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 👇
Sales Call Scripts
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My cold call pick-up rate is 22.2%. Here's what Jeff Bajorek and I are learning from daily cold calling: ✅ Optimize call times to maximize pick-up rates My best pick-up rate is 7:57am local time for the prospect. I catch them right before the workday starts. It's close enough to 8am that no prospect has mentioned anything. 8-9am local time for the prospect remains the highest pick-up rate window. ✅ Use multiple data sources We pull as many as 3-4 phone numbers across two data providers to get the right phone number. Then, we make sure to mark bad phone numbers so we don't call them again. Rarely is the first number the correct one. ✅ We call mobile numbers This one's obvious for many of you. But there's still reluctance, yes, in 2024—to call cell phones. You just have to do it. And deal with the OCCASIONAL angry prospect. ✅ Double & triple touches No "naked activities." We never call without emailing. We never send an email without calling. Salesloft data shows that this type of "combo prospecting" (a la Tony Hughes) increases contact rates by 3.1x. It works. My ideal workflow: → Call first. Things happen way faster on the phones. Feels like less work for me this way. → LinkedIn second. Send a blank connect request. → Email last. Send the email last. I do this all at once. Then give it two days to rest and hit with a double touch of phone + email. ✅ Prioritizing calling prospects who open emails For all the talk out there about innacurate open rating tracking—pick-up rates are much better when I prioritize prospects who open emails. We have an automated call task created after 3 email opens. ~~~ That's it. We follow fundamental sequencing best practices. How are you maximizing cold calling pick-up rates?
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Listen up. I’ve coached thousands of sales calls and most reps sabotage their own deals without realizing it. When I started in 2007, I nearly got fired for not understanding how language impacts buyer psychology. Now, after helping teams double revenue in 90 days, I can spot the hidden mistakes instantly. You're probably killing your win rate with these “harmless” phrases. Here are 6 phrases that are absolutely DESTROYING your deals (and what to say instead): 1) "Sorry to bother you..." Starting with an apology tells the prospect, “I’m not worth your time.” You’ve lost before you’ve begun. Top 1% performers NEVER apologize for delivering value. They command attention through absolute certainty. ✅ POWER MOVE: "Hey Alice, Marcus here from Venli. I'm reaching out because we helped Company X increase their pipeline by 37% last quarter, and I noticed your team might be facing similar challenges..." 2) "Just following up..." This lazy phrase screams, “I’ve got nothing to offer, but want your money.” Total momentum killer. Elite reps are wildly precise with their words and always reference specific commitments made in previous conversations. ✅ POWER MOVE: "Alice, you mentioned you were going to discuss our proposal with Charles during your leadership meeting yesterday. I'm curious … what feedback did you receive that we should address?" 3) "I know you're really busy..." Say this, and you’ve just made yourself irrelevant. Game over. Remember: YOUR time matters. Top performers signal status through subtle positioning every time. ✅ POWER MOVE: "I was just wrapping up a strategy session with Lisa, the CEO over at Company X, and wanted to quickly connect about next steps before my afternoon gets packed..." 4) "What are the next steps?" This signals poor process control - no system, no playbook, no real method. The sales machines I build don’t ask for direction - they GIVE it. They own the process. ✅ POWER MOVE: "Based on what we've discussed, here's what typically happens next: First, we'll schedule a technical review with your team for next Tuesday. Then, we'll deliver a customized implementation plan by Friday. How does that sound?" 5) "To be honest..." Wait, Wait... so everything before this wasn’t true? Nothing kills credibility faster. When I turn around failing sales teams, eliminating this phrase is always one of the first habits we break. ✅ POWER MOVE: "That's an excellent question, Alice. Here's exactly how our solution addresses that challenge..." 6) "What do I have to do to get your business?" Is this 1988? This pushy close screams desperation and kills trust instantly. The best reps I've coached understand that closing isn't an event. It's the natural outcome of a well-executed sales process. ✅ POWER MOVE: "It seems like you're hesitating about X. I'm curious … what specific concerns do you have that we haven't fully addressed yet?" Which of these six phrases have YOU been using without realizing it?
