Littlefield Agency

At Littlefield Agency, it’s a family affair—but all are welcome at the table. 

Founder David Littlefield opened the advertising company in 1980 out of his home in Stillwater, Oklahoma with just one client (Stubbs Sporting Goods) and one employee (himself). The business grew and evolved over the next four decades and in 2021 his son, Sam Littlefield, bought the successful organization from his father. 

These days, Littlefield Agency occupies a 10,000-square-foot office space in downtown Tulsa with approximately 25 employees and a nationwide clientele.

“My father started the agency because he knew brands back then would have a sales challenge, and he would be able to provide the solution they needed,” Sam Littlefield said. “Over forty-five years later we exist for that same situation, and our best clients are the ones who we get to help grow in the years to come. That’s what gets us out of bed every morning.”

Since the early 2000s, the CEO noted, the agency has specialized mostly in business-to-business manufacturers and financial institutions. They do work with some regional brands throughout the Midwest, but their national outbound marketing and sales strategies specifically fall within the B2B and FI universe. 

When it comes to concrete plans of action, Littlefield opined the agency’s superpower is lead generation. 

“Our creative and account teams work with our media and analytics department to help our clients find the most efficient use of their marketing dollars to provide the best results,” he said. “Our best-case scenario with a client is leveraging a full funnel media activation for their campaigns and constantly optimizing so they see the results they are looking for.”

An important lesson Littlefield said he’s learned over the years is to be as transparent as he can with clients. If a tough conversation needs to be had, he or one of his personnel now addresses it “up front and early.” 

In 2020, Littlefield Agency made the decision to work only with clients who are like-minded and value the services they bring to the table. Prospective clients also need to respect the employees—something Littlefield said hadn’t always been the case. 

“If a client is in any way rude or disrespectful to our team, we fire them very quickly,” he said. “I have zero tolerance for that.” 

Another important change which took place in 2020 was to eliminate the agency’s account planning department and start an in-house media and analytics offering instead. They’d been partnering with a media group in Dallas, Texas, for a decade, but felt it was time to bring lead generation back to their home base in Tulsa. 

Littlefield said that determination was “hands down” the most pivotal and best decision the company has made within the last decade. In 2022 they also merged their growing media and analytics departments. 

“These decisions are what help shape the future of our agency to make sure we evolve and stay relevant to continue our legacy on,” Littlefield said. 

It’s clear the company in its current iteration is thriving. On Littlefield Agency’s website, their homepage features a montage of grinning employees in festive holiday attire taking turns holding up an Ad Age award. The annual award ceremony is hosted by “Advertising Age” magazine and gives props to the best agencies in marketing in the nation. 

In 2024, 2025, and 2026, Littlefield Agency was voted one of the Best Places to Work by Ad Age, an industry accolade Littlefield is intensely proud of. 

“Culture is the most important thing to our agency, so the fact that we won this back-to-back-to-back speaks to how we are focusing on the right things as an agency,” he emphasized, adding that 2024 was the company’s biggest year in its storied 45-year history. 

Similarly to how one might commemorate a family member’s job success with a big party or an intimate dinner gathering at a fancy restaurant, Littlefield decided to up the ante and surprised his staff with something bigger and better. 

“We took the entire agency to Vegas for 24 hours to celebrate,” he said. “It’s probably the coolest thing we’ve ever done as a group and created memories that will last a lifetime.”