What Founders Get Wrong About GTM Efforts


This podcast episode explores why companies should move beyond a one-size-fits-all “mono strategy” in outbound marketing. We explore the significant benefits of deep market segmentation and tailored outreach, illustrating how these strategies ensure more personalized and effective communication. 

This conversation between Kellen Casebeer (Founder of The Deal Lab) and Collin Stewart highlights the strategic matrix approach. It shows how it operationalizes segmentation to adapt campaigns based on real-time feedback, enhancing engagement and conversion. 

This approach aligns marketing efforts with current market realities and emphasizes strategic agility and depth, which are crucial for sustained success in dynamic business environments.

The Danger of the Mono Strategy

One key issue highlighted in this episode is the tendency towards a ‘mono strategy,’ where companies adopt a one-size-fits-all approach. This strategy often lacks empathy and specificity, leading to generic messaging that fails to resonate with any particular audience segment.

The Importance of Deep Market Segmentation

Kellen advocates for detailed segmentation rather than treating the market as homogeneous. This involves breaking the market into finely tuned segments with tailored strategies that address specific needs and characteristics. 

Such granularity allows for more personalized and effective outreach, moving beyond superficial characteristics to understand deeper needs and pain points.

Operationalizing Segmentation for Precision in Outreach

Kellen explains the process of operationalizing segmentation for effective go-to-market strategies. This starts with identifying different market segments and understanding the unique aspects of each. 

For example, the approach to a company with a revenue of $100 million would differ significantly from a smaller enterprise. He stresses the importance of not just segmenting for the sake of it but doing so to enhance how messages are tailored to each group.

Segmentation as a Bridge Between Sales and Marketing

The conversation also touches on the convergence of sales development methodologies and traditional marketing tactics. Segmentation in outbound sales is likened to creating highly defined audiences in paid advertising, where messages are crafted based on detailed demographic and behavioral data. This strategy ensures that each interaction is relevant, increasing the likelihood of engagement and conversion.

Balancing Granularity with Execution

While deep segmentation is critical, Casebeer acknowledges the challenge of balancing detail with practical execution. There’s a risk of becoming too theoretical, which can delay direct action. He emphasizes ‘speed to value,’ ensuring that while segments are meticulously defined, the strategy remains agile enough to adapt based on real-time feedback and results. 

This approach helps identify ‘hotspots’ of resonance and areas of underperformance, continually refining the segmentation model based on actual outcomes.


Embracing Market Signals

Collin and Kellen also touch on the complexities of achieving genuine product-market fit and the often misunderstood concept of message-market fit. Their discussion underscores a critical lesson for founders and marketing leaders: the importance of interpreting market feedback as an opportunity to refine and adapt their offerings.

Collin shared an anecdote about a customer tempted by a competitor’s promise of significantly more meetings for a lower cost. This scenario illustrates a common pitfall in the SaaS industry: chasing seemingly lucrative offers that sound too good to be true. Collin’s advice to “see if it’s real” reflects a broader philosophy of skepticism and verification that businesses should adopt.

The Importance of Resonance with Market Needs

Kellen highlights the importance of securing meetings and ensuring these interactions resonate with the market’s needs. He introduces the concept of “message-market fit,” which he distinguishes from product-market fit. 

According to Casebeer, it’s not enough for a product to meet technical requirements; its messaging must also align with what the market genuinely desires and responds to. This alignment is crucial, especially when traditional metrics suggest a high close rate upon engaging customers. If broader outreach efforts like cold emails fail to generate interest, it suggests a disconnect not with the product’s quality but how it’s being presented to an unengaged audience.

Collin reiterates the importance of fit, whether it’s about the product fitting into a market or a message fitting into a market strategy. 

He likens it to a child’s puzzle, where sometimes a small angle adjustment can make all the difference. This analogy powerfully reminds us that achieving market fit isn’t always about major overhauls; sometimes, minor tweaks can significantly enhance how potential customers perceive and embrace a product.

Potential Pitfalls of Marketing Channels

The discussion also touches on the potential pitfalls of different marketing channels, particularly in how they align with specific audiences. For example, the challenge of engaging engineers through cold emails exemplifies the concept of “market-channel fit,” further complicating the process of effectively reaching and resonating with target segments.

