Strategies to Close 6-Figure IT Project Deals

Most reps are trying to close bigger deals by writing better cold emails or using the latest AI automation. That might get you meetings. But it won’t get you contracts. You want to close multi 6 and 7 figure deals consistently? You need to master the skill almost nobody is willing to talk about. ➡️Business acumen. Here’s what that actually looks like (and how I used it to close massive enterprise deals in my career). #1 Study how businesses really work. I dove into profit and loss statements, earnings transcripts, and cash flow reports. Not because it was “fun.” Because I needed to understand how my buyers thought about money, growth, and risk. Salespeople who don’t know how their prospects make decisions will always be treated like amateurs. #2 Read what your customers are reading. I’ve read over 1,000 books. Not just sales books. Business books. Leadership books. Biographies. Decision-making frameworks. If an SVP or CFO mentioned a book in passing, I bought it and read it. Most reps can’t hold a real business conversation because they’re stuck in “sales rep speak.” That’s why they get ghosted by execs. #3 Get in the rooms where decisions happen. I invited myself to cross-department meetings. Ops. CS. Finance. Product. I wanted to see how they thought and what they prioritized. Later, I sat in on executive strategy meetings. I wasn’t there to pitch. I was there to listen, learn, and think like a decision-maker. #4 Go visit clients. In person. While everyone else hid behind email, I went onsite. I watched how their teams worked. I asked real questions. I walked the floor. When it was time to pitch, I wasn’t pitching a product. I was pitching a custom solution for how they actually operated. Game changer. #5 Play the long game. I followed up with prospects for years. No “just checking in.” I added value. I solved problems. I worked with other stakeholders at no revenue to me. When they were ready to buy, I wasn’t the vendor. I was the obvious choice. #6 Demonstrate deep preparation. I carried what I called my “blue folder.” Every ENT meeting, I pulled out a thick file. Notes. Research. Earnings reports. Highlights. Workflows. Historical context. Prospects would literally pause and say, “Wow. You’ve really done your homework.” It built instant trust and credibility. Most reps are out here trying to sell like it’s 2018. Good emails. Decent social content. Basic follow up. That’s table stakes. If you want to close real deals, you need to do the unsexy work. Deep business acumen. Long term relationship building. Creativity. Critical thinking. That’s how you go from sales rep to trusted advisor. And why buyers choose you when it’s time to sign. Want to go even deeper? Check this out, the REAL reason $500k sales rep outperform everyone else: https://lnkd.in/gDn-UHd4

You got a $500K inbound. Pause. If you just caught a half-million dollar lead and your head is racing, pause. I have a few notes before you blow it. I say this because I once watched a $30K deal turn into a $500K close in three days. It was an anomaly. It happened because we reached power fast and we pulled the whole company into the deal. The rep did not “crush it.” She orchestrated it. Here is what to do the moment that big lead hits your inbox. 1) Get to power fast: - Ask on day one: who can sign at this amount. Not who likes us. Who signs. Do your own research first so you can suggest who this person might be when meeting with your original stakeholder. - If your primary contact cannot sign, you are networking, on top of selling. - Use your leaders. Use your CEO if needed. A warm intro from the top beats your third discovery call. 2) Quarterback your company: - Make a one-page brief so leaders can help without asking for context. Problem. Impact. Ask. Next step. - Pull product for the one question that really matters to the exec. - Pull CS for a reference that speaks their language. - Pull finance to clear vendor setup early. Big deals die in paperwork. 3) Change your process because the deal is not normal: - Ditch the standard demo. Execs want outcomes, not feature tours. - Propose a mutual action plan with dates, owners, and the signature path. - Map legal and security as early as the value you've landed allows. Get the NDA signed while you set the first meeting if possible. - Pricing needs a clean one-pager. No riddles. Tie the number to business impact. 4) Use the room the right way: - When you finally meet power, stop pitching. Ask what changed inside their business that created this budget. - Repeat their words back. Align on three outcomes they will defend internally. - Offer the shortest path that meets those outcomes. Fewer steps win. 5) Fix small frictions that kill big deals: - Calendar control. Send three exact slots. Include your exec. Make it easy to say yes. - Email subject lines that get opened by power. “Decision path and dates,” not “Quick catch up.” - Silence management. Daily update to the customer until closed. Even if the update is “waiting on security response.” - Internal rumor control. Keep your team aligned on who speaks to whom. One voice to the customer. 6) Know when luck helped you: That three-day $500K close I mentioned. We had a relationship that reached power in one call. That was luck. The part that was not luck was how fast we moved when the door opened. Brief ready. References lined up. Execs prepped. Pricing clear. No chaos. The bottom line: Big deals are not won by working harder on the wrong person. They are won by getting to power and pulling the right people in at the right time. Your job is not to be the hero. Your job is to conduct the win.

