Sales Opening Techniques

“Call a lead within 60 seconds and you’re 10× more likely to win the deal.” Cool stat. But I’ve never bought anything just because someone was fast. I buy when someone makes me feel understood. And making people feel understood doesn’t come from speed. It comes from presence. From a pause. A reflection. A moment that says: “I see get you.” “What I hear you saying is…” “It sounds like…” “What’s your theory on why that is?” “What would a win look like for you?” “Why not do this in house?” These aren’t closing techniques. They’re acts of respect. Because people don’t trust what you recommend until they feel like you understand them. So yes, respond promptly. But not toward the sale. Toward understanding. Speed to lead gets you in the room. Speed to trust keeps you there.

Want more opens, more clicks, and more sales from email? Start with these 7 simple changes. 1) Optimal Sending Time Schedule emails when your audience is most likely to engage. Analyze past open rates to identify peak days and times that have performed well. For example: Tuesday and Thursday mornings PST. Test different timings & refine based on performance data. 2) Reflect Your Brand’s Tone & Value in the Sender’s Name If your brand is playful, use a friendly, informal name like ‘Your buddy Jack at [Company]’. For a more professional tone, opt for ‘Jack, CEO at [Company]’. This alignment enhances brand consistency & recognition. 3) Craft Irresistible Subject Lines Incorporate these elements into your subject line: Numbers/data Specificity Power words Curiosity Emojis Questions This is how you make it impossible to ignore. 4) Leverage the Preview Text Use your preview text to: Tease a benefit Offer an incentive Provide a sneak peek The preview text gives people a second nudge to open your email. Make the most of it. 5) Implement a Call-To-Open Call-to-opens are phrases like: “Open to discover…” “See what’s inside…” “Click here to learn…” Incorporate these in your subject line or preview text. The simplest way to encourage an open is by directly requesting it. 6) Optimize for Mobile Ensure your emails display well on small screens. Shorten subject line/preview text Check the sender’s profile picture Ensure correct character display Most people check their email on a mobile device. Neglecting them means losing a lot of opens. 7) Strategically Resend to Non-Openers Resend with a tweaked subject line or a note like: “In case you missed this…” This approach can recapture attention without seeming repetitive. Bookmark this and follow Chase Dimond for more great tips.

We tend to complexity sales (sometimes), but Sales = Trust 3 steps framework I use since 2015 👇 1. Set-Up: It’s all about the prospect Before you talk about your product, you need to earn the right. The first 10 minutes? You’re not selling. You’re listening. Hard. You're asking real questions. You're clarifying assumptions. You're pushing on the pain and helping them feel it. If they’re doing most of the talking early, you're doing it right. Use the ACE Framework to open strong: - Appreciate – Thank them, and lead with a custom insight about them or their company - Check – Confirm what you know about their pain. Ask, “Did I get that right?” - End goal – Align on the purpose of the call: “We’re here to see if this is a fit. Sound good?” This tells them: You’re not winging it. You came prepared. - - - 2. The Feature Ask-Flow Now that you’ve unpacked their pain — it’s your turn to shine. But not by dumping every feature you’ve got. Focus on three features. Max. Each one should map directly to a pain point they confirmed. Here’s how you present each one: Show the feature — clearly, simply, relevantly Ask: A. “Does this solve the problem you mentioned?” B. “What would the impact be if you implemented this?” C. “Can you see your team using it?” These questions do two things: → Keep them engaged → Make them imagine the future with you in it - - - 3. The Close: The Rocket Demo Builder - You’ve shown the pain. - You’ve shown the solution. - Now, don’t fumble the close. Summarize what you heard: “You’re trying to [X], and the biggest blocker is [Y]. We showed you how we solve it with [Z].” Then make the ask. Not pushy. Just clear: - “Is this something you want to explore further?” - “Should we look at what rollout would look like?” Too many sellers talk at prospects. Great ones build a path with them. The difference is process.

