The modern wealth management landscape is often a tug-of-war between rigid risk management and the need for authentic leadership.
As the President and COO of Berkshire Money Management, Wheeler represents a new breed of operational leader – one who leverages sophisticated technology to create space for radical candor.
For Wheeler, operational excellence isn't just about the "how"; it’s about the courage to say what needs to be said. She’s built a career on the belief that you must find your voice when it’s most uncomfortable – because that is precisely when it is most needed.
"My advice is just speak up," Wheeler says. "Be curious and look around about what you can do to help others."
Early on, Wheeler realized that "status quo" is just another word for stagnation. You don't evolve an organization by nodding along; you do it by poking holes in the way things have always been done. She noticed that many in the industry are "scared to step up and say, 'Hey, I think we need to make this improvement here.'"
Her advice to other operational leaders? Use your voice as a tool for evolution, not just execution. That sounds great on a slide deck, but in practice, it’s gut-wrenching. It means raising your hand to flag a flaw in a partner’s favorite project or proposing a radical change to a legacy system.
For Wheeler, this brand of transparency isn't about being a contrarian –it’s about a practical shift in mindset. She’s made peace with the idea that being wrong isn’t a failure; it’s a data point.
"It's okay if you're wrong. It's okay if you make a mistake," she explains. "It's okay if someone isn't happy about a change you want to make, but if you feel confident in what you're going towards, it's just built inside."
Most firms treat mistakes like a PR crisis – they’re quietly scrubbed or buried. At Berkshire Money Management, they’re practically celebrated. Wheeler describes a culture where leadership actively rewards employees for identifying errors.
"My boss actually gave the company [a challenge]: 'If you make a mistake, I will give you this bonus,'" she laughs. "It was almost like: make a mistake because it's okay if you do, I'm going to reward you for it. I thought that was the coolest thing ever."
This creates a feedback loop that actually works. When people aren't terrified of losing their jobs over a typo, they become the firm’s best line of defense. Wheeler actively maintains this through constant communication. "I have one-on-ones with all our team members and I’m always asking: 'How do you feel the culture and morale is?' If they say it's great, I want to know why. What are we doing right?"
On the technical side, Wheeler is a believer in the "magic" of workflows baked into the firm’s CRM system. To her, a workflow isn't just a digital checklist; it’s the firm's central nervous system.
"Workflows are the magic ingredient," she says. "They add that structure. They make sure nothing is going to fall through the cracks from A to Z."
But Wheeler refuses to let the process kill the personality. She intentionally weaves human touches into these automated systems. For example, when a prospect is added, the workflow triggers a celebratory internal tone, saying, 'Congratulations! You now have a prospect.' I'm hoping when someone sees that, they get amped up."
Whether it’s a "welcome experience" full of literal confetti or a tailored dashboard, the goal is to make sure neither the client nor the employee feels like a ticket number. "We want to make sure from the second we have that first 15-minute conversation, they feel heard, they feel welcome, they feel already like they're family," Wheeler reports.
The COO role in a financial firm is a bit of a catch-all. On any given Tuesday, Wheeler is toggling between high-level operations, compliance, and HR.
Managing that chaos requires radical visibility. Since joining the firm in 2020 and immediately facing SEC audits, she had to ensure no gaps existed in their documentation. She now runs regular "scenarios" to stay ahead. "If [auditors] came in tomorrow, can we show them that we're getting the verbal confirmation from our clients when they're requesting cash? It’s super important," says Wheeler.
Wheeler is a fixture in the industry, often found swapping "war stories" with her peers. But her message remains consistent: your job isn't just to keep the engine running.
Operational excellence is about where you're steering the car. The most effective leaders aren’t the ones with a folder full of answers. They’re the ones willing to ask the "dumb" questions, invite the hard conversations, and build a space where their team feels safe enough to do the same. "I am just a curious person," Wheeler says. "We're going to dive into it, we're going to pull some things out– what are we not using? – and let's just figure that out."
In the end, great firms aren't built on iron-clad processes. They’re built on people who are brave enough to speak up and leaders who are actually listening.