100 Sales Calls for Startup Success

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 👇

In 2022, I tried cold calling like it was 2010. Result? 0 meetings booked. Why? Buyers are smarter, busier, and less patient. But here’s the thing: Cold calling works—if you adapt. Here’s how I turned it around and booked 60 meetings in 20 days becoming a Top Sales Performer in a Startup Unicorn: 1️⃣ Do Your Homework No more blind dialing. Research your prospect: → Recent news about their company → Their pain points based on their industry → Key decision-makers (know their names!) My mistake: I used to pitch without knowing their challenges. My fix: I spent 5 minutes researching before every call. 2️⃣ Open Strong Don’t waste 15 seconds introducing yourself. Hook them right away: “Hi [Name], I noticed [specific insight about their company], and I think we might be able to help you solve [key challenge]. Do you have 2 minutes?” My mistake: I started with, “Hi, I’m Carlos from Sales Titans.” My fix: I led with value and got their attention in 10 seconds. 3️⃣ Focus on THEM, Not You Cold calls flop when you start with “We do this…” Instead, ask questions: → “What’s your biggest challenge with [their area of interest]?” → “How are you currently solving [specific problem]?” My mistake: I talked about my services before understanding their needs. My fix: I flipped the script and made it about them. 4️⃣ Have an Objection-Handling Plan 90% of first objections are smokescreens. When you hear “I’m not interested,” ask: “Totally understand. Before I go, let me ask: are you seeing [specific industry trend]? That’s something we help companies navigate.” My mistake: I took objections at face value. My fix: I used objections as opportunities to educate. 5️⃣ Book, Don’t Sell Your goal isn’t to close the deal—it’s to schedule the next meeting. “Why don’t we hop on a quick call next week to dive into this further? How’s Tuesday at 10?” My mistake: I tried to close on the first call. My fix: I focused on booking the next step. 🎯 The Cold Calling Rules for 2025 → Be prepared. → Focus on adding value, not pitching. → Always aim to move the conversation forward. Cold calling is still a skill, and those who master it are thriving.

90% of salespeople are sleeping on ChatGPT for sales call prep. It’s not just a toy. It’s a tactical advantage. Here are 10 sharp prompts that make your discovery calls, demos, and objection handling way stronger: 1.) Discovery Call Decoder “Based on this company description: {paste}, give me 5 discovery questions tailored to a {job title} at a {company type}. Focus on uncovering pain points and priorities.” 2.) Objection Anticipator “I’m selling {product} to {persona}. What are the 3 most likely objections I’ll hear—and how should I respond with confidence and value?” 3.) Call Opener Generator “Write a 60-second intro for a discovery call with a {job title}. Make it sound natural, curious, and low-pressure—not scripted.” 4.) Deal Killer Detector “I’m prepping for a call with this company: {paste LinkedIn or website text}. What signs suggest they’re a bad fit or time-waster?” 5.) Competitor Contrast “Our biggest competitor is {name}. Give me 3 clear, honest ways we’re different—no bashing, just value-focused contrast I can use live.” 6.) ROI Talking Points “List 3 business outcomes I can tie {product} to when speaking with a {seniority level} buyer. Keep it punchy and high-level.” 7.) Persona Cheat Sheet “Create a quick snapshot of {job title} at a {company type}. What are their goals, metrics, and daily frustrations?” 8.) Demo Setup Lines “I’m about to show {product} to a skeptical buyer. Write a 2-line intro that frames the demo around their goals—not our features.” 9.) Story-Based Social Proof “Give me a short customer story I can tell about how {company} solved {pain point} using {product}. Make it conversational, not salesy.” 10.) Confidence Reps “Act as a skeptical {job title} and role-play a discovery call with me. Ask tough questions, and let me respond.” These prompts = sharper calls, better deals, fewer stalls. — 📌 Save this. Share with your team. 🚀 Want the high-res PDF version and 21 bonus sales resources? Grab it here → https://buff.ly/8rE7ZPV ⚙️ Want to go deeper? Check out the AI Sales Mastery Program - designed to help reps close faster, prep smarter, and dominate the new era of selling: → https://buff.ly/HJ1cIhf