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Nobody tells you this about enterprise sales The biggest deals are lost in the first 5 minutes. Not because of your pitch. Not because of your price. Not because of your product. But because of the language you use. Here's what I discovered after analyzing 1000+ sales calls: The higher the deal value, the simpler the language needed to win. Example: $5K deal (Lost) Rep: "Our value proposition addresses critical pain points in your tech stack integration, offering seamless scalability..." $50K deal (Won) Rep: "We help companies stop losing customers due to slow website loading times." See the difference? I tested this with a struggling SaaS team: Before: Complex sales language - 22% close rate - 108-day sales cycle - $127K average deal After: Plain English only - 41% close rate - 71-day sales cycle - $198K average deal Simple change. Massive impact. The truth is, every exec can smell rehearsed "sales talk" from miles away. Want to close bigger deals? Drop these phrases: - "Value proposition" → Say how you help - "Pain points" → Say what problems you solve - "ROI analysis" → Say how much money they'll make - "Scalable solution" → Say how you grow with them - "Best-in-class" → Say why you're better Top performers don't sound like salespeople. They sound like trusted advisors who happen to sell. Start talking like a human. Watch your deals grow. What's the worst sales jargon you've heard lately? P.S. If you need help with your sales, send me a message Let's talk about finding your breakthrough strategy
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Here's a discovery technique that feels manipulative but isn't: The "go back in time" question. I learned this after watching hundreds of discovery calls go sideways. Here's the problem: You get on a call with an inbound lead. They're ready to see the product. They want to talk solutions. But you need to understand their pain first. If you start asking: "So what are your biggest challenges?" They get annoyed. "We already told your SDR. Can we just see the product?" You've lost control. Here's what works instead: Start by meeting them where they are. Ask: "What motivated you to look into [your category]?" They'll tell you about the solution they want. Let them talk for 2-3 minutes. Then say this: "Interesting. Can I go back in time with you for just a second? What was the ORIGINAL challenge going on in your business that caused you to prioritize looking into a solution like this to begin with?" Boom. Now they're telling you about the pain. Not the solution. Why this works: You respected where they were in their buying journey first. You didn't force them to go backwards immediately. You earned the right to ask about pain by first acknowledging they're ready to talk solutions. The pattern: 1. Meet them where they are (solution-focused) 2. Ask 1-2 questions about what they want 3. Use the "go back in time" transition 4. Now you're in pain-based discovery I've used this hundreds of times. It works like magic. Try it on your next inbound call. You'll never go back to generic discovery questions again. P.S. These 7 strategies will help you CLOSE more deals in a GTM crisis: https://lnkd.in/d_DkYTSH
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Head over heels in love with this phrase a newer AE has been using in her disco convos that she shared during one of our Peer Groups last week: "I'm still learning the ins and outs of your job and what your everyday looks like." And apparently, it works every single time. Not "I understand your challenges." Not "I work with companies like yours." Just admitting she doesn't fully get their world yet. The prospects slow down a bit and start explaining things differently. They become teachers instead of prospects. Apparently, one VP of Supply Chain spent 47 minutes mapping out his entire operation after she.…..just said she was still learning about all things supply chain. Weird, right? The funniest thing is that this is probably what a lot of reps are all thinking but don’t say. They sit through these disco calls nodding along while acronyms fly over their heads. They pretend that 3-day onboarding somehow made them experts in their industry. They may even memorize persona cards that say "CFOs care about ROI" and act like we've unlocked some Rosetta Stone shit. Meanwhile, I'd wager most buyers would know that they're faking it. But when you admit you need their help understanding their world? That level of vulnerability works. - They tell you why your competitor won't work (saving you weeks of positioning). - They explain which stakeholders will kill the deal. - They literally draw you a map of how to win. Gong's data backs this up, btw...reps who use phrases like "help me understand" have 23% HIGHER close rates. Probably because it sounds human? Another rep in the group mentioned they tried something similar with a CISO. Eight years of selling experience, knows security cold. But instead of the usual dance, he goes: "I know software, but I don't know your specific environment. Walk me through what breaks." CISO ended up explaining exactly how to position against the incumbent. Even suggested which features to ignore during the demo. So maybe you should stop pretending. Stop nodding when you're lost. Stop using discovery scripts that assume every VP is the same VP. The smartest person in the room is usually the one asking the dumb questions. I'm not saying that expertise is useless or that you shouldn't strive for it. Not at all. What I AM saying is that maybe your buyers don't need someone who pretends to know more than them about THEIR INDUSTRY. Maybe they need someone who cares enough to actually understand their mess before suggesting solutions. Expertise is overrated. Curiosity closes deals.
