When HR and Finance Can’t Agree, Employees Lose
Clip of Vincent Catalano and Ali Payne, Senior Partner of People Solutions, The People Co. on “HR Can’t Do Math”
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A conversation with Ali Payne, Senior Partner of People Solutions, The People Co.
There is a meeting that happens inside almost every mid-market organization at least once a year. HR walks in with the benefits renewal. Finance is either not in the room or barely paying attention. Numbers get presented. Some get remembered. Most don’t. And somewhere between the broker’s slide deck and the CFO’s budget spreadsheet, the people who actually depend on those benefits get lost entirely.
Ali Payne has seen this movie more times than she can count.
As Senior Partner of People Solutions at The People Co., Ali has spent nearly two decades embedded in the HR strategies of organizations ranging from scrappy growth-stage companies to complex mid-market employers. She’s watched HR teams get handed more responsibility than any one function can reasonably manage. She’s watched finance teams treat benefits like a line item to minimize rather than an investment to optimize. And she’s watched brokers default to the path of least resistance, usually an RFP, when a real conversation would have served everyone better.
Ali joined Vincent Catalano on the CLEARly Beneficial Podcast to talk candidly about all of it. What came out of that conversation was a frank diagnosis of one of the most persistent structural problems in the American workplace: when HR and finance operate in silos, employees are the ones who pay the price.
HR Is Being Set Up to Fail
The first thing Ali makes clear is that the problem isn’t HR people. It’s what HR people are being asked to do.
“HR people are being asked to do so much more than what they — and maybe it isn’t necessarily they’re asking to do more. There’s just more to do. So how do you make sure that they have the resources at the right time?”
The scope of what falls under HR has expanded dramatically over the past decade. Compliance. Culture. Recruiting. Workforce planning. Benefits management. DEI initiatives. Manager training. Employee relations. All of it lands on the same team, and often the same person, without a commensurate increase in headcount, budget, or strategic support.
The result is an HR function that’s perpetually in catch-up mode. And when you’re always putting out fires, strategy becomes a luxury you can’t afford.
Vincent, who spent over two decades as a benefits consultant working inside some of the industry’s largest firms, has a blunter take: “HR is that function in an organization that is overworked, underpaid, understaffed, least respected. And they’re the ones that strategically probably play one of the most valuable parts of what an organization can do to deliver what their mission is.”
The irony is painful. The function most responsible for attracting, retaining, and developing the people who actually execute the business strategy is often the last one invited to the table where that strategy gets made.
The Table Nobody’s Sitting At Together
Ali’s work at The People Co. is built around a deceptively simple premise: people strategy and business strategy have to be developed together, or one of them will fail.
“We spend hours and hours talking about our business strategy and we spend zero time talking about our people strategy. And if you don’t have a people strategy that can marry your business strategy, you’re going to fail. At some point those two things are going to come to a head and you’re going to say, we don’t have the right people to get us to where our business needs to go.”
In practice, this shows up in ways organizations don’t always recognize. A company sets an aggressive growth target for the next three years but hasn’t invested in the leadership pipeline needed to manage that growth. A firm enters a new market without thinking through what skills and roles are required to compete there. An organization rolls out a new product line without asking whether its people have the training and support to sell and service it effectively.
These aren’t strategy failures in the traditional sense. They’re people strategy failures. And they’re preventable.
The People Co. was built specifically to address this gap, offering fractional, project-based, or ongoing HR support to organizations that need more than their internal team can deliver. What Ali finds, consistently, is that clients come in thinking they need one thing and actually need something else entirely.
“A lot of times we get called because they have a specific issue. They say we need an engagement survey. And we get in there and we start to talk to people and we actually find out that it’s actually not the engagement strategy they need. It’s actually that they need a strategy in general.”
One client came to The People Co. convinced their turnover problem was a hiring problem. Ali’s team dug in and found something different: “Once we get in there and we find out it isn’t necessarily your hiring — it’s that you’re showing up as something different than who you hired. When you hire your people, what you say on the outside has to match what’s actually happening on the inside.”
