Closing Strategies for Tech Sales Professionals

I recently closed a six-figure deal with an enterprise client. While most deals this size take 6-8 months, I closed this one in under 60 days. Here's exactly how I did it: When selling to an enterprise company, it's easy to get trapped in long deal cycles. To avoid this from always happening, here are the 4 steps I take to expedite my enterprise closing process: 1. Subject Matter Expertise Plays    Most sellers pitch products. We pitch proven expertise in their space. This shifted the entire conversation from "vendor" to "expert." • Pitched as an industry expert, not influencer • Showed proven processes from our team  • Focused on vertical expertise vs following Expertise beats influence every time. 2. Multi-Threading     Instead of focusing on one champion, I built relationships across the organization. Each stakeholder had different things that made this a win for them. • Built relationships with seven key stakeholders • Sent a recap email to each buying department so everyone knew what was going on • Had notes for each department's goals and why they wanted to win Throughout the deal, I always asked who would feel left out if they weren't involved. Every time I found a new person, I made it a point to meet them. That means more allies for the deal to sell internally. 3. Weekly Momentum Building    Most deals need more momentum. That's why I keep the energy high. • Sent weekly videos to keep my POC informed • Highlighted each stakeholder's priorities • Highlighted work we were doing along the way Momentum beats perfection. 4. Procurement Fast Track This is where deals typically go to die. Not today my friends. This is where the party starts. As soon as I get introduced to procurement, I ask for a quick 15-minute call so I can quickly text edits as my lawyer goes back and forth. • Asked for concerns up front • Built solutions into proposal • Asked what do you people typically redline when they approach you Being proactive beats being reactive every time. Because doing the little things well will always yield great results. P.S. Have a favorite step?

Most sellers think the biggest obstacle is the status quo. They’re wrong. I’ve coached 1,000+ reps and closed over $100M in enterprise software deals— And I can tell you firsthand: Your biggest competitor isn’t “do nothing.” It’s fear. Here’s how to de-risk deals and overcome buyer indecision: Buyers don’t lose sleep over doing nothing. They lose sleep over messing up. Because if they do nothing? Nothing happens. If they choose you and it fails? Their job’s on the line. That’s the real reason you get ghosted. Not because they want to stay in the status quo— But because they’re terrified your solution won’t deliver. Here’s how top sellers overcome that fear: 1. Get brutally honest, fast. Read their energy. Watch their face. If something feels off, call it out. “I’m sensing some hesitation. Where do you feel risk?” or “What would make you feel comfortable moving forward?” Don’t wait for objections—extract them. 2. Land and expand. Big deals create big fear. Instead of pushing the whole $1M rollout, start with one team. Prove results, build credibility, then go enterprise-wide. Smaller deal. Faster close. More trust. 3. Get creative with contracts. You don’t have to choose between ‘yes’ or ‘no’. Invent a ‘yes that feels safer.’ Here are 2 ways I’ve done that: A. Carveouts: We put experimental products on a 1-year agreement, while the core was 5 years. Result? They said yes to both—without getting locked into unproven tech. B. Price ramps: Instead of $5M up front, we ramped: $3M → $4M → $5M. They only paid what they could actually use—and that made all the difference. 4. Conservative ROI. Don’t sell the dream. Sell the floor. Buyers don’t want inflated projections—they want numbers they can defend. Let them plug in the ROI and stand behind it. Remember: The real reason deals stall? It’s not lack of urgency. It’s lack of confidence. Help your buyer feel safe— Or watch the deal die in “maybe.” Be the rep that makes saying yes easy. De-risk everything. Win more. P.S. If you're an AE who wants to work with me as your sales coach in 2025, we have a few 1:1 spots left. You can apply here: https://lnkd.in/gf3zQSPy

