Dereka M. Smith | B2B Marketing Insights

Tag: business

  • Don’t Follow the Herd: How Being Different in Sales Strategies Drives Results

    Don’t Follow the Herd: How Being Different in Sales Strategies Drives Results

    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

    Gif from the movie, Wolf of Wall Sreet

    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.

  • Craft Emails That Engage, Not Annoy Prospects

    Craft Emails That Engage, Not Annoy Prospects

    Cold email outreach isn’t dead—it’s just evolved.

    Response rates are plummeting across the industry, countless “revolutionary” outreach strategies are being misused and overdone. The companies that are thriving in this new era are ones who understand that beneath all the tech noise, we’re still dealing with humans who want to feel understood, who crave authentic connection, and can smell insincerity from three time zones away.

    2025 has changed the terrain with tightened filters, flooded inboxes, and redefined what it means to reach out. So I’ve changed, too. Here’s what still holds weight, and what no longer does.

    1. Personalization Is Still Queen👸🏾—But Relevance Is Her Throne

    I’ve written cold emails since before sales leaders realized that “Hey {First Name}, saw you went to {College}” was more parody than personalization. I used to believe, back in my early SDR days, that referencing a funding round or a company’s new office was enough to pierce through the digital noise. I would spend fifteen minutes sculpting these handcrafted intros that danced around the actual point. And prospects ignored them, politely and thoroughly.

    Everyone preaches personalization. Few understand its anatomy. Without relevance, personalization is just a warm pat on the back—comforting, maybe, but directionless.

    You have to understand that personalization is not flattery or a prospect’s LinkedIn activity. It’s about framing their pain in a way that feels like it was plucked from their Slack messages.

    Here’s How to Make It Work:

    The 3-Layer Research Framework:

    1. Layer 1 – Company Context (2 minutes): Recent product launches, leadership changes, or market shifts
    2. Layer 2 – Role Reality (3 minutes): LinkedIn posts, any podcast appearances, or conference talks that reveal their actual priorities
    3. Layer 3 – Pain Patterns (5 minutes): Industry forums, Reddit threads, or Glassdoor reviews that expose what keeps their team up at night

    The Opening Formula That Works:

    “Noticed [specific observation about their business challenge] while [credible source of insight]. 

    Most [their role] I work with struggle with [related pain point]. 

    Curious if you’re seeing the same thing at [company]?”

    Example: Instead of: “Saw you raised $20M in Series B funding – congrats!” Write: “Saw your engineering team grew 3x after the Series B. Most CTOs tell me their deployment velocity actually slows down during rapid scaling. How are you keeping ship velocity high while onboarding?”

    What we’re witnessing now is the death of surface-level personalization, and while it’s been painful for many salespeople to watch their carefully crafted templates become ineffective, I’d argue this shift is actually beneficial—it’s forcing us to dig deeper, to develop real empathy, to become students of our prospects’ industries and challenges rather than just collectors of their publicly available information.

    2. Intent Data is a Strategy

    We’ve become obsessed with signals. A download here, a webinar registration there, a glance at a pricing page. But these are breadcrumbs. Treating them like coordinates to a hot lead is the fastest way to overlook the other 97% of your total addressable market.

    Yes, I pay attention to intent data, but not to build my lead list. I use it the way one reads weather patterns: to understand where the winds are shifting, what topics are heating up, what anxieties are forming underneath industry smiles.

    Mini Intent Data Playbook:

    Use Intent Data For:

    • Timing your outreach (not selecting your targets)
    • Understanding trending pain points in your industry
    • Crafting emails that match current concerns
    • Building talk tracks around active problems

    Intent-Informed Emails: Track what content your market is consuming, then mirror that language:

    • If they’re downloading a “cost optimization” guide → “Quick question about (company’s) infrastructure spend”
    • If they’re attending “AI implementation” webinars → “Your ML ops stack”
    • If they’re downloading “remote work productivity” resources → “Async collaboration for (company)”

    The key is making it feel like a natural continuation of their research journey rather than obvious tracking.

    3. The AI Paradox: When Perfect Becomes Perfectly Forgettable

    Photo by cottonbro studio on Pexels.com

    AI is efficient. It’s even helpful—if you use it to gather language, observe tone, track forum conversations, or spot patterns you might otherwise miss. But what AI generates is, at best, scaffolding. And scaffolding doesn’t move people.

    The mistake I see now is salespeople (and people in general) outsourcing not just their writing but their thinking to a robot. You can’t automate understanding and business acumen.