I just deleted 147 cold emails without reading them. Here’s what they all got wrong: Every morning, my inbox looks the same. A flood of pitches from people trying to sell me something. Most days, I just mass delete them. But this morning, I decided to actually read through them first. Within 5 minutes, I spotted a pattern. Everyone was making the exact same mistake. They were all trying to close the deal. ALL IN THE FIRST MESSAGE 🥵 Let me show you what I mean (with two small examples): APPROACH A: "The Wall of Text" Send 100 cold emails with full pitch, calendar link, and case studies. • 3 people open • 0 responses • 0 intros This looks exactly like the 147 emails I just deleted "Hi [Name], I noticed your company is scaling fast! We help companies like yours optimize their marketing stack through our proprietary AI technology. Our clients see 300% ROI within 90 days. Here's my Calendly link to book a 15-min chat: [LINK]. Looking forward to connecting! Best, [Name]" BORING!!! APPROACH B: "Micro Conversations" Same 100 prospects, broken down into micro-convo's. Email 1: "Do you know [mutual connection]?" • Send 100 • ~40 open • ~20 respond Email 2: "They mentioned you're scaling your marketing team. I'd love to connect about [specific thing]." • Send to 20 who responded • ~15 continue engaging Email 3: "Would you mind if they made an intro?" • Ask 15 engaged prospects • ~10 intros Final score: • Approach A: No intros • Approach B: 10 intros How to Apply These Lessons (Tactical Summary): 1. Focus on Micro-Conversations: Break your cold outreach into smaller, manageable steps. Build rapport before making any asks. 2. Personalize Everything: Reference mutual connections, specific company milestones, or shared interests in every message. 3. Play the Long Game: Aim for replies in the first message.. not conversions. If you’ve been struggling with cold outreach, you might just need a new approach. Give this one a try and lmk how it goes.

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

When I started coaching an SMB AE, he was a quota ghost—5 months straight, barely cracking 25% close rates. His company could have fired him. Instead they brought me in We tore into 1:1s, call replays, deal autopsies. By month 7, he was closing 60% of his demos and got promoted to Sr. AE. Here’s the 5-step gut-punch playbook we used to turn his sales around: 1/ Kill the Product Hype: He’d lead with ‘Let me give you a walkthrough of [product]’—and lose them in 5 minutes. We flipped it: ‘Out of [all the problems mentioned], whats #1 on your list to solve in next 90 days?’ Discovery became the star; the product waited its turn. 2/ Name the Bleed, Then Bandage It: He’d rattle off features like a spec sheet. I taught him how to alley-oop it to the feature. Example: "You said [PROBLEM] is killing you—here’s how we stop it." Pain-first hooks them; solutions seal it. 3/ Drop the Commission Chase: He’d oversell every deal, gunning for the fattest paycheck. We flipped it: "This solves your headache—nothing more, nothing less." Honesty built trust, and deals started closing faster. 4/ Cut to the Chase: His demos dragged with fluff—prospects checked out. We slashed the word salads, hit their pain point in 3 minutes: Example: "This is why you’re here; here’s the fix." Speed won them over. 5/ Sell the Win, Not the Widget: He’d geek out on feature details—felt like a CS onboarding call. We reframed it around solving the prospects problems in the shortest period of time. Example: "Here’s how this gets you [GOAL] faster." He stopped being a demo monkey. SMB reps have the chops—they just need the right lens.

Sales are simple when you understand this secret: The moment you start selling, you've lost. I used to be terrified of sales calls. Now my team and I close without ever feeling like we're "selling." Using a proven system I call “Pitch OS”. I've taught this exact system to founders who went from struggling to book calls to closing 30-50% of their prospects. Here's the 6-step sales system: 1. Lead With Curiosity Most salespeople start by talking about themselves. Big mistake. Instead, ask open-ended questions: • "What are you looking to achieve?" • "Tell me about your current situation" • "What made you book this call today?" Then shut up and listen. 2. Clarify Their Challenges You can’t help your prospect if you don’t truly understand their situation. Some great follow-up questions I use: • "Tell me more about that" • "Why is that important to you?" • "What impact does that have on your life?” Care about what they say here. The key is to dig deeper: • "How long has this been an issue?" • "What happens if this doesn't get solved?" Their answers become your roadmap. 3. Co-Create Their Ideal Outcome Once you understand their challenges, help them paint a picture of what success looks like: • "What's the ultimate goal here?" • "What would this allow you to do?" This creates a vision they're emotionally invested in. 4. Contrast Cost of Inaction vs. Investment Most people aren't afraid of the cost of your solution. They're afraid of making a change. Ask them: "If nothing changes, where will you be in 6 months?" Help them see what inaction will cost them. 5. Present Your Solution As The Bridge After successfully going through steps 1-4, I transition into the bridge: "Based on what you've shared, I think I can help because of my experience in [solving their problem]. Here's how we'd get you to [their ideal outcome]." I structure my solution around 3-4 clear pillars that directly address their challenges: "The first thing we'll do is build out what I call [Pillar 1], which will solve [Challenge 1 they mentioned]." Then, I’d go through each one in detail, following the same format. 6. No Manipulation I never use: • Fake scarcity ("only 2 spots left!") • False urgency ("price doubles tomorrow!") Instead, I'm radically honest about what my solution can & cannot do. Sales don't have to feel gross. Remember: Trust is built before the call, not during it. That's why my Content GPS makes sales effortless: • Monthly workshops with immense value • Weekly newsletter building a true relationship • Daily content on social media solving real problems By the time someone books a call, they're pre-sold on your expertise. __ Enjoy this? ♻️ Repost it to your network and follow Matt Gray for more. Want to learn how to build a sustainable founder-led brand that grows even when you’re not around? Join my free live Workshop on August 21st (4 days away) to steal my homework: https://lnkd.in/eXgiGXxS