I watched 300 sales calls. The best closers never actually close. They do something that sounds like business suicide: They give prospects permission to say no. I implement this is all my Video Sales Funnel landing pages and on DM's. Here's what I discovered after analyzing top performers vs average reps: Average rep: "So are you ready to move forward today?" Top performer: "I'm sensing some hesitation. What's holding you back?" Average rep: 23% close rate Top performer: 67% close rate The psychology is backwards from everything we're taught. When you push for the close, the brain activates defense mode. When you acknowledge their resistance, the brain relaxes. It's the same principle I use in video CTAs. Traditional video CTA: "BOOK YOUR DEMO NOW!" My CTA: "Not sure if this is right for you? Here's how to find out..." One demands action. One invites exploration. The Anti-Close Close framework: 1. Acknowledge their reality "I know you're comparing multiple options..." 2. Remove the pressure "This might not be the right fit, and that's okay..." 3. Shift to curiosity "What would need to be true for this to work for you?" Real client example: E-commerce brand's sales video Old close: "Start your free trial today!" → 2.8% conversion Anti-close: "Still not convinced? See what happens when..." → 11.3% conversion Same product. Same price. Different psychology. Why this works: Your prospect expects you to push. When you pull back instead, their guard drops. Suddenly they're not defending against a sale. They're exploring a possibility. The data from those 300 calls: Hard closes: Created resistance 89% of the time Soft closes: Created curiosity 73% of the time But here's what really shocked me: The calls where reps said "This might not be for you" closed 4x faster than aggressive pitches. Because when you're not desperate to close, they stop looking for reasons to run. Common objection: "But won't they just leave if I give them an out?" The ones who were going to leave will leave anyway. The ones on the fence lean in when you stop pushing. My highest-converting video funnel ends with: "If you're still reading this, you're either really interested or really bored. Either way, here's what to do next..." 31% conversion rate. Because humor + honesty beats pressure every time. The implementation checklist: 1. Delete every "Buy now!" CTA 2. Replace with curiosity-driven questions 3. Acknowledge their skepticism upfront 4. Give them an honorable exit 5. Watch them choose to stay The uncomfortable truth: The best way to close a sale is to stop trying to close it. Let them close themselves.

There’s a reason your deal isn’t closing — and it’s not because of the price. Inside big orgs, decisions follow politics, process, and personal agendas. That’s why closing a deal means helping your buyer 𝘴𝘦𝘭𝘭 𝘪𝘵 𝘪𝘯𝘵𝘦𝘳𝘯𝘢𝘭𝘭𝘺, too. Here’s how: (𝟭) 𝗠𝗮𝗽 𝘁𝗵𝗲𝗶𝗿 𝙞𝙣𝙩𝙚𝙧𝙣𝙖𝙡 influence, not just their title. It’s easy to sell to the person with the right title. But real traction comes when you understand who 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 moves decisions forward internally. Titles can be misleading—find the person who can champion your cause in the rooms you're not in. They don’t just have access; they have sway. Ask: “Who else needs to say yes?” and “Who really owns the outcome of this project?” (𝟮) 𝗪𝗵𝗶𝘁𝗲𝗯𝗼𝗮𝗿𝗱 𝘁𝗵𝗲 𝗳𝘂𝗹𝗹 𝗮𝗽𝗽𝗿𝗼𝘃𝗮𝗹 𝗽𝗮𝘁𝗵 𝘁𝗼 𝗮 “𝘆𝗲𝘀”. Your champion isn’t always your decision-maker. That’s why our best reps always map out the approval journey: → Who needs to sign off? → What triggers procurement or legal involvement? → At what dollar amount does this escalate to the CFO? When you know the answers, you can preempt roadblocks, and arm your buyer to drive it through. The fastest path to a “yes” is in removing friction from the buying process. (𝟯) 𝗦𝗲𝗹𝗹 𝘁𝗼 𝘁𝗵𝗲 𝗽𝗲𝗿𝘀𝗼𝗻𝗮𝗹 𝗺𝗼𝘁𝗶𝘃𝗮𝘁𝗶𝗼𝗻 𝗼𝗳 𝘁𝗵𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗺𝗮𝗸𝗲𝗿. In enterprise sales, you’re asking a person to bet their reputation on you. So make it worth it. Understand what they care about: → What does success look like for them? → How’s their bonus structured? → What are they trying to prove (or avoid)? If your solution helps them win, they’ll go to bat for you because value beats price (especially when it’s personal). 𝗧𝗵𝗲 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆: Don’t just pitch. Partner with the buyer, with the process, and with the politics. Do that, and price stops being the issue.

Most AEs lose deals because they can't build urgency. They find pain. They demo features. They quote price. But they never answer the million-dollar question: "What happens if we do nothing?" Here's how to build the cost of inaction (and close more deals): 1. Find a metric that's suffering. Pain without numbers is just complaining. You need something measurable: • Revenue lost per month • Time wasted per week • Customers churning per quarter If they can't give you a number? Ask who can. 2. Reverse-engineer the cost of waiting. I once had a VP of Sales want $10K off a $50K deal. He said: "We'll wait until January when hiring ramps up." So I asked: "How many reps are you hiring in January?" "10 reps." "How long to ramp them?" "4 months." "What's each rep worth when ramped?" "$40K ARR." 3. Do the math out loud. "So if you're one month late on those 10 hires... That's 10 reps × $40K = $400K knocked off your annual plan. You want $10K off. But waiting costs you $400K. Which sounds more expensive?" He signed at full price. 4. Make the invisible visible. Customers aren't thinking about compound costs. Your job? Bring the horse to water and make them drink. Show them what "doing nothing" actually costs. 5. Use this exact question: "What metric is suffering as a result of that problem?" If they can't answer, ask: "Who would know that number?" Now you're opening doors to power. The cost of inaction drives your timeline. Not discounts. Not "budget cycles." The fear of losing $400K while trying to save $10K. 💡 What's the biggest "cost of inaction" you've ever built? P.S. These 7 strategies will help you CLOSE more deals in a GTM crisis: https://lnkd.in/d_DkYTSH

