Personalizing Sales Outreach

We analyzed 4 million recruiting emails sent through Gem. Most get opened. But only 22.6% get replies. Half those replies are "thanks, but no thanks." We dug into what actually works. Here are 8 factors that drive REAL responses: 1. Strategic timing beats everything else - 8am gets 68% open rates. 4pm hits 67.3%. 10am lands at 67% - Most recruiters blast at 9am when inboxes are flooded - Avoiding peak times alone can boost your opens by 7-10% 2. Weekend outreach is criminally underused - Saturday/Sunday emails get ≥66% open rates consistently - Why? Empty inboxes. Zero competition. Candidates actually have time - Yet few recruiters send on weekends. Their loss is your gain 3. Keep messages between 101-150 words - Shorter feels spammy. Longer gets skimmed - You need exactly 10 sentences to nail the essentials - Every word beyond 150 drops performance 4. Generic templates kill response rates - Generic templates: 22% reply rate - Personalized outreach: 47% increased response rate - Even adding name + company to subject lines boosts opens by 5% 5. Subject lines need 3-9 words - Include company name + job title for highest opens - "Senior Engineer Role at [Company]" beats clever wordplay - 11+ words can work if genuinely intriguing, but why risk it? 6. The 4-stage sequence is optimal - One-off emails are dead. Send exactly 4 follow-up messages - You'll see 68% higher "interested" rates with proper sequencing - After stage 4, engagement completely flatlines. Stop there 7. Get the hiring manager involved - Having the hiring manager send ONE follow-up boosts reply rates by 50%+ - Yet most recruiters don't use this tactic - Weekend advantage: Minimal competition for attention 8. Leadership involvement is a cheat code - Role-specific timing (tech vs non-tech) matters - Technical roles: 3 of 4 best send times are weekends - Engineers check email differently than salespeople. Adjust accordingly TAKEAWAY: These aren't opinions. This is what 4 million emails tell us. Most recruiting teams are stuck in 2019 playbooks wondering why their reply rates won't budge. Meanwhile, recruiters who implement these 8 factors see dramatically better results. The data is right there. The patterns are clear. The only question is: will you actually change how you operate? Or will you keep sending the same tired emails at 9am on Tuesday? Your call.

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

After creating hundreds of thousands of presentations, Nancy Duarte discovered a framework in 2010 that changed her life. She mapped it over Martin Luther King's "I Have a Dream" speech and Steve Jobs introducing the iPhone. Both aligned perfectly. She cried in her office - the pattern she'd been desperate to find was real. See, most founder pitches fail the same way. You stack all the customer pain points at the start, then demo your product at the end. By the time you reach your solution, people have already decided if they're interested. They tuned out at slide 8. Duarte's Sparkline does the opposite. You alternate between “what is” and “what could be” throughout the entire pitch. Pain, solution. Pain, solution. The pattern works because contrast commands attention and open loops create psychological discomfort. The brain needs recurring tension to stay engaged: - MLK toggled between injustice now and "I have a dream" repeatedly. - Jobs contrasted clunky smartphone limitations with iPhone capabilities throughout the 80-minute presentation. - JFK alternated between the US’s space limitations and “we choose to go to the Moon in this decade.” Each toggle made staying in the current state unbearable. The execution: 1. Make your customer the hero by using their exact words Interview five target customers or investors before you build slides. When they describe frustrations, use their language verbatim. This proves you understand their reality before pitching your solution. 2. Paint “what could be” with sensory detail Not better accommodations. Instead: a family arrives in Paris, their Airbnb host left fresh croissants and a handwritten neighborhood guide on the kitchen table. They feel like locals, not tourists. Concrete outcomes stick. Abstract benefits are forgotten. 3. Alternative problem/solution throughout - never batch Pain 1, solution 1, pain 2, solution 2, pain 3, solution 3. Never group all problems then all features. Batching lets investors and customers mentally check out before you finish. 4. End with an immediate next step (24-48 hours) For investors: “By Friday, confirm the partner meeting date and three references you want to call.” For customers: “By tomorrow, send three use cases and I'll record a custom demo by Wednesday.” Make the decision immediate and concrete. Watch for these signals mid-pitch: You're losing them when investors lean back, check phones, or pivot to questions about your burn rate and competition. You're winning when customers interrupt to describe their specific use case, ask about implementation timeline, or want to loop in their team immediately. When every startup in your category has similar features, the pitch that creates unbearable tension wins the round, the sale, and the talent.

