How to Close High-Ticket B2B Deals

One of the biggest reasons deals stall isn’t that buyers doubt your solution—it’s that they doubt their ability to make the right choice. Matt Dixon's research for The JOLT Effect found that 40% of lost deals are driven by customer indecision, not preference for a competitor. And Brent Adamson's new book The Framemaking Sale highlights that customers with high decision confidence are TEN TIMES more likely to make a purchase. Here are a few ways you can help buyers build confidence in themselves: 1. Reduce Decision Complexity According to Gartner, 77% of B2B buyers report their last purchase was “very complex or difficult." Streamlining options, providing decision guides, or recommending a clear best-fit reduces “analysis paralysis” and gives buyers confidence they aren’t missing something. 2. Reframe Risk in Personal Terms Buyers often fear personal blame more than organizational failure. Use case studies and peer validation to show how people in their role succeeded—helping them feel safe and supported in their choice. 3. Provide Buyer Enablement Tools Tools like ROI calculators, pre-built board decks, or checklists reduce the burden on them and demonstrate that they have what they need to decide. 4. Normalize Their Concerns The JOLT Effect also emphasizes “normalizing indecision” as a critical skill—buyers need to know hesitation is common and that you can guide them through it. Framing uncertainty as a normal step in the process reduces the shame that often delays action. 5. Signal Post-Decision Support Harvard Business Review highlights that buyers who see strong post-sale support are more confident in making initial commitments. Show them the path forward—onboarding, customer success, peer communities—so they know they won’t be left alone after purchase. Helping buyers feel personally confident and protected is as important as proving your product’s value. The most successful marketers and sellers don’t just build confidence in the solution—they build confidence in the decision-maker.

I closed a client in 2 calls. Here's what I did differently. No pitch deck. No "let me send you my packages." No pressure. A senior industry veteran in his mid-60s reached out via LinkedIn DM. He wanted to show up on LinkedIn and share his insights with startups. Most people would've jumped straight to pricing. I didn't. Here's what I did instead: **Call 1: I just listened.** ↳ What are your goals? ↳ What's stopping you from posting? ↳ What does your voice sound like when you're not overthinking it? 60 minutes. No selling. Just understanding. **Call 2: I went deeper.** ↳ What hesitations do you have about working with someone? ↳ What would success look like for you in 6 months? ↳ What's your budget comfort zone? Yes, I asked about budget. Not to quote my highest rate. But to understand what feels right for them. Here's the thing most service providers get wrong: They quote before they understand. I evaluate what someone can genuinely pay before I quote. Not to undercharge. But to build a partnership that lasts. This client has been with me for 5 months now. He signed personally after his company backed out. Why? Because the relationship was built on trust, not transactions. If you're a service provider struggling to close high-ticket clients, try this: ↳ Stop pitching on the first call ↳ Ask about their hesitations openly ↳ Understand their budget before quoting ↳ Make them feel heard, not sold to The close happens when trust is already built. 🩷 PS: What's your approach to closing clients? I'd love to know.