That gap between the promise and the reality is one of the most common and most damaging problems Ali encounters. Employees show up expecting the culture they were sold in the interview process and find something different waiting for them. The disillusionment sets in fast, and the exits follow.
The Generational Shift That’s Rewriting the Playbook
Layered on top of these structural HR challenges is a generational shift that’s forcing organizations to rethink how they manage, develop, and retain talent.
Ali points to a Forbes article that stopped her cold: 43% of employers report having parents present during job interviews with younger candidates. When she was speaking to a group of employers in Marshalltown, Iowa, a place she expected might be insulated from coastal workplace trends, she decided to test it.
“I asked the audience of 19 or 20 employers: have any of you had parents alongside when you do job interviews? And six hands went up.”
The stories that followed ranged from parents sitting in on Zoom calls to physically showing up to the interview site. One HR professional had to tell a parent to go wait in the car.
Ali doesn’t frame this as a character flaw in younger workers. She frames it as the predictable outcome of how this generation was raised, with more scaffolding, more coaching, and more personalized support than any generation before them.
“If you think about how we’ve raised these kids — they come out of college with having someone, everything from a guidance counselor at school to some sort of college coach to a career coach inside college. Everybody gets a trophy.”
The challenge for employers is real: these employees arrive expecting a level of development, feedback, and individualization that most organizations simply aren’t set up to provide. And rather than adapting, many companies respond by complaining about the generation, which doesn’t solve anything.
“How do you help your leaders adapt to having these younger generations join you? I’m not saying you have to throw everything out. But you still have to figure out how do you adapt — and then how do you personalize it — because if you think about our world, our world is personalized. Everything we do now is personalized.”
She’s direct about what happens when organizations resist that adaptation: “If you’re not willing to adapt quicker than maybe what you were before, you are going to lose that talent just as fast as you get them. Because they’re not going to wait around.”
AI Is Here. Most Organizations Are Responding With Fear.
No conversation about the future of HR in 2026 gets far without landing on artificial intelligence. And Ali’s perspective is worth sitting with.
She shares an early example of how not to handle it: when ChatGPT first launched, the organization she was working for at the time didn’t study it, pilot it, or develop a thoughtful policy around it. They shut it down entirely.
“They literally cut off all access to people. You had to fill out this form on what you were going to use it for and how you were going to use it for it to even be okay to be on your laptop.”
At that point, Ali notes, employees were mostly just using it to write emails. The fear was wildly out of proportion to the actual risk. And it sent a signal to employees, particularly younger ones who had grown up comfortable with new technology, that the organization wasn’t interested in thinking creatively about the future.
Vincent has thought carefully about AI’s implications for the benefits brokerage world specifically. In a conversation with a former insurance industry colleague, the two spent about twenty minutes deconstructing the traditional role of a broker and concluded that AI could likely handle around 95% of the work. Quote and analysis generation. Plan comparison. Strategy development. Even client-facing communications.
“I’ve tried this experiment where I type stuff into ChatGPT, giving it an employer scenario, and it spits out a strategy that I would have come up with — and then some.”
Ali’s take on what this means for people and organizations: “If we can get organizations to understand how AI can help their business, I think it can help their humans be more efficient. How do you help your teams get more efficient using AI? That’s really where we can continue using AI in a way that isn’t necessarily going to just eliminate jobs.”
The key, she argues, is approaching it with curiosity rather than fear. “We got to be curious about it. Because if we don’t figure it out, the younger people coming in are not afraid to try and use it.”
And regardless of how capable AI becomes, Vincent draws one important line: “In everything we do, there’s the last mile. And the last mile is that touch point where something has to get done from human to human.”
The Finance-HR Divide That’s Costing Employers Millions
The most consequential part of the conversation, and the one with the most direct dollar impact on organizations, is the relationship between HR and finance when it comes to employee benefits.
Vincent frames it starkly: “I’ve maintained for many years that HR, and forgive me for saying these words, but HR really can’t do math.”
