Why Most Mid-Market Companies Fail at Marketing—And How to Fix It

Marketing Strategist Joseph Upton Offers a Bold Diagnosis and a Clear Path Forward for Businesses Between $1M and $100M

Chicago, IL, 7th May 2025, ZEX PR WIRE, According to Chicago-based marketing expert Joseph Upton, most mid-sized businesses are getting marketing wrong—and it’s costing them growth, customers, and long-term brand value. With 14 years of hands-on experience advising companies in the $1 million to $100 million revenue range, Upton says the issue isn’t lack of talent, technology, or even budget. The real culprit? A broken mindset around marketing itself.

“Too many companies in the mid-market treat marketing like a series of disconnected tactics,” Upton explains. “They invest in paid ads, redesign their website, or start posting on social media—without a clear strategy guiding those actions. It’s like building a house without a blueprint.”

This opinion, though provocative, is backed by Upton’s extensive track record as a growth advisor to founders, CEOs, and investors. Formerly Chief Growth Officer at a private equity-backed firm, Upton now runs a portfolio of ventures focused on marketing strategy and advisory services. His insights are grounded in hundreds of engagements across both B2B and B2C markets.

The Mid-Market Marketing Trap: Why It’s So Easy to Get It Wrong

Mid-market companies face a unique challenge: they’re too big to operate on hustle alone, but often not big enough to attract the kind of senior marketing leadership or strategy resources available at enterprise level.

“The result is what I call ‘Frankenstein marketing,’” Upton says. “You’ve got a patchwork of efforts—an agency running ads, someone in-house doing emails, maybe a freelancer on social media—but no unifying strategy that ties it all to business outcomes.”

This scattered approach leads to what Upton refers to as “activity without impact”—a high volume of marketing work that delivers low ROI and unclear metrics. Many of these businesses operate with outdated assumptions, often copying what larger competitors are doing without understanding the context or scale.

The Four Key Symptoms of a Broken Marketing Strategy

According to Upton, there are four key symptoms that indicate a marketing strategy is not working as it should for mid-market companies:

1. Tactic-Driven Marketing Instead of Strategy-Driven Marketing
   

    “Marketing is not a set of isolated tasks. If your marketing plan consists of a list of tactics—like ‘run ads,’ ‘send emails,’ ‘post on social media’—you’re missing the point. Strategy must come first,” Upton explains. A successful marketing plan begins with a clear understanding of the company’s goals, target audience, and how marketing will support those objectives.

2. A Lack of Clear Customer Positioning and Narrative
   

    Mid-market companies often fail to articulate a compelling brand story or clear positioning. “Your brand’s message should answer two important questions: Who is it for, and why should they care? Without a compelling narrative, even the best tactical campaigns will fall flat,” says Upton.

3. Silos Within Teams and Vendors
   

    Another symptom of a broken strategy is the siloing of marketing efforts. When different vendors, agencies, or departments operate independently, it results in disjointed messaging, inconsistent execution, and missed opportunities for cross-collaboration. “Marketing should be a seamless operation, with clear communication between all players,” Upton advises.

4. Misaligned Metrics
   

    The fourth red flag for Upton is a mismatch between the marketing team’s focus and the company’s core business goals. “If your marketing team is focused on vanity metrics like impressions, clicks, or likes, but your CEO cares about revenue and leads, you have a problem,” Upton warns. Metrics should always be tied directly to business outcomes, ensuring that every marketing dollar spent contributes to the company’s growth.

The Problem with Viewing Marketing as a Cost, Not an Investment

At the heart of the issue, Upton believes, is a widespread misconception about the role of marketing within mid-market companies. Too many business leaders see marketing as a discretionary cost rather than a critical growth lever.

“Marketing isn’t an expense—it’s an investment,” Upton says. “But it’s only an investment if approached with the same strategic thinking that goes into decisions about hiring, capital, or operations. Marketing has to be treated as a growth engine, not as a department that simply makes ads or sends out emails.”

To illustrate this point, Upton draws a parallel to other core business functions. “If you think about it, CFOs don’t just oversee finance—they guide investment strategy. Similarly, COOs don’t just handle logistics—they’re responsible for optimizing operations for long-term efficiency. Marketing needs the same level of strategic depth and clarity. It’s not just about running campaigns—it’s about creating lasting brand equity and driving revenue growth.”

Upton’s Proven Framework: Strategic Marketing That Actually Works

So, how can mid-market companies break free from the “Frankenstein marketing” trap and build a strategy that leads to real business growth? Upton offers a five-step framework to help businesses of all sizes implement strategic marketing that actually works:

1. Positioning First
   

    Upton emphasizes that positioning is the cornerstone of any marketing strategy. “The first question every business needs to answer is: Who are we for, and what makes us different? Don’t move forward with any marketing campaign until you’ve nailed down your position in the market.”

2. Set Clear, Actionable Strategic Goals

    Clear goals are essential to ensuring that marketing efforts support the broader business objectives. These goals should include revenue targets, brand positioning goals, and customer acquisition objectives. “Everything marketing does should be aligned with the bigger business goals,” Upton advises.

3. Create Message-Market Fit

    The key to a successful marketing campaign is ensuring that your messaging resonates deeply with your target audience. Upton stresses that message-market fit is not just about delivering the right message—it’s about ensuring that message directly addresses the real needs and challenges of your audience.

4. Integrated Marketing Execution

    Marketing should not be a fragmented collection of tactics. Upton’s framework emphasizes integration across all marketing activities. “Break down the silos between in-house teams, agencies, and consultants. Marketing is a system, not a collection of isolated parts,” he says. Unified execution leads to a more powerful and cohesive brand presence.

5. Measure What Matters

    Finally, Upton stresses the importance of measurement. “Without clear metrics, there’s no way to know what’s working and what’s not. Every marketing activity should be measurable, and that data should inform future decisions,” Upton says. This approach allows businesses to optimize campaigns in real-time and make informed decisions about resource allocation.

The Bottom Line: Don’t Wait Until It’s Too Late

Upton concludes with a call to action for mid-market business leaders: “The best time to build a strategic marketing function is before you need it. Don’t wait until your revenue growth plateaus or your competition outpaces you. By then, it’s too late to catch up.”

Marketing isn’t a one-time investment or a series of random campaigns—it’s a process that requires constant refinement, adaptation, and commitment. By adopting the right mindset and applying strategic principles, mid-market companies can avoid the common pitfalls and create a marketing engine that drives both short-term wins and long-term growth.

About Joseph Upton

Joseph Upton is a strategic marketing consultant based in Chicago with 14 years of experience helping mid-market companies accelerate growth and build strong, lasting brands. His firm works with startups, private equity-backed ventures, and established businesses, offering marketing strategy, growth consulting, and advisory services. Upton’s expertise spans B2B and B2C sectors, and he is recognized for helping businesses scale efficiently and effectively.

He resides in Chicago with his wife Emily, a UX designer, and their two children. Outside of his work, Upton enjoys photography, travel, and immersing himself in new cultures around the world.

Media Contact:
Upton Marketing Consultancy
Marketing Consultant and Growth Partner
www.josephupton.com
316 N Blue Island Ave, Chicago, IL 60607, United States