Most sales presentations fail in the first 10 seconds. (And most people do not even realize it.) Prospects are busy, distracted and have little attention. If you do not capture attention fast, You will lose them fast. So how do you hook them instantly? Start with: 𝗪𝗵𝗮𝘁 𝗶𝘀 𝗶𝗻 𝗶𝘁 𝗳𝗼𝗿 𝘁𝗵𝗲𝗺? 📌 Instead of starting with: ❌ "Here is an introduction of myself." ❌ "I will be sharing our new products with you." ❌ "Let’s begin with a background of our company." 📌 Try this: "I will be sharing about how you can X with/without Y so that you can Z." X = Results (E.g. Generate quality leads) Y = Your method (E.g. Without running ads) Z = Bright future (E.g. Be stress-free from finding sales) See the difference? Your audience needs a reason to listen. Keep it clear. Keep it specific. Keep it about them. 𝗣𝗦: 𝗪𝗵𝗮𝘁 𝗶𝘀 𝘁𝗵𝗲 𝗯𝗲𝘀𝘁 𝗽𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 𝗼𝗽𝗲𝗻𝗲𝗿 𝘆𝗼𝘂 𝗵𝗮𝘃𝗲 𝗵𝗲𝗮𝗿𝗱?

I analysed 100 of our best-performing outbound campaigns The ones getting the most replies have 3 things in common: 🍿 A no-brainer offer The best cold outreach offers something instantly useful. A free audit. A shortcut. A valuable insight. Think: “I’ll do this bit of work for you — no strings.” The aim? Leave them thinking “Why wouldn’t I say yes to this?” 🤙 An informal tone of voice People buy from people (yes, even in B2B!) Casual, clear, human messages build trust fast. Remember: You’re talking to a person on the other end! 💭 A soft CTA We’re seeing better results with low-pressure closes: “Worth exploring?” “Want me to send more info?” “Can I show you how we’d approach it?” It opens the door without slamming them with a meeting link and lets the prospect stay in control. 💬 Curious what others are seeing... Are you noticing similar shifts? Or are you still finding success with the old-school approach?

They put me on the spot. Cold calling for a product I don't sell. 5 minutes to build a script. And only 5 connects to book a meeting. There's nothing worse than a "sales trainer" teaching cold calls who doesn't know how to do it themselves, am I right? 30 Minutes to President's Club put me to the test. Here was my approach: ✅ The opener: nailing the first 30 seconds I need to grab the buyer's attention in a unique way. Every great opener has a strong Reason To Meet (RTM): - Trigger: Why should I engage now? - Tension: Why should I consider change? - Trust: Why should I continue talking with you? Not necessarily in that order. And not all at once. I like the initial opener to have the trigger. It might sound like this: "Hi Dave, saw you're hiring AEs right now. It's Jason with Outbound Squad. Can I share why I'm calling you specifically?" Bonus points if you can include more than one of the Ts in the opener like this: "Hi Dave, saw you're hiring AEs right now. It's Jason with Outbound Squad. Our clients like Shopify are very focused on making sure those AEs can self-source their own pipeline right out of onboarding, which we help support. Have a minute for me to share more about why I'm calling?" Trigger, tension, trust...the entire RTM all in the opener there. ✅ The tension Next, I need to really understand the buyer's problem. The tension they're feeling on a daily basis that makes them take action. My approach here is always to "chunk up" We have two types of tension: - Strategic tension: problems that affect the business (execs care more about this) - Surface tension: problems that affect the day-to-day for those executing the work If I'm calling execs, I want to focus on strategic tension and how problems affect revenue and profit ~~~ Spoiler: I had a 20% conversion rate into a meeting for a product I do not sell. This was a fun one. I'd highly recommend the full breakdown, where you can listen to me get rejected and analyze what happened. Check it out here: https://lnkd.in/gx9zUfQx