Women in Road Construction: Ebony Jennings' Legacy | Scaling Legends S2E2

Key Takeaways

• Legacy is a launchpad, not a crutch. Ebony inherited her grandfather’s asphalt company name and reputation, but she had to completely rebuild the operations, systems, and client base from the ground up.

• Women in construction face real structural barriers. From bonding requirements designed for established players to the informal networks that exclude women, the obstacles are systemic, not just cultural.

• Modernizing operations is non-negotiable for growth. Ebony replaced paper-based tracking with digital estimating, GPS fleet management, and automated scheduling, cutting overhead by over 30%.

• Government contracts can be a growth engine. Minority and woman-owned business certifications opened doors to municipal and state projects that provided steady revenue while building the company’s track record.

• Hiring culture matters more than hiring speed. Ebony built a crew that respected her leadership by being on-site, understanding the work, and never asking someone to do something she wouldn’t do herself.

• Strategic partnerships beat going it alone. Teaming with larger general contractors on joint ventures let Ebony’s company take on bigger projects while building capacity and credibility.

• Patience and persistence win contracts. Some of Ebony’s biggest wins came from relationships she built over 2-3 years of consistent follow-up and flawless execution on smaller jobs.

From Her Grandfather’s Hands to Hers: Ebony Jennings’ Asphalt Origin Story

There is a particular kind of weight that comes with carrying a family name in business. It is heavier when the business is in construction, heavier still when you are a woman, and heaviest of all when the person who built it is no longer there to guide you.

Ebony Jennings knows that weight. Her grandfather, Raymond Jennings Sr., started a small asphalt paving operation in the early 1980s in the Southeast. He ran crews, bid on municipal jobs, and built a reputation one parking lot, one subdivision road, one church driveway at a time. By the time Ebony was a teenager, “Jennings Paving” was a known name in three counties.

But like many family construction businesses, the company’s knowledge lived in one person’s head. When Raymond Sr. passed, the business didn’t transfer cleanly. Equipment was aging. Key employees left. Contracts lapsed. By the time Ebony decided to bring the company back, she wasn’t inheriting a going concern. She was inheriting a name and a pile of challenges.

“People told me I was crazy,” Ebony shares in this episode. “They said the name doesn’t mean anything if the trucks don’t run and the contracts aren’t signed. And they were right. But the name meant something to me. It meant my grandfather believed a Black family could build something permanent in this industry. I wasn’t going to let that die.”

The Reality for Women in Construction: Numbers Don’t Lie

The construction industry remains one of the most male-dominated sectors in the American economy. According to the Bureau of Labor Statistics, women make up roughly 11% of the construction workforce in 2026, and the vast majority of those roles are in office and administrative positions. On the field side, in the trades, running crews, operating heavy equipment, women represent less than 4% of workers.

Ownership is even more skewed. The National Association of Women in Construction (NAWIC) estimates that woman owned construction companies account for approximately 13% of all construction firms, but they capture less than 5% of total industry revenue. The gap between ownership count and revenue share tells a story: women-owned firms tend to be smaller, have less access to bonding and capital, and face steeper barriers to scaling.

Ebony ran headfirst into these realities. Her first major challenge wasn’t winning work. It was getting bonded.

“Bonding is the gatekeeper in construction,” she explains. “You need a surety bond to bid on most public work. But to get a bond, you need a track record, financial reserves, and usually a personal relationship with a bonding agent who believes in you. When you’re a young Black woman restarting a company, those doors don’t just open because you knock.”

She spent her first 18 months focused entirely on smaller private jobs, residential driveways, small commercial lots, anything that didn’t require bonding. She used the revenue to build financial statements, establish banking relationships, and create a paper trail that eventually got her bonded for her first $250,000 municipal job.

Modernizing a Legacy Construction Operation

One of the most compelling parts of Ebony’s story is how she approached modernization. Her grandfather ran the business the way most small contractors did in the 1980s and 1990s: estimates on paper, scheduling by phone call, accounting in a ledger book. That system worked when one person held all the relationships and all the knowledge.

Ebony knew that wouldn’t scale. And she knew that to compete for larger contracts, she needed systems that could demonstrate professionalism, accuracy, and capacity.

Her modernization playbook included several key moves:

Digital estimating and takeoff software. She invested in construction estimating software that allowed her to produce accurate, professional bids faster. This was a direct competitive advantage, as many small asphalt contractors were still doing manual takeoffs and sometimes underpricing jobs because of calculation errors.