What makes a decision-maker actually reply to your LinkedIn message? I wanted to find out. So we ran an experiment. At my recent Get Paid To Speak Bootcamp, I invited Brian Tee, Head of Sales at SingPost, as one of our corporate guests. Why? Because I wanted my aspiring speakers to hear directly from someone who hires speakers: what gets their attention, what turns them off, and what actually gets you booked. So here’s what we did: Everyone in the room had to reach out to Brian on LinkedIn. No scripts. No templates. Just thoughtful outreach. Brian received 95 connection requests and he took the time to go through every single one. Then he shortlisted the messages that stood out to him and shared WHY they worked. That’s what this post is about (you might want to bookmark this post!) Here are five things the best outreach messages had in common: 1. They anchored to a real, shared moment. “I really appreciated your insight at GPTS, especially when you said ‘leadership today requires empathy and adaptability.’ That stayed with me.” 2. They focused on Brian first not their pitch. “May I ask what business challenges you're currently facing? How do you envision inspiring your sales team in 2025 and beyond?” 3. They asked meaningful, open-ended questions. “What’s your take on vulnerability in the workplace? Does it have a place in leadership today?” 4. They aligned their offer with Brian’s values and goals. “Given your focus on transformation, I believe my talk on resilience could complement your vision at SingPost.” 5. They offered to add value without sounding transactional. “If there’s any way I could contribute to your work at SingPost, I’d be happy to explore how.” One big lesson from this? The best outreach doesn’t try to impress, it tries to connect. Respect. Curiosity. Relevance. That’s what opens doors. A huge thank you to Brian Tee for being so generous with his feedback, this was GOLD for every speaker in the room. And now, for you reading this: If you’re trying to reach high-value contacts, use the above five insights as your blueprint. Your turn: if you were a potential client, how should we reach out to you that will elicit a positive response? #LinkedInTips #GetPaidToSpeak

Just got off a call with a founder who's sent 1,000+ cold emails with ZERO responses... Let me ask you something... Have you ever crafted what you thought was the perfect outreach message, only to be met with complete silence? One of my clients (a SaaS founder) just shared their frustrating experience that might sound familiar... They spent weeks perfecting their message, researching prospects, and personalizing every email. The result? Radio silence. Zero responses. Zero meetings. Zero opportunities. And here's what really hurts... Their competitor, with an inferior product, was landing meetings left and right with the same prospects. After analyzing thousands of outreach campaigns, I’ve discovered that trust isn't built through volume - it's built through three specific elements that buyers actually care about. Here are the 3 trust drivers that actually get decision-makers to reply: 1) Social Proof That Matters Stop leading with generic logos. I've found buyers instantly engage when you share specific results from companies in their exact industry. They need to see themselves in your success stories. ✅ POWER MOVE:  Reference a similar company's specific metrics improvement (e.g., "We helped Company X increase their conversion rate by 47% in 60 days") 2) Thought Leadership Signals Your prospects are drowning in "experts." I've tested this extensively - buyers respond when you demonstrate deep industry knowledge through specific insights about their business challenges. ✅POWER MOVE: Share a unique observation about their market position or recent company changes that others missed. 3) Micro-Deliverables This is the game-changer most miss. I've seen response rates triple when founders offer immediate value before asking for anything in return. ✅POWER MOVE: Provide a quick competitive analysis or specific growth opportunity they can implement today, regardless of whether they reply. The data is clear: 89% of cold outreach fails because it focuses on what YOU want instead of what THEY need. These aren't just theories - I've watched these exact strategies transform response rates from 2% to 20%+ across hundreds of campaigns. Here's the real question: How many of these trust drivers are you actually incorporating in your outreach right now? #ColdOutreach #B2BSales #TrustBasedSelling #OutboundMarketing #SalesStrategy

