get ahead there. But I gave you the quote earlier, that people say right now it's, AI's not gonna replace people, but it will replace people who don't use it.

And so really taking the time to learn and understand, and I think a lot of our employees are still not there. They're still trying to figure out like, how can I even use this to my benefit? Is it gonna be helpful or not? And so the learning has been a big thing that we focused on first, which is getting some learning out to all of our employees.

Just Hey, what is ai? How does this help you? How does this help your work, your day-to-day work? [00:13:00] And then also encouraging people to experiment with it. In our team we did just a teams chat and said, Hey, I don't care what it is, personal business. Just put your story of what you.

Played with an AI out there just so that people can get an idea of all the things that they can do. And then once they had have that comfort, then they'll be more apt to experiment on it. But, we're a very, we're a technology company that serves banks and credit unions, so very high security and making sure that our people understand what to put in there, what not to put in there, what sites to use.

So we've had to go through I'm on the AI executive strategy team. And you're just trying to determine what do we block, what do we allow, and giving the instructions and all of that, which is really important for all companies, especially for us. 

Cindy Lu: Yeah, absolutely. It's interesting, Mandy, thanks for joining as well.

And Bridget Mandy talks about how you have to teach the ai, right? Some of the lessons learned Yeah. Around you gotta teach the ai not just your [00:14:00] employees. But what's interesting, and I probably brought this up last week and worth bringing up again 'cause I do think it's. Such a cool merger. There's chief AI and people officers and chief people and AI officers.

Now the role is getting merged. And it makes a lot of sense because if you think about our coworkers in the future, they may not be flesh and blood. Yeah. There's gonna be digital twins. There's going to be agents that can do the work that nobody else wants to do in any country. So many amazing opportunities.

I think this is the gonna be so exciting. I hear about some people, like close to retirement going, oh, I'm so glad I don't have to deal with it. I'm like, I could not be more excited about this topic and what it's gonna do. Yeah. 

Holly Novak: I'm actually a big nerd, so I love playing around with it. I probably am not as advanced as other people, but I love experimenting with it and seeing what it does from a work and personal standpoint.

I think that. As we think through what AI can do for us from a business [00:15:00] standpoint, it's really important. To think through, as we lose a position or a person in the role, taking that time to zero base and say, Hey, not just backfilling it, but what does this position do?

What can AI help with, on this? Can, can we take half of a position and give it to ai? And then, add some other duties back to this role. And so really making sure that we go through the org design process and focus on ways that we can gain that efficiency. I think it's really hard when you're thinking from a budget standpoint to put a cost or a dollar number to AI efficiency unless you're replacing headcount, right?

But your everyday efficiency, I think is something that we're trying to think through. Like how do we measure that? Savings and what does that look like and how you calculate it. So it's gonna be interesting.

Cindy Lu: I have some opinions around that. Do CEOs ever say, we want a really great culture and I wanna measure the AI or the return on [00:16:00] investment for having a really great culture.

We all know it's the right thing to do, but how do that, how do you measure it? Measure that. Now I know this is viewed in the lens of technology. Yep. But it's also like maybe it needs to be talked about in the terms of consequences, 

Versus return. Yeah. If you don't do it. Okay.

So here's an example. If you don't talk to your kid about sex ed. Does that mean they're not gonna have sex? Yeah, probably not. So if you don't, if you don't invest in the governance around ai, people are just gonna go shadow spend on their own. 

Yeah. Maybe they don't expense it and maybe they're like, it's just worth it.

I get to work 20 less hours this week because yeah, I'll just pay for it myself. Yeah. So then is your data out there right in the middle of the ether versus being on a team? Where they're not learning from your technology or. If you don't know and you don't put it in notebook LM versus you put it in the, unpaid chat GBT [00:17:00] what can that mean for your organization?

I think, I hate to do the scare tactic thing, but yeah, I'd be curious from the group, it's the cost of not doing it, right? Yeah. The cost of not doing, sometimes we, without knowing exactly what the RO, who knows what the ROI is right now. Maybe there's some ways to measure it. Certain parts of hr, like even like talent acquisition, it's a lot easier to measure ROI for anything in TA because you've got numbers and metrics that are very firm.

Holly Novak: So Yeah. Oreven instructional design, right? Utilizing it to build trainings faster than you've ever imagined. Yeah. 

Cindy Lu: Or they can deliver faster. So our CH school.com, you know that free resource that we provide? Yeah. HR leaders. So I had recorded a bunch of these lessons and most of them take.

