Ashly Rieman – Milestone Contractors

For most drivers, Interstate 69 is a simple stretch of highway connecting cities across Indiana. For Ashly Rieman, project manager at Milestone Contractors, it represents years of coordination, collaboration, and determination. The I-69 Finish Line project—connecting Indianapolis to Martinsville, Bloomington, and Evansville—is the newest interstate in the state and completing it has been a generational milestone for Indiana’s infrastructure.

“It’s a big deal to have this project completed,” Rieman says. “There were people at the ribbon-cutting ceremony who had been talking about this road for more than seventy-five years.”

When the final section opened in 2024, the event drew three sitting or former governors, countless state officials, and construction crews who had spent years bringing the vision to life. For Rieman, who joined Milestone Contractors nearly eight years ago after earning her degree in Construction Engineering Management Technology from Purdue University, Indianapolis, the celebration was a personal and professional high point.

“I started this job in 2021,” she explains. “At the time, I was transitioning from multiple smaller projects to this massive joint venture with Walsh Construction. For the past three years, this was my sole focus.”

Navigating a generational project

Headquartered in Indiana and part of The Heritage Group, Milestone Contractors is a fully integrated heavy construction company specializing in highway, bridge, asphalt and concrete paving, and site development.

Known for prioritizing safety, innovation, and teamwork, the company has built a reputation as one of the Midwest’s most reliable contractors. Its collaborative culture encourages ideas from all levels of the organization, ensuring the best solutions rise to the top regardless of job title or tenure.

That inclusive mindset proved invaluable on I-69, a project with enormous scope and complexity. The Finish Line extended Indiana’s interstate network, filling the gap between existing sections to create a continuous highway from Indianapolis to Evansville. Once complete, the route cut commute times in half for thousands of residents and opened new economic corridors across southern Indiana.

The work itself was demanding. Over several years, Rieman and her colleagues coordinated across multiple engineering firms, managed intricate staging plans, and implemented countless design adjustments to meet both state specifications and real-world field conditions. Flexibility was crucial.

“There were so many stakeholders, from the state of Indiana to local municipalities and utility partners,” she says. “Our job was to make sure everyone’s needs were heard while still keeping the project on track and, above all, safe.”

Milestone’s culture of open communication aligned perfectly with Rieman’s leadership style. A believer in servant leadership, she focuses on empowering her team members, valuing every contribution, and fostering an environment where questions and ideas are always welcome. That approach not only builds trust but also helps avoid misunderstandings that can lead to safety incidents or schedule delays.

“Safety is our No. 1 priority,” she says. “To get there, you have to make sure people feel comfortable speaking up and sharing what they see in the field. That’s how we find solutions before they become problems.”

Mentoring the next generation

While the I-69 Finish Line might mark a significant chapter in her professional career, Rieman’s influence extends beyond the job site. As chair of the Indiana branch of Women of Asphalt, a national organization dedicated to advancing and supporting women in the paving industry, she’s working to make construction a more visible and welcoming career path for young women.

“I’m definitely seeing an increase in interest from women, but we still have to get out there and tell people they can do these jobs,” Rieman says. “You can be a part of a big project and see the result in something tangible—that’s what makes construction so rewarding.”

Through Women of Asphalt, she helps coordinate outreach efforts to schools, career fairs, and community events. One of her favorite initiatives is the Golden Shovel Competition, a high-school event that lets students operate equipment and compete in hands-on construction challenges. The program introduces teens to the industry long before they begin thinking seriously about college or career tracks.

Rieman also leads mentorship programs that connect industry veterans with newcomers, ensuring knowledge is shared across generations.

“We’re reaching out not just to field workers but to people in administrative or support roles too,” she says. “Construction has so many paths, and there’s a place for everyone.”

Her outreach stems from her own unexpected journey into construction. Originally pursuing a different degree, she found herself at a crossroads after running out of money for tuition. Looking for a practical path forward, she researched top-paying majors and discovered construction engineering. The field combined her childhood fascination with building—sparked by designing theater sets in high school—with the challenge and satisfaction of tangible results.

“I fell in love with it,” she says. “I love asphalt. I’m passionate about what we do.”

Lessons in leadership and perseverance

Outside of work, Rieman continues to build—literally. In 2020, she bought a 1935 Cape Cod-style home and has spent years teaching herself how to renovate it, tackling everything from refinishing floors to reframing walls. The process mirrors her professional life: persistent, curious, and hands-on.

“I’ve had to fend for myself for most of my life,” she says. “Nobody gave me anything. I had to work for it.”

That self-reliance has become a cornerstone of her leadership. On the I-69 project, she often juggled long days, complex logistics, and tight deadlines, but she never lost sight of the bigger picture—the people who would one day drive those roads or the colleagues who made it possible.

During one stretch of the project, she brought a young acquaintance to the site. The girl was fascinated by the equipment and the crew’s energy.

“Two years later, she’s still talking about that experience,” Rieman says with a laugh. “She might not end up in construction—she’s thinking about nursing—but she saw what it means to build something real.”

That’s the kind of exposure Rieman hopes more young people will have. She regularly visits middle and high schools to discuss career opportunities in the trades, emphasizing that the work is not only meaningful but also well compensated and supported by strong unions.

“The trade workers are paid well, and the unions take care of them,” she says. “You just have to pique people’s interest early. Once they see what this industry can offer, a lot of them get hooked.”

Her advice to students—and to anyone considering a career shift—is simple: find something you’re passionate about and commit to it fully.

“If you’re not passionate about what you’re doing, you’re not going to make it,” she says.

Paving the future

As the final punch-list items wrap up on I-69, Rieman is already thinking about what comes next. Smaller jobs will follow—roundabouts, resurfacing, and other infrastructure improvements—but the lessons from I-69 will shape her work for years to come. The project tested every facet of her leadership and strengthened her belief in collaboration, safety, and mentorship.

For Milestone Contractors, projects like I-69 exemplify the company’s broader mission: to build safely, inclusively, and with integrity. That mission extends beyond the pavement, into classrooms, community events, and future generations of builders.

Rieman plans to continue growing with Milestone and with the Women of Asphalt network, ensuring that the next wave of engineers and project managers—especially women—see construction not as a closed door but as an open invitation.

“We’re trying to do a lot with supporting programs in schools,” she says. “You must start them young. Once they see the possibilities, they realize this isn’t just a job. It’s a career where you can make a real impact.”

For Rieman, that impact is already visible—in miles of new highway, in the safety and pride of her crews, and in the spark she sees in the eyes of the next generation discovering construction for the first time.