Joey Gilkey

SMB AEs stuck at $5K per month make the same mistake when it comes to creating urgency in deals. They try to manufacture it. "This promo ends Friday" "We only have 2 licenses left" "Pricing is going up next week" Prospects see right through it, and worse, it cheapens the deal (and your product). The best AEs making $10K-$20K don't fake urgency. Here's how: 1. Tie to their calendar, not yours: Instead of “my end of quarter,” they anchored next steps to their business timelines, hiring pushes, seasonal peaks, upcoming product launches, etc. 2. Stack the cost of waiting: They don't say “sign up now or else.” They show what waiting 30 days actually cost (lost deals, more $ spent, etc). 3. De-risk fast action: They reduce friction in the deal by addressing prospect's major FUD (Fear Uncertainty and Doubt) and de-risk the decision for them. Before my AEs go after a big deal, I tell them to lay out the prospects: → problem → timeline → reason timeline → benefit to switch now on paper and role play the talk track by tying it all together. When buyers see the cost of waiting, you don’t have to push. They’ll pull the deal forward themselves. P.S. If you liked this, you'll love my Monday morning newsletters 6,000+ sellers are reading: https://lnkd.in/dkuDYfnn

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Most salespeople don't know how to "create" urgency. It is hard to do. And there are not many ways you can actually do it. What is one way you can improve? You likely are satisfied too early with the information you get from prospects. You are not asking enough. Let's go into an example: This salesperson is in a discovery meeting. Here is how the discussion unfolds: 🕵🏾 Salesperson: "Why are you taking the time for this meeting?" Prospect: "I want to learn more about your tool. We would like to make our salespeople's lives a bit easier and introduce some new technologies that can reduce admin effort and help us improve our conversion rates." ---- 70% of salespeople are satisfied with that information and move on to the demo. ---- Meanwhile, the other 30% dives deeper: 🕵🏾 Salesperson: "Okay, could you please elaborate a bit on what admin tasks you are talking about that you see some potential for making lives more efficient?" Prospect: "Our salespeople spend way too much time entering data into the CRM. Additionally, they go from meeting to meeting and often do not have time to properly follow up with the customers. That leads to lost deals." ---- Another 20% of salespeople are satisfied now and move on to talking about their product. ---- Meanwhile, the remaining 10% dives deeper: 🕵🏾 Salesperson: "Besides obvious consequences such as lost time and frustration, what other impacts do you see from people spending too much time entering CRM data?" Prospect: "Well, actually, the main problem is that because most salespeople are not doing it properly, we often lack information when a sales cycle is very long or has some changes in the sales force. That annoys many future customers of ours." ---- Another 5% stop asking questions here and move on. ---- The remaining 5%: 🕵🏾 Salesperson: "It seems like your company is still running despite these pains. Why not continue doing things the way they're done now?" Prospect: "We estimated that we lost 5 larger deals with an average of 50'000 ARR last year because of all that I have said above. And we were actually 200'000 short of our target?" ---- The last 1%: 🕵🏾 Salesperson: "Uh that sounds rough. How did that affect you personally?" Prospect: "I got all the frustration from our Board and our CEO...." ---- That is the meat to the bone 🍖 That is what will open their eyes and make them aware of how severe that challenge actually is. Try to be with those last 1%. Be genuinely curious until you understand business and personal Value. It will be the basis of the urgency of any deal.

