The title and escrow industry is built on trust, precision, and hard work. For nearly 40 years, Cheryl Baillis has operated as a quiet architect of change and innovation within this demanding field, reshaping it from the shadows of giants like Old Republic, First American, and Zillow. She’s led thousands, forged enduring relationships, and tackled challenges that would daunt most, yet she recoils at the idea of self-promotion. “I’m terrible at talking about myself,” she confesses with a laugh, her discomfort palpable during a rare interview from her home. She’s a dynamo on panels, unraveling industry complexities with ease, but ask her to recount her own triumphs, and she’d rather champion her team.
This conversation pushed her to reveal a tale of defiance, camaraderie, and a fire to turn “you can’t” into “just watch” a career so remarkable it begs to be celebrated, even if her humility keeps her from the stage.
It all started in a lively Cleveland office, pulsing with teamwork, where manila folders and recipe cards tracked files in a pre-digital haze. Cheryl, a college student scraping by to pay tuition, landed an escrow assistant job at a small title company. The outdated tools and manual processes, like push button check imprinters, sparked her curiosity. “There’s got to be a better way,” she insisted, her knack for tackling complex challenges like decoding an escape room already evident. But colleagues waved her off. “You can’t rethink that system,” they would say. Fueled by their doubts, Cheryl didn’t just prove them wrong; she rocketed to escrow officer, setting the stage for a career that would redefine the industry.
Her mentor, Augie Pachetti, a Cleveland title legend, gave her a mantra: “Do your best to make it right, because it’s our job to protect the consumer.” Those words became her anchor, guiding her to tie every transaction to a family’s dream. She joined a larger firm, juggling customer service and title examination, burning the midnight oil to master her craft. But the 1990s economic downturn threw a curveball, forcing her to pivot to international law firms, where she grappled with mergers, acquisitions and contracts. The shift was daunting, yet it honed her puzzle solving instincts, a skill she deems essential for success. “You need a curious, inquisitive and strategic mind for this work,” she says, “one that thrives on solving tough problems.”
When the title industry rebounded, Cheryl charged back, but the stakes were higher. At Old Republic, she teamed with visionary Joe Casa to pioneer a centralized operation for refinance and home equity products - a daring leap from local norms. It was the first of many forward-thinking opportunities that established her reputation for driving transformation and innovation within organizations. Her career led her to multiple opportunities at large organizations, where she continually faced new challenges. But her motto, “Let’s show them what we’ve got,” drove her leadership at each stop over the next 20 years.
Over those years Baillis has led thousands, and amidst all of it, has learned to always prioritize the person over the priorities. “The two things people want are to be valued and to add value,” she says warmly, her leadership rooted in listening and empowering. She’d meet teams, absorb their struggles, and ignite their potential, turning shaky operations into powerhouses. Her roles were vast: streamlining global systems, driving revenue, optimizing operations and implementing innovative solutions. And most importantly, not losing sight of the client’s experience along the way. Each step tested her, as market shifts and corporate demands loomed. She met every challenge with a vow to leave the industry stronger, a promise tied to her Ohio farm roots, where her parents drilled in a work ethic that never quits.
Now at Flueid, Baillis has risen from board member to Chief Relationship Officer, a title she insists on over “Revenue.” “Relationships are this industry’s pulse,” she says, her passion fierce, a mindset she’s embraced fully in this role. She ensures Flueid’s decision engine platform, not only empowers title companies however also serves as a broader solution to help the real estate industry better understand the importance of insuring risk and protecting consumers. “I’ve long advocated for innovation and technology to improve efficiency - without compromising the vital role of title insurance. Today, that balance is more important than ever. Her push for collaboration mirrors a career spent bridging gaps and bringing the industry together with forward-thinking solutions.
Looking back, Baillis reflects on the warmth of those manila folder days, when recipe cards and shared purpose knit her team like kin. “That camaraderie is what sets this industry apart,” she says, her gaze softening. She treasures the colleagues, even rivals, who’ve answered her calls over decades, their wisdom fueling her rise. But as she reflects, those folders and cards take on deeper meaning - not mere tools, but emblems of a collective spirit that drove her to contribute, connect, transform. “They sparked it all,” she says softly. “They remind me why I’m here: to make a difference, one relationship and transaction at a time.” Baillis may shun the spotlight, but her legacy, forged through relationships, puzzle solving grit, and a refusal to bow to “you can’t” burns bright, a testament to a woman who’s changed an industry while lifting everyone around her.