Category: sales

I’ll never forget my first day in sales. I was on a cramped team with ten other fresh SDRs, all of us holding the same scripts and call lists. “Stick to the script,” they told us. “Make x calls/emails a day. Sales is a numbers game.” But after weeks of dial-tone monotony, a light bulb went off—I needed to be different. The script was holding me back, and more importantly, it was boring the people on the other end. So, I tried something new. I sent personalized emails, handwritten notes, and even a few quirky gifts (yes, a few Dunkin Donuts cards went a long way). Suddenly, prospects responded. They remembered me. And more importantly, they converted.

In today’s market, where sales pitches are as common as spam, it’s those daring enough to break the mold who drive real results. Here are some unconventional strategies I’ve learned that can help you with standing out from the crowd.

Strategy 1: Master Copywriting and Content Marketing

As more organizations are starting to see sales and marketing as “one unified revenue funnel,” great salespeople are also expected to be great marketers, and content is their secret weapon.

Example: A colleague of mine publishes insightful LinkedIn articles on common industry pain points, which then became conversation starters in emails. This not only drove engagement but also positioned them as a trusted industry voice, leading to inbound inquiries they hadn’t even sought.

This shows the impact of blending storytelling into your outreach. Instead of pushing a hard sell, share success stories, industry insights, or even lessons from a failed campaign. 

Strategy 2: The Multichannel Rebellion–Going Where Others Fear to Tread

Multichannel outreach has turned into a predictable pattern: email, LinkedIn, maybe a phone call, and perhaps a direct mail piece if you’re feeling particularly crafty. However, if you are truly curious about where your prospects spend their time and are willing to explore the spaces where they learn, complain, seek advice, and connect with peers, you will uncover opportunities that your competitors are either unaware of or too risk-averse to pursue.

Your ideal customer profile (ICP) might be developers who spend their evenings contributing to open source projects on GitHub, who seek solutions to technical challenges on Stack Overflow, and who engage in surprisingly deep discussions about architecture decisions on Reddit. Maybe your prospects are finance leaders who participate in industry-specific Slack communities, attend virtual meetups, and follow particular thought leaders on LinkedIn you’ve never considered part of your sales strategy.

The key insight here is that people behave differently in different contexts: the same person who ignores your LinkedIn message might engage thoughtfully with your contribution to a technical discussion they care about, might appreciate your insights when they’re genuinely helpful rather than transparently promotional. This is where AI can actually be useful—not to automate your outreach but to help you understand the language, the concerns, and cultural norms of these communities so you can contribute authentically rather than intruding awkwardly.

Strategy 3: Attend In-Person Events 

There’s something about a handshake, an unforced laugh over coffee, or the energy of a live event that no Zoom call can replicate.

During an industry lunch-n-learn event, a small chat with an industry peer about our chickpea salad bowls turned into an insightful conversation on how we helped out another company that was adjacent to what the prospect’s company does. A week later, they decided to get on a disco call with us. This shows that in-person interactions build a type of trust that emails or calls often can’t.

I would encourage salespeople and especially founders to attend a few key industry events each year. Before you go, research the attendees and map out a few goals for the event. The effort will pay off in unforgettable connections.

Strategy 4: Execute Fun, Thoughtful Campaigns

Sales doesn’t always have to be serious nor hay-wire like a scene from the Wolf of Wall Street. In fact, a little fun can go a long way in breaking through the monotony of traditional outreach.

Examples

• Holiday Letters: For the holiday season last year, I sent handwritten letters to my most engaged prospects. It was simple, personal, and surprisingly effective. Plus, it helped me express my inner holiday joy!
• Dunkin’ Donuts Cards: For prospects who frequently engaged with my emails, I sent a virtual coffee invite with a Dunkin’ gift card. It turned a cold email into a warm introduction that converted into a $60k deal.
• Hawaiian Shirts for Summer: Something you can try that I wanted to do is send Hawaiian shirts to select prospects with a note about “bringing the vacation to them.” This will be a great campaign to do during the infamous summer vacation season.

Think about a campaign theme that reflects your brand’s personality or the season. Make it genuine and memorable. People respond to creativity, and it’s often what sets you apart from the hundreds of other emails and calls they get.

Strategy 5: CC Executives/Senior Prospects with Custom Case Studies

This strategy is more for warmer leads or account executives who have extra time to craft memorable outreach.

By crafting a customized case study and CC’ing executives on an observation or problem that I identified and how our solution could help them, I generated internal buzz that opened doors within a company. This approach led to quicker decision-making and got the attention of multiple stakeholders.

When CC’ing executives, be sure your email highlights their specific needs and concerns. A targeted case study shows that you’ve done your research, making it harder for them to ignore your outreach. 

When you send tailored case studies to decision-makers, you’re not only showcasing your value but also sparking internal conversations that can speed up the sales process.

Note: Of course, this strategy is meant for your key accounts that are likely to convert. It’s not advisable to do this with every account you target.

Different is Memorable, and Memorable Drives Results

When everyone follows the same playbook, it’s us the rule-breakers, the creative thinkers, and the bold who drive real results. Differentiate yourself by being unconventional in your outreach, and you’ll soon find that standing out is much more than a strategy—it’s a pathway to success.

Ready to stand out and drive results? Pick one of these strategies, try it in your outreach this week, and see how it changes your game. After all, blending in is easy, but bringing in new business and forming impactful connections with your prospects is what truly matters.

If you’re a sales leader or founder whose team or sales outreach lacks excitement, visit my website to learn more about my expertise and work.