If my CEO asked me to bring $1000 MRR by tomorrow 5PM, here’s exactly how I’d do it. No fluff. No theory. Just actions that actually move the needle. First, the math: $1000 MRR = 5 deals at $200/month. Or 10 deals at $100/month. Assuming: 20% close rate after conversation 10% reply rate on first touch 30% pickup rate on cold calls I need about 400 multichannel touches to be safe. Not impossible. But no time to waste. Here’s the plan: 1️⃣ List Building (3 hours max): → Define ICP: SaaS founders with 5–50 employees, $500k–$5M ARR → Pull 300–500 contacts using Linkedin Sales Navigator or Clay → Verify emails via lemlist or NeverBounce by ZoomInfo - Enrich phone numbers using Lusha or lemlist No random contacts. Only high buying-intent people. 2️⃣ Offer Crafting (1 hour): The message is simple: “Hey [FirstName], noticed [specific pain point]. Helping [similar companies] fix this with [outcome]. Can show you in 5 mins if you want.” No links. No PDFs. No decks. Just a conversation starter. 3️⃣ Channel Strategy: Forget cold emails alone. Go full speed on: → LinkedIn DMs → Cold calls → Cold emails (only if no reply elsewhere) Tools: lemlist (for multichannel outreach and automation) Pipedrive or HubSpot (to track conversations) The goal before noon: 150 LinkedIn DMs 100 cold calls 150 cold emails Personalize the first line. Automate the follow-ups. 4️⃣ Execution: 8AM–12PM: Prospect 12PM–1PM: Lunch + quick reply check 1PM–5PM: Qualification calls + Closing Speed-to-call is king. If someone replies, call them within 5 minutes. Book same-day meetings. Not “next week.” 5️⃣ Pitch Framework: Ask: “What’s your #1 priority today around [pain]?” Then pitch: “Here’s how we solve it. Here’s the price. You can start today. Want to see it live?” Simple. Direct. No overtalking. 6️⃣ Closing: Send Stripe link,Docusign, or PandaDoc quote on the call. Push for same-day signature. If they say “let me think,” ask: “What’s missing for you to decide today?” 7️⃣ Follow-up (4PM): Use manual LinkedIn voice notes for high touch follow-up. One follow-up nudge can close the deal. In short: 400 touches → 25 conversations → 5 closed deals → $1000 MRR. All inside 24 hours. Speed wins. Volume wins. Clarity wins. If you had to bring $1000 MRR by tomorrow, how would you approach it?

The ultimate guide to 0-to-1 sales with Jen Abel Jen and her team at JJELLYFISH have worked hands-on with over 300 early-stage startups, teaching them how to do sales, early customer discovery, and to set up a repeatable sales motion. In our conversation, Jen explains 🔸 What to do at step of the enterprise sales process 🔸 What three channels work best for outreach 🔸 What to say (and not say) on your first call, and subsequent calls 🔸 How to craft outreach messages 🔸 Where to find the good leads 🔸 How to maintain momentum with prospects 🔸 Strategies for navigating procurement 🔸 How to avoid common pitfalls in the sales process 🔸 Why founder-led sales is so crucial early on Listen now 👇 - YouTube: https://lnkd.in/g6hnrm2v - Spotify: https://lnkd.in/gxMKpiDs - Apple: https://lnkd.in/ghYK8RhJ Thank you to our wonderful sponsors for supporting the podcast: 🏆 Brave — A smarter way to search: https://brave.com/lenny 🏆 Vanta — Automate compliance. Simplify security: https://vanta.com/lenny 🏆 Paragon — Ship every SaaS integration your customers want: https://lnkd.in/geirC2qS Some key takeaways: 1. As a founder, you are the best person to sell your product in the early stages. No one knows your vision and product as deeply as you do. Use that knowledge to connect with potential customers. Salespeople can’t replicate the passion, vision, and insights you can offer. 2. The typical enterprise sales process includes: a. Initial outreach and qualification b. Discovery call c. Demo/proposal d. Co-authoring scope of work e. Procurement f. Signature and closing 3. When crafting outreach messages, focus on: a. Relevance to the prospect’s role b. Presenting a counterintuitive or novel insight c. Focusing on the problem, not the solution d. Keeping it concise (3 to 4 sentences maximum) 4. When reaching out to potential leads, don’t just tell them your product is “better”—show them why it’s fundamentally different. Share a shocking insight or counterintuitive observation that’ll make them stop and think. If they read your message and think, “That’s interesting,” you’re already halfway there. 5. In the early stages, founder-led sales should focus on learning about customer pain points, not just closing deals. Treat sales conversations as research opportunities to gather insights, validate problems, and refine your product based on real feedback. Look for “budding insights”—those subtle hints of deeper needs—that can guide product or pitch adjustments. 6. You may think cold emailing and LinkedIn DMs are your only routes to outreach, but cold calling is surprisingly effective. In fact, the response rates can be much higher than with email in some cases. So don’t shy away from picking up the phone—especially when you can deliver that personal touch that makes people want to engage.

