- Susan Stewart
- 2 days ago
- 5 min read
Ann Riley Allard – Finding the Joy in Every Chapter.
This week’s Her.Collective Spotlight shines on a woman whose career is as inspiring as it is impactful — Ann Riley Allard, of Old Republic Title, who has spent nearly three decades shaping, teaching, and uplifting others in the title industry.
Rooted in Real Estate and Resilience.
Ann’s journey in title insurance began long before she ever joined the industry. What started as an after-school job at a law office during high school quickly became a calling — one that intertwined her love of law, people, and property.
Mentored by a generous attorney, Ann learned every aspect of the business: from title examination to client relations and lender coordination. One summer, she worked on a fascinating project for the Department of Natural Resources, tracing titles for abandoned railroad tracks that would later become walking trails and bike paths across Massachusetts.
“I spent my days in courthouses and my evenings soaking in Cape Cod’s charm — beaches, gift shops, and baseball games,” she recalls. “That experience sparked my lifelong love for both the work and the world of real estate.”
After gaining years of legal experience, Ann took an entrepreneurial leap, co-founding a real estate paralegal business that supported law firms across the region. “It was an innovative idea at the time,” she says. “And it taught me how to listen, solve problems, and build something from the ground up.”
When the 2008 financial crisis hit, Ann — like so many — faced uncertainty. But she used that season to serve, volunteering for a presidential campaign where she applied her sales and leadership skills in a whole new arena. The experience reignited her passion for connecting with people and eventually led her to Old Republic Title, where she’s thrived since 2009.
Today, Ann serves in Agency Educational Training and Business Development, where she designs and delivers impactful training programs, mentorship initiatives, and business growth strategies — helping agents and professionals nationwide rise to their full potential.
Women Who Inspire.
In a time when women leaders in title were few and far between, one woman made an unforgettable impact on Ann — Annie (AG), the only female associate at a law firm where Ann once worked.
“She was brilliant, tireless, and courageous,” Ann remembers. “Even when she faced resistance, she advocated for herself and pursued partnership until she became a Probate Court Judge. Watching her navigate her career with conviction taught me that women can break barriers, and that we must also reach back to lift others as we climb.”
Challenges that Shape and Strengthen.
Ann’s career hasn’t been without challenges. One of her toughest lessons came early, learning to manage former colleagues who were also friends. “I wish I’d recognized that dynamic sooner and sought advice from someone who’d walked that path,” she reflects. “It taught me the importance of boundaries, humility, and grace in leadership.”
Words of Wisdom for Women Entering Title.
Ann’s advice for the next generation of title women is both heartfelt and practical:
Find a mentor. Someone who will guide, challenge, and champion you.
Use your voice. Speak up and take risks — even when it feels uncomfortable.
Explore your path. If one area doesn’t light you up, there’s another waiting for you.
Protect your balance. “There are no real emergencies in title,” she reminds. “Save your energy for the true ones — the family moments that matter most.”
The Heart of Her ‘Why.’
At her core, Ann is driven by a deep sense of integrity and purpose. “My why has always been about finishing what I start, honoring commitments, and helping others grow,” she says.
“There’s nothing more rewarding than watching someone find their confidence, especially when they didn’t see it in themselves yet.”
Finding Strength in Her Roots.
Ann credits much of her strength to her mother, a woman who survived polio in the 1950s and went on to live a full, determined life. “She learned to walk again with crutches and braces and even drove a car with hand controls,” Ann shares. “Her resilience taught me that strength doesn’t need to be loud. It just needs to be steady.”
Joy, Family, and the Power of a Village.
Ann’s world is filled with family, laughter, and love. She’s one of four siblings — “the best gift my parents ever gave me” — and a proud mother of two grown children. “My daughter and I grew up together,” she smiles. “When my son arrived eight years later, I was more grounded and ready for the ride.”
And now, there’s Lilly, her granddaughter and self-proclaimed “treasure of my soul.” “Her joy is contagious,” Ann says. “She reminds me daily of what matters most: love, laughter, and leaving a legacy that matters.”
Surprises, Songs, and Standing Tall.
Outside of work, Ann is always up for a challenge — whether it’s tackling a new skill or conquering a literal leap of faith. At a leadership retreat, she once climbed a 50-foot pole, stood at the top, and jumped to grab a trapeze bar. “I’m not an athlete,” she laughs, “but that moment taught me that if I stay focused, I can do hard things.”
Her first concert? The Beatles, live at Suffolk Downs. “It was pure magic,” she says. “And yes — I still remember every lyric!”
The Legacy She Hopes to Leave.
Ann’s professional mantra is simple but profound: Find the joy!
“I’ve learned that joy is a choice — and it changes everything,” she says. “Whether it’s celebrating a client win, guiding a new hire, or solving a tough problem, I try to find the joy in every moment.”
When asked about her legacy, her response captures her spirit perfectly:
“I hope to be remembered as someone who showed up for others — who encouraged, included, and believed in what’s possible. If I’ve helped even one woman find her voice or take a risk she might not have otherwise, then I’ve done something that matters.”
Final Thoughts for the Women of Her.Collective.
Ann leaves us with words that encapsulate her grace, strength, and optimism,
“To all the women in title: you belong here. Your voice, your ideas, your leadership — they matter. Don’t wait for permission to rise. Lift others as you climb. Lead with courage, character, and joy. That’s how we change this industry — and the lives within it.”
Ann Riley Allard is proof that true leadership isn’t about titles, it’s about impact. Through every chapter of her journey, she’s led with wisdom, humor, and heart, reminding us that in both business and life, the real success lies in finding the joy along the way.
*Connect with Ann here: aallard@OldRepublicTitle.com I LinkedIn
