How to Use Personalization in Sales Pitches

Most AEs fail on the phone for one simple reason: They’re cold calling people who’ve never heard of them. In 2025, that’s just lazy. Here’s how I would book executive meetings without sounding like a desperate sales rep: I used to teach cold calling techniques. Tonality. Pacing. Objection handling. And while that still matters... It’s not the reason I consistently get meetings with C-level buyers. The secret? I never cold call anymore. I warm call. Here’s how I do it: Step 1: Start with a personalized, relevant email. Do some quick research. Make it about them. For example, if I’m reaching out to a CRO, I’ll highlight a drop in quota attainment from RepVue and explain how I can help upskill their team in tough times. Step 2: That same day—a few hours later—I call their cell phone. (ZoomInfo or LinkedIn can get you that. No excuses.) DO NOT call the office. DO NOT waste time dialing assistants. If you can’t get a cell, send a LinkedIn connection request with a DM or video message. Step 3: When I call, I say: “Hi, this is Ian Koniak—did you happen to see the email I sent this morning?” If they say no: “No problem. I sent it because I saw your team’s quota attainment is down since 2022. I think I can help based on what I’ve done with other clients. Do you have a couple minutes now, or should we find time to connect on Zoom?” It’s not a pitch. It’s a reference to something you already sent that’s about them. That’s what makes it warm. Step 4: If they don’t respond, wait 2–3 days. Then reply to the original thread with more context: – Mention the training or workshops you offer – Share real results (e.g., 20% increase in quota attainment) – Ask: “Is this something you’d be open to learning more about?” Always lead with interest, not a hard ask for time. Step 5+: Stack 6–8 touchpoints total. Each one builds on the last—adding more insight, examples, testimonials. Mix in: – LinkedIn videos – Client stories – Relevant frameworks Each message = more value. That’s how you break through. It can take 8-12 touchpoints to get a meeting. Most reps quit after 1-3 touchpoints. Or worse—just send the same “following up” message. No value. No relevance. No shot. This process works. It’s not magic. It’s just real sales effort with a real strategy.

We all want the shortcut to personalization, but peep this email we received today and see why my mantra of those that put in the effort, that Show Me You Know Me, are the ones that will continue to win in these coming years: "Hey Samantha, kudos on fueling your competitive spirit since sixth grade—still got that portable TV? I especially love it when I see people who like coaching & mentoring others ;)" **This is pulled directly from my About section and has no authentic tie to the person; further, I do still have the tv - it says so right there in my profile. 😉 The second sentence is unrelated, so a clear demonstration of the use of {{ }} in a sales engagement tool. Instead, find something that you can relate to, that you can admire for a reason, that you can tell a story on, etc.** "Based on your expertise, you’d have a lot of impact if you’d create a course about social selling ." **Wait, you took the time to look at my profile and then...didn't notice that we already multiple courses on social selling? Weird... 😉** "Would you mind if I share my plan with you? PS: I couldn't help but be intrigued by your start in door-to-door sales for a noble cause; it seems like your prize-winning portable TV could be dubbed the original trophy of your flourishing competitive streak." **Thank you for mentioning my portable TV, again..." ******************************************************************************* Imagine instead if he'd looked at my profile and sent this: SUB: #samshorts on social selling + CO NAME BODY: Sam, I love that you offer your shorts on social selling already! My company specializes in XYZ and with over 50,000 students, social selling has been in huge demand. In looking at your courses, I have an idea on how I can help you get even more traction. Have you considered (this specific tangible thing that we probably haven't considered, which you know because most of your clients have this same challenge or ah ha moment) ? If not, it's an easy way to do XYZ and something we commonly tackle with our clients. Would love to chat if you're up for it - let me know a day/time that suits you and I'll send along a calendar invite. Cheers, Name *************************************************************************** You can't fake this stuff. Your buyers are numb to spray/pray and personalization-at-scale. There's no faster way to discredit yourself than by taking the lazy route. Sellers, click on #SMYKM and look at the infinite ways you can level up. Or, hey, we have a #samshorts for that. 🙃 Leaders/enablement, your sequences deserve better, we can help! #samsales

