Unlock Your Business’s Potential with Win-Loss Analysis

At Margo, we’re all about helping small business owners build marketing that works — and that means understanding what actually resonates with your customers. In our latest episode of Fluent in Marketing, I had the pleasure of chatting with Drew Giovannoli, founder of Buried Winds, an agency that specializes in win-loss and competitor analysis.

Drew’s story is packed with insight, but one thing stood out loud and clear: if you want your marketing to work, you need to talk to your customers — and listen.

Here are a few key takeaways from the episode that can help you use customer feedback to improve your marketing today:

Win-Loss Analysis Isn’t Just for the Big Guys

Most small businesses don’t think about win-loss analysis, but they should. Why did a prospect not choose you? Why did they? You probably have hunches, but talking directly to customers gives you actual answers—and those insights are gold when it comes to refining your offer, messaging, and targeting.

Try this: After a sales conversation (whether you close the deal or not), send a quick note and offer a small gift card in exchange for a 15-minute chat. Ask what stood out, what confused them, and who else they considered. You’ll be surprised how much people are willing to share.

Let the Customer Be the Voice in the Room

Drew talked about the power of sharing actual customer clips—those 20-30 second nuggets where someone says exactly what they liked or didn’t. When you share that kind of raw insight with your team or even just reflect on it yourself, it grounds your strategy in real experience instead of assumptions.

Pro tip: Use voice memos or video recordings (with permission!) and save them. They’re not only powerful for internal clarity—they can also become killer testimonials later on.

Feedback Isn’t One and Done

Customer insights shouldn’t be a one-time research project. Drew has shifted from thinking about win-loss as a single moment to viewing it as an ongoing tactic you can use throughout the entire customer journey—from sales pipeline to churn prevention.

Start small: Pick one touchpoint—like recent customers or lost leads—and build a repeatable process for reaching out and capturing what they experienced. Over time, layer in other stages like post-onboarding or canceled subscriptions.

Don’t Be Afraid to Ask

People will talk to you. You just have to ask—and sometimes incentivize. As Drew shared, people usually say yes because of one of four reasons: incentive, goodwill, guilt, or passion. So make it easy, offer something valuable in return, and show them you’re genuinely interested in their experience.

Consistency Beats Perfection

When it comes to turning those insights into action—whether through content, campaigns, or product changes—it doesn’t have to be perfect. Drew reminded us it’s better to be above average for a long time than exceptional once in a while. Keep showing up. Keep listening. Keep iterating.

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Final Thought

Whether you're a solopreneur or running a team, making time to understand why people buy—or don’t—can completely change your marketing. It helps you speak more clearly, build stronger relationships, and make smarter decisions.

At Margo, we believe small businesses deserve tools that bring clarity, not complexity. That’s why we’re building the marketing OS that helps you track your customer feedback, marketing performance, and growth—all in one place.

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About Drew Giovannoli

Drew Giovannoli is the founder of Buried Winds, an agency that helps B2B companies unlock competitive insights through strategic win-loss and customer research. A former VP of Marketing and seasoned product marketer, Drew’s experience spans scrappy startups to scale-stage tech companies like Bizarre Voice and Rev. He’s passionate about helping teams close the gap between what they think customers want—and what customers are actually saying. Through Buried Winds, Drew turns customer conversations into clear, actionable narratives that drive smarter decisions and stronger growth.

Connect with Drew: Buried Wins Website | Drew Giovannoli on LinkedIn