20, 25 minutes and our intern, Aidan Huurman actually just. Put it all into synthesia, which is the learning Yeah. App that we use. I don't know if you guys are familiar with it, but Yeah. We use that too. Yep. [00:18:00] Yeah. Literally it took the same script and I must talk really slow because it was like eight minutes versus 25 minutes.

Holly Novak: Oh, wow. 

Cindy Lu: And it was. Just more clear, more concise, and yeah. We put my, it's amazing. Yeah. We put my digital twin on it. So it looks just like me saying all the stuff, but I just saved you, almost 20 minutes. Yeah. Yeah. Looks like we have a question. Oh yes. Let's see. Can you look at the additional value your team is generating because they aren't doing what AI's now doing?

Can you monetize these outcomes? That's. Great question. 

Holly Novak: We're doing that in a couple of different areas. And, it just takes the time to, to track the hours, to log the hours that you're saving per employee or per task. And then you can definitely monetize that. Yeah. It's a good example.

Of course if you reduce the whole headcount to turn to ai, that's an easy way to, to. To as well. 

Cindy Lu: Yeah. See, Mandy says, I learned last week from a new study done that [00:19:00] to speed transformation, you need to focus on the full potential of data technology and people, those who don't focus on the people as well, are 7% less than likely to succeed.

Yeah. Makes a ton of sense. Yeah. Holly, what do you think other challenges? With corporations implementing ai. 

Holly Novak: One of the biggest things that just popped into my head as we were talking, that we've been dealing with at Jack Henry is related to fraud and and ai and I think that is a huge topic that I.

HR people aren't quite thinking through as much as they should, and really investigating how to protect their companies against it. 'Cause these people are getting super good. Getting into organizations and utilizing deep fakes and all this other stuff to get into the application process.

And so I think that's, I think that's a challenge. It's a risk that we we've, we're in the process of redoing our whole. Onboarding, interview, everything around making sure that [00:20:00] we're protecting against deep fakes and threat actors and all of those things. And so I think that's a huge challenge that is gonna get harder and harder the more sophisticated AI gets that were paying attention to.

Cindy Lu: Yeah, for sure. That's been going on for years. Yeah. They're just 

Holly Novak: getting really good at it. Yeah. Yeah. 

Cindy Lu: My cousin, who has a niece in China years ago, I think it was like on WhatsApp or something. Some kind of FaceTime type program. And she got on, she's oh, my audio's not working.

And got him to send her or. No, how'd it go? They pretended like they were him. And he asked his fake, deep, fake, asked her for money and it was almost like a month's salary. Oh wow. She was sending him, so Yeah. Pretty bad. Pretty scary. 

Holly Novak: It is. And honestly, our recruiters right now are having to be a little investigators.

They have to, they, if they see anything that looks off. They go through a whole process of investigating social [00:21:00] media and addresses and phone numbers and comparing them to other ones, and just making sure we've found groups of five North Korean actors that are in our system applying for one job.

And our recruiters have been great and some of our managers have been great at really identifying, hey, something's off here that we need to dig into a little bit more. And then we find, a whole group and none of them are real. It's been increasing. Substantially over the past couple of months, 

Cindy Lu: just AI bots that are out applying.

Holly Novak: Well, a lot of 'em are real people that are applying just in different ways, but we've also had some deep fakes. We also had some just true identity, identity stealing happening too. But yeah. 

Cindy Lu: Scary. Okay. Folks that have just joined us, Hey, can you guys drop in the chat what AI tool you use today potentially, right?

Still we'll use. So I had chat GPT work out on me today before mastermind meeting, and I was like, Ugh, I gotta get all my notes from the last meeting so I can see what everybody talked about. And we have our cohort [00:22:00] meetings only every other month and I just can't remember it all anymore.

Yeah. And so I was like, okay, let me switch over. To another one. And it's pays right to be able to know about multiple ways to leverage it. But it's so cool because I am like, can you take this, these transcripts? And this is I'm not letting them learn in a open environment, right? It's notebookLM. So these transcripts are not going out to the public, but I'm just like, Hey, just tell me what everybody said in the group alphabetized by first name, and tell me what they're last. Thing is that they were interested in, solving for or working on. So then I have that at my fingertips and you can't believe how much time that saves me.

