From Freight Brokerage to Tech Startup: The Art of Authentic Marketing in a Volatile Industry
Nine years at one company is practically unheard of in today's job market. But for Jennie Ruiz, Head of Marketing at Transfix, those nine years represent something even more remarkable: a front-row seat to one of the freight industry's most dramatic transformations. What started as a marketing role at a traditional freight brokerage evolved into leading the marketing charge for an innovative freight tech company—complete with a company-wide pivot that would test every assumption about brand identity and authentic communication.
"I feel like I kind of grew up with the company," Ruiz reflects. "I spent all my 30s here, and I'm literally going to enter a new chapter with them in my 40s."
The Great Transformation: When Everything Changes Overnight
In June of last year, Transfix made a decision that would fundamentally alter its identity: the company divested its freight brokerage operations to NFI and pivoted entirely to the freight technology solutions they had been quietly developing for internal use. In an instant, a company known as one of the top three freight brokers in the country—mentioned alongside Uber Freight and Convoy—became a relatively unknown tech startup.
“We were listed with the top three as a top three freight broker in the country,” Ruiz explains. “You couldn’t hear Uber Freight, Convoy, or JB Hunt without Transfix. And then now we are retelling, or telling a new story in our livelihood.”
This transformation wasn’t just a business pivot—it was a complete reinvention of everything Ruiz had built as a marketer. Brand recognition, customer relationships, market positioning, even the fundamental value proposition had to be reconstructed from the ground up.
The Advantage of Battle-Tested Solutions
While the brand transformation presented challenges, Transfix’s new tech focus came with a significant advantage: their solutions weren’t theoretical. Every product they now offered to the market had been developed and refined through years of internal use serving major clients like Heineken and Unilever.
“All the tedious processes that we have to deal with, especially when it comes to RFPs, and having to reformat and spend sometimes weeks because one person is out and they have the only access to the spreadsheet—we thought, ‘This is really annoying. We don’t have the manpower to do this. How can we automate this?'” Ruiz describes.
This real-world testing created something rare in the freight technology space: solutions built by people who actually understood the pain points they were solving. The company’s pricing solution, in particular, represents what Ruiz calls their “secret weapon”—a system developed by people who are still with the company and have watched it evolve through multiple market cycles.
Navigating the Noise: Freight Fluencers and Information Overload
One of the most significant challenges facing freight industry marketing today isn’t competition—it’s information overload. The rise of what Ruiz coined “freight fluencers” has created a landscape where everyone seems to be an expert, and authentic voices struggle to break through.
“When you’re scrolling, you come across these long posts about how ‘this is where I think the market is going,'” Ruiz observes. “When you see it so frequently, you wonder, like, who are these people? Where are they coming from, and how can I trust what they’re saying?”
This phenomenon creates a particular challenge for freight companies, where buying strategies are highly specific to individual businesses. “When you’re a freight brokerage, your buying strategy is specific to your buying pattern. It’s not going to be the same as broker A to broker B.”
The New Normal: Embracing Volatility as Strategy
For freight industry professionals, discussions about returning to “normal” market conditions have become almost meaningless. As Ruiz points out, “How long have we been talking about the new normal? This concept of a new normal—we’ve been talking about it for like five years. Bro, this is your normal now.”
This acceptance of volatility as the default state has profound implications for marketing strategy. Instead of waiting for conditions to improve, successful companies are using uncertainty as a competitive advantage.
“You have to get risky in times like this,” Ruiz argues. “I’m not saying get 100% risky, but test the waters. See what works, see what doesn’t. And if you get a glimmer of hope that this is the right path, run in that direction.”
The Single Marketer Challenge: Creative Solutions Under Constraints
As Transfix scaled down from a 300-person freight brokerage to a lean tech startup, Ruiz found herself in a position familiar to many B2B marketers: running a one-person marketing operation. “I’m a one-man team,” she admits. “Kudos to anyone who’s running the one-man show, because I don’t know how y’all do it.”
This constraint forced creative solutions and strategic prioritization. Rather than trying to execute traditional marketing playbooks that require large teams, Ruiz focused on what she could do authentically and well: building genuine relationships through content and conversation.
Learning the Language: The Reverse Engineering Approach
One of the most creative solutions Ruiz developed was addressing her own industry knowledge gap. Coming from a finance background, she needed to quickly develop credibility in freight and logistics. Her solution was both ingenious and honest.
