Titan of Tech - Jayme Fishman of Avalara

Jayme Fishman didn't initially set out to be a tech executive. His career began in a courtroom, not a boardroom - suited up as a litigator, where he argued cases and navigated legal complexities.

However, it didn't take long before a perceptive boss saw something else in him.

"You look like a businessperson trapped in a lawyer's body," the mentor told him at the time. That exact moment is what sparked a career pivot that would eventually position Fishman at the helm of one of the most innovative companies in global tax compliance.

As EVP, Chief Strategy and Product Officer at Avalara, Fishman leads with a rare blend of legal intellect, operational grit, and visionary instinct - skills honed across decades in software, consultancy, and regulatory strategy.

His path is anything but conventional, and that's exactly what makes his leadership so compelling.

"I never looked back, and that was over 25 years ago," he told TechDay during a recent interview.

Fishman's relationship with Avalara long predates his official start in 2020.

In the early 2000s, while working at a company operating in the same space, he encountered Avalara's founding team and was instantly struck by their radically different approach.

"They were born in the cloud, they made tax tech accessible, and they weren't afraid to be bold - literally, showing up to trade shows in bright orange gear and tiki hut booths while everyone else wore grey suits," he said.

That early admiration led to a partnership, but it would take him another 16 years - and a world of experience - before he officially joined the company.

"I was on my own journey," he said, speaking of the delay. "Working with clients globally, managing software portfolios, sharpening my skills - I think it all made me better for Avalara in the long run."

That self-awareness fuels his current role, where he toggles between high-level strategy and hands-on execution. "I spend a lot of time looking at green projects and asking, 'Are they really green?'" he said. "Because green is the most dangerous status - it hides risk."

Now leading a global team of over 150, Fishman is focused on scaling Avalara's influence at a time when the tax landscape is undergoing seismic shifts.

At the centre of this transformation is artificial intelligence, which Avalara has embedded into its DNA long before AI became a boardroom buzzword.

"It's reshaping how we support customers, how we process documents, even how we think," he said. "It's not just innovation - it's reinvention."

Another key focus is e-invoicing, where Fishman sees regulatory urgency aligning with technical opportunity.

With governments worldwide racing to digitise and monitor transactions to combat tax loss, Avalara is helping businesses stay ahead by connecting them to a unified global platform—one that enables seamless compliance across borders, systems, and industries. "It's the most transformative thing we've seen in decades," he said.

Fishman credits Avalara's success to its foundational philosophy: make complex things feel simple. "We're democratising capabilities that used to be locked away in enterprise-level projects," he said.

That starts with over 1,400 signed partner integrations ensuring that nearly any business system can plug into Avalara's platform - and continues through intuitive onboarding and AI-powered automation.

"We've built something where businesses can be up and running in five minutes," he said. "That's an incredible achievement."

Under Fishman's watch, Avalara keeps up with a fast-moving regulatory environment – for instance, helping businesses cope with waves of new tariffs with its cross-border compliance products and services – and the company is also anticipating the next wave.

Whether it's new mandates, market shifts, or technological breakthroughs, his team is constantly scanning the horizon, betting boldly and building fast. "We want to be part of every transaction in the world," he said. "That means embracing automation, being obsessive about customer experience, and never standing still."

Competition, he believes, only makes the company stronger. "It keeps you sharp, pushes you to improve. Without it, my job would be pretty boring," he laughs.

From small startups to sprawling multinationals, Fishman has worked across the spectrum - and those experiences have taught him that details matter, scale is earned, and agility is everything.

At Avalara, he's found a place to "put all of it into action."

"My head's on Zoom all day, pinging across time zones, but it's all worth it," he said. "Because we're building something meaningful. Something that works beautifully for customers around the world."