Forager’s Chief Operating Officer on Starting a Company, Flawless Hauls, and Everything in Between

Every part of a business is important. Without Sales, you won’t have any customers. Without Product, you won’t have anything to sell those customers. Without Finance, who knows if your business is growing or burning through cash like there’s no tomorrow.

But, if you had to split hairs and identify a crucial piece of every single company, the one that’s always behind the scenes ensuring everything runs smoothly (and in the same direction), it’s Operations.

And, standing at the helm of Forager’s small, growing, and mighty cross-border operations, is one of Forager’s fearless leaders and co-founders: Chief Operating Officer Jessie Essman.



Entering the logistics game

A Highland Park native with a passion for cheese fries and community engagement, Essman originally planned to become a teacher in the Illinois public school system. “I went to a small school called Trinity International University where I got a teaching degree. It was what I always wanted to do, but when I graduated in 2011 there weren’t a lot of teaching jobs. The market was still really suffering from the 2008 recession.”

As she was job hunting, Essman got an unexpected phone call from old friend (and future Forager co-founder), Matt Silver. Was she interested in foregoing teaching and joining the world of…logistics? “Matt and I met in high school through a school trip and we kept in touch in college. He heard through the grapevine that I was looking for a job and gave me a call about an opportunity at Coyote Logistics. He said, ‘You’d be great at this. You’re so organized, you’re a master problem solver, this is what you should be doing.’”

Lucky for Silver, Essman was up for a new adventure. “I took the job, and I haven’t looked back!”

Jessie looking out the window

Jessie Essman, Forager’s Chief Operating Officer.


Mastering the operations ropes

Essman started out in a coordinator role on the brokerage floor at Coyote, but within nine months the organized self-starter was tapped for a variety of operations projects. She jumped in feet first.

“One of the most impactful projects I worked on was helping Coyote run their ISO-9001. It gave me a bird’s eye view of the entire organization. I learned how departments were organized, how they functionally operated, and how they collaborated and worked with one another. It was very helpful to have that framework of a well-run business with an employee base that loved their jobs and their company.”

From then on, Essman became an integral part of Coyote operations and delved even deeper into the inner workings of a massive, respected logistics company. “I worked on a variety of different operational functions while I was there. I did quality control, compliance, human resources processes. I even worked with engineering where I supported software releases. I did a little bit of everything with incredible depth.” Six years later, Essman helped run a mammoth bid for one of the company’s largest customers.  She hadn’t just learned the ropes, she’d mastered them.


Transforming business operations

After Coyote, Essman joined Stepan Company in Northbrook, Illinois as Project Manager of Business Transformations. “I had a dream job at Coyote, then I was recruited to my dream job at Stepan! I worked on project management for business transformations which are large projects sometimes with 100+ person project teams, multi-million-dollar endeavors, and huge stakeholder groups. They require expert project management, change control, and excellent communication. It was a phenomenal experience.”

Beyond hiring Essman to flex her full operational skill set, the company also wanted to sponsor her enrollment in an MBA program. “It was one of the reasons I joined Stepan. Not only were these projects exciting and complex, there were also opportunities for continued growth and development.”

And then Silver called again, this time with a dream opportunity.


Co-founding Forager

Silver and Essman had stayed in touch throughout their overlapping time at Coyote and beyond. “We’d been friends for years at this point, and we were always talking about our goals and visions, our successes and failures. We were logistics career buddies.” But when Silver called her, it wasn’t just to catch up. It was about starting a company.

“Forager didn’t even have a name at that point. Matt just had this burning idea about transforming cross-border shipping. I was hooked right away. I said, ‘You’re right, you’ve already started doing this, we can do this, I have so many ideas.’ And so we did. We started envisioning and creating Forager.”

Jessie writing on a whiteboard

A customer operations brainstorm with the team.

Essman’s home office in Northbrook is where the magical mayhem of start-ups began. “Matt and Jordan [Salins, co-founder and VP of Finance and Analytics] would trek up to the suburbs and we would crash in the office for hours over the weekend. We talked about how complex and expensive cross-borders shipping was. We discussed all the ways domestic shipping was failing businesses with cross-border supply chains. We started putting together a business plan and talking with vendors, and we quickly realized we were really onto something special.”


Building best-in-class operations

Two years, thousands of loads, and a lot of changes later, Forager is still transforming cross-border supply chains. The company has an array of investors, 65 team members, and a new all-remote workforce.

But whether it’s building a company from scratch or managing massive business changes, Essman is ready for it all. “My role as COO is to really elevate our operations. Right now, that means creating and maturing processes, then finding experts who can come in and take them over. I like to say we have all these ‘green shoots’ emerging right now. Instead of it being all-hands on deck like it was at the beginning, we have more and more people who can take what we’re building, see it to fruition, and expand.”

The three Forager founders

The three Forager founders: CEO Matt Silver, COO Jessie Essman, and VP of Finance & Analytics Jordan Salins

Operational diligence is crucial given the company’s fast growth. “Business operations are the heart of the company. What do all the departments do? How do they do it? Are those processes written down? What governance do we need in place? We don’t want to build a business where everything’s tribal knowledge. Information needs to be documented, referable, and teachable. That helps our team expand, provide the best service externally, and stay efficient and confident internally.”


Creating a flawless cross-border experience for customers

That internal attention to business operations is reflected in Forager’s customer operations, another major part of Essman’s role. “Our customer’s priority is to make the product that they sell, not to deal with the logistics of that product. We want to take that burden off their plate. I’m very proud of our team. We have a truly exceptional customer operating process. We take a magnifying glass to our customer’s supply chain. We assess their network, learn how their freight works, get into the tiny details about how they manage shipments.”

The goal of this intensive review? “It helps us better operate their freight and mitigate challenges. We want every Forager customer to have a flawless first load. We want them to see and feel from day one that we’re experts; that we’re serious and good at what we do. They can trust our technology, service, and expertise.”


Looking toward the future of Forager and cross-border

Between a growing team of start-up professionals and the latest release to SCOUT by Forager, Forager’s cross-border shipping portal, there’s a lot to be excited about at Forager. Essman is excited about it all, but especially the tech and talent. “Our product is amazing. It keeps me up at night in the best way, because our engineering team is doing a phenomenal job, and some of them have been working for Forager almost since we started the company. To see their growth and SCOUT’s growth, you realize how much more we can offer to customers in the future.”

Laptop with SCOUT screenshot

SCOUT by Forager, the only self-service cross-border shipping portal.

Essman is also happy to see so many new employees embrace Forager’s culture and the unique challenges and opportunities of start-ups. “Working at a start-up is difficult.  It requires someone who’s comfortable with ambiguity, someone who can be an independent self-starter. But the personal growth opportunity? Unparalleled. It’s great to have people who want that opportunity and who seize it.”


Making sure those “green shoots” keep growing

Essman and the rest of Forager plan to keep that momentum going, but that doesn’t necessarily mean customers and carriers will be hearing big news about its internal operations any time soon. “With operations, a lot of it is behind the curtain. If ops are doing a good job, if everything is working smoothly, then it’s silent. If something is broken, you feel it and see it immediately.”

For the record, Forager’s operations don’t break. “I’m proud of our team, of our company. We know we’re building something special and we treat each building block with care. Those green shoots are growing quickly, and we plan to keep it that way.”


Jessie on a couch

What can we say? She’s a boss.