By weaving together insights from real-world experiences and strategic advice, Collin and Kellen’s conversation provides valuable lessons for businesses striving to improve their market engagement strategies. They emphasize the importance of embracing market feedback, even when it challenges cherished assumptions about a product’s market fit. This openness to learning and adapting is portrayed not as a concession but a strategic advantage in the ever-evolving marketplace.

Refining Market Engagement with the Strategic Matrix Approach

Unlocking the secrets to successful market engagement often involves peering into the complex web of customer segments, personas, and their unique pains or needs. A well-structured strategic matrix can be a game-changer, offering a systematic approach to understanding and targeting potential customers.

The strategic matrix‘s core is integrating native market insights with in-depth primary research. This dual-layered analysis helps businesses avoid common pitfalls and craft strategies that resonate authentically with their audience. 

Starting at the market level, businesses categorize their audience broadly, such as differentiating between B2B SaaS companies and manufacturing firms. From there, the matrix dives deeper into specific segments and personas, tailoring strategies to address varied customer backgrounds and needs.

One critical aspect of this approach is identifying and leveraging “angles.” Customers might express specific concerns or frustrations even in casual settings like a morning conversation at home. This level of detail allows businesses to craft messages and solutions that speak directly to the heart of the customer’s daily challenges.

The matrix guides the development of targeted campaigns by mapping out these elements (market, segment, personas, and pains). These campaigns might vary in form, from video analyses by a founder to detailed case studies or direct meeting requests. This specificity ensures that each campaign is highly tailored to the audience’s needs, increasing the likelihood of resonance and engagement.

How to Manage the Matrix

To manage this complex system, businesses often rely on tools like Excel to maintain an organized and accessible view of their strategic efforts. Campaigns are tracked by linking strategies directly under the relevant segment and persona in the matrix, providing a clear visual representation of ongoing and past marketing efforts. 

This structured approach helps visualize the strategies and evaluate their effectiveness, ensuring that the business isn’t merely throwing strategies at the wall to see what sticks but is making informed decisions based on real feedback and results.

The strategic matrix isn’t just a static tool; it’s dynamic, evolving with each campaign’s outcomes. It requires constant refinement and iteration, allowing businesses to pivot quickly based on real-time feedback. If a particular angle or message isn’t resonating, it can be adjusted or abandoned in favor of more promising strategies.


Effective Outbound Marketing: Beyond Immediate Results

Thorough preparation, especially in market segmentation and domain warming, is critical to long-term success in outbound marketing. Quick-launch strategies, like acquiring expiring domains, can occasionally speed up this process but might bring unforeseen issues like poor deliverability due to potential negative reputations associated with these domains.

A carefully considered setup phase, which includes detailed segmentation and tailored messaging, is not a delay. It’s an investment. This preparation ensures that the messaging resonates deeply with the intended audience, increasing the likelihood of engagement.

Marketers need to manage client expectations from the beginning. Clients eager for immediate results may need to understand that these strategic investments in preparation are crucial for effective campaigns. Transparency about the processes involved and the reasons for their duration helps align client expectations with the campaign’s goals.

Furthermore, regular updates through outcome reports can give the marketer and the client insights into what strategies are working and which aren’t, allowing for timely adjustments. These reports should detail responses, engagements, and feedback from different market segments, thus informing future strategies.

Ultimately, the success of an outbound marketing campaign hinges on the balance between meticulous preparation and the ability to adapt strategies based on real-time feedback. This ensures that every step, from segmentation to messaging, is aligned with client expectations and market realities.


Embracing a nuanced approach to market segmentation allows businesses to connect more effectively with their target audiences, moving beyond generic strategies that often fall short. Companies can better align their offerings and needs by integrating in-depth market insights and continuously refining tactics based on actual outcomes. This strategic flexibility improves engagement and conversion rates and positions businesses to respond adeptly to market changes and opportunities.

Learn more about how The Deal Lab can optimize your outbound efforts with bespoke segmentation and precision targeting.

Discover how Predictable Revenue can transform your sales process through tailored outreach strategies. Explore our solutions.


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