Holmes Lilley – Chartwell Staffing Solutions

Putting the title on his story

When Holmes Lilley became executive vice president and general counsel at Chartwell Staffing Solutions in 2016, after “the longest job interview of my life,” he inherited a department that was spending well into seven figures on legal expenses.

Even for a $350 million company, Lilley knew such outlays were unsustainable. Through a combination of tech innovation and staff realignment, within two years he’d helped transform the department into a lean, efficient machine.

Holmes Lilley – Chartwell Staffing Solutions Vanguard Law Magazine

His efforts were so appreciated, in fact, that Chartwell saw fit to give Lilley a reward: a promotion to CEO.

“When you’re a general counsel, you wake up every day thinking about the various legal and regulatory problems and issues you have to solve that day,” says Lilley, who assumed his new post in late 2018. “Now, I wake up thinking about taking care of 12,000 employees. So the scope is a bit different.”

It’s a leap few attorneys get the chance to take. Then again, Lilley’s career—and his life—seem to have always been about bucking trends.

Finding his way

His journey began in a two-bedroom house on a dirt road in “Middle of Nowhere, North Carolina,” with a single mom who often worked three jobs just to put food on the table. When the work wasn’t enough, the family relied on welfare.

With the help of a family friend, Lilley was able to attend prep school in Lynchburg, Virginia, where he cultivated a love of reading—and plenty of connections.Holmes Lilley – Chartwell Staffing Solutions Vanguard Law Magazine

“I always felt like I met the right people at the right time,” Lilley reflects. “It’s sort of been a through-line in my life.”

One of those connections came during his final year at the University of Mississippi, where Lilley was about to graduate with a degree in English. Unsure of his next step, Lilley began talking with the uncle of a former boarding-school classmate, who also happened to be an Ole Miss alum—and a practicing lawyer.

On the advice of his newfound mentor, Lilley decided to give law school a try, enrolling in Elon University School of Law. After earning his J.D. in 2009, he joined the North Carolina firm of Karen McKeithen Schaede, PLLC, where, over the next four years, he focused on issues ranging from corporate health care litigation to M&A.

In 2012, serendipity struck again. After concluding a presentation focused on health care litigation, Lilley was approached by the medical director for HMS, a health care claims integrity company. They were looking for attorneys, he said, and wanted Lilley to join the team.

Rung by rung

Lilley spent four years at HMS, representing the company at federal administrative hearings, working on complex contracts and providing time-sensitive research for all manner of litigation. When Chartwell came calling in 2016, the decision wasn’t an easy one—for either side.

“I think the interview took six months start to finish,” Lilley recalls with a laugh. “Ultimately I felt I was ready to take that next step, to be a full-fledged general counsel with a seat at the business table. It was the right time—and the right place.”

There was, however, one major red flag: The company was incurring millions a year in legal costs, owing to not enough management and over reliance on outside counsel.

Lilley’s first move was to implement new software that automated much of the billing process. It also helped trim expenses by creating rules stipulating that any bill older than 90 days would be reduced by a set amount.

More important still, the software provides in-depth insights into a firm’s billing practices, giving Lilley and his team the information necessary to leverage more competitive rates.

“One thing everyone kind of takes for granted is that firms have set fees. Well, those can be negotiated,” Lilley explains. “So if you can talk them down on the hourly rate, while promising them more work based on what you’ve learned about their firm, that’s something a lot of firms are willing to do.”

By 2018, Chartwell had reduced its legal outlays by more than 70 percent. While far from the only reason for Lilley’s eventual promotion, the accomplishments underscored a knack for bolstering the bottom line.


As CEO, Lilley hopes to capitalize on Chartwell’s recent growth, which saw the company leap from $50 million in earnings to over a $350 million in less than three years.

With U.S. unemployment at near record lows, that means looking to places like South America, where Chartwell’s offerings—temporary staffing, direct hire and temp-to-hire services and more—are seen as a bridge between the region’s huge workforce and its growing economies.

Holmes Lilley – Chartwell Staffing Solutions Vanguard Law Magazine

Still, Lilley says the lessons he learned as a general counsel are never far from his mind. With 36 offices in 13 U.S. states—each with their own rules and regulations—managing Chartwell’s compliance efforts remains a priority.

To strengthen the company’s posture, Lilley is working on crafting compliance “playbooks” based on laws currently in place in highly regulated states like California, Chartwell’s largest revenue generator and home of some of the country’s strictest employment and commerce regulations.

“The logic is that, if we’re compliant in California, we’ll likely be compliant everywhere else,” Lilley explains. “That’s saved us a lot of time having to research individual states and crafting playbooks tailored specifically to those laws.”

And while the legal business juggling act is one he’ll always embrace, Lilley says his tenure will be defined by a hands-off approach—giving Chartwell’s departments leeway to work, and grow, on their own.

Indeed, when it comes to finding success, it’s the only formula he’s ever known.

“I think I’ve always been able to envision what’s ahead and work around whatever road blocks arise,” Lilley says. “Life will throw a lot your way, and so will business. You just have to have the right people around you. And I feel Chartwell has that.”

Published on: February 19, 2019


Showcase your feature on your website with a custom “As Featured in Vanguard” badge that links directly to your article!

Copy and paste this script into your page coding (ideally right before the closing tag) where you want to display our review banner.


It was a great honor to be featured in Vanguard Law. Working with every member of the team, from the initial interview with Erin Clark, through production with Victor Martins, writing the article with Taryn Plumb and creating the final content with Dave Gushee, was a true pleasure. Everyone was very professional, enthusiastic and supportive, and their creative approach and positive attitude clearly came through in the final product.
– Kevin C. Rakowski, Senior Vice President, Deputy General Counsel, Compliance with Radian Group Inc.
As promised in advance, my feature in Vanguard has increased my visibility within the profession and prompted more than a few people I have not communicated with recently to reconnect. One of the Italian law firms I have used in the past is now in the process of interviewing me for an article on their website and tweeting out the feature story. Activity and the number of people connecting with me on LinkedIn has soared, which is great. The Vanguard writers and editorial staff were great to work with—highly professional and made the effort to make the experience both fun and rewarding (they were also respectful of the time pressures and demands all lawyers face). I was very pleased with the experience and the final outcome. Needless to say, I have been very pleased. All in all working with Vanguard has been a very positive experience which generated good publicity for both Shawcor and myself. My sincere thanks.
– Tim Hutzul, General Counsel, ShawCor Ltd.
The piece highlighting my company, Bob Baker Enterprises, Inc., came out fabulous. Our company is in the new and used car sales and service industry. Everyone was great to work with and extremely professional. They produced a high-quality product and have provided expert assistance and guidance post-production of the article.
– Wade Poulson, General Counsel, Bob Baker Enterprises Inc.
I was honored to be the subject of an article. I enjoy reading Vanguard articles and seeing how other attorneys got to their positions and see their jobs. It's also interesting to see how different law firms partner with the subjects of the articles.
– Henry Marquard, in-house counsel, Stanley Consultants Inc.


Summer I 2024



  • * We’ll never share your email or info with anyone.
  • This field is for validation purposes and should be left unchanged.