    How to Use AI Without Losing Your Soul:

    AI for Research (Good):

    • Extract key themes from their company’s last 5 blog posts
    • Identify patterns in their LinkedIn activity
    • Generate industry-specific terminology lists

    AI for Writing (Dangerous): Never fully rely on AI to write your actual email or other sales content. Instead:

    1. Write your first draft with pure human insight
    2. Use AI or a tool like Grammarly to check for jargon or unclear phrases
    3. Ask AI to suggest alternative ways to phrase your subject lines or CTAs
    4. Always rewrite in your voice

    The Humanity Test: Before sending, ask:

    • Would I say this out loud to someone?
    • Is this something I would say to this person at a networking event or industry conference?
    • Does this sound like something only I could write?
    • Is there at least one line that might make them smile/think/react?

    People don’t buy from companies; they buy from people who make them feel understood, who can articulate their frustrations better than they can themselves. Prospects want brands that can tell stories that resonate not just with their logical mind but with their emotional reality. 

    Your emails need to make prospects feel heard, seen, maybe even challenged—they need to create that moment of recognition where someone thinks, “Finally, someone who gets it.”

    4. Real “Value” Is Educational and Emotional

    We’ve diluted the word “value” into something toothless.

    Value is not always a tip, a blog, or a whitepaper. Sometimes value is a sentence that makes someone stop scrolling or a truth they’ve avoided naming out loud. Sometimes it’s just the perfect echo of their own doubt.

    The Value Hierarchy That Actually Converts:

    Level 1 – Recognition (Weakest): “Here’s a blog post about sales productivity”

    Level 2 – Insight (Better): “Your sales team is probably spending 64% of their time on non-selling activities”

    Level 3 – Revelation (Strongest): “Every sales leader I know says they want their team selling more. But then they add another tool, another process, another meeting. What if the problem isn’t productivity—it’s permission?”

    The Email Structures That Create Emotional Value:

    The Confession: “I used to think [common belief]. Then [specific event] happened. Now I realize [contrarian insight]. Seeing anything similar at [company]?”

    The Question: “Quick question: When your [team] says they need [common request], what are they really asking for?”

    The Pattern: “Talked to 4 [their role] this week. All mentioned [specific challenge]. All tried [common solution]. None of it worked. There’s a different approach that’s worth exploring…”

    The companies that are winning understand that cold email is about joining conversations their prospects already having, about providing value that exists independent of any potential sale, and building the kind of trust and credibility that makes people want to engage.

    A 6-Email Sequence Framework That Doesn’t Annoy Prospects

    Here’s the exact sequence framework I use that generates 50-60% open rates and 4% reply rates, and doesn’t annoy prospects.

    5. Email deliverability can be a constraint or a catalyst

    Photo by cottonbro studio on Pexels.com

    I hate deliverability.

    But I respect it.

    Google, in all its algorithmic majesty, has raised the bar. If your domain isn’t properly authenticated or your emails look like they’re part of a generic twenty email sequence sent from a ghost domain–you’re out. Possibly, digitally exiled.

    The Technical Checklist You Can’t Ignore:

    Domain Setup (Do This First):

    • SPF, DKIM, and DMARC properly configured
    • Separate subdomain for cold outreach (e.g., reach.yourcompany.com)
    • 3-4 week warmup period before full volume
    • Daily sending limits: Start at 20/day, increase by 10 every 3 days

    Email Hygiene Rules:

    • Validate every email with tools like Instantly
    • Remove anyone who hasn’t engaged after 3 touches
    • Maintain <2% bounce rate and <0.1% spam complaint rate
    • Use varied subject lines (no more than 3 emails with same subject)

    Show legit activity in your inbox:

    • Subscribe to 5-10 industry newsletters from your sending address
    • Reply to some of them occasionally
    • Send personal emails to colleagues from the same domain
    • Vary your sending times (no blast at 9:00 AM sharp)

    Email deliverability is tedious house-keeping, but it must be done in order to reach your prospects.

    Final Thoughts

    I write cold emails that don’t apologize for taking space in someone’s day. I write for the reaction, the double-take, the half-smile, and the skeptical curiosity that becomes interest.

    So no, cold outreach isn’t dead.

    It’s just become a mirror. And if your email reflects nothing of value, humanity, or insight back to the reader then maybe it deserves to be ignored.

    But if you follow the frameworks above, you’ll find that the inbox still rewards those who treat it like a conversation between humans, and not a transaction between logos.

    Want to turn your inbox into a revenue generating machine? Contact me here.

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