I'm watching salespeople leave money on the table every day. The data doesn't lie. B2B deals require 6.8 stakeholders to reach consensus. Yet most reps focus on ONE relationship. This single threading approach is why deals: = Go dark without warning = Disappear when priorities shift = Get cut first when budgets tighten = Take 2X longer to close than necessary After coaching 500+ AEs who've collectively closed $750M+ in revenue, I've found the solution hiding in plain sight. It's Account Mapping in LinkedIn Sales Navigator. But not just basic mapping. Strategic multi-threading. Here’s the play: 1. Pull up your target account in Sales Navigator 2. Click "View Account Map" (shockingly, most reps don't know this exists) 3. Identify key players in the buying committee 4. Assign roles: Decision-Maker, Champion, Influencer, User, etc. 5. Develop personalized outreach for EACH stakeholder When you deploy this strategy, something magical happens: One stakeholder goes dark? You have 5 other active relationships Technical objection arises? Your champion in Engineering addresses it internally Budget concerns surface? Your Finance contact provides insider perspective Decision-maker changes? You're already connected to their peer group Here’s a real world example: Last month, my client was working a $500K deal that seemed solid. Their single point of contact suddenly stopped responding for 3 weeks. Dead deal? Not quite. We implemented the multi-threading approach, mapped the account, and connected with 4 additional stakeholders. Turns out, their champion was on medical leave but the team was still evaluating solutions. Deal closed 40% faster than their average cycle. By the way… my favorite question to get me multi-threading from the get go? During discovery calls, I teach reps to ask: "Besides yourself, who else will be involved in evaluating this solution?" Then follow up with: "And who else might influence this decision, even indirectly?" “Who else?” Map these names immediately in Sales Navigator. Look for connections between them. Identify potential champions at EACH level of the organization. While your competition waits for ghosted emails, you're having productive conversations with multiple stakeholders. All moving toward consensus. The biggest deals CANNOT be won through a single relationship. Stop leaving commissions on the table. Start multi-threading today. Check out my Sales Navigator deep dive video (and how to use AI with it). : https://lnkd.in/gtE-FWax

Long-Cycle Sales Are Not Won with Pressure… They’re Closed with Precision. Most sales reps treat enterprise contracts like short-term quotes. Big mistake. You’re not just selling a service. You’re managing a complex decision-making process across multiple stakeholders, risk profiles, and compliance fears. Sound familiar? - Months-long buying cycles - Procurement reviews - Budget objections etc... You’re not in transactional sales anymore. You’re in enterprise sales. Here’s what the top closers are doing differently: 1. Build Trust Like a Consultant, Not a Closer 87% of B2B buyers say trust is the #1 factor in their decision. > Not price. > Not speed. > Not ROI. That means: - Leading with insight, not pressure - Admitting when you’re not the best fit - Knowing their industry as well as your own Your credibility is the contract. Lose it, and the deal’s dead... 2. Create Urgency Without Destroying Trust Artificial deadlines? Gimmicks? Buyers see right through it and they vanish. Instead: - Show the cost of inaction (lost revenue, failed audits, poor reviews) - Tie your timeline to their goals I.E. what's important to there business. - Offer exclusive benefits for early adopters Urgency works best when it feels like alignment, not pressure. 3. Guide the Buying Journey with a Mutual Action Plan (MAP) 77% of B2B buyers say their buying process is overwhelming. If you’re not leading the process, you’re losing it. The best reps co-create a roadmap that outlines: - Who’s involved - What needs to happen - What success looks like This removes friction. It keeps momentum. And it positions you as the pro who’s orchestrating success... 4. Engage Every Stakeholder… Especially the Skeptics Most pest control reps talk to their champion and hope for the best. Elite closers multi-thread across departments: - Ops - Legal - Procurement They ask: > “Who else needs to be involved so we can get this done right?” - They find the skeptic. - They win them over early. - They never leave the champion to fight alone. 5. Close with Proof, Not Pressure In the final mile, trust alone won’t close the deal. You need: - ROI calculators - Case studies - Visual proposals - Risk mitigation data Make the business case so strong… The only rational answer is “Let’s go.” What Sales Reps Must Remember: You’re not just selling a solution. You’re selling safety, reputation, and operational continuity... And if you're still relying on pressure tactics instead of enterprise precision? You’re going to lose. But if you’re ready to start closing like the pros? - Lead with trust - Anchor urgency in reality - Back it all with proof Then you’ll not only win the deal. You’ll own the process... "Lead Different. Sell Smarter. Win with Purpose." --- ♻️ Share this post with a sales leader who needs to hear it. 👉 Click here: Follow me on LinkedIn: https://lnkd.in/eA7csH2q Join our community of 39,000+ sales professionals today! P.S. Thanks for reading!