You don’t really lose Enterprise deals to price. Even if that’s what buyers tell you. It’s more like: Hidden stakeholders popped up, process out of control, champion winged it… Real reason? Buyer CHAOS. I’ve hired 100s of AEs who closed 6-7 fig deals, and one skill stood out every time – Project Management. 10 examples: 1. Work-Back Planning PMs start from the delivery date and work backward. Ent AEs do the same: co-create Mutual Action Plans with champions backwards from value delivery. 2. Stakeholder Mapping PMs wouldn’t run a project without a RACI chart (Responsible, Accountable, Consulted, Informed). Ent AEs don’t run deals without mapping champions, influencers, blockers, and economic buyers – mapped in one big Miro board. 3. Risk Management PMs identify risks early and have mitigation plans. Ent AEs do the same: assume deals will die, spot red flags, and proactively derisk with pilots, exec sponsors, or extra champions. 4. Resource Orchestration Like PMs align engineers, designers, QA – Ent AEs rally SEs, execs, product, and CS at the right moments. Lone wolves lose big deals. 5. Async Communication Projects fail when all updates happen only in meetings. Same with deals. Ent AEs master the between calls moments: Deal Rooms to keep key topics & assets organized across teams. Recaps & updates across Slack/Email/Deal Room. 6. Documentation & Version Control PMs maintain one source of truth. Ent AEs are fanatics at organizing POCs, business cases, resources, etc. in a way that makes it easy for buyers to align (vs 50 lost email threads, files, and links). 7. Change Management PMs expect scope changes mid-project. Ent AEs expect new stakeholders, shifting priorities, and budget freezes. It’s how they adapt quickly without losing momentum. 8. Time Management & Prioritization PMs manage competing priorities ruthlessly. Ent AEs do the same. It’s so easy to get swallowed up in Enterprise. They balance 6–10 big opps, obsess over quality in deals or situations that truly require it, and move fast where they can afford it. 9. Consensus Building PMs align cross-functional teams. Ent AEs facilitate consensus across buying groups – building single-threads with stakeholders to problem-solve and align, while arming champions with tools to win internal debates. 10. Dependency Management PMs know some tasks can’t move until others are done. Top AEs know the same: you can’t rush commercials if the POC is still shaky. They sequence dependencies, but also know how to run parallel streams so deals move fast. —— Enterprise deals don’t reward basic sales skills. They reward PM level of discipline, structure, and execution. The AE who facilitates the internal chaos, wins. Simple as that. P.S. We built Aligned to help manage the deal complexity of Enterprise Sales. 100% FREE Deal Room used by 50,000 sellers. Try it: https://lnkd.in/d_49kHZE

🚨 The #1 reason AI, automation, and no-code agencies aren't landing six-figure enterprise deals? They’re treating enterprise like a bigger SMB. One week into the Anti Roadmap Roadmap Club—an accelerator helping Zapier Solution Partners land their first $100K deal—and one thing is crystal clear: breaking into enterprise isn’t just about leveling up your sales… it requires a completely different playbook. 1️⃣ Enterprise isn’t buying a tool—they’re buying risk reduction They care about de-risking operations, not just speed. Build trust with use case-based content and strategic partnerships. 2️⃣ Fast ≠ Enterprise-Ready Speed is nice, but stability, compliance, and long-term viability win deals. Have a clear support plan and security readiness from day one. 3️⃣ Inbound leads won’t cut it Enterprise doesn’t Google solutions—they buy from trusted experts. Outbound sales, multi-threading, and LinkedIn networking are non-negotiable. 4️⃣ Scope creep will kill your margins Enterprise clients assume “just add this” is easy. Use pre-set add-on pricing and formalized scope changes to stay profitable. 5️⃣ If they don’t push back on pricing, you’re too cheap Price signals legitimacy. Enterprise expects to pay more—position your offer around business impact, not hourly rates. 6️⃣ Saying yes to everything makes you a vendor, not a partner Define three core offerings and say NO to anything outside that scope. Guide them—don’t just take orders. 7️⃣ Custom builds don’t scale Enterprise wants repeatability. Package your solutions into fixed-scope offerings that can be easily deployed. 8️⃣ Procurement is the final boss SOC 2, security reviews, and vendor approvals take months. Start preparing now or lose deals before they start. 9️⃣ Your case studies need to sound like them, not you Show impact in enterprise terms: “Reduced processing time by 47%,” not “We built a cool automation.” 🔟 You’re closer than you think Most agencies already have the technical skills—what’s missing is the sales & positioning strategy. Start enterprise conversations now. 🚀 If you’re trying to land bigger contracts, what’s been your biggest challenge? Drop it below 👇 Let’s talk.

