There’s a strange dichotomy in my relationship with sales. On one hand, I genuinely dislike being on the receiving end of a sales pitch. My internal skeptic kicks into high gear; I dissect arguments, poke holes in value propositions, and generally make myself a tough nut to crack.

Yet, on the other hand, I enjoy the art of selling. Some of my most formative professional experiences came during a college summer selling Cutco knives door-to-door. Against the odds, I became one of the top sellers in Texas that year, relishing the connection, the persuasion, and the satisfaction of closing a deal.

This duality has never been more apparent to me than now, as the founder and CEO of DemoHop. I’m building an enterprise solution, and the success of my company hinges on reaching B2B decision-makers. The irony? I’m trying to reach people who behave exactly as I did during my executive tenures at Target and UnitedHealth Group – which is to say, almost entirely unreachable.

The blissful inaccessibility of an executive

Looking back at my time as a tech executive, I unwittingly architected a near-impenetrable fortress against unsolicited outreach. My office phone? Purely decorative. All important calls came to my closely-guarded personal cell. Corporate email was a twice-a-day chore, a necessary evil quickly scanned and archived, while real work and communication happened in Slack or Microsoft Teams. Physical mail? It piled up in a distant mailroom, a relic of a bygone era I might sift through quarterly, if at all. I’d log into LinkedIn perhaps once a week for a cursory scroll, largely immune to its charms.

In short, I was a ghost in every marketers’ CRM database. The only predictable window of access was the handful of hours I might dedicate to walking an exhibition floor at a major industry conference each year. And honestly, I loved that “new world order.” It allowed for focus, minimizing distractions in a hyper-connected world.

The other side of the coin: selling in the new wilderness

Fast forward to today. As a founder, the landscape I once navigated with ease as a buyer now feels like an obstacle-laden Tough Mudder. It’s not just that executives are busy; the traditional avenues to reach them have crumbled or become prohibitively noisy.

Consider the old playbook versus today’s reality:

• Google Search: Once dominant, now eclipsed by ad-free AI chat.
• Display Ads: Routinely blocked, their B2B effectiveness has always been debatable.
• Email: Everyone’s drowning in volume so now largely ignored for internal Teams/Slack.
• TV Advertising: A B2B longshot, now further lost in B2C-centric streaming.
• YouTube Ads: Not shown to most execs due to ad-free premium subscriptions.
• Direct Mail: Only occasionally reaches the execs’ eyes, even more rarely in hybrid workplaces.
• Phone Calls: Office lines are ghosts; personal cells although findable are too intrusive.
• Yellow Pages: A moment of nostalgic silence for this relic.
• Events and Conferences: Still a key opportunity, though hybrid formats mean fewer attend in person.
• Social Media (Instagram,TikTok etc.): These are B2C powerhouse, but not where execs hunt for business solutions.
• LinkedIn: The designated “business” social media network, but now a noisy echo chamber of AI self-promotion.
• Reddit: Emerging, but approach with caution: high noise, demands nuance.
• Content Marketing & SEO: Authentic voices now battling a flood of AI-generated content.
• Billboards and Radio: Less commuting means less impact; podcast ads are a promising yet costly substitute.

This isn’t to say these channels are entirely dead, but their effectiveness for B2B outreach to senior leaders has drastically diminished. While B2C marketing might be enjoying a golden age of hyper-targeted, personalized advertising that feels almost clairvoyant, the B2B world feels like it’s regressed into a communication dark age.
For DemoHop, our outreach reality means a highly focused, almost surgical approach. We lean on hyper-targeted, meticulously researched cold email and LinkedIn messaging (no more than 300 characters allowed!) – quality over quantity, always striving for relevance. Beyond that, we’re strategically investing in sponsoring and attending a few key industry events each year, hoping to capture those valuable face-to-face moments.

The irony isn’t lost on me. The very communication moats I helped dig and enjoyed as an executive are now the barriers I’m persistently trying to bridge as a founder. There’s no easy answer, no silver bullet. It underscores the relentless evolution of communication.

But that old Cutco-selling tenacity, the drive to connect and solve a problem, still burns bright; it’s just adapting to this new terrain. Back then, I was literally knocking on doors to show how a great product could improve someone’s daily life. Today, with DemoHop—a platform we designed specifically for enterprise tech teams to run genuinely engaging virtual planning sessions and impactful demo days—we’re on a mission to help companies bridge that internal virtual distance. We aim to foster the very kind of connection and silo-busting engagement that has become so elusive in far-spread technology orgs.

So, in this crazy era of digital overwhelm, where executives are harder to reach than ever, maybe the most radical act is to go full circle and re-sharpen our approach. Perhaps it’s time to get back to those Cutco basics, when a direct, personal touch was the keenest way to connect.

Don’t be entirely surprised, fellow Twin Cities leaders, if you hear a knock on your office door – or heck, even your front door, considering how many of us are still embracing the hybrid life. If you see me standing on your stoop, please, try not to hit ‘ignore’ on your Ring app. I promise it’s not knives this time, but I do have a fantastic enterprise SaaS solution I’m incredibly excited to show you!

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