He’s not saying it to be dismissive. He’s saying it because he’s watched the dynamic play out hundreds of times. The broker delivers the renewal to HR. Big binders. Complex spreadsheets. A polished presentation. HR absorbs about ten percent of it. Then they walk into the CFO’s office and try to translate it into a budget conversation, without the financial fluency to make the case effectively or defend the numbers under scrutiny.
“You’re not in the room, Mr. CFO, even though you should be. HR gets the renewal, big spreadsheets, big binders, all the things. Broker does their dance. HR remembers about 10% of what broker told them. Then they tell you.”
The result is a communication breakdown that plays out in slow motion every renewal season. If the increase is modest, everyone breathes a sigh of relief and moves on. If it’s significant, fingers get pointed, usually at HR, which had the least control over the outcome and the least context to explain it.
Ali confirms what Vincent suspects: in nearly two decades of HR consulting, she has not seen a single mid-market example of an HR team and a finance team genuinely partnering to build a sustainable health strategy together.
“It’s like they’re never at the same table together. The CFO is thinking about it from a money perspective and the HR person is thinking about it from a people’s perspective. And it’s like they cannot figure out how to come together.”
The financial stakes of that disconnect have never been higher. Vincent puts it in context: when he started in the industry in the early 2000s, a single health premium for an employee was around $150 a month. A family plan ran about $450. Today those numbers have effectively added a zero. And yet the strategic collaboration between finance and HR that this level of spending demands has not materialized.
“Benefits are one of the hardest costs that a company has to eat. Because if benefits get too expensive, people don’t get raises, products don’t get developed, marketing doesn’t get budget.”
Stop Buying Things. Start Understanding What You Have.
Ali’s prescription for HR teams trying to navigate this environment isn’t another vendor. It’s clarity.
“Just understanding really what you need and what you don’t need. We’re spending so much money in the benefit space that — yes, medical insurance coverage is expensive — but you’ve got all this other stuff that in some cases is just noise.”
The point solutions market has exploded in recent years. Vendors with compelling pitches for mental health apps, financial wellness platforms, caregiver support tools, and dozens of other supplemental benefits have flooded HR inboxes. And many HR teams, trying to check boxes and respond to employee feedback, have said yes to more than they can effectively manage or communicate.
Ali’s advice: stop. Take stock of what you already have. Find out whether employees actually know it exists and whether they’re using it.
“So many times we never go back and we say, of all these things we offer — are people using it? Is it providing the value that it should be providing? Do my people know about it?”
She describes clients who hired The People Co. after realizing their benefits communication had broken down entirely. They had assembled a solid suite of offerings but communicated them so poorly, or so infrequently, that employees didn’t know they existed. The solution wasn’t more benefits. It was better communication about the ones they already had.
Vincent drives the point home with a reference that will resonate with anyone who has sat through open enrollment: “You give them that 85-page PDF at open enrollment and say, here you go, I’ve done my job. Knock yourself out, buddy.”
The RFP Reflex and What to Do Instead
Which brings Ali and Vincent to the part of the conversation that hits closest to home for brokers and HR teams alike: the reflexive, often counterproductive overuse of the RFP process.
Ali identifies a dynamic she has watched play out inside some of the largest brokerage firms in the country: brokers who have come to believe that their value lies in running RFPs. Not in understanding clients. Not in building strategy. In producing a process.
“So many times, the broker thinks their value lies within doing RFPs. So they’re like, I’m going to do an RFP for you for a new vendor for whatever point solution it is. Instead of taking a step back and saying, what’s actually working and what’s not working — and why is it not working — before we go through the exercise of doing an RFP.”
The RFP process is exhausting for everyone involved. Vendors spend enormous resources responding to requests from clients they’ve never met, for evaluations that are often already decided. HR teams spend months managing a process that pulls them away from everything else. And at the end, as Ali notes, the analysis that took a hundred hours often leads right back to where it started.
“No one likes doing RFPs — answering them or reading them or analyzing them. And then at the end of the day they do all the analysis that took someone a hundred hours and they’re like, yeah, we’re just going to stay with who we have today.”
Both Ali and Vincent are clear: if your relationship with your broker isn’t working, the first step isn’t an RFP. It’s a conversation.