One of the most expensive phrases in 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗦𝗮𝗹𝗲𝘀: "I'll get back to you with another proposal" One of the biggest mistakes founders make when presenting price or negotiating is to chase procurement's request for a better price. 𝗧𝗿𝘂𝘁𝗵 𝗶𝘀— If you're going back to get a better price without context, you're a puppy dog chasing after an impossible ball. You end up: • Guessing what discount percentage is going to get the deal done. • Wondering why the list price you presented doesn't work. • Second guessing the value of your product. • Undercutting the ultimate price you could close the deal with. Skilled negotiators from the competition aren't guessing what discounts or deal structure are going to get the deal done. They're pushing back on nebulous discount requests and are engaging in rich realtime negotiation. So the next time you're asked to come back with a better price, here's what you can do: 1. 𝗥𝗲𝘀𝘁𝗮𝘁𝗲 𝘁𝗵𝗲 𝘃𝗮𝗹𝘂𝗲 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗰𝗼𝗻𝗳𝗶𝗱𝗲𝗻𝘁𝗹𝘆 → "The price is the price because..." 2. 𝗔𝘀𝗸 𝘄𝗵𝘆 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁 𝗱𝗼𝗲𝘀𝗻'𝘁 𝘁𝗵𝗶𝗻𝗸 𝘁𝗵𝗲 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗽𝗿𝗶𝗰𝗶𝗻𝗴 𝘄𝗶𝗹𝗹 𝘄𝗼𝗿𝗸 → "This is our view but it'd be great to get a sense for how you think about budgeting for a platform like this." 3. 𝗔𝗰𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 𝘆𝗼𝘂𝗿 𝗯𝘂𝘆𝗲𝗿'𝘀 𝘃𝗶𝗲𝘄 𝗼𝗳 𝘁𝗵𝗲 𝘄𝗼𝗿𝗹𝗱 𝗢𝗥 𝗼𝗯𝗷𝗲𝗰𝘁𝗶𝗼𝗻 𝗵𝗮𝗻𝗱𝗹𝗲 𝗶𝗳 𝘆𝗼𝘂 𝗱𝗶𝘀𝗮𝗴𝗿𝗲𝗲 → "That makes sense so thank you for providing that context" → "I'd view our product in a bit of a different light because..." 4. 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗮 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝗽𝗿𝗶𝗰𝗲 𝘁𝗵𝗮𝘁 𝘄𝗼𝘂𝗹𝗱 𝘄𝗼𝗿𝗸 𝘁𝗼 𝗴𝗲𝘁 𝘁𝗵𝗲 𝗱𝗲𝗮𝗹 𝗱𝗼𝗻𝗲 → "Can I ask what price would work for you? Is there a magic number you have in mind?" 5. 𝗖𝗼𝗻𝗳𝗶𝗿𝗺 𝘄𝗵𝗲𝘁𝗵𝗲𝗿 𝗼𝗿 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗰𝗼𝘂𝗻𝘁𝗲𝗿 𝗽𝗿𝗶𝗰𝗲 𝗶𝘀 𝗿𝗲𝗮𝗹 𝗼𝗿 𝗻𝗼𝘁 → "If we don't miss that price are we in a place where this deal doesn't get done?" 6. 𝗔𝘀𝗸 𝗵𝘆𝗽𝗼𝘁𝗵𝗲𝘁𝗶𝗰𝗮𝗹𝗹𝘆 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗮𝗯𝗹𝗲 𝘁𝗼 𝗺𝗲𝗲𝘁 𝘁𝗵𝗲 𝗰𝗼𝘂𝗻𝘁𝗲𝗿 𝗽𝗿𝗶𝗰𝗲 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂 𝘄𝗼𝘂𝗹𝗱 𝗴𝗲𝘁 𝗶𝗻 𝗿𝗲𝘁𝘂𝗿𝗻 → "If we're able to meet that price can we sign the contract this week?" → "If we're able to meet that price, can we move forward with the legal terms as is?" etc. 7. 𝗖𝗹𝗼𝘀𝗲 𝘁𝗵𝗲 𝗰𝗮𝗹𝗹 𝘄𝗶𝘁𝗵 𝗮 𝗰𝗼𝗺𝗺𝗶𝘁𝗺𝗲𝗻𝘁 𝘁𝗼 𝗴𝗲𝘁 𝗯𝗮𝗰𝗸 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗯𝘂𝘆𝗲𝗿 𝗾𝘂𝗶𝗰𝗸𝗹𝘆 𝘄𝗶𝘁𝗵 𝘄𝗵𝗲𝘁𝗵𝗲𝗿 𝗼𝗿 𝗻𝗼𝘁 𝘆𝗼𝘂 𝗰𝗮𝗻 𝗺𝗮𝗸𝗲 𝘁𝗵𝗲 𝗻𝘂𝗺𝗯𝗲𝗿𝘀 𝘄𝗼𝗿𝗸 → "I'll need to discuss with my cofounders but can commit to getting back to you tomorrow" With an approach like this you: • Have an opportunity to reposition the value of your product • Gain clarity around a deal structure that will work • Can accelerate the deal vs. slowing it down Want more sales & negotiation tips? Follow me and check out the resources in my featured section. S/O to Chris Do for the hook and post format inspiration ✨