“HubSpot partners don’t go upmarket.” “Just stick to SMBs.” “You’ll never close a 6-figure deal.” Cool story. Now tell that to the partners closing 100+ seat Service Hub deals and multi-hub enterprise contracts. Want to be one of them? Here are 14 actions to take: 🔒 SECURITY & CREDIBILITY 1️⃣ Get SOC II, or don’t bother. Enterprise clients don’t ask if you have security standards - they assume you do. No SOC II? You’re getting stuck in procurement purgatory. Chat w/ BD Emerson for help. 2️⃣ Carry liability insurance that matters. Enterprise legal teams will ask. $1M policies are the floor, not the ceiling. 3️⃣ Have a formal data privacy policy. GDPR, CCPA - you need to know these terms cold. Enterprise clients need to trust you with their customer data. 📦 OFFERING & SERVICE DELIVERY 4️⃣ Package your solutions for multi-hub. Don’t just “offer HubSpot services.” Build clear offerings like “Revenue Platform Overhaul” that solve for business value (across hubs) 5️⃣ Create a true RevOps advisory service. Executives don’t just want a “CRM setup.” They want a partner who aligns Sales, Marketing, and Service processes 6️⃣ Develop a multi-phase engagement model. Big companies hate “one-and-done projects.” Build a 3-phase offering: -> Phase 1: Platform Strategy & HubSpot Blueprint -> Phase 2: Hub Implementation + Change Management -> Phase 3: Ongoing Enablement & Optimization 7️⃣ Get good at data migrations. Enterprise clients have data sprawled across Salesforce, Zendesk, custom ERPs. If you can’t migrate and map data across platforms, you’re not getting the deal. 8️⃣ Master complex Sales Hub setups. Lead routing. Territories. Custom objects. The Sales Hub complexity is where the money is. SMBs don’t need this - enterprises do. 9️⃣ Offer post-implementation enablement. Enterprise clients don’t want “here’s your portal, good luck.” They want 6-12 months of adoption support. Train their teams. Build their playbooks. Embed with them. 💼 SALES & POSITIONING 🔟 Stop selling “HubSpot.” Start selling “Business Outcomes.” Enterprise execs don’t care about “Marketing Hub Pro.” They care about shorter sales cycles, better customer retention, and revenue growth. 1️⃣1️⃣ Learn how to talk to CFOs. These deals will always involve Finance. You need to prove ROI and justify spend over time. 🔑 PARTNERSHIP & REPUTATION 1️⃣2️⃣ Position yourself as a “CRM Implementer,” not a “Marketing Agency.” Enterprise clients don’t need more ads - they need RevOps transformation. HubSpot knows this. They’re sending the big deals to process-focused partners 1️⃣3️⃣ Get certified beyond the basics. Data Migration Accreditation. Advanced Implementation. These certifications signal you can handle complexity. Get them. 💡 BRAND & PERCEPTION 1️⃣4️⃣ Raise your prices. Enterprise clients don’t trust cheap partners. Pricing too low signals you don’t understand their complexity (yes, RAISE WHAT YOU CHARGE). stay Supered⚡ -matt

I've managed 500+ enterprise deals over $100K. When late-stage deals stall, 90% of reps send "checking in" emails and pray. That's not momentum. That's desperation. Here are the 5 moves that actually unstick stalled deals: 1. Social Proof That Hits Different Send a screenshot of a customer Slack message celebrating their win with your product. Not a polished case study - raw, authentic excitement from someone just like them. I used this exact strategy on a deal that had been stalled for 6 weeks. Deal closed within 10 days. One I've used at UserGems 💎 is in the example photo. ($1,004,400 deal) 2. Direct Legal-to-Legal Connection Stop being the middleman in contract negotiations. Introduce your legal team directly to theirs. Even better: get both teams on a single call to hash out terms. This cuts review time in half and shows you're serious about closing. 3. Executive Alignment Above Your Head Connect your C-suite with their C-suite for a single line of communication on negotiations. When execs talk directly, deals move faster. Your champion will thank you for getting leadership buy-in they couldn't secure alone. 4. Technical Resource Direct Access Introduce your SE/SC directly to whoever handles their IT review. No more playing telephone with technical questions. This removes the biggest bottleneck in enterprise deals and shows you understand their process. 5. Implementation Preview = Decision De-Risking Set up a Customer Success overview showing exactly what happens post-signature. Buyers need to see the path to value, not just the product. This removes "what if this doesn't work" anxiety that kills deals in legal review. — Friction reduction beats follow-up frequency. Every single time. Stop chasing. Start facilitating.