Hours. Of Oh 

Holly Novak: yeah. And we're doing some of that. We're just about to implement a new data tool where you can literally tie all of your different data together and then you can just type in a question that is, Hey, what is the biggest. What is the biggest future area that we need to focus on for trending, and then it'll pull [00:23:00] in, utilizing all the different data.

And so you're having those real time discussions with the AI tool and super excited to play with that and dive into that from an HR perspective. So yeah. Yeah, tons of tools out there are amazing. 

Cindy Lu: The one I'm really excited about is using chat GPT as a thought partner. Oh how be a counselor?

Yes. Yes. So one of the business coaches I work with, she has a chat that she shared with us about overthinking. So sometimes entrepreneurs can overthink things so that they just stall, they don't launch anything 'cause they're like just still thinking about whether or not they want to do it. And some of it's fear based, but this GPT literally will.

Keep asking questions and then be like, okay, what about this? And what about that? And now I'm overthinking it. And I never thought that AI would be good at that kind of thing. Do you know what I mean? I'm like, okay, combine two spreadsheets, great. But I never thought that it would be such a good counselor, and it just sounded like she was in my head.

It was her voice. Yeah. It's fascinating. I was like, okay, this [00:24:00] is really cool. All right. Looks like we've got lots of chatt. Yeah, I have. 

Holly Novak: I see a question there. Before implementing AI tools, do you feel confident about the data? You know what? We're working on our data right now, so as we're in the implementation process, no, I wouldn't say that I feel confident about our data, and I do think that's super important.

I will say a lot of the AI tools out there right now will help you clean your data as part of the implementation. And yeah, so I, I think that's a really good point. You do wanna make sure that your data is good or pretty decent before, before connecting it. 

Cindy Lu: I also think it highlights when your business processes are a mess.

Holly Novak: Yeah. But, and implementing some of these tools help you work through that process again, right? And re redo it so that you're, you have a cleaner process. 

Cindy Lu: Looks like we got a winner here, Eric Raz, Apollo, higher quotient, all the things, Gemini, perplexity, and of course chat. It sounds like Eric, you need to come and do do your LinkedIn live pretty soon.

Alright quick plug for [00:25:00] our big CHRO event this year, September for sitting CHROs at companies over 500 employees and our mastermind members. We have, we're bringing in Chris McKay and team to talk about this very topic and they've got a framework for companies to use. So you have to try to figure out,

Holly Novak: oh, that'll be fascinating.

Cindy Lu: Yeah. And they've used it with many large organizations. So Holly, just before we leave any parting words of wisdom to those who are rising CHROs or in the role and struggling, any last minute thoughts of inspiration? 

Holly Novak: Yeah, I would say, I've been in the role for about three years and I think one of the biggest things is this job is extremely demanding and lots of pressure and emotional challenges.

You never know what you're gonna, face during the day. And so I think one of the biggest things is having a really good support system around you. I think it's been amazing to be part of your team and really. Have the CHROs around me that I just, when [00:26:00] I need a question or just, I'm like, I feel like I'm failing and I need somebody to either validate that or tell me something better to do.

So I think that's super important. And really taking your rest and making sure that you, like you, you could work yourself to death if you wanted to. I could work 24 hours a day, but you have to force yourself to really. Give yourself that care. And otherwise you're not gonna have the resilience that you need to be able to handle the hard things and and then build that group of community around you.

I think it's super important to have that. 

Cindy Lu: Yeah. Thank you for saying that, Holly. Yeah, I did not ask her to say that. You guys. Yeah, but actually I was just listening to the McKenzie podcast and they talked about resilience. Like not resilience or pre like building. Yeah. One of those things was friends, having friends.

And whether it's professional or otherwise it's known to extend people's lives. It's known to make you happier, so yeah. Yeah having friends e even if they have a HR title,

Holly Novak: yeah. Then we don't have to. Eric doesn't, but we still like him, [00:27:00] yeah. 

Yeah. 

Cindy Lu: All right guys.

Hey, thank you so much. Put in the chat your thank yous for Holly. For joining us today. Thank 

Holly Novak: you for having me. It's been good. 

Cindy Lu: Yeah. I dunno how you guys do it. You're so busy and you probably really have time to use the bathroom, but that, yeah, you take time to back and share with others. So I hope somebody's been inspired or you learned something from our LinkedIn Live today.

Thanks everyone. Oh, and thank you. Hi to everybody on YouTube as well. Yeah. Hi. Okay, thanks. Take care. 

Holly Novak: Bye.