If you had told Kathy Kwak after law school that she’d one day be the COO of a major title insurance company, she probably wouldn’t have believed you.
Like many in the industry, her path wasn’t a straight line—it was a winding road of opportunities, pivots, and unexpected lessons that eventually led her to Proper Title in Chicago.
She started in real estate law, then moved to Chicago Public Schools where she reviewed leases and property agreements. But the traditional legal path wasn’t enough. She wanted more—more impact, more opportunity, more challenge.
So, she took a leap.
"I saw a job posting on LinkedIn for a National Commercial Underwriting Counsel at First American, and I thought, ‘That sounds important. I like the title. I’ll apply.’”
She got the job. And just like that, she was in title insurance.
Over the next decade, she mastered commercial underwriting, agency management, and operations, gaining a deep understanding of how title companies work at every level. Now, as COO of Proper Title, she’s focused on scaling the business by increasing its market share of residential closings, expanding its national commercial services division and growing its construction escrow business.
The Industry’s Biggest Untapped Resource: Knowledge That’s Walking Out the Door
Kathy has big plans to help improve the title insurance industry, but she also sees a major problem: a knowledge gap that’s growing every day.
"If I could snap my fingers and change one thing, it would be to capture the knowledge of the retiring generation before it disappears.”
Title insurance is an industry built on deep, specialized knowledge—but too much of it is locked away in the minds of professionals who have spent 30, 40, even 50 years solving complex property issues, deciphering handwritten records, and making nuanced underwriting decisions.
And now?
"They’re retiring. Some are being forced out. And when they leave, all of that knowledge leaves with them."
Kathy believes the industry needs a structured way to document and transfer this expertise—not just for the sake of history, but to ensure the next generation has the tools to succeed.
“I’d love to have a dedicated person whose job is just to sit with these experts, document everything they know, and turn it into a real resource for future professionals,” she says. "Because if we don’t do it, we’re going to find ourselves scrambling to fill the gaps in 10, 20, 30 years."
Technology is Moving Fast—But People Still Matter
Kathy has seen major progress in automation, e-recording, and digital workflow management.
Software tools like SoftPro have transformed how her team operates, making workflows smoother and reducing manual errors. But while technology should make title work more efficient, she’s not convinced it can replace the human element entirely.
"A lot of people were hyped about blockchain replacing title a few years ago," she says. "But the reality is, title insurance isn’t just about recording transactions. It’s about solving problems when things go wrong."
Even the most advanced systems still rely on people to input, interpret, and verify data.
"What happens when there’s a break in the chain of title? When a deed is handwritten and hard to read? When a document needs to be recorded in a specific order? Tech alone can’t fix those things. We still need experts who understand the details.”
That’s why, even as AI-driven tools continue to evolve, Kathy believes the real future of title lies in a mix of technology and human expertise.
The Future of Title: More Collaboration, Less Competition
Looking ahead 20 to 30 years, Kathy hopes to see a cultural shift in how title companies, underwriters, and industry players work together.
"When I first started, everything was about competition. Underwriters were competing with each other. Title companies were competing with each other. No one was really collaborating.”
But during the pandemic, something changed.
"There was a moment when we were all in it together. Everyone was facing the same challenges, and for the first time, it felt like we were truly working as a unified industry."
She wants that cooperation to continue—not just in times of crisis, but as a long-term strategy for industry growth.
Instead of keeping solutions siloed, she envisions a future where:
- Title insurance professionals openly share best practices.
- Underwriters and agents collaborate on training and knowledge transfer.
- New talent is intentionally recruited and mentored—rather than ‘falling into’ the industry by accident.
We Have to Be More Intentional About Who We Hire
One of Kathy’s biggest priorities as a leader is ensuring that title insurance remains a career worth pursuing—not just a job people stumble into.
"I make a point to meet every single person we hire, no matter the role," she says.
For entry-level positions, she looks beyond traditional resumes.
"I’ve started hiring from the service industry, such as bartenders and restaurant workers, because they have something I can’t teach—hustle. I can train someone on title insurance. I can’t train someone on work ethic.”
For leadership positions, she’s just as intentional.
“These roles aren’t just about experience. They’re about alignment, culture, and long-term vision.”
She sees succession planning as a critical part of her job—not just filling positions today but building a leadership pipeline that ensures the company thrives decades from now.
"I’m already thinking 10 years ahead,” she says. "Because if we don’t plan for the future now, we’re going to wake up one day with no one ready to lead."
Final Thought: The Power of Relationships
For Kathy, the future of title isn’t just about technology, processes, or hiring strategies—it’s about relationships.
Whether it’s mentoring young professionals, collaborating with underwriters, or building strategic vendor partnerships, she believes the industry will thrive only if people commit to working together.
"I’ve never worked with a team as collaborative and dedicated as the one at Proper Title," she says. "And that’s what I hope to see more of across the industry—people putting aside competition and focusing on what’s best for the future of title as a whole."
Because in the end, the success of the industry won’t be measured by how many deals get closed—but by how well it adapts, innovates, and supports the people who make it all happen.
The Growth & Scale Report is published by CloseSimple, and explores strategies for growth and tools for scaling your title or escrow company. The report emphasizes the art of balancing growth and scale, with a focus on personal and organizational success stories. It aims to share insights from industry leaders who have navigated these challenges, providing a platform for broader conversations in the business landscape.