Struggling with cold intros that don't convert?  My client was too, and it made her lose heart. She could get referrals, but thought she couldn't close because she disliked selling herself. Most advice focuses on perfecting the offer. Wrong place to start. You don't need the best offer to close. I've sold $50M deals at Fortune 100s,  and netted $100K in 100 days solo. These are the 11 common mistakes I learned kill referrals, and the fixes that get closes: ❌Talking data only and overloading the audience ✅Be curious. Ask questions. Let them tell you what they need. 💬”What prompted you to want to meet today?” The goal is 40-60% buyer talk-time. ❌Pitching features instead of belief ✅Check their belief in you as the solution they need. 💬”What do you think delivers the biggest unlock for you?” Winning discussions have 28% more buyer questions. ❌Positioning as a general problem solver ✅Be the 32MM drill bit for the 32MM hole they need. 💬”Here is how and where I have solved this before.” Specialists are 2.9X more likely to command $10 K-plus project fees. ❌Skipping urgency ✅Show a loss-or-gain case. 💬”Would you burn another $160K trying to figure this out on your own.” An urgency cue lifts revenue 27% in studies. ❌Not establishing a decision expectation ✅Be clear about your direction. It is fair to set the agenda. 💬”I will ask for a decision by the end of this call.” Calls with a clear expectation have a 70% higher close rate. ❌Believing what you do is easy ✅Own your expertise was hard won and unique. 💬”I delivered X by doing Y for this client.” Generic social proof drops win rates 22%. ❌Expecting your experience is sufficient ✅Show leverage, talk method. Method > Experience. 💬”I used my 5 step framework to get the same outcomes at 20 clients.” 78% of clients pay a premium when they perceive exceptional, niche expertise. ❌Not demonstrating your impact ✅Quantify and connect outcomes to their needs. 💬”The result of this was a 20% increase in X.” Value-based pricing raises revenue up to 25% over hourly billing. ❌Focusing on your objectives, not theirs ✅First, demonstrate value, then explore mutual fit. 💬”Given your problem, here is how you accelerate. This is my method.” Buyers talk 28% more in calls that close. ❌Coming across as desperate ✅You choose whether you make an offer. 💬”I'm really excited for this opportunity," not "I really need to close to pay my kid’s tuition.” Discounting too early correlates with a 27% drop in win rates. ❌Treating an ask as dirty ✅Believe in yourself and your offer. 💬”If I feel we are a fit, I will tell how I work and ask for a decision at the end of this call.” Fastest sales cycles spend 53% more time clarifying next steps in the first two calls. My client made these easy fixes. Her close rate increased by 50%. Her confidence in herself? Up 100%. Try these easy fixes in your next call. Watch your close rate soar. Which do you believe will make the biggest difference?

I built a lead-gen system powered by 60 AI agents that now replaces an entire outbound team. Booked 22 calls last week using it. The system, built across 6 categories of agents, covers: → Prospecting (ICP, buyer intent, decision-maker mapping) → Outreach (DM writing, follow-ups, objection handling) → Enrichment (company intelligence, persona research, lead scoring) → Pipeline conversion (qualification, forecasting, churn detection) → Messaging & funnel (angle creation, timing optimisation, CTA testing) → Intelligence & automation (trigger tracking, pricing signals, CRM sync) Each agent runs a specialised task and hands off to the next. The output is a fully-automated, multi-agent engine that finds, qualifies, nurtures, and books meetings — without manual effort. I ran the system on a new niche last week before building an outbound flow. The agents identified: – 3 fast-growing companies expanding headcount – A founder posting frustration signals around lead quality – A competitor’s funnel weakness – 17 high-intent prospects with matching tech stacks One click later, the outreach agents activated: → Personalised openers from the DM Agent → Social-aware timing from the Engagement Tracker → Objection handling scripts from the Handler Agent → Automatic call prep summaries from the Meeting Prep Agent Booked 14 calls in 7 days — all from cold. The use cases go far beyond outbound: For businesses: → Build accurate ICPs using behavioural + firmographic signals → Detect buying intent before prospects reveal it → Run multi-channel nurture without extra headcount → Build a “virtual SDR team” with zero hiring cost For freelancers: → Run high-volume outreach with personalised angles → Offer lead research as a premium add-on → Qualify clients before wasting hours on calls For employees: → Prepare for stakeholder meetings with AI-built dossiers → Automate weekly reporting and CRM hygiene → Track market and competitor movements in real time Everything runs on publicly available data and internal logic. It removes busywork, increases precision, and de-risks outbound. Comment “AGENTS” and I’ll send you the full 60-agent system (+ quickstart guide) __ P.S. I drop 2 new tutorials weekly. Follow so you don’t miss them :)

