Behind the Leadership

Cyndi Whelpley, SR/WA, R/W - RAC

Cyndi Whelpley’s IRWA journey began in 1992 when a Caltrans coworker invited her to her very first Chapter meeting. Starting as a quiet observer, Cyndi soon found herself at the heart of Chapter activities—especially after chairing the Golf Tournament in 2000, an experience she describes as both fun and foundational. That volunteer role sparked her ongoing commitment, leading her to take on increasing leadership responsibilities, ultimately joining Chapter leadership. For Cyndi, it’s all about community: “Building and nurturing relationships has always been a core value of mine. IRWA gave me the chance to lean in, contribute, and grow alongside dedicated, like-minded professionals.”

As the current International Vice President, Cyndi’s responsibilities span strategic planning, supporting regional leaders, collaborating with committees, and guiding key IRWA initiatives. What she enjoys most is connecting with members across chapters—hearing their stories, brainstorming new ideas, and translating those ideas into programs that make a real difference. “Leadership isn’t just about the title,” she says, “it’s about listening, showing up, and serving a community that cares.”

Cyndi encourages everyone to step up and get involved—whether by chairing an event, joining a committee, or simply volunteering. “You don’t have to know everything—just be willing to engage and offer what you can. If you’ve ever thought, ‘I wonder if I could do that,’ the answer is YES!”

Her advice to emerging professionals in the right of way field is clear: integrity and ethics must guide every decision, no matter how small. “Always do the right thing, especially when no one’s watching. Your reputation is built on the unseen moments. Be fair, transparent, and keep your promises—people may not remember every detail, but they will remember how you made them feel.”

Of all her IRWA experiences, the 2008 Education Conference in Dallas stands out. For Cyndi, it was a turning point, revealing the scope and passion of the right of way profession and resulting in lifelong friendships and a broader professional network.

When she’s not leading or mentoring, Cyndi’s adventurous side takes center stage: she’s parachuted over Hawaiian pineapple fields, is a self-professed Disney roller coaster enthusiast, and loves balancing thrill-seeking with relaxing beach days and good music.

Asked what IRWA chapter she’d visit if given the chance, Cyndi enthusiastically chooses Chapter 14 in Washington, D.C.—a city that inspired her early dreams of public service and remains close to her heart through her Navy Reserve service and time working at the Pentagon. She’s looking forward to visiting the area later this month to teach with fellow IRWA member Krista Chambers.

Cyndi’s message to fellow members: “You don’t have to be in Congress to create meaningful change. Every role matters. Lean into leadership, stay curious, and never underestimate the power of showing up. Big change often begins with small, intentional steps—and when those steps are taken by people who genuinely care, their impact can be far greater than imagined.”