Want to sell £30k packages without burning out? Here’s how. High-ticket sales don’t come from one perfect email (although everyone loves that narrative 🙄) They come from a clear nurturing journey that respects how premium buyers actually make decisions. Think of it in three stages: STAGE 1 — Familiarity: “Who are you and why should I care?” Goal: Turn a cold subscriber into someone who actually looks for your name in their inbox. Your emails here should: ✅ Use their words to speak to their problems. ✅ Show you understand their world/ constraints ✅ Give useful insights they can apply quickly ✅ You’re building relevance not rushing a pitch. STAGE 2 — Depth: “Do you think like someone I’d trust at this level?” Goal: Shift from “this is interesting” to “this person gets how I operate.” Your emails here should: ✅ Share how you think and make decisions. ✅ Walk through recognisable real scenarios. ✅ Name the trade-offs, risks and realities of high-ticket investment. STAGE 3 — Decision: “Is this the right move, right now, with you?” Goal: Make the yes/no feel clean, not pressured. Your emails here should: ✅ Clearly position who the offer is and isn’t for. ✅ Show what working together looks like. ✅ Help them weigh this against other options they already have. You’re building confidence in their decision, not trying to “overcome” them. When your email strategy walks someone through: 1️⃣ Familiarity 2️⃣ Depth, and 3️⃣ Decision Selling 30K offers stops feeling impossible and starts feeling like the logical next step. What resonates most about what I’ve said? (cannot wait til my hair’s this long again 🤩)

Last week, I did a fireside chat with 30 founders on how we closed our first $1M ARR. Here's the advice I wish someone had given me 2 years ago: The reality of early traction isn't glamorous. It’s brute force. We used hustle, plane tickets, and a lot of late nights. Here is the reality of what it takes to close your first few deals: 1/ Write your own outbound In the early days, I wrote cold emails from 9 AM to 9 PM. I'd dig through their website, screenshot specific parts, circle the problem, and write exactly how we'd fix it. When you automate too early, you numb yourself to the feedback loop. Writing the message and getting ignored forces you to think like the buyer. You feel the failure viscerally. That's how you get good. 2/ Sell the plane while you build it We closed our first customer with a demo running on my laptop at localhost:3000. We didn't have a full product yet, so we onboarded them into a "sandbox environment." If a feature was missing, we could say "oh, that's a limitation of the sandbox environment, give us a bit and we'll enable it for you." Then we’d crank out code for the next 3-4 hours, ship the feature, and deploy it to their account. It allowed us to sell the vision but deliver the code just-in-time. 3/ A fast "no" is a gift What you should actually fear is a "no" after 6 months of your time. If a prospect can't tell me their use case, volume, current solution, and specific pain points — I know it's going to be a no eventually. I'd rather find out today. On the flip side, learn to spot real signals. 10+ people in a shared Slack channel? Serious. Champion inviting their manager? No one spends political capital like that unless they mean it. Pushing back on pricing instead of just asking? Real intent. 4/ Deals don't close over Slack and Zoom. They close over cocktails and iMessage. I've taken more last-minute flights than I can count. Minnesota, Texas, India. We still have a 100% close rate on in-person meetings. Most people won't get on the plane. That's exactly why it works. 5/ Never step away from sales Every founder I've talked to who hired a sales team and then stepped away from sales has regretted it. You need to stay close to what customers and the market are saying, because it's always changing. What we do now: AEs manage the deal cycle and pull me into strategic moments (a 30-minute 1:1 here, a dinner there). The first 10-20 customers are a slog. But it compounds quickly, so just hang in there. Anything else I'm missing?

