ESSG Blog: News & Insights on Workforce Management

Riding the Cycles: Winning New Clients and Keeping the Job Orders Coming

Written by Mike Lillemo | Oct 22, 2026, 6:28:35 PM

After more than two decades of owning staffing agencies, I've seen our industry go through a lot of changes. But I don't believe we've ever seen staffing evolve at the pace we're experiencing today.

Technology, automation, and now AI are changing how we recruit, communicate, and do business. COVID accelerated that change, pushing staffing toward a more transactional, commodity-driven business with less personal interaction between staffing companies, their clients, and candidates. While technology has made us more efficient, I believe we've also lost some of the personal relationships that made this industry successful in the first place.

Today, staffing companies have better CRMs, recruiting software, LinkedIn, automated emails, and AI tools that can accomplish in minutes what used to take hours. I'm a strong believer in technology and the efficiencies it brings, but we can't forget that staffing is, and always will be, a relationship-driven business. Technology should give us more time to build relationships, not replace them.

I've always believed that if you're simply a vendor, you're replaceable. If you're a true partner, you become part of your customer's success. That doesn't happen through automated emails or AI. It happens by picking up the phone, getting in front of people, asking questions, understanding their business, and doing what you say you're going to do.

The fundamentals that worked for me 20 years ago still work today. The tools may have changed, but the importance of relationships hasn't. And most importantly, you have to keep building those relationships and selling, even when business gets busy.

The Best Time to Win New Clients Is Before You Need the Business

One of the biggest mistakes I see staffing companies make is treating sales like something you turn on and off.

When business slows down, everybody suddenly focuses on sales. Then a big customer calls with 30 openings, everyone gets busy, and sales activity gets pushed aside. Six months later, that customer cuts its workforce, loses a contract, or brings in another staffing company. Suddenly, you're scrambling again.

I've lived through that cycle more times than I can count. My advice is to keep selling, even when you're busy. A healthy book of business gives you the freedom to be selective about the opportunities you pursue and walk away from accounts that aren’t a fit.

Owners need to be part of that effort, too. You can hire great salespeople, but nobody knows your business, your story, or what your team can deliver better than you do.

Quit Selling Staffing, Sell a Solution to Their Problems

Those conversations become more valuable when you stop leading with everything your staffing company does. Most staffing companies pitch pretty much the same thing. We have great recruiters, customer service, and candidates. Prospects have heard it before.

What they really want to know is whether you understand the problem they're trying to solve. Maybe turnover is hurting production. They could be struggling to staff a second shift, or supervisors might be spending hours interviewing instead of managing their teams.

Finding that problem should come first. Ask where the business is growing, which positions cause the biggest headaches, and what happens when those jobs stay open. Find out what they wish their current staffing partner did better. Then listen.

The more I understood about a customer's business, the easier it became to figure out where we could make the biggest difference.

Protect Your Value Instead of Racing to the Bottom

That understanding also changes the conversation around what your service is worth. There will always be somebody willing to do the work cheaper. You don't have to chase them to the bottom.

Staffing companies have real costs, and an account can generate a lot of revenue without generating much profit. Know your economics and the point where an account stops making business sense. Sometimes saying no is the right decision.

Price will always be part of the conversation. Give customers other reasons to keep working with you by showing them the impact you're having on their operation.

The First Job Order Is Where the Real Sale Begins

Of course, earning the business is only the beginning. The real test starts when that customer hands you the first job order.

A client might have 50 openings and give you five. Those five should become some of the most important openings in your office because the client is watching what happens next.

Keep them informed and share what you're seeing. If a position is difficult to fill, explain what's getting in the way. Address any issues early and work through them with the customer.

Staffing is rarely perfect. What matters is how you communicate, respond, and help clients move forward. Do that consistently, and those first five openings can turn into 10, 20, or eventually all 50.

Don’t Overlook the Customers You Already Have

Everybody wants new clients. But some of the best opportunities I found came from accounts we were already servicing.

Stay curious about what's happening inside your customers' businesses. Visit when there isn't a problem to solve or an invoice to collect. Ask what the next six months look like. Are they adding a shift, opening another location, or preparing for new business? Understanding where they're headed helps you anticipate what they'll need and where the relationship can grow.

Whenever you can, have those conversations face-to-face. Walk through the facility, meet the supervisors, and see the jobs you're asking your recruiters to fill. An hour inside a customer's operation can teach you a lot about their business.

Consistency Wins in Sales

Most prospects aren't going to need you the first time you interact with or call them. Three months from now, they may land a new contract or suddenly need 40 people. When that happens, you want your name to be one they remember.

That takes consistency. I'd rather have a salesperson make 20 quality calls every day than make 100 calls a day for a week and disappear.

Give people a reason to pay attention when you reach out. Share what you're seeing with wages, applicants, or the labor market. Bring them information they can use. Owners need to make sure that activity is happening, too. A CRM can help track it. Clear expectations and accountability keep the sales process moving.

Keep Riding the Cycles

There are going to be good years and difficult years in staffing. Customers grow and shrink, companies get bought, management changes, and industries shift. You can't control when those things happen, but you can control how prepared your business is when they do.

Keep building relationships when business is good. Stay close to your customers. Know the problems you're solving and the value you bring. When someone gives you an opportunity, make the most of it.

I've seen plenty of sales tools and strategies come and go over the years. The fundamentals haven't changed nearly as much. It's pretty simple; you just have to keep at it.

That's how you keep riding the cycles, winning new clients, and keeping the job orders coming.

At ESSG, I work with staffing agency owners every day who are navigating these same challenges. If you want to talk through what you're seeing in your business or where you're trying to grow, get in touch with our team.