The Work Isn't Going Away - It's Changing - Center for Transformation

Technology is advancing faster than the profession’s ability to rethink its workflows.

In a profession often defined by structure, standards, and well-worn career paths, Donny Shimamoto opens a different kind of conversation in a recent Accounting ARC episode—one that challenges assumptions about what it means to build a career in accounting. His guest, Danielle Supkis Cheek, embodies that challenge.

As senior vice president of AI, analytics and assurance at CaseWare, Supkis Cheek operates at the intersection of technology, methodology, and human judgment. But her path there was anything but linear—and that, Shimamoto suggests, is exactly the point.

Rethinking what accountants do
Supkis Cheek describes her role less as a technologist and more as a translator. “I like to think of myself as someone who translates across domains,” she says, explaining how she helps software companies understand how accountants actually work—and how technology can reshape those workflows.

Her focus is not on automating existing processes for efficiency alone. Instead, she challenges whether those processes should exist in their current form at all. In one example, she flips a traditional audit workflow on its head: rather than narrowing a dataset first and then completing a checklist, she envisions applying checks broadly and using AI to surface insights afterward. The goal is not speed—it is better judgment. That mindset reflects a broader shift in the profession, where the value is moving from execution to interpretation.

A nontraditional path—by design
Supkis Cheek’s career includes public accounting at EY, launching her own firm before age 30, teaching at Rice University, and working in standards and regulatory environments. That mix was intentional.

Early in her career, she recognized that credibility could be questioned—not because of capability, but because of age. So she built what she calls a “national voice,” pursuing leadership roles, credentials, and affiliations that would make her expertise undeniable. “I needed to make sure my age wasn’t my undoing,” she says.

The strategy worked—but it also exposed her to a broader view of the profession, one that extended far beyond traditional firm roles. That perspective ultimately led her to the vendor side, where she could spend more time solving complex, systemic problems—particularly in data analytics and AI.

The reality of running a firm
The conversation does not romanticize entrepreneurship. Supkis Cheek candidly describes the tension of running a growing firm: strong demand, steady revenue, and high-quality work—paired with operational stress, talent challenges, and the constant pressure of payroll. “Payroll gets scary,” she says, describing the moment when growth shifts from exciting to risky.

Her firm succeeded in many ways, particularly in building a stable client accounting services (CAS) base. But that stability created a different problem: it began to crowd out the forensic work she was most passionate about. That trade-off—between stability and purpose—is one many firms face but rarely articulate so clearly.

AI will not eliminate “tedious” work—it will redefine it
For all the discussion of AI, Supkis Cheek offers a grounded perspective on what it actually changes. The profession has long viewed automation as a way to eliminate repetitive tasks. But she argues the nature of that work is simply evolving. “The new tedious is going to be fact-checking,” she says.

In other words, AI may generate outputs, but professionals remain responsible for validating them. That requires not less thinking, but more. Her advice to early-career professionals reflects that reality: stay curious, even in the most routine tasks. The ability to notice what does not make sense—and ask why—remains the differentiator. She shares a story of a junior team member performing painstaking transaction tracing on a forensic engagement. By staying engaged, he identified a pattern no one else had seen—uncovering a new fraud scheme in the process, illustrating how insight often hides inside the work people are most eager to rush through.

The human side of expertise
While much of the episode focuses on technology and career strategy, the most striking moments center on emotional intelligence. Supkis Cheek recounts a case where she had to override a client’s instructions—forcefully—to prevent a costly mistake that could have resulted in a $20 million liability. It required judgment, confidence, and a willingness to be unpopular in the moment.

At other times, the role demands the opposite: empathy, patience, and the ability to support clients through crises. “The hero status,” she says, “is being what the client needs you to be.” That duality—technical expertise paired with emotional awareness—emerges as a defining theme of the conversation.

Expanding the definition of an accounting career
Shimamoto, founder and managing director of IntrapriseTechKnowlogies LLC and founder and inspiration architect for the Center for Accounting Transformation, underscores what Supkis Cheek’s journey represents: the profession offers far more pathways than many realize. Too often, students and early-career professionals see only a narrow set of options—public accounting, industry roles, or internal audit. This episode challenges that view, highlighting opportunities in technology, data, policy, education, and beyond.

The message is not just that alternative paths exist—but that they may be essential to the profession’s future. At a time when AI dominates headlines, this Accounting ARC episode avoids hype in favor of substance. It reframes AI not as a replacement for accountants, but as a catalyst for rethinking how work is done—and what skills matter most.

It also reinforces a broader truth: the profession’s value has never been in the tasks themselves, but in the judgment, curiosity, and humanity behind them.

For listeners navigating their own careers—whether just starting out or considering a pivot—this conversation offers both practical insight and a subtle challenge: Don’t just follow the path. Question it. Redesign it. And stay curious enough to see what others miss.

Listen to the full episode