Your prospect has 147 unread emails. Yours just got added to the pile. What makes them open YOURS instead of the other 146? After sending thousands of cold emails and generating over $700M in sales throughout my career, I've identified the #1 mistake destroying most cold outreach: ZERO RIGHT PERSONALIZATION. Most reps "spray and pray". Sending the same generic template to 1,000 prospects hoping something sticks. Then they wonder why their response rate is 0.5%. Here's the cold email framework that consistently gets 20%+ response rates:  → Make your subject line about THEM, not you. Use recent news, achievements, or common pain points to spark curiosity. Example: "Your Inc 5000 ranking" or "Austin expansion" 1. Keep your email so simple it doesn't require scrolling. It MUST be mobile friendly, as 68% of executives check email primarily on their phones. 2. Use this 3 part structure:  → Personal opener: "Hey [Name], [specific personalization about them]"  → Show understanding: "In chatting with other [title] in [industry], they're typically running into [pain point]"  → Soft CTA: "Got a few ideas that might help. Open to chat?" 3. Research these personalization sources: • Company website (values, mission page) • Press releases • LinkedIn activity • Earnings transcripts (for public companies) • Review sites The hardest territory to manage isn't your CRM. It's the six inches between your prospect's ears. They don't care about your product. They care about THEMSELVES. Recently, one of my clients was struggling with a 1.2% response rate on cold emails. We implemented this framework, and within 2 weeks they hit 17.4% - with prospects actually THANKING them for the personalized outreach. Find your sweet spot on the personalization spectrum. You can't do hyper personalized video for everyone, but you can't blast the same generic template either. — Hey reps… want another cold email strategy? Go here: https://lnkd.in/gKSzmCda

A Lesson from a Birthday Voicemail: The Power of Authentic Connection in Sales Recently, I experienced a moment of pure joy and authenticity, one that resonates deeply with me a sales professional. On my birthday, a couple weeks ago, among the chorus of off-key family renditions in my voicemail, I received an unexpected message from a colleague, Precious L. Williams "Killer Pitch Master". She didn’t just wish me a happy birthday; she sang it! Precious, an outstanding speaker known for her insights into pitching and sales, exhibited a fearless, genuine spirit. This small, personal act encapsulated why she is so successful: she understands the importance of truly “SEEING” people. In an era where AI tools craft our emails and streamline client interactions, it's crucial we don’t lose the human touch. As sales professionals, our challenge is to genuinely connect with our clients, to see them not just as leads, but as individuals with unique values, missions, and stories. Here are three actionable ways to make our clients feel seen and valued: 1️⃣ Personalize Your Approach: Before hitting send on any email or LinkedIn message, take a moment to personalize it. Refer to a recent post or article they’ve written or acknowledge a career milestone. This shows you’ve done your homework and value their contributions. 2️⃣ Celebrate Their Successes: If your client achieves something noteworthy, be it professional or personal, acknowledge it. A simple congratulatory message can go a long way in building a stronger, more personal relationship. 3️⃣ Take a Risk with Creativity: Don’t shy away from doing something out of the ordinary. It could be as simple as sending a handwritten note or sharing a relevant article or book. These small, creative gestures can make a big impact in a digital world. Incorporating these tactics isn’t just about improving sales; it’s about building genuine, empathetic connections. As sales professionals, let’s strive to be more like Precious – fearless, authentic, and always ready to truly see the person behind the client. #SalesStrategy #Sales #AuthenticConnections #PersonalTouch #SalesSuccess

We talk so much about the horrible sales reps doing this or that... Well, here is the Best Sales Outreach I've Ever Received 🏆 (And It Wasn't Even a Cold Call!) As an avid teacher and consumer of #sales training and a #CEO, I've encountered countless outreach attempts over the years (literally thousands). But one particular interaction stands out - not just for its effectiveness, but for its sheer brilliance. By far it wins the award of BEST SALES OUTREACH of all time. It was from Caleb Parsons, an Account Executive at Oracle. Caleb reached out to me via LinkedIn, and within minutes, I knew this was different. Why? Two reasons: 1️⃣ Caleb embodied the golden rule of prospecting: To be Interesting, You must be Interested. 2️⃣ He leveraged the Omni-Channel (email, LinkedIn, FlyMSG) the SAME day. Caleb didn't just give me a run-of-the-mill sales pitch like everyone else does. Instead, he took the initiative to truly comprehend my company, the work I do, and my interests. He did several things: 1. He sent a personalized connection request ✅ 2. He triangulated that with an email using FlyMSG.io ✅ 3. He SIGNED UP for FlyMSG!!! ✅ 4. He invited me to an event! ✅ This personalized approach instantly piqued my curiosity. I felt respected, not just as a potential customer, but as a fellow professional. He embodied my saying to sellers: "show me that you know me." Caleb's message wasn't just about selling; it was about building a connection based on an interest that he knew I was passionate about. He demonstrated a genuine interest in me, our company and products, my work, which sparked an instant "Yes, let's talk." Here's why Caleb's approach was so effective: * Personalization: He did his research and tailored his outreach to my specific interests. * Value-driven: Umm, he used my own product on the CREATOR! * Building rapport: He focused on establishing a connection, not just spraying and praying automation. Caleb's outreach wasn't just impressive; it was transformative. It showed everyone who watches this 7-min video the power of personalized, value-driven prospecting that prioritizes building relationships over his personal focus... "booking a meeting." I've been teaching prospecting for eight years, Vengreso | The Creators of FlyMSG.io. FlyMSG is over 3 years old. Nobody, and I mean nobody, has taken the time to engage with me as a buyer like he did! Caleb's outreach is the best I've ever received. It's a shining example of how to connect with prospects authentically and effectively. Watch this 7-min video or read this article I wrote about him. While I couldn't be one of his buyers... he deserved the praise. https://lnkd.in/gFQK-ZmH What are your thoughts on Caleb's approach? John Barrows 🏄♂️ Scott Leese • Richard Bliss Richard Harris™ Shari Levitin Chris Gandolfo Jordan Bauer Liz. Bishop Casey (Case) George Mike Levy Any exceptional sales outreach experiences? Share your stories 👇