The exact steps I took to close a $250,000 deal as an AE (5X more than any other deal in company history… 1. I built a web of relationships throughout the customer organization. My deal was 10 mini-deals woven together. I ran dozens of demos with teams across 3 continents. I had contacts from C-level executives to second-year analysts. When they finally made the decision, it felt less risky because we had created champions everywhere. 2. I outlasted everyone else. This deal took two years from start to finish. There were a lot of meetings that went nowhere. I got left on read. I heard a lot of "We've already got a solution" and "Not right now, check back in 6 months". I kept showing up. 3. I built a deal team. By the final meeting, we had 16 people in the room - 10 from their side, 6 from ours. We brought our CEO and CTO. That was literally 20% of our entire company at the time. 4. I created a shared vision, internally and externally. We didn't actually have what they needed when we started talking. I sold something we had never sold before. I spent as much time making the internal case to our product team as I did building credibility with the client. Eventually, we all realized their vision represented the future of their industry and it was something we should build. This was years ago, but these strategies still work today. The only difference is they're now becoming essential for deals half this size. Which of these are part of your process?

During my time at Qwilr, I’ve seen THOUSANDS of proposals. Here are 4 proposal plays that the best sellers use to close deals: #1 Lead With Problems Start your proposal by articulating your prospects' problems, ideally in their own words. Using quotes from relevant stakeholders within their organisation will grab your buyers’ attention and show you understand their problems. This immediately demonstrates that this isn’t just a generic pitch – you actually understand them and are focused on their specific issues. Doing this also puts decision-makers in somewhat of a tricky situation. They must either… 1. Disregard the opinions of their team as incorrect 2. Acknowledge they’re facing a problem, but decide not to look for a solution 3. Look for a solution (which you are providing in the rest of your proposal) Most (good) leaders will opt for the latter and will read on to better understand your offering. #2 It's Easy to Digest You MUST ensure your proposal is clear, straightforward and easy to understand. Remember, the folks who will be reviewing your proposal are incredibly busy and don’t have time to decipher endless information, searching for what is relevant for them. If your offer is easy to understand, it’s easier to say yes to. Avoid dense walls of text, and use images, graphics and interactive elements to simplify complex ideas. Always steer away from jargon. While it might showcase a level of expertise, you have to keep in mind that it’s likely a number of people will review your proposal. You need to make sure that EVERYONE will buy in. #3 Make It Relevant Buyers want to know that you’ve helped organisations that look like them, or the type of organisation that they aspire to be. Making sure that your proposal speaks to your buyers’ industry, needs, challenges and objectives will increase the likelihood of engagement Build your case by including concrete data and case studies that resonate with your client’s situation. CAUTION: It can be tempting to litter your proposal with logos and quotations from your “biggest” clients. You should not (always) do this! Instead, focus on featuring logos of similar companies or aspirational peers, not just massive brands. Remember, just because a company is “big” to you, that doesn’t mean your client will care. They want to know you can help THEM! #4 Keep Next Steps Simple It’s essential that you break down your proposal into clear, actionable steps – giving your client a roadmap on how to proceed and what will happen when they sign. You should also educate your champion on how to position the proposal to the buying committee, arming them to sell internally. Meet with them and go through your proposal, asking what needs to be removed and added (for other stakeholders) and how they plan to share it more widely. Want to send proposals that impress buyers and close deals? Try Qwilr for free at https://getqwilr.com

