Joel Vandendriessche belongs to a rare club in today’s workforce. While frequent job changes and nonlinear career paths have become the norm, Vandendriessche has done the opposite, spending 40 years building a distinguished career at Old Republic Surety Company (ORS).
The surety veteran joined ORS when it was formed in 1986 through the consolidation of three surety companies under Old Republic International Corporation. Four decades later, he has witnessed and helped shape the company’s evolution from a small, regionally focused operation with limited contract bonding capacity to a national surety leader supporting bonds in excess of $100 million and serving more than 4,800 independent insurance agencies.
“I feel very fortunate and fulfilled,” says Vandendriessche. “When you work for a company for that long, you really feel like you’re part of something larger than yourself. You get to see the people evolve, the challenges, the strengths — all of it.”
He calls ORS’s 40th anniversary a “great accomplishment,” crediting Old Republic International for providing the foundation, financial strength and independence that have allowed ORS to grow steadily and sustainably.
“There are very few companies that stay consistent and stable enough to support a 40-year career,” he notes. “When you work somewhere from age 22 to age 63, there’s a lot of change, both in the individual and the company. It takes tolerance and patience on both sides to make it work. In many ways, that’s a metaphor for life.”
A career defined by change
Vandendriessche’s four decades at ORS have been anything but static. He spent his early years with the company in Kansas City before moving to Des Moines, Atlanta and finally Milwaukee, where he lives today.
As a self‑described “small‑town guy,” he says he “loved the opportunity” to travel, gain perspective and better understand both the business and the world around him.
Over the years, Vandendriessche transitioned through a wide variety of roles and responsibilities, ultimately landing in his current role of Vice President – Underwriting in June, 2004, with a focus on contract bonds.
“With all the shifting duties and constant industry change, it’s been like working at 10 different companies,” he says. "Some people have the desire and temperament for assembly line for 40 years. That’s not me, and that’s not what ORS wanted me to be.”
Instead, he describes ORS as a company of “intrapreneurs” who are given opportunities for advancement, growth, change and challenges — or as Vandendriessche puts it, “a lot of complicated fun.”
40 years of change
Over his career, Vandendriessche has seen the business world shift from a slow, paper‑heavy environment to one driven by speed, automation and data.
He has watched ORS take these changes in stride. He recalls the company’s introduction of fax machines in the late 1980s, describing it as a “big upgrade” that marked a new era of faster, more responsive service. That momentum continued with email, mobile technology and, more recently, the adoption of artificial intelligence (AI), automation and data analytics for enhanced efficiency, underwriting and service delivery.
“Just like society, business has shifted toward an expectation of instantaneous responses,” he explains. In surety today, that translates into online systems that allow agents to input a few details and, particularly in commercial surety, immediately issue bonds, which is a dramatic departure from the manual processes of the past.
ORS has also evolved operationally during Vandendriessche’s long career. Over the past decade, the company moved from a flatter organizational structure to a more layered regional model led by vice presidents, strengthening management, consistency and training across the board.
“I’ve also seen a shift toward online marketing and business sourcing,” he adds. “We operate through the independent agency and broker channel. The changes they’re making and how they’re adapting to a more online environment instead of the old-school model of close, community-based relationships represent a big shift in the surety industry.”
A trusted surety partner
Amid all this change, Vandendriessche stresses that some things have remained constant. Chief among them are the company’s core values of integrity, respect and its unwavering commitment to strong underwriting. The latter, he says, is critical in such a complex industry that blends finance, accounting, legal issues, construction dynamics and risk analysis.
The surety market moves in cycles, often mirroring broader economic and construction trends. Currently, the market is soft, with abundant capacity and competitive pricing. In these conditions, strong underwriting can be overlooked.
“But one big event or economic downturn sorts things out quickly,” Vandendriessche warns. “In good times, anybody can stay in business. In tough times, only disciplined underwriting prevails.”
That discipline is one of ORS’s greatest strengths, he claims.
Strong underwriting, he says, begins with deep financial analysis — understanding whether ORS is prepared to bond a contractor — but continues with relationship‑driven work that some surety providers shortcut in soft markets.
“We meet contractors with our agents and brokers and ask tough questions about related companies, key people, longevity and succession planning,” Vandendriessche says. “Those granular details matter. They help us understand the contractor and prepare them for long-term success.”
Good contractors, he adds, appreciate the rigor: “They see us as a partner, an integral part of their business. It comes down to integrity, professionalism and taking the time to truly know each other.”
What comes next?
“I get to retire,” Vandendriessche says with a grin, though not immediately. When the time comes, he says he’ll step away prepared, supported by ORS’s retirement benefits, and reassured that his knowledge, responsibilities and values have been passed on to the next generation.
Looking ahead, he predicts continued growth in the surety industry, supported by government infrastructure spending and increased bonding demand. But he also cautions that an economic downturn will come and when it does, many professionals will experience it for the first time.
“Seventy‑five percent of the industry hasn’t seen a real downturn. When tough times hit, they reshape your approach to underwriting. It will create opportunities for those who truly understand the fundamentals.” And that, he says, is why surety remains such an exciting career path.
“It’s a vibrant, challenging industry with a great future,” he says. “AI and new technologies aren’t replacing people in surety; they’re enhancing what we can accomplish. Here at ORS, you’re treated as an individual, and you get to be an intrapreneur. You’re not just a cog in a machine; you get to use your skills, make decisions and shape your career while adding real value.”
After 40 years, Vandendriessche still speaks with the enthusiasm of someone who chose the right place and the right profession.
“I’ve been very fortunate,” he says. “If you’re looking for a fun, thriving, energetic and challenging situation, this is the industry and this is the company for sure.”
