Navigating Entrepreneurship, Building Dimmo, and the Future of B2B Sales, with Troy Munson

Entrepreneurship isn’t just about taking leaps—it’s about calculated steps, continuous learning, and adapting to an ever-evolving landscape. In a recent conversation, Troy Munson, founder of Dimmo, shared his journey from being an account executive to building multiple successful ventures, including Dimmo—a platform revolutionizing the way buyers explore and evaluate tech. Here are the top takeaways from our conversation with Troy, highlighting key lessons in entrepreneurship, referrals, and the future of B2B sales.

Start Small, Think Big

Troy’s entrepreneurial journey began with side gigs that allowed him to test ideas and validate their potential while maintaining the safety of his AE role. His first two ventures scaled modestly, generating $15,000 and $50,000 in ARR before being sold to software companies. These experiences provided crucial lessons in growing a business while minimizing risk.

The tipping point came with Dimmo, an idea born from observing the friction buyers faced in evaluating software solutions. Inspired by a simple question—how could he pay off his mortgage without relying on his W2 income—Troy created Dimmo Days, events where companies could showcase their products and receive qualified leads. The success of these events highlighted an essential lesson: starting small and validating ideas early allows entrepreneurs to scale intentionally while mitigating risk.

Leverage Your Network

One of Troy’s most significant early advantages was his ability to tap into his LinkedIn network. With approximately 10,000 followers, he promoted Dimmo Days and drove initial registrations. Recognizing the need for broader reach, he partnered with Sarah Brazier, a sales influencer with a larger audience. This collaboration not only filled seats at Demo Days but also solidified LinkedIn as a cornerstone for building awareness and driving traffic.

Troy also underscored the power of referrals as an underutilized tool in sales. His advice? Don’t settle for vague asks like, “Do you know anyone who might be interested?” Instead, research the right person, craft a thoughtful introduction message, and make the process seamless for the referrer. By incorporating referrals into measurable KPIs, sales teams can consistently generate high-quality leads with minimal effort.

The Future of B2B Buying: Hybrid and Human-Centric

As Dimmo evolved, Troy observed a growing trend: buyers increasingly prefer platforms that enable self-service research and evaluation. He envisions a future where buyers can explore and compare tech solutions independently, engaging sellers only for complex or high-value transactions. Dimmo’s design reflects this shift, offering a centralized platform where buyers can view product demos, compare competitors, and make informed decisions—all without the need for lengthy sales cycles.

Despite advancements in AI and automation, Troy believes sales roles like enterprise account executives will remain essential. For complex deals requiring relationship-building and strategic alignment, human expertise will continue to play a critical role. Sellers who adapt to this hybrid model, focusing on educating and guiding buyers rather than simply pitching, will thrive in this new landscape.

Adaptability is Key

Entrepreneurship requires both vision and the ability to pivot when necessary. Troy shared a recent decision to shelve a major initiative for Dimmo: creating private communities where buyers could exchange insights about software. While promising, the project wasn’t aligned with Demo’s immediate goals of increasing traffic and revenue. This decision underscores an essential entrepreneurial skill: prioritizing initiatives that deliver the most value and revisiting others when the time is right.

Takeaways for Sellers and Entrepreneurs

Troy’s story is rich with practical lessons:

• Start small and validate: Side gigs can serve as a low-risk way to test and scale ideas.
• Build and use your network: Platforms like LinkedIn and well-executed referral strategies are invaluable for growth.
• Prepare for the hybrid future: Adapt to buyers’ preferences for self-service tools while maintaining human-centric expertise for high-value deals.
• Stay adaptable: Focus on initiatives that drive measurable results, and don’t be afraid to pivot when necessary.

Troy’s journey from AE to founder of Dimmo demonstrates the power of thoughtful action, leveraging networks, and staying adaptable. Whether you’re building your business or refining your go-to-market strategy, his insights offer a valuable roadmap.

For more lessons from Troy, follow him on LinkedIn and stay tuned for his upcoming podcast!

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