Rethinking an Industry: Kirsten Liston on Building a Company by Listening to the Market

Entrepreneurship is often described as a leap of faith, but in reality it usually begins with something much quieter. It starts with noticing a pattern. A frustration that keeps showing up. A problem that everyone in an industry seems to accept even though it clearly could be solved better.

For Kirsten Liston, founder and CEO of Rethink Compliance, that realization came after more than a decade working inside the compliance training industry. By the time she decided to launch her own company in 2015, she had already spent fifteen years helping global companies train employees on complex legal and ethical expectations.

She knew the market well. She knew the clients. And perhaps most importantly, she knew what was not working.

What she saw was an industry that had stopped evolving while the world around it had changed dramatically. Employees consumed information differently, technology had advanced, and expectations around digital learning had shifted. Yet many compliance training programs still looked almost exactly like they had in the early 2000s.

Clients were asking for something different.

Eventually Kirsten realized that if no one else was going to build it, she might have to.

A Career Built on Communication

Before Kirsten ever worked in compliance, she was a writer. She studied English in college and began her career in journalism during the final years of the traditional newspaper industry.

Writing had always been her strength, but she was also deeply interested in business. Early in her career she found herself thinking about how those two interests might intersect. She once described it simply: she did not want to write about the product. She wanted the writing to be the product.

That perspective ultimately led her to a small startup in Boston in 2000 that was experimenting with delivering compliance training online. At the time, both the internet and the compliance profession itself were still evolving.

Many large organizations did not yet have formal compliance programs. Training employees about ethical and legal responsibilities was still a relatively new concept, particularly for multinational companies that needed to communicate these expectations across languages and cultures.

The work required a unique skill set. Compliance professionals had to translate complicated laws and ethical guidelines into practical communication that employees could understand and apply in their daily work.

For Kirsten, the role turned out to be a perfect fit. It allowed her to combine writing, strategy, and communication in a way that directly influenced how organizations operated.

Over the next fifteen years, she developed deep expertise in how compliance training works and how employees actually engage with it.

Seeing the Problem from the Inside

As the compliance training industry grew, several large vendors came to dominate the market. They built extensive libraries of training courses and secured long-term contracts with major corporations.

From the outside, the system looked stable.

But from the inside, Kirsten was hearing a different story from clients.

Technology was changing quickly. Digital media had become more visual, more interactive, and more engaging. Employees were used to consuming information through short videos, graphics, and storytelling. Yet compliance training programs still relied heavily on long modules and outdated formats.

Clients were beginning to push back.

They wanted training that employees would actually pay attention to. They wanted communication tools that reflected how people learned in the modern workplace. They wanted something that felt more relevant and less like a mandatory exercise.

Kirsten began experimenting with new ideas. She developed prototypes for whiteboard videos, visual training formats, and shorter learning modules that made compliance concepts easier to understand.

When she showed these ideas to clients, the response was immediate.

They wanted them.

But inside the company she worked for, there was little appetite for change. Established vendors had long contracts, predictable revenue, and little incentive to disrupt their own products.

At some point, the situation became clear. The market was asking for something the industry was not prepared to deliver.

Leaving Security to Build Something Better

In 2015, Kirsten made the decision that defines many entrepreneurial journeys. She left her leadership role and founded Rethink Compliance.

The early days of the company were anything but glamorous. Like many founders, she relied on consulting work to fund the business while building its long-term vision. Her former employer hired her as a consultant, and several other projects provided financial stability while she developed Rethink’s core offerings.

At one point she was effectively running four professional engagements at the same time while trying to build the company.

The arrangement provided both income and valuable insight. It allowed Kirsten to test ideas about how compliance training could be created differently, without the overhead of a large development team.

Still, entrepreneurship brings moments that test even the most confident founders. During the company’s early years, several anticipated projects fell through unexpectedly. One client disappeared after a major layoff inside their company. Other opportunities simply did not materialize.

For a period of time, the business had almost no revenue.

Many founders describe this stage as the point where doubt becomes unavoidable. It is when the difference between having an idea and building a company becomes very real.

Yet Kirsten never seriously questioned the opportunity she had identified. Her confidence came from years of experience talking to clients who were asking for exactly the kind of solution she was building.

She believed the demand existed. The challenge was simply getting in front of the right people.

The Moment the Market Revealed Itself

A major turning point for Rethink Compliance came in 2018 when Kirsten and her colleague Patty decided to take a more proactive approach to business development.

They organized a series of visits to companies in several cities, reaching out to contacts and offering to share trends in compliance training and demonstrate their work.

What they heard during those meetings surprised them.

Many of the companies they spoke with were deeply dissatisfied with their existing vendors. Complaints about outdated technology, poor service, and lack of innovation surfaced in nearly every conversation.

Driving between meetings, Kirsten and Patty began to realize something they had not expected.

They had assumed Rethink would become a niche company that handled specialized projects for organizations already working with large vendors. Instead, it appeared that companies were actively looking for alternatives.

The entire market might be ready for change.

That realization transformed the company’s strategy. Rethink began building a full training library capable of competing directly with the established vendors that dominated the industry.

Building a Company with a Different Structure

As the company began to grow, Kirsten made another unconventional decision about how to build her team.

Many startups begin by hiring junior employees and gradually promoting them into leadership roles. Kirsten did the opposite. She focused on recruiting experienced professionals who could operate at a high level immediately and eventually build their own teams as the company expanded.

This approach required trust and collaboration, but it allowed the company to scale more effectively. By bringing in leaders who already understood the industry, Rethink was able to maintain a high standard of expertise while expanding its services.

Today the company employs around thirty professionals and serves more than 125 organizations worldwide. Its training materials reach millions of employees across global companies.

A Culture Built on Honesty and Respect

While the growth of Rethink Compliance is significant, Kirsten often speaks just as passionately about the company’s culture.

From the beginning, she wanted to create an organization where people were treated as individuals rather than interchangeable employees. Many early team members were professionals returning to the workforce after raising children, and flexibility became a defining part of the company’s identity.

Rethink also emphasizes direct communication. One of the company’s core values encourages people to speak honestly and address issues openly.

In Kirsten’s view, strong teams are not built by avoiding difficult conversations but by handling them with respect and transparency. Disagreement is inevitable in any organization doing meaningful work. What matters is how those disagreements are managed.

The Lesson at the Center of the Journey

When Kirsten reflects on building Rethink Compliance, one lesson stands out more than any other.

Most of the things founders believe they must know before starting a business are actually learnable along the way.

Running a company requires understanding finance, marketing, operations, leadership, and strategy. Very few entrepreneurs begin with expertise in all of these areas. What separates those who succeed is not perfect knowledge but the willingness to learn continuously and adapt as the business grows.

For Kirsten, the most important realization has been that more is possible than most people initially believe.

As she often reminds entrepreneurs, the companies, products, and systems that surround us were built by people who were not necessarily smarter than anyone else. They simply decided to try.

In that sense, the story of Rethink Compliance is not just about one company disrupting an industry. It is about what happens when someone decides that the better solution they imagine is worth building.

And sometimes, that decision starts with a simple question.

Why not us?