Eleanor Dorfman, xHead of Sales @ Retool has overseen $1B+ in B2B Sales & trained hundreds of top reps. If you listen to her full episode on the recent 30 Minutes to President's Club, sales leaders will drop what they’re doing & immediately put in place these 3 key bans: 1/ Ban reps from saying your own company name on Discovery Calls ---- To win deals you need to train your reps to do excellent discovery. But excellent discovery is more about listening than talking. 95% of reps make the same mistake: bragging about the product they sell instead of listening. One tactical way to force reps into asking questions and minimizing “I” statements and “My company” statements is to forbid your own company name. Eleanor has her rep’s call recordings surface ANY mention of their own company and coaches reps to stop this. 2/ Ban reps from saying feature names on Deep Dive Calls ---- To win deals you need to train your reps to value-sell, not feature-sell. Bragging about features is cool, and champions might like it, but real decision makers want to have their top level problems solved with value-based business cases, not a laundry list of neat features. Words to ban: - Role-based access controls - SSO - front-end UI - anything big on your marketing site - etc Remember: buyers are trying to launch in a new market, they’re trying to drive efficiency in their engineering department, they are revamping their old SEO practices. They are NOT: waking up in the morning hoping to that their new tool has SSO. Feature selling might work for 4 or 5 figure deals, but it won’t work for 6 or 7 figure deals 3/ Ban buyers from starting POCs / Trials without answering business value questions. ---- POCs are an AMAZING place to discover business value. Prospects are eager to try out your tool and are willing to put in work to get it going. Use this to your advantage by making the prospect do work in the POC to help you pre-figure out your negotiation / closing tactics through your business case. As part of your POC onboarding ask: - What is the value you’re hoping to see? - What is the value the budget holder if hoping to see? - Which business problem will our product solve for you? - Which budget will the final payment come from? Squeeze these into the normal POC questions like “who needs access?” and “which CRM are you going to integrate with?” These are the bans that Eleanor uses to win 7 figure deals at Retool. Which bans have you implemented in your sales process? #sales

Quick reminder to sales teams closing out Q2: You cannot create urgency. It’s just not going to happen. You can find it. You can agitate and accelerate it. You can create speed and momentum in a buying process. But you CAN’T make your product urgent if their problem isn’t. And if you try (fake) urgency tactics, you won’t just waste your time. You’ll kill trust. - Expiring offers - Trial shutdown threats - High-pressure closing moves Throw it all away. It’s not 2021 - buyers smell that nonsense a mile away. And when they’re finally ready, they’ll choose your competitor. Instead, ask yourself: Is there an urgent, growing problem here? Not sure? Reach out and ask directly. No clear signals? Move on. Seriously. Then, focus on your *real* deals and do this: 1. Build together a workback plan from their target date—back to TODAY. 2. Map every strategic move clearly with your manager—leave zero surprises. 3. Daily brainstorm with your team—for moves, motivation, and momentum. 4. Set EOQ to June 25 (not 30th)—because deals slip. Always. 5. Co-create a compelling Cost of Inaction they can't ignore. 6. Get your execs to reach out NOW—confidence closes deals. 7. Move FAST. Urgency mirrors urgency—buyers match your pace. 8. If CSM bandwidth is tight—flag it today and lock them in early. 9. Just ask: “John, what exactly needs to happen to sign by June 25?” 10. Use their end-users to nudge internally: “Can you help us get this signed?” 11. Negotiating? Don’t hide deadlines—let them “beat you down” (Chris Voss). 12. Incentives as last resort—if there’s already urgency, and they’re making asks. Do it. Now. You won’t create urgency out of thin air. But you WILL move faster. P.S. A quarter-closing 'war mode' isn’t about aggression or ego. It’s about being focused. Sharp. Strategic. And doing whatever it takes. I'm writing this as Iranian missiles fly over Israel 🇮🇱 Real war mode. We keep going.