“We had a podcast called ‘The Transfix Take’—it was a weekly market update. I hosted it with Justin Mays, who is incredibly knowledgeable,” she explains. “It was wildly intimidating for me to take on the task of co-hosting with him.”
Her solution? “We recorded this not live. I backtracked my voice and my narration from his recording. So he would record the market update for me, then I would go in and figure out a question, so that when he gave a response, it was like he was responding to that.”
This approach allowed her to learn industry language and concepts while creating authentic-sounding content. After a full year of this reverse engineering approach, Ruiz felt confident enough to conduct live conversations. The strategy demonstrates the importance of authenticity over perfection—she found a way to learn publicly while still providing value to her audience.
The Podcast Strategy: Authentic Relationship Building at Scale
Ruiz’s podcast approach differs significantly from typical corporate strategies. “This is not, by any means, a commercial,” she emphasizes. “We can save that for the end, but it’s not going to be that throughout the whole show.”
The podcast, “Supply Chain Decoded,” serves multiple strategic purposes: community building, thought leadership, and authentic content creation. At its peak, “The Transfix Take” generated 7,000 listens per episode. Even after rebranding, “Supply Chain Decoded” maintains 1,000-2,000 downloads per episode—impressive numbers for a niche B2B audience.
Cross-Functional Collaboration: The New Marketing Reality
The lean startup environment forced closer collaboration between traditionally siloed departments. “We bring everyone to the table at every prospect meeting. You have sales team, you have the CEO. Everyone is involved in this process, because maybe there was something that we didn’t think about that we could put on our roadmap.”
This integration ensures that marketing insights directly influence product development, while product capabilities inform marketing messaging. The result is more authentic communication because the marketing team truly understands both product capabilities and customer needs.
The AI Integration Challenge: Tool vs. Crutch
Like many marketers, Ruiz grapples with AI’s role in content creation. She’s found success using AI for brainstorming and operational tasks while maintaining human control over strategic decisions.
“That’s when it’s a good brainstorming partner for me,” she explains. “What is the challenge here? What are the risks if we use this sort of messaging versus this messaging?”
However, she’s mindful of the risks: “I just get worried for myself that it’s a slippery slope of, ‘Oh, I’m always going to use this every time I need something,’ and now I can’t even use my own brain.”
Measuring Success: Beyond Vanity Metrics
Ruiz tracks podcast success through both quantitative and qualitative measures, but she prioritizes meaningful engagement over raw numbers. “I want to walk away from a show knowing that they are going to be able to use that for their own marketing material, and that it’s not a commercial but rather a passionate conversation.”
This approach reflects a broader shift in B2B marketing measurement. While download numbers and website traffic remain important, the focus has shifted to relationship quality and authentic engagement.
The Authenticity Imperative: Being Human in B2B
When asked for her key advice, Ruiz doesn’t hesitate: “You have to be authentic to who you are. If you’re dorky, own it. If you are a geek, own it. If you have a trucker’s mouth, own that shit.”
This philosophy extends beyond personal branding to corporate communication strategy. In an industry flooded with generic content and AI-generated posts, authenticity becomes a competitive differentiator.
“Have an opinion,” she continues, “because what’s worse than not being authentic is you’re just saying yes to everybody. You’re going with the flow. That’s boring.”
But she adds an important caveat: “Don’t be an asshole, because we all screenshot, we all share.”
The Secret Sauce: Authenticity in Action
Ruiz’s journey from freight brokerage marketer to tech startup marketing leader illustrates the broader evolution happening across B2B industries. Traditional boundaries between sectors are blurring, customer expectations are rising, and authentic communication has become essential for success.
The companies that thrive won’t be those with the biggest budgets or the most sophisticated technology. They’ll be the ones that maintain genuine connections with their communities, adapt quickly to changing conditions, and never lose sight of the human relationships that drive business success.
For marketers navigating similar transformations, Ruiz’s experience offers both inspiration and practical guidance. Success comes not from having perfect conditions or unlimited resources, but from embracing authenticity, building genuine relationships, and never stopping the learning process. The future belongs to marketers who can be genuinely human in an increasingly digital world.
FR8 Marketing Gurus
A podcast where freight, logistics, and supply chain leaders come to talk real marketing.
