Enterprise Sales Strategies for Large ACV Deals

Enterprise Sales is a different beast. You’re thinking about it all wrong. The difference between a $50K and a $500K deal is NOT fancy Negotiation skills or Disco tactics. You need to learn BUSINESS ACUMEN like a VP. I’ve worked 100s of $6-7 fig deals. Here are the 5 hardest lessons I wish I knew before going upmarket: 1. AEs Don’t Close Deals—They Rally The Troops Lone wolves don't close 7-fig deals. Enterprise AEs are like film directors—connecting champions, execs, and influencers across both companies, so the deal feels inevitable. It’s never about one hero; it's about orchestrating every player: CEO who shares the vision, VP Product who tackles tough questions, Exec Sponsor who secures buy-in. High-stakes deals demand the best your company can offer. Great AEs know how to get it. 2. Complex Sales = World Class Project Management In enterprise deals, you’re more PM than a seller. Big deals die in the details: missed tasks, unaligned stakeholders, and endless email threads. New people jump in mid-cycle, each needing context. Your job: bring order to chaos. Protect momentum, keep everyone aligned, and ensure nothing slips. Top AEs co-create timelines, organize materials in Deal Rooms and tailor every detail. 3. AEs Master Buying (not Selling) My biggest breakthroughs came not from sales training but from buying software and interviewing CXOs. That’s when I realized: If you understand how budgets, approvals, and internal priorities work, you don't need sales tactics. Empathy becomes your superpower because you know what each stakeholder needs (financially and politically) to say YES. Want to excel at enterprise? Study how companies justify ROI, CFOs think, and champions navigate approvals. 4. There’s No Sales Process—Only a Buying Process Your buyer doesn’t care if you’ve hit Stage 3 in your CRM. They care about their own maze of priorities, budgets, and internal politics. Top AEs ‘dance’ around the sales stages. They choreograph moves based on what the deal needs next—like looping in a board member to champion them behind the scenes or going after end-users to outshine a competitor who started at the top. 5. AEs Think Transformation, Not Pain Points Execs won’t write $1M checks to fix a clunky spreadsheet workflow. They need to see a solution driving company-wide impact—like a strategic pivot or entering a new market. If you’re only uncovering small headaches, expect a small deal. But connect those symptoms to a transformation—and the CFO listens. —— Enterprise sellers think and act like business leaders. Not salespeople who want to close deals. Yes, they know the fancy sales tactics. But that's not the point… When buyers see you think like them. When you work a deal like it’s their internal project. You unlock trust that deserves 6-7fig budgets. P.S. We built Aligned to help manage the complexity of Enterprise Sales. A 100% FREE Deal Room used by 40K sellers. Try it https://lnkd.in/dwX_Zizk

In large deals, the real competition is rarely another product. It is inertia. The most effective large deals are often shaped early. When the business user begins exploring a problem, and the right conversations start happening at that stage, the deal gradually evolves into a sole-sourced decision rather than a late-stage RFP comparison. Because once a deal reaches a formal RFP stage, many vendors appear to be at the finish line. In reality, the direction of the deal was usually influenced much earlier. Many deals look healthy for months. The champion is engaged. The demos land well. The value is understood. And then, close to the finish line, the deal slows down… or quietly becomes “No Decision.” More often than not, the issue is not price or product. The deal simply never travelled far enough inside the organisation. Large buying decisions are rarely made by one person. They are shaped by a group. The business user evaluates usability. IT looks at integration. Security looks at risk. Finance looks at cost. Leadership looks at long-term impact. Each of them is solving a different problem. If the conversation is only happening with one or two people, the deal remains fragile. This is where relationship mapping becomes one of the most important disciplines in selling large deals. Not just knowing your champion, but understanding the ecosystem around the deal. Who influences whom? Who signs. Who can block progress quietly? Who needs confidence before the decision moves forward? Building that map takes time. It means asking better questions. • Who else will review this internally?  • Who will be responsible for implementation?  • Who owns the budget?  • Who needs to see this before we move ahead? As more people across the organisation understand the value, the deal becomes stronger. It stops being one person’s initiative and starts becoming a shared decision. And shared decisions move forward with far less resistance. The best sellers know that closing large deals is not just about presenting a solution well. It is about shaping the deal early and building alignment across people, priorities, and perspectives. #LargeDeals #Enterprises #SST

I just watched an AE lose a $1.2M deal after running a "successful" product trial that the prospect LOVED. After 8 weeks of work, the CFO killed it with five words: "Let's try our current vendor." This happens because most reps treat trials as product demos instead of what they actually are: RISK ELIMINATION EXERCISES. After analyzing 200+ enterprise sales cycles at companies like Salesforce, HubSpot, Thomson Reuters, and Workday, I've identified the exact framework that separates 80%+ trial conversion rates from the industry average of 30%. Here's what most reps get wrong: They skip qualification and jump straight into the trial. Big mistake. Before any trial, ask these 3 questions: → "What happens if you don't solve this problem in the next 90 days?" → "How have you tried solving this before?" → "Who else is affected by this problem?" These eliminate 68% of unqualified trials before they start. Next, define success upfront: → Technical requirements that must work → Business metrics they expect to see → Timeline for implementation → User adoption patterns needed Get confirmation: "Just to confirm, if we demonstrate these criteria, you'd be ready to move forward with purchase by [date]. Correct?" Map every stakeholder: → Technical buyers (include every trial user) → Economic buyers (CFO/budget holder) → Political influencers (who can kill deals) → Current solution advocates (who benefits from status quo) For each person, document their personal win/loss scenarios. Have legal review agreements BEFORE starting trials. "We typically have legal review the agreement structure ahead of time so there are no surprises later. Would you be open to having them review a blank agreement while the trial is running?" Finally, handle the current vendor objection upfront: → "Have you discussed these challenges with your current vendor?" → "What was their response?" → "What specific capabilities do they lack?" Document these answers to build your business case. Results from this approach: ✅ Trial conversion: 32% to 83% in 60 days ✅ Deal size increased 40% ✅ Sales cycle shortened 37% ✅ Forecast accuracy improved 92% ✅ 43% less time on unsuccessful trials Stop running trials. Start running risk elimination exercises. — P.S. Sales Leaders, want to ACTUALLY move the needle in your org and find an extra $2 to $10 million of hidden revenue? Go here: https://lnkd.in/gDexefD5