Many sellers inadvertently lower their status with their "rapport building". Want your prospect to actually respect you? Try this approach: The easiest way to earn your prospect's respect and get them to "like" you: 1. Show you respect their time 2. Show you know their business 3. Show you're prepared for the call To accomplish all 3, our team follows the 𝟵𝟬 𝘀𝗲𝗰𝗼𝗻𝗱 𝗿𝘂𝗹𝗲 in sales meetings: In the first 1.5 mins of the call, say something that SHOWS we prepped for the meeting and know their business. Examples: 1. For our newsletter sponsorships, we might comment on a new product feature they just released: "𝘐 𝘸𝘢𝘴 𝘱𝘳𝘦𝘱𝘱𝘪𝘯𝘨 𝘧𝘰𝘳 𝘵𝘩𝘪𝘴 𝘢𝘯𝘥 𝘴𝘢𝘸 𝘵𝘩𝘦 𝘯𝘦𝘸𝘴 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘦 𝘭𝘢𝘶𝘯𝘤𝘩 𝘰𝘧 𝘵𝘩𝘦 𝘢𝘶𝘵𝘰-𝘦𝘯𝘳𝘪𝘤𝘩𝘮𝘦𝘯𝘵 𝘧𝘦𝘢𝘵𝘶𝘳𝘦 - 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘸𝘦𝘴𝘰𝘮𝘦. 𝘏𝘰𝘸'𝘥 𝘭𝘢𝘶𝘯𝘤𝘩 𝘨𝘰?" ^This is likely something they'd want to promote in a newsletter -- 2. For our Club Pass sales training program, we'll might comment on something we read on a job posting for an AE: "𝘋𝘢𝘯, 𝘐 𝘸𝘢𝘴 𝘳𝘦𝘢𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘰𝘱𝘦𝘯 𝘑𝘋 𝘺𝘰𝘶 𝘢𝘭𝘭 𝘩𝘢𝘷𝘦 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘌𝘕𝘛 𝘈𝘌 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯. 𝘗𝘳𝘦𝘵𝘵𝘺 𝘤𝘰𝘰𝘭 𝘵𝘰 𝘴𝘦𝘦 𝘺𝘰𝘶'𝘳𝘦 𝘭𝘰𝘰𝘬𝘪𝘯𝘨 𝘵𝘰 𝘦𝘹𝘱𝘢𝘯𝘥 𝘪𝘯𝘵𝘰 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵 𝘷𝘦𝘳𝘵𝘪𝘤𝘢𝘭𝘴 𝘣𝘦𝘺𝘰𝘯𝘥 𝘫𝘶𝘴𝘵 𝘴𝘦𝘯𝘪𝘰𝘳 𝘭𝘪𝘷𝘪𝘯𝘨 𝘤𝘰𝘮𝘮𝘶𝘯𝘪𝘵𝘪𝘦𝘴. 𝘏𝘰𝘸'𝘴 𝘵𝘩𝘢𝘵 𝘨𝘰𝘪𝘯𝘨?" ^Selling into new verticals often leads to VPs wanting to upskill their teams. -- Done right, you differentiate yourself from every other crummy sales call they've taken this quarter AND get a chance to feel out how much they care about the thing you called out. If I get a lackluster response about the new feature release...I know that's probably not something they're going to want to promote in the newsletter, and I know not to waste time asking more about it! Don't waste everyone's time attempting to schmooze about the cold weather in Toldeo in an obvious attempt to butter 'em up...instead, find ways to demonstrate credibility and your calls will kick off so much smoother.