GPS fleet management. Every truck in her fleet got GPS tracking. This wasn’t about surveillance. It was about efficiency. She could see where every vehicle was, optimize routing, track fuel consumption, and provide real-time updates to clients on delivery timing. For an asphalt business, where material temperature matters and timing is critical, this was a significant operational upgrade.

Project management software. She moved from phone-call scheduling to a proper project management system. Crews got digital work orders. Progress was tracked in real time. Clients could see project status without calling the office. This alone reduced her administrative overhead and freed up time she had been spending on coordination calls.

Financial systems and job costing. Perhaps the most important upgrade. Ebony implemented proper job costing so she could see profitability on every project, not just at the end of the year. This allowed her to identify which types of work were most profitable and which were eating margin. She discovered that certain small residential jobs were actually losing money when she accounted for mobilization costs, and she adjusted her pricing and targeting accordingly.

“My grandfather could hold all of this in his head,” Ebony says. “I respect that. But I can’t scale a company on one person’s memory. Systems let me grow beyond myself.”

Winning Major Contracts as a Minority and Woman-Owned Business

Ebony’s WBE (Woman Business Enterprise) and MBE (Minority Business Enterprise) certifications became strategic assets, but not in the way most people assume.

“People think you just get the certification and the work rolls in,” she says. “That’s not how it works. The certification gets you in the room. It gets you on the bid list. But you still have to be the best bid, or close to it, and you still have to execute flawlessly. The certification opens a door. You have to walk through it and deliver.”

Ebony used her certifications strategically. She targeted state DOT (Department of Transportation) projects that had DBE (Disadvantaged Business Enterprise) participation requirements. She positioned her company as a reliable subcontractor for larger general contractors who needed DBE partners to meet their compliance goals.

This was smart on multiple levels. First, it gave her access to larger projects than she could have won as a prime contractor. Second, it built relationships with established GCs who could mentor her on larger-scale operations. Third, it created a track record on big projects that eventually allowed her to bid as a prime contractor herself.

“I wasn’t too proud to be a sub,” Ebony shares. “Some people think being a subcontractor is somehow lesser. But I learned more working under experienced GCs than I ever could have on my own. And every project we completed added to our bonding capacity and our resume.”

Within three years, Ebony’s company went from doing residential driveways to paving municipal roads, school parking lots, and sections of state highway projects. Revenue grew from under $500,000 to over $3 million annually.

Building a Crew That Respects the Mission

Ask any contractor what their biggest challenge is, and most will say labor. Finding good people, keeping good people, building a crew culture that performs consistently. For a woman in construction leading field crews, this challenge has additional layers.

Ebony doesn’t sugarcoat it. “Some guys didn’t want to work for a woman. Period. I could tell in the first week. And I didn’t waste time trying to change their minds. I let them go and found people who wanted to be here.”

Her approach to crew building was deliberate:

She was on-site. Not every day on every job, but enough that her crews knew she understood the work. She could talk about compaction rates, asphalt mix temperatures, and grade tolerances. She wasn’t a paper owner. She was an operator who happened to also run the business.

She paid above market. Not excessively, but enough to attract experienced operators and laborers who had options. She paired competitive pay with consistent work schedules and respectful management, a combination that is surprisingly rare in the industry.

She promoted from within. Her two lead foremen both started as laborers. Promoting internally built loyalty and created a culture where people saw a future, not just a paycheck.

She invested in training. CDL training, equipment operation certifications, safety certifications. Every investment in her people’s skills was an investment in her company’s capacity and quality.

“My grandfather used to say, ‘Take care of your people and they’ll take care of your customers.’ That’s the one thing from the old business I kept exactly the same,” Ebony says.

How to Grow an Asphalt Company: Lessons from Ebony’s Playbook

For contractors listening to this episode and wondering how to grow an asphalt company, Ebony’s path offers a practical blueprint:

1. Start with what you can control. Don’t chase big contracts before you have the systems, equipment, and people to execute them. Build your foundation on smaller work that lets you refine processes and build cash reserves.

2. Get certified early. WBE, MBE, DBE, SBE, whatever certifications are available to you. The application process takes time, and the sooner you’re on bid lists, the sooner opportunities start flowing.

3. Invest in systems before you think you need them. The time to implement project management software, job costing, and fleet tracking is before you’re drowning in work, not after. Systems installed under pressure never work as well as systems implemented thoughtfully.

4. Build relationships with GCs. General contractors need reliable subcontractors. Be that reliable sub. Show up on time, hit your quality marks, and communicate proactively. These relationships become your pipeline to bigger opportunities.