Over the last 5 years, personally I’ve closed 11 deals that were 7 figures of ARR. Also over those same 5 years, I’ve lost 42 of them. Reality does still exist out here somewhere on LinkedIn. Every one of them (won and lost) had multiple things in common: - Started with cold outreach. Yep… - Took in-person interaction to build progress. Events, onsites, etc - Required maniacal multi threading and an army of teammates working alongside me. - 2 months of contract review and security review. 💰If you want to be closing big deals, prepare to: Research like a maniac, then cold outbound to get then in. Then, prepare to: 1️⃣Lose more than you think. You’ll win, but not as much as you think you will. 2️⃣Be a project manager. You’re not playing hero ball. You’re playing facilitator, except managing execs internally and externally throughout the deal. It’s exhausting, but rewarding. 3️⃣Invest time in person. It’s near-impossible to close these entirely remote. 4️⃣Steel yourself for the absolute buzzsaw of procurement and legal. They will break you or your champion - make it easy for them to get through their process, but keep it on track. It’s longer than you think. 5️⃣ Keep control of a deal by not being controlling. Guide the buying team with clarity. Fight for clarity to drive next steps. Big deals are INCREDIBLE to close and entirely worth it. Be prepared to play the long mental game. Only the sellers with the best process survive. Embrace your process, trust it, win with it.

The most overlooked part of closing a deal? Equipping your champion to sell it internally. You’ve built the relationship. You’ve shown value. Your product solves a real problem. But your contact isn’t the final decision-maker. That means your close is only as strong as their internal pitch. District leaders are tired. They’re juggling a million end-of-year tasks. They’re not going to write a new business case from scratch. So if you want this deal to close, your job isn’t just to convince your champion, it’s to equip them. That might look like: Sending a summary email that outlines the problem, the solution, and the funding source. Drafting messaging they can send to a supervisor or decision-making committee. Offering to join a final call with leadership to answer any remaining questions. And if the internal process requires documentation, procurement paperwork, or vendor approval steps, send them everything they need in one clean package. You’re not asking your contact to work harder. You’re making it easier for them to say yes without doing all the heavy lifting themselves. That’s what partnership looks like in the final stretch of the year.

What’s the fastest way to compress your sales cycle when selling large deals to Enterprise accounts? Here's what you DON'T do: - meet with department heads - demo your product and get them excited - have them attempt to sell upstream Instead, try using my Yo-yo sales framework. Here’s what it looks like. Step #1: Connect with power first, understand the most important problem(s) they need to solve, why they want to change, and the costs of not changing.If it’s a problem you can help solve, get their sponsorship for your discovery process. Ghost write a note they can send to their team to begin discovery Step #2: Meet with their department heads, get the real deal on what their day to day challenges look like, and grab some quotes which capture their biggest pain points. Seek to understand, not sell. Dig deep - understand the people, processes, and steps involved in doing the painful things which you can help improve or automate. Step #3: Package everything you’ve uncovered into an Executive Summary and Business Case and deliver back to Exec Sponsor and their team. Demo only what’s relevant. Close. Power compresses deals. This insight was key to me becoming the number one AE at Salesforce. It's how I went from averaging $240K/year my first four years to averaging $720K my final four years (including two years cracking 7 figures). Want to learn my process for closing huge enterprise deals? Tune-in to my full conversation on the 30 Minutes to President's Club podcast. Listen here: https://lnkd.in/gCJ4x7HZ