“Have a pretty good sit down with the broker to figure out what exactly are they doing. Start with just a conversation. Don’t put everyone through the ringer just because you feel like you need to add more value.”
Vincent takes it a step further, surfacing a question that most HR professionals have never thought to ask: do you actually know what you’re paying your broker?
“I can’t tell you how many people, whether it’s HR or CFOs, tell me as I’m talking to a potential client: I don’t even know what I pay my broker. And I just happen to have the 5500 with me. And I’ll go, well, here’s your latest 5500 and it’s $250,000 or whatever the number was. And they’re appalled by that.”
The 5500 is a federal form that discloses broker compensation, and many of the people whose signature is on it have no idea what’s inside it. That opacity isn’t an accident. It’s a feature of a commission-based model that has historically benefited brokers at the expense of client clarity.
Vincent’s prescription is straightforward: “The smart brokers would do more of that — come up with a number that made sense for everybody. When brokers start to prospect new business, they look at a company and say, look at the commissions in that, I want to go after that. But the truth is they should ignore that and really come up with a value prop that makes sense for the clients.”
What Better Actually Looks Like
Ali closes the conversation with a challenge, not just to HR teams, but to every organization that claims to take its people seriously.
The thesis is simple: you cannot build a sustainable, competitive organization without a people strategy that is as carefully developed, resourced, and measured as your business strategy. They are not separate conversations. They never should have been.
“We believe that there is going to be, and has to be, change in this industry. And we believe helping your HR teams get smarter and faster and fitter — that’s the thing that we just think is such an important element to helping organizations grow.”
For HR professionals, that means getting financially fluent enough to have the benefits conversation at the executive level, not just receiving the renewal and passing it along. It means understanding what they’re paying their brokers, what value those brokers are actually delivering, and when a conversation is more appropriate than an RFP.
For finance teams, it means recognizing that benefits are not simply a cost to contain. They are the mechanism by which an organization attracts and retains the people who execute the strategy. When that mechanism breaks down because costs spiral out of control, because employees don’t understand or value what they have, because the broker relationship isn’t working, the whole organization pays.
And for brokers, it means being honest about where your value actually lies. Not in running processes for their own sake. Not in generating commissions from products your clients may not need. In doing the hard work of understanding your clients’ actual situation and building strategy around that.
The employees caught in the middle of all of this, the ones using the benefits, making decisions during open enrollment with a PDF they can barely parse, hoping their plan covers what they think it covers, deserve better than a system that’s optimized for everyone’s interests except theirs.
About Ali Payne
Ali Payne is the Senior Partner of People Solutions at The People Co., where she leads transformational work helping organizations create workplaces where people thrive. An award-winning thought leader in employee experience and organizational wellbeing, Ali was named Employee Benefit Adviser’s Wellness Adviser of the Year in 2018. She holds a leadership certificate from Harvard Business School and has nearly two decades of experience leading wellbeing and engagement strategy at some of the industry’s most respected firms. Ali is also a global keynote speaker sought after for her insights on the future of work, workplace culture, and people-first leadership. Learn more at www.thepeople-co.com.
About Vincent Catalano & CLEAR Healthcare Solutions
Vincent Catalano is the CEO of CLEAR Healthcare Solutions and host of The CLEARly Beneficial Podcast. With over 23 years of experience in the employee benefits and insurance brokerage industry, including time at Arthur J. Gallagher, Catalano founded CLEAR Healthcare Solutions to provide independent, unbiased healthcare benefits consulting. The CLEARly Beneficial Podcast features solution-oriented conversations with healthcare innovators, industry leaders, and benefits professionals. His unique position as an independent consultant allows him to have frank conversations about healthcare issues that corporate-employed professionals cannot address. New episodes release weekly on Tuesdays at 8:00 AM across all major platforms. Learn more at www.clearhcs.com.
Disclaimer: The information provided in this podcast is for educational and informational purposes only and should not be construed as legal, financial, or professional advice. Listeners should consult with qualified professionals regarding their specific situations.
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