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Meeting show rates: 72.5%+ is the golden standard Here's Gong's latest analysis with 30 Minutes to President's Club on show rates: 🔴 - 56.9% 🟡 - 57-72% 🟢 - 72.5% You're leaving massive amounts of revenue on the table if prospects aren't showing up to meetings. Here's how to fix this problem: ✅ 1) Should the meeting have been set in the first place? - Strong ICP fit - The right persona - A problem worth exploring If they don't meet that criteria, don't set the meeting ✅ 2) Make it easy Leverage best practices from executive assistants: - Convert to their timezone - Manually suggest days/times - Provide a meeting link - Let them know you're happy to work with their EA ✅ 3) Phone confirmations - Get the prospect to accept the invite live, on the phone, while you have them: "Sometimes these end up in spam. Would you mind quickly accepting the calendar invite on your end to make sure it went through?" - Text them a confirmation - Double down on the agenda for the meeting and what's in it for them ✅ 4) Customer-centric calendar invites/agendas Don't label things in a way that makes you look like a vendor. Meeting Title example: "Demo with Outbound Squad" looks like a sales call "AE self-sourcing + PipeGen" is more like an internal invite ~~~ If you're dealing with no shows, take an idea or two from this list and try it. How else do you prevent no shows? P.S. Join me, Colin Specter🥇, and Calvin Flax next Wed 8/27 for a free training on cold calling. You’ll get tons of data-backed tips to help you land more meetings from the phone. Register here: https://hubs.ly/Q03B6wgP0

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3 Things you should never say in Sales: 1. ‘That competitor sucks’ Quickest way to lose credibility. Instead, acknowledge that they’re good companies But outline 3 reasons why companies choose you. 2. ‘Can we get your boss on the next call?’ Leaves a big chance of being shut down. Instead, map the account before Learn the first name of the ‘boss’ Build a valuable next step & recommend they join. 3. ‘We can offer split payments no worries!’ Small things like this CAN be easy to get approved. But when negotiating, Never give anything without getting: → Isolate their request (Is this the only thing you need?) → Confirm if that’s it (If we approve this we’ll move forward?) → Agree on a signature date (I can try but we’ll need to sign by X) What would you add to this list? 680+ Sellers are subscribed to my newsletter 😁 Tonnes more insights shared there: https://lnkd.in/e4b9FAvP

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I interviewed 150+ B2B buyers in the last 6 months. Here’s the most surprising thing I learned: AE's asking for a 30 minute demo call kills pipeline For a buyer, 30 minutes is a HUGE ask. And if you are using a scheduling link and making them wait 2 weeks for that call, you're dead on arrival.    There are over 1,000,000 sales reps in the United States. These 30 minute demo calls add up to millions of decision maker hours every month. You need to use your buyers time (and attention) more responsibly Buyers want instant answers. They do not think 30 min is fair ask just to get clarity on a few questions The problem isn’t the demo but how and when you do it. Here’s what's actually working for sellers today: 1. ChatGPT: Get the answers to your qualifying questions on ChatGPT and spare the buyer with obvious questions 2. Trust : Use the time to build trust and “really” understand the buyer needs. Ask “What value can I provide you with today to earn the right to another call?” 3. Actively Listen: Let the buyer speak. Listen between the lines. Record the call and listen to it again. 4. Reduce time: Reduce the time for discovery calls to 15 min but try to do it within 24-48 hours 5. Solve problems : 30 minutes isn’t enough to build trust. Trust develops over repeat interactions through consistent problem-solving. Get the process started. 6. Many 15 min calls: Try to do multiple 15 min calls with emails or slack. Use the cadence that works best for the buyer to get immediate value. 7. Provide Micro Value: In every call try to deliver something of value - content, free demo, insights, recommendations or introductions. Ask how you can be useful. When buyers reach out they are often looking for expertise and not a demo Sooner they get the answers, the faster they can move through the buyer’s journey Don’t try to slow them down with relentless qualifying questions or irrelevant demos. The future of sales will not be driven by 30 min demo calls It will be won by sellers that respond fast, solve real buyer problems and earn trust in every interaction.  At Zeer AI, we are building research tools that make this future possible. Until then review your content for the 30 min demo calls and keep earning the right to your buyers time.

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Too much sales outbounding still starts with the same lines:  ☑️ “Just checking in.”  ☑️ “Hope you're doing well.”  ☑️ “We help companies like yours…” The future of selling is rooted in real connection, not automation. Every touchpoint is a chance to differentiate or disappear. Personalization is more than using a name or company, it’s about showing you’ve done the work to understand what matters. That’s how conversations start. Sellers win when they treat outreach as a conversation, not a template. Revenue is a team sport — and that starts with every seller showing up with empathy, insight, and intent. Let’s raise the bar. The buyer deserves it. So does your pipeline.

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