Your deal just died in a Slack thread you'll never see. It wasn't your champion. It was the Head of Data Infrastructure who got looped in 48 hours before signature and killed it over "integration concerns." This is the fun part about selling these days. You're not just convincing one person. You're playing chess against an entire department. That's why you should stop treating your SEs like post-demo cleanup crew. They're your closers now. 🙂 Some ideas to consider: 1. SEs start in DISCOVERY. Not after the demo. Not when things get technical. From call one. They shape how pain maps to product before you even open slides. What this looks like: Your SE is asking about current architecture, data flows, and integration points while your AE is still qualifying budget. They're building the technical narrative that makes your solution inevitable, not optional. 2. Forecast stages require SE sign off. You can't call it "proposal" if your SE hasn't validated technical fit, or "commit" if they haven't walked the deployment path. Maybe add SE checkboxes to your CRM stages: - Discovery -> SE has mapped current tech stack - Demo -> SE has customized use cases to their environment - Proposal -> SE has reviewed security requirements with their team - Negotiation -> SE has walked implementation timeline with IT 3. SEs become content creators. They're building competitive breakdowns, ROI calculators that speak IT language, and security checklists that kill objections before they start. Example: Instead of generic ROI decks, have your SEs create technical business cases. "Based on your current API call volume and processing delays, here's how our architecture saves you 47 hours of dev time monthly." That's $180K annually in developer productivity that IT can defend to finance. 4. Deal velocity lives in SE credibility. Procurement trusts your SE more than your AE. Your champion's IT team trusts your SE more than your marketing deck. Gangster SEs become technical advisors, not just vendor reps. They're the ones saying, "Here's how three other companies in your space handled this exact integration challenge" and actually knowing the architecture details. 5. Pay them like closers. If SEs are shortening cycles and unblocking security reviews, they deserve variable comp tied to those wins. Progressive comp structures: - Base salary + 2-4% of closed-won ARR for deals they actively supported - Milestone bonuses: $2K for security approval, $3K for technical win vs. competitor - Acceleration kickers: Extra 1% for deals that close 30+ days ahead of forecast - Team multipliers: Additional bonus when AE/SE pairs exceed joint quota tl;dr = you used to close with confidence and charisma. Now you need confidence, charisma, and credibility. Your SE is your credibility. Put them on the front lines, or keep losing deals to technical objections you never see coming. Unless James disagrees, of course. Then just ignore everything I said. 🫣

I recently closed a $15,000 deal with the potential of being a $100K deal. We had 3 discovery calls w/ 2 presentations. Here are 6 strategies I did to close this in less than 30 days that you can copy: 1/ Shared My Research: I did my homework on the company, industry, and buyer persona. I got to the call and shared my notes about my research and how I connected the dots. E.g. "Btw, from my understanding, you're dealing with a really antiquated buyer persona for the most part who is either using a competitor or some old school method of doing things, like managing their tasks on Excel..." Don't keep your notes private. 2/ Be Radically Transparent: Most salespeople try to hide that they're taking notes and looking at another screen, but prospects want to feel like you're taking their problems/goals seriously. E.g. "Btw, if you see me look at another screen, it's because I am. I'm writing some notes and ideas down as we talk through this, which I'll share at the end." Be candid. 3/ Looked For Problems: Salespeople hate opening a can of objections during a call, but I'd argue that is your best bet for maintaining control of the deal. I asked questions that would get me and my business in trouble. The prospect ends up selling you on why you'd be a better fit. E.g. "You mentioned you used to use [COMPETITOR] training program, why not just continue with them since the team is sold on it already?" Unsell yourself. 4/ Gave Value Before The Pitch: Most prospects expect you to spend more time pitching your services or product, but I flipped it on its head. I spent more time giving them strategies and advice on how to better run their department. E.g. "Whether you go with me, another provider, or none at all, here's what I recommend you do in the next 30-60 days.. [INSERT VALUE ADD]." Always teach something new. 5/ Set Up Next Steps Upfront: Most salespeople set up next steps at the end of the call, but that's when prospects are out the door. I like to set them up front because there's the least amount of resistance. E.g. "Assuming this would be fit, you'd probably want another call to dive deeper into your process so we can scope out the work and proposal, so let's set some time in the end to do that later this week for 30 minutes, sound good?" Make next steps worth it for them to agree. 6/ Recapped In The Beginning: At the beginning of our follow-up discovery call, I recapped their challenges/goals from our last call, but I did it by sharing my screens and showing them my notes. E.g. "Based on our last call, these were top of mind for you [LIST CHALLENGES/GOALS] - 1) What's missing from here? 2) And are these still top of mind? Use slides strategically. The takeaway: prospects don't want to be sold to, they want to be helped. #helpmedontsellme P.S. Here are my top 24 discovery questions to quantify pain that helped me close this deal: https://lnkd.in/edAVrn2v