How many times have you logged on to Linkedin and found yet another email that starts with: "Hey [First Name]," followed by a generic pitch that does not concern your interests or needs. Sound familiar? We've all been there. And it's frustrating. As a fractional CMO/Consultant, I've seen this happen repeatedly. Businesses think they're doing personalization right but need to do better. It's not enough to use someone's name or company. 👉🏾 True personalization is about understanding their challenges, goals, and needs. For example, on LinkedIn, scroll through their feed and see what they post, talk about, like, and comment on. This helps as a starting ground on how to approach them and what to discuss. So, instead of sending a LinkedIn message that says: "I'd love to connect and learn more about your business," try something like: "I noticed you're working on [specific project]. I have some ideas on how you could [achieve a specific goal]. Would you be open to a quick chat?" See the difference? It's not just about being personal; it's about being relevant. And when you're relevant, you're not annoying — you're helpful. 👉🏾 So, think about this the next time you craft a personalized outreach campaign. →"Would I find this message valuable? →Does it address my specific needs and interests?" If the answer is no, it's time to return to the drawing board. 👉🏾 Also, tools like Crystal Knows help you fine-tune your message and tone when reaching out to maximize the impact of every conversation. Let's aim for genuinely helpful messages, not just another annoyance in their inbox. What do you think about personalized outreach? #b2bmarketing #demandgeneration #leadgeneration #ABM

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.

If you ask (and answer) this 1 question before starting cold outreach, you'll be on track to see 2x results from your outbound in 2025. 📌 The question is simple: Does this matter to THEM? Too often, outbound efforts are built around what we want: to book a meeting, to hit quota, to close the deal. But here’s the reality: no one cares about your goals unless they align with theirs. This is where my #EarnTheRight approach comes in. Before you send an email, pick up the phone, or craft a LinkedIn message, stop and ask yourself: “Am I talking about what matters most to my prospect?” Taking the time to create email copy and phone talk tracks that align with their priorities is critical. This is not about prospect-specific personalization. This is about RELEVANCE. ➡️ Here’s why: Relevance drives response. When you speak to the challenges and goals that matter the most to your prospect, you’re no longer interrupting them—you’re engaging them. Want to stand out in 2025? Believe me when I say the bar is low and stealing this strategy will help you 2x your results this year. Most outreach is about the seller: “We offer X,” “Our platform does Y.” Flip the script by focusing on the prospect’s world instead, and you instantly differentiate yourself. Trust builds faster when your messaging reflects that you’ve done the homework. In 2025, relevance isn’t just important—it’s essential. Buyers are busier than ever, and generic outreach is the quickest way to get ignored. When your outreach centers on what truly matters to your prospects, you earn the right to their time, their attention, and eventually, their business. 📌 How are you ensuring your team’s messaging speaks to what matters most to your prospects?