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How I run sales meetings that lead to next steps 90% of the time. Running a successful sales meeting involves clear communication before, during, and after. Often, attendees aren't sure what to expect, so we have to make sure to set the tone before the call even happens. So I send an agenda 24 hours prior to the call and include the following. • What topics will be discussed • Questions to answer beforehand • Use cases if applicable Also, make sure to do some research about the company so you have context. No one likes an unprepared sales rep. During the call immediately set expectations. • Ask if they have a hard-stop • Refer back to the email to set the agenda for the call • Mention that you did some research and tell them what you found Be an active listener and ask deep discovery questions to uncover pain. As the call wraps up, make sure to leave 7-9 minutes to guide them through the next steps. Here is an example: "Typically, when we see a problem like this, we would most likely include (x person) and (y person) on the next call to discuss how we help in that area. Would Thursday at 10am EST work for you?" I book these meetings directly from Calendly's browser extension while still on the call because it's quick, smooth, and instant. Calendar invites are sent before we end the call so you remove the possibility of being ghosted after. We still have work to do after you nail down the next steps. We ain't done yet. Send a summary email, not to do more selling but to recap for accountability. • What their main goals/priorities are • Timeline • Next steps When you have a system to run better meetings, it leads to great results. P.S. Do you agree with this framework? #BetterMeetings
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My average sales cycle for 5-figure B2B training deals is 2 weeks (inbound). Here's how I run the sales cycle step-by-step👇 1. Intro Discovery: Before the call I spend 30 minutes researching the account & persona I speak to. This allows me to focus on pain, impact and need-payoff questions (check out SPIN). I use a standard business case template to help my prospect understand the Cost Of Inaction (COI) of not making a decision. We agree on a proposal call within 3-5 business days. 2. Proposal Call: I use tl;dv - AI Meeting Assistant to summarise all the information from the 1st call. Budget is often not defined, therefore I work out 3 flexible pricing options of different scope. My prospect is usually not the economic buyer, so I will get their input before we present to a decision maker. We schedule a decision maker call 1-2 days later. 3. Decision Maker Call: I walk the economic buyer through my proposal: challenges, objectives, training scope & methodology, timing, joint responsibilities and commercials. I always expect to negotiate, so I prepare 3 scenarios of making concessions that protect my time and hourly rate. 4. Implementation Call: Once the agreement is signed I set up a call with my champion to schedule all training workshops, get the list of participants and prepare everything for kick-off. They key takeaway: → Closing inbound deals is all about buyer experience. → Run a smooth sales cycle & remove barriers to buy. → YOU are the expert in what you sell, so lead the way. What's your best practice inbound sales process?👇
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I’ve done 350+ discovery calls in the past 3 years and closed 7+ figures in contract value. I always structure my 1st call in the same 5-step format: Great sales is nothing more than a structured approach to help prospects make a decision. It shows them that I’m understanding and have their best interest at heart. I consider sales to be part of the service. It’s consulting. Here's how my discovery calls look: 𝟭. 𝗚𝗲𝘁 𝗧𝗵𝗲𝗶𝗿 𝗦𝘁𝗼𝗿𝘆 I want to find out as much as possible about them. My goal is to understand their journey & personality, and also make them feel heard & understood off the bat. They talk, I shut up. If they jump straight into business, I gently steer them back. ___ 𝟮. 𝗔𝗻𝗮𝗹𝘆𝘇𝗲 𝗙𝗶𝘁 Next, I dive into their business model, bottlenecks, and top goals: • Who’s your ICP? • What do you offer? • What’s your marketing status quo? • etc. I figure out if a collaboration makes sense and whether they need our help or something else entirely—like coaching, a new tool, a different vendor, or just advice on improving their current setup. ___ 𝟯. 𝗜𝗻𝘁𝗿𝗼𝗱𝘂𝗰𝗲 𝗠𝘆𝘀𝗲𝗹𝗳 I recap what they’ve shared and then introduce myself. Here, I try to mirror how they shared their story: • what topics did they focus on? • how far back did they go? • what did they highlight? At the same time, I look for similarities between us to create relatability. Then at the end, I explain what I do on a high level. ___ 𝟰. 𝗞𝗲𝘆 𝗧𝗵𝗲𝘀𝗲𝘀 & 𝗥𝗼𝘂𝗴𝗵 𝗕𝘂𝗱𝗴𝗲𝘁 𝗥𝗮𝗻𝗴𝗲 From there, I introduce the 3 key theses they need to believe for us to work together. • Thesis 1: The decisions we make are influenced by the people we trust and the content we consume. • Thesis 2: Content helps build relationships & trust at scale. • Thesis 3: Content is an infinite game If they're not aligned with this thesis, it usually indicates we're not a fit. At the same time, I also discuss the rough budget range to make sure we're on the same page about expectations early on. ___ 5. 𝗕𝗼𝗼𝗸 𝘁𝗵𝗲 𝗡𝗲𝘅𝘁 𝗦𝘁𝗲𝗽 If it feels like a fit, I lock in a follow-up call right then. I never leave this for later—it just adds uncertainty and hassle. If it’s not a fit, I still try to offer value—maybe I send some free resources or give advice. ___ 𝗕𝗲𝘀𝘁 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲𝘀 𝗜 𝗙𝗼𝗹𝗹𝗼𝘄: • I call out any elephants in the room. • I recap what they say to confirm my understanding and give them a chance to add details. • This also helps me process what they’ve shared. • I always leave room for their questions. • Their needs are #1 priority. #b2bsales #founderledsales #consultativesales
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Top reps ask 4x more implication questions than average ones. Here’s why SPIN Selling still works. Most reps jump straight into pitch mode. They ask a few surface questions, then start talking features. That’s not selling. That’s presenting. SPIN flips the script. It gets the buyer to sell themselves. Start with Situation questions. Learn their current state, but keep it short. Experienced reps ask fewer of these than you’d expect. Move to Problem questions. Uncover what’s not working. Where they’re stuck. What’s costing them time or money. This is where small deals get won. But for complex sales, you need more. That’s where Implication questions come in. Show the consequences of inaction. What does this problem cost them? How does it affect other areas? What’s the revenue impact? Top performers ask these 4x more than average reps. They build urgency without being pushy. Finally, Need-Payoff questions. Let the buyer articulate the value. How would solving this help? What would the impact be? Why is this important? When they say it, they believe it. Here’s the key insight: Buyers don’t just want you to solve their problems. They want to understand why solving them matters. SPIN gives you the framework to guide that conversation. Not through charm. Not through pitch decks. But through the right questions in the right order. Save this framework. Use it on your next discovery call. Watch how fast urgency builds.
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