5. Know your numbers cold. Understand your cost per ton placed, your mobilization costs, your equipment utilization rates. Contractors who guess at pricing either leave money on the table or take losses they don’t discover until it’s too late.

6. Protect your bonding capacity. Every completed project successfully builds your bonding capacity. Never take on a job that could blow up your bond if something goes wrong. Growth should be steady and manageable, not reckless.

7. Market your results, not your promises. Before and after photos, client testimonials, project case studies. Let your completed work sell your next job.

Breaking Barriers in the Construction Industry: What Still Needs to Change

Ebony is clear-eyed about the progress that has been made and the distance still to travel. Breaking barriers in the construction industry isn’t just about individual stories of success. It’s about changing systems that were never designed to include women or minorities.

“I celebrate every win,” she says. “But I also know that for every woman who makes it in this industry, there are ten who got pushed out. Not because they couldn’t do the work, but because the system made it too hard to even get started.”

She points to several systemic issues that still need addressing:

• Bonding requirements that effectively exclude new entrants without established financial histories

• Informal networking that happens at golf courses, hunting clubs, and industry events where women are often the only one in the room, if they’re invited at all

• Access to capital that remains disproportionately difficult for women and minority-owned construction firms

• Mentorship gaps where young women in construction don’t see role models who look like them in leadership positions

“I want to be the person I needed when I was starting,” Ebony says. “That’s why I talk about this stuff publicly. Not to complain, but to map the obstacles so the next woman coming through can navigate them faster.”

The Legacy Continues: What’s Next for Jennings Paving

Today, Jennings Paving operates a fleet of trucks, pavers, and rollers across a multi-state region. The company employs over 30 people and has completed projects for municipal governments, state DOTs, school districts, and commercial developers.

Ebony’s vision for the next five years includes expanding into concrete work, adding a materials testing division, and potentially acquiring a small asphalt plant to control material costs and supply chain timing.

“My grandfather started with one truck and a dream,” Ebony reflects. “I restarted with his name and my stubbornness. My kids are going to inherit a real company with real systems and real opportunity. That’s the construction legacy business I’m building.”

Frequently Asked Questions

How do women get started in the construction industry?

Start by identifying the specific trade or sector that interests you. Get certified through programs like NAWIC (National Association of Women in Construction), pursue relevant licenses for your state, and connect with mentorship programs. Many states have women-in-construction advocacy groups that provide training, networking, and business development resources. Consider starting as a subcontractor to build experience and a track record before pursuing larger prime contracts.

What certifications help a woman-owned construction company win more contracts?

The most valuable certifications are WBE (Woman Business Enterprise), DBE (Disadvantaged Business Enterprise), and SBE (Small Business Enterprise). These are recognized by federal, state, and local governments and open access to projects with diversity participation requirements. The SBA’s 8(a) program is also valuable for minority-owned firms. Each certification has its own application process and eligibility requirements, so start the paperwork early.

How profitable is an asphalt paving business?

Asphalt paving businesses typically operate on net margins of 5-15%, depending on the type of work, regional market conditions, and operational efficiency. Municipal and state DOT work tends to have tighter margins but more predictable volume. Commercial and private work can offer higher margins but is more competitive and seasonal. The key to profitability is accurate estimating, tight job costing, and efficient equipment utilization. Companies that own or lease modern equipment and invest in operator training tend to outperform those running older, less efficient fleets.

What’s the biggest challenge for family construction businesses trying to scale?

The most common challenge is the transition from owner-dependent operations to systems-dependent operations. Many family construction businesses rely on the founder’s personal relationships, knowledge, and work ethic. Scaling requires documenting processes, implementing technology, hiring management talent, and building a culture that can operate without the founder being involved in every decision. This transition is uncomfortable but necessary for any construction business that wants to grow beyond one or two crews.

How do you build bonding capacity as a new construction contractor?

Bonding capacity is built incrementally. Start with smaller bonded projects and complete them successfully. Maintain strong financial statements with good working capital ratios. Build a relationship with a surety agent or broker who specializes in construction. Be transparent about your financials and your growth plan. Many surety companies offer mentorship programs for emerging contractors. Each successfully completed bonded project increases your capacity for the next one.

Related Episodes and Articles

• S2E1: From Solo Contractor to Scaling Legend: The CEO Mindset Shifts

• Women in Construction: Breaking Through the Barriers That Still Exist in 2026

• How to Scale a Family Construction Business Without Losing Its Soul

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