Here's 2 testimonial formats that don't sound like bullsh*t: It’s tempting to showcase your most effusive reviews, but that’s a missed opportunity. We got this one last week: "I've been an entrepreneur for almost 30 years and this is the best thing I've ever done. Wish I did it 30 years ago.” I love reading testimonials like that! But I don't post them on our site. Why? Because they sound like bullsh*t. Think about it from your prospect’s perspective: If they read a review that says “This product is awesome!” will they think “Wow, this product must be awesome. Lemme grab my credit card…” (No. No, they will not.) Effective testimonials don’t just say “It's awesome,” they break through by addressing prospect’s specific goals and fears. Like this... 𝗛𝗲𝗿𝗲'𝘀 𝟮 𝘁𝗲𝘀𝘁𝗶𝗺𝗼𝗻𝗶𝗮𝗹 𝗳𝗼𝗿𝗺𝗮𝘁𝘀 𝘁𝗵𝗮𝘁 𝘄𝗼𝗿𝗸 𝗵𝗮𝗿𝗱𝗲𝗿 𝗢𝗽𝘁𝗶𝗼𝗻 𝟭: 𝗪𝗵𝗮𝘁 𝗲𝘅𝗮𝗰𝘁 𝗼𝘂𝘁𝗰𝗼𝗺𝗲 𝗶𝘀 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁 𝗵𝗼𝗽𝗶𝗻𝗴 𝗳𝗼𝗿? Share quotes from people describing that exact outcome. For example: • “We cut production times by 30% while lowering defect rates, I didn’t think that was possible.” • “We quadrupled the engagement rates of our outreach campaigns, now we actually need to hire more salespeople.” • “We were able to achieve 100% FCA compliance without hiring additional people." 𝗢𝗽𝘁𝗶𝗼𝗻 𝟮: 𝗪𝗵𝗶𝗰𝗵 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝘄𝗼𝗿𝗿𝘆 𝗶𝘀 𝗯𝗹𝗼𝗰𝗸𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁 𝗳𝗿𝗼𝗺 𝘀𝗶𝗴𝗻𝗶𝗻𝗴 𝘂𝗽? Call it out and knock it down. Examples: • “Normally my sales reps hate new software and refuse to use it, but they love [product] and they’re 24% more productive after the first week.” • “I thought migration would be a huge hassle, but we were up and running in 2 hours, no engineering required.” • “Our CEO was watching this project closely, so I was nervous about working with software from a startup. But [product] not only did the job, it made my whole team look like rockstars." For both options, the key is 𝘴𝘱𝘦𝘤𝘪𝘧𝘪𝘤𝘪𝘵𝘺. The more directly you can address the reader’s exact desire or blocker, the more the quote will resonate with them – and the less it will sound like bullsh*t. 𝗕𝗼𝗻𝘂𝘀 𝘁𝗶𝗽: What if your customers don’t give you the right words for your ideal testimonial? You can always reply to a happy customer and ask “Would you mind if we phrased your testimonial this way instead?” They’ll usually say yes. Who else needs to read this? Tag them 👇🏼 Are you a little smarter than you were 2 minutes ago? Follow me: Matt Lerner so you don't miss my future posts.

The answer to your outbound problems isn't: ⛔️ AI ⛔️ More volume ⛔️ SDR agents ⛔️ More relevance ⛔️ Dialers It's your OFFER. Let me explain... Most reps reach out with something like: “Just want to introduce myself and our company…” “Let’s do a quick call so you know your options when budgeting season comes around...” The problem? You have NOTHING to offer. If there’s no immediate need, there's zero reason to take a meeting with you. So you need a way to entice buyers to meet when they have a problem, but are not actively shopping. Here are three types of offers you can use to entice buyers to meet with you: ✅ Offer #1: Good - Pitch The Blind Date Position who the buyer will be meeting with. Hype up the AE, sales engineer, or yourself. Show them that meeting with you will be worth their while. Example: A client of ours sells an automated welding solution. The manufacturing industry is facing a massive shortage of welding talent. Their SDRs pitched it like this: “I’d love to introduce you to Eric. He’s worked with a dozen manufacturers like Caterpillar, Karavan, and more, who are all facing similar challenges. He’ll walk you through how they’re automating the most difficult welds and dealing with the labor shortage. Even if nothing comes of it, you’ll walk away with a better understanding of how the industry is solving this.” Even if the buyer isn’t shopping, they gain value from the conversation itself. ✅ Offer #2: Better - 1:Many Offers These are high-quality, reusable insights that still feel tailored. Think: competitive benchmarks, industry research, or best practice guides. Example: We have a client that sells to ecomm brands. They conducted a mystery shop of 400 competitors to analyze response times, customer service channels, etc. Their reps used those insights to open cold calls with: “Hey Katie, I submitted a ticket on your site, and it took about 48 hours to get a response. It was about 3x longer than folks like Patagonia and the North Face. Again, it’s Jason. Mind if I share more about why I’m calling?” That’s an offer that feels immediately relevant and valuable. It gets a conversation started immediately. ✅ Offer #3: Best - 1:1 Offers These are custom-tailored experiences or resources created specifically for the prospect. It’s you and your organization putting in serious effort to customize the offer. This works best at the enterprise & strategic levels. Examples: - A cyber risk analysis - A benchmarking analysis - A workshop - A personalized audit of a website checkout flow. - Visiting and experiencing the brand firsthand, then sharing insights. - Offering free data, licenses, or pilots. These take more work, but they convert like crazy. ~~~ Which one's most applicable for you?