Most sales reps don’t realize they’re losing deals before they even start, because of bad data. Every time you dial a wrong number or email a dead inbox, you’re wasting time and missing revenue. Here’s how bad data vs. good data impacts your outbound results when making 100 cold calls: Bad data → 100 calls - 70 calls go to disconnected or incorrect numbers - 25 calls reach the wrong contact (not the decision-maker) - Only 5 calls turn into real conversations - 0 meetings booked → 0 deals closed → $0 in revenue Good data → 100 calls - 60 calls connect with valid phone numbers - 30 calls reach decision-makers at the right company - 15 calls turn into real conversations - 4 meetings booked → 1 deal closed → Revenue generated Same effort. Same 100 calls. Very different results. If your connect rate is under 10%, the problem isn’t your pitch, it’s your data quality. Bad data wastes time, burns your leads, and kills your pipeline before it even starts. What you should do: → Always validate phone numbers and emails before calling → Enrich your leads with verified contact details → Track your connect rates—if they’re low, your data is costing you money → Invest in better data so every dial has a real chance of success Stop wasting effort on the wrong contacts. Fix your inputs, and your pipeline will follow.

I studied 3 startup CEOs with $3M+ in pipeline. Only one had a system that worked. Here’s what he did (and what you can steal): 1) Talk to buyers • No scripts • No shortcuts Just honest conversations. 8 calls/week → 3 trials/month Your best pipeline yet starts here. 2) Qualify fast You don’t need to convince everyone. You just need to find fit. Look for: • A problem • A budget • A decision-maker Missing one? Kindly move on. 3) Set a clear goal for each pilot Before your pilot starts, write the goal down. • Keep it short • Repeat it often Example: “Cut dispute time 30% in 30 days.” Your goal keeps everyone focused. 4) Show value in 7 days or less Quick wins build trust. • Set up the tool with them • Follow up the next day • Solve something painful They won’t forget you. 5) Keep your pipeline clean No date? No next step? It's not likely to close. Every Friday: • Cut what’s cold • Double down on what’s warm 6) Find a champion One person can move your deal forward. • Text your customer • Line up a C-suite sponsor 7) Plan to grow Don’t guess. Plan. • Day 30: 1 team • Day 60: 2 teams • Day 90: 3 teams Land → expand → go! 8) Review weekly Keep it simple. • Check pilots • Note wins • Communicate Time kills deals. --- In my 10+ years of sales (and tons of failure), you don’t always need to hustle harder. You just need a system that works. If this could help a tech founder you know, ♻️ send this their way. P.S. I recorded a fun video this morning walking through the first two steps.

Most reps are terrible at cold calling because they wing it. Here's the framework I've used to book thousands of meetings. Even during the last recession: #1 Build a Hyper Targeted List Stop calling random people and hoping for the best. Your list should be laser focused on your exact ICP. —Same role/responsibilities —Same industry/company size —Same use cases and pain points If you're calling 100 random prospects, you're doing it wrong. If you're calling 20 perfectly matched prospects with research, you're doing it right. Enterprise reps: This is non-negotiable. Do your homework. #2 Use a Simple Opener Forget the "How are you doing today?" nonsense. Here's what I say: "Hey Alice, it's Marcus with Venli. Thanks for taking my call!" Three things happening here: #1 Clear name recognition #2 Establish who I am upfront #3 No fake pleasantries… get to the point Sound confident. Sound like an equal. Don't sound desperate. #3 State Your Clear Purpose Most reps dance around why they're calling. I go direct: "The reason I'm reaching out is because I listened to your Q4 earnings call and saw that you're aiming for 10% top-line growth while maintaining 30% margins. I'm working with sales orgs at Stripe, ZoomInfo, and HubSpot to help them blow their targets out. We may be able to help your org too. Do you have time to discuss this Thursday at 3?" Notice what's happening: —I did my homework (earnings call reference) —I'm tied to their biggest initiative —I have credible social proof —I'm asking for a meeting, not trying to sell on the spot I've taught this framework to thousands of reps across dozens of industries. It works when you EXECUTE it with the right tone and attitude. Stop winging your cold calls. Have a system. Do your research. Be direct. == Want even more cold calling scripts? Go here: https://lnkd.in/gZVxaRqQ