10 Barriers to Closing Sales (and How to Break Them) Closing sales isn’t some mysterious art reserved for a select few; it’s a teachable skill. If you’re struggling to seal the deal, it’s time to identify the barriers holding you back. Let’s dive into the top 10 obstacles I've come across and how to overcome them. 1. Not Showcasing the Product as a Solution The best sales reps are their product's biggest fans. However, they often get lost in features rather than focusing on the buyer’s dominant motive (DBM). Nail down the DBM, and your presentations will be shorter and more impactful. 2. Missing Customer Cues Focusing too much on your pitch can make you miss critical customer signals. Pay attention to their reactions; they’ll tell you if they’re ready to buy or if you need to pivot your approach. 3. Avoiding Hard Questions Sales require grit. Asking tough questions might feel uncomfortable, but it’s essential. If your prospect knew what they needed, they’d have already bought it. Don’t shy away from pressing them for answers. 4. Thinking Price Seals the Deal Price is not the primary driver of sales. Instead of discounting, focus on building value around your product. A strong connection to the DBM will overshadow any price concerns. 5. Going In Without Intention Your mindset matters. Approach every prospect with the intention to close. If you believe every customer is a done deal, you’ll project confidence, making it easier for them to say yes. 6. Skipping Soft Closes Remember: buyers are often 57% ready to purchase before they even talk to you. Use trial closes to gauge interest without pressure. Phrases like, “Have you heard enough to make a decision?” can move you closer to the sale. 7. Hiding the Price Until the End Don’t wait to reveal pricing. Being upfront allows the buyer to weigh value against cost from the start, preventing them from fixating on the price alone. 8. Ignoring Influencers in the Decision-Making Process Always identify the decision-maker, but don’t neglect their advisors. Addressing the concerns of influencers will help you gain credibility and close the deal more smoothly. 9. Using Freebies as a Crutch Offering discounts or freebies might seem tempting, but it signals that you don’t value your product. Instead, focus on showing its worth and building value. 10. Failing to Create Urgency Urgency is crucial. Don’t let clients walk away to “think about it.” Instead, emphasize the immediate need for your solution, validating their reasons for buying now. The Key to Overcoming These Barriers: Sales can feel daunting, especially for newcomers. The solution? Practice. Role-play tough scenarios, refine your pitch, and strengthen your sales techniques. Commitment to training is essential if you want to see results. Mastering the close is a powerful tool that will serve you and your clients. You owe it to yourself and your future success. Be Great! #Sales #Marketing

I warmed up a prospect for 3 months on LinkedIn before our first call. They signed a £75K deal in 3 days. Modern selling demands a new approach: cold outreach fails, warm relationships win. Think about it... That prospect had consumed 47 of my posts. Watched my videos. Read my articles. Engaged with my content. By the time we jumped on that first call? They already trusted me. They already knew my approach. They already understood the value. I didn't have to sell them. They'd already sold themselves. Here's my framework for turning content into closed deals: 👇 1. Build trust at scale BEFORE the pitch Stop spraying and praying with cold messages. Start building relationships through value. Each post builds trust. Your insights mark credibility. Stories create connection. Your content is doing the heavy lifting while you sleep. 2. Let buyers self-educate on THEIR timeline Modern buyers don't want to be sold to. They want to discover solutions themselves. ↳ 70% of the buying journey happens before they talk to sales ↳ They're researching you before you even know they exist ↳ Your content is either attracting or repelling them Give them what they need to make informed decisions. 3. Recognize the REAL buying signals Forget MQLs and SQLs. Think about PQLs (product qualified leads) Here's what actually matters: - Multiple engagements across different posts - Bringing colleagues into the conversation - Asking specific, detailed questions - Moving from public comments to private messages These aren't leads. These are pre-qualified buyers. 4. Keep momentum BETWEEN meetings Here's where most deals die: The 167 hours between your calls. While you're chasing other prospects, your buyer is: ↳ Getting cold feet ↳ Talking to competitors ↳ Forgetting why they were excited Smart sellers stay present even when they're not there. This is where tools like Consensus come in. They let buyers explore demos on their own time. Answer their questions at 10 PM. Share materials with their team. Stay engaged between touchpoints. It's how you keep social selling momentum right through the demo stage. https://lnkd.in/ePVWw-Bi 5. Close with confidence, not pressure When trust is already built? When value is already proven? When buyers are already educated? Closing feels natural, not like a battle. The best deals I've ever closed felt inevitable. Because the relationship started months before the opportunity. Here's what this approach delivers (in my experience): ✓ Significantly faster sales cycles ✓ Much higher close rates ✓ Bigger deal sizes (pre-sold = less negotiation) ✓ Happier customers (they chose you, not the other way around) Stop thinking of social selling as "nice to have." Start treating it as your primary sales strategy. Your next big deal isn't in your CRM. They're scrolling LinkedIn right now. What content are you creating to catch them? #ConsensusPartner