Take notes, folks. Seriously. And show that you care. I was once pitched by a vendor and, in conversation, the sales rep learned my wife, pet human and I are big travel buffs. I mentioned a trip we had planned for a few months down the road, and also told him that we didn't need his product at that time, but it could be a good fit down the road. I also mentioned we were evaluating some competitors, and obviously weren't in a big rush to make a decision. He sent me an email thanking me for the time, and also included the name of a restaurant in the city we were headed to that he heard was awesome. About a month later, he sent me another email. The only thing in it was a recommendation for another place to eat during our trip. 4 months later, an email with the subject line "How was the trip??" landed in my inbox. There was no text in the body. I bought from him later that month (after filling him in on our trip, obviously). We all know you want to get the deal - so do I - but you’re better off nurturing the process rather than rushing a decision. Some buyers need more time. On top of that, if a potential client feels like you know them as real people...not just prospects...they’ll be more inclined to give you the bidness. It's the way the world works. Do you need to establish a strong use case, prove that there will be ROI (or COI per Jen), and all of that stuff? Of course. That's table stakes. When you personalize that connection with customers and create an emotional relationship, you get closer to a sale. Especially when you're in the midst of a competitive sale.

Over 20 years of running companies, I’ve seen three traits that consistently separate the top salespeople: volume of activity, personalized outreach, and delivering value in every interaction. In a world of AI and automation, these things are more important than ever. Volume of activity There is a strong correlation between the number of calls, emails, and LinkedIn messages a salesperson sends and the number of meetings they book. That was true 20 years ago and it’s true today. At my first company, we didn’t have dialers. Reps manually punched in every number, I know… old school. One rep asked for a headset so he could move faster. He instantly doubled his daily dials and exceeded every goal we set. Today, there are more channels, more tools and more noise than ever, but the best reps know how to leverage automation to consistently execute a high volume of activities against the right accounts. Personalized outreach This is important because just pure volume isn't going to do it. You need to have strong personalization to your outreach to get people's attention because so much is being written by AI, is templated, etc. The best reps do real research on their prospects and use it to tailor their message. This might include referencing a shared connection, a recent announcement, or even a personal interest (I’ve seen reps find crazy stuff about prospects with some basic internet stalking). One of the best outreaches I ever received came from a rep at a bank who had been trying to get my attention. He sent a package with a framed New York Times article I was featured in, along with a handwritten note about why it resonated with him. He showed me I wasn’t just a name on a list. I had to take the meeting. Value in every interaction High activity and personalization go a long way, but the best reps consistently bring value to every conversation. That might mean sharing relevant trends, customer stories, or internal research. Most reps forget that even if they’ve never done the job their prospect does, they speak to more people in that role than most practitioners ever do. Sometimes it means connecting prospects with people or ideas they wouldn’t otherwise access, like the rep’s CEO or a high-profile customer. One of my top reps had a gift for becoming a kind of therapist. She would listen closely, reflect what she was hearing, and share examples of others facing similar challenges. It helped prospects feel understood. But all of it has to tie back to the value your company and product can deliver. When reps get this right, prospects actually look forward to their calls. The most interesting thing is that I have been saying this for many years to every rep I work with and only a very small portion will actually do these things. The truth is that none of this is easy. It takes time, effort, and discipline. But these are the three things that set the best apart.

It took me 2 years to learn what makes personalization work. I’ll teach you in 2 minutes. Most people think personalization means… ❌ First name ❌ Company name ❌ A compliment pulled from LinkedIn That’s not personalization. That’s pattern-matching. And your prospects know the pattern. Here’s what real personalization looks like: ✅ Context - Why this message, why now? ✅ Signal - What buying behavior did they show? ✅ Relevance - How does your offer solve their current friction? Let’s break it down: Start with intent Are they hiring? Funded? Shifting strategy? That’s your “why now.” Anchor in pain Lead with what they’re trying to fix, not what you’re trying to sell. Mirror their language Read how they talk on their site or in interviews and reflect that back. Offer a next step Not a meeting. A win. → “Saw X. Helped Y solve it with Z. Want the teardown?” Bad personalization flatters. Good personalization understands.