Last week I spoke with Salesloft CEO David Obrand about the massive 40,000 seat deal they closed with IBM. Here are the 3 critical elements of their enterprise sales playbook: 1. Non-tech GTM orchestration and product marketing Ensure that you have coordinated revenue motions for each industry vertical you are targeting. Historically, the big VC-backed sales and marketing tech companies have grown on the backs of selling into tech itself.  But the future of sales and marketing tech sits within the true enterprise and most of the true enterprise is decidedly not tech.  To enter the healthcare, financial services, industrials, or government services markets you’ll need dedicated sales teams, services teams and account-based marketing motions that make it clear to the buyer you deeply understand their problems and their issues.  It’s not going to come from super bowl ads.  2. Leverage ecosystems Going it alone into the enterprise can be a daunting task. To effectively drive enterprise adoption, you’ll need support and assistance from partners and ecosystem players in the space.  IBM isn’t just a Salesloft customer, they’re also a partner, helping introduce the concept of revenue orchestration to thousands of their customers.  If you don’t have relationships with the big IT consulting arms of the major strategy firms (eg Deloitte), make sure you begin to develop them. They are critical trusted entry points into the enterprise. Being on the AWS app exchange isn't enough. You need deep partnerships that give confidence to enterprise buyers you are a bet worth making and that there is infrastructure capable of supporting you.  3. Invest in Customer Success and introduce them pre-sale Introducing a new workflow product to a company with 40,000 employees isn’t a “set it and forget it”. Getting 40,000 people to do anything, let alone use your new product, is hard.  Whether you call it strategic account management, customer success, or something else doesn’t matter. What matters is that you are focused and have a plan for driving usage and adoption and that the plan begins before the sale happens. Investing in CS pre-sale also helps drive GTM alignment and makes sure that the sales team is selling something the services team can stand behind. TAKEAWAY: The enterprise will decide who wins the B2B SaaS wars. Few companies actually have experience building deep and lasting relationships within the enterprise.  If you want to do it, you’ll need a playbook. This is a great place to start.

I’ve sold 1M dollar deals, 10M dollar deals, and 50M dollar deals — Here are 3 things I learned from those deals that you won’t find in any playbook: 1. Secure Micro-Commitments Throughout the Process Big deals don’t close with one big “yes.” They’re built on a series of small, intentional, but effortless agreements that create buy-in over time. Here are two of my strongest micro-commitments: * Have senior leaders attend the end of the POC (Proof of Concept). Here’s how I frame it: “Mrs. Senior Leader, we’ve run these POCs many times, and there are key elements that, when executed in the right order, deliver the outcomes you need. This session will give you the clarity to decide whether to move forward.” * Keep the process time-bound. POCs that drag on for months risk losing momentum—or worse, rolling into the next fiscal year. Set expectations upfront: “Let’s agree to keep this time-bound and wrap up by [specific date]. That way, you get the insights you need without unnecessary delays.” 2. Multi-Thread Like Your Deal Depends on It (Because It Does) In enterprise sales, relying on a single point of contact is a gamble you can’t afford. You need to create multiple layers of engagement: * Champions (at least 1): These are your internal sellers—they’ll pitch your solution when you’re not in the room. Champions are personally invested in your success because it aligns with their goals. * Coaches (3 or more): They will share critical internal insights, recommend actions, and help you navigate the organization’s decision-making process. * Contacts (5 or more): These are people directly affected by the problem you solve. They’ll provide feedback, share experiences, and engage in conversations that shape the deal. If your main contact goes dark, your deal doesn’t have to. You’ve already built relationships with 5-10 others who can keep the momentum alive. 3. Engage Executives Early and Often Big deals require buy-in from the top. Here’s how to involve executives early in the process: *Facilitate peer-to-peer conversations: Have your executive meet their executive 1-on-1. These discussions foster trust and set the tone for collaboration. * Run a whiteboard session with your head of product and their technical team: Let your product expert demonstrate value while you step back and observe. This creates a deeper, more technical connection between teams. * Bring in your sales leader for pricing negotiations: Position them as the "closer" and let them handle the tough conversations, ensuring you maintain the relationship. — High-performing sellers know the truth: Closing big deals isn’t about luck—it’s about strategy. But they are missing the secrets that transform big-deals into mega-deals. If you are ready to disclose them, join my session this Friday. Seats are reserved for experienced sellers only. Comment “The Forum” to get your invite.

One strategy I'm DYING to try at an enterprise software / cyber company is the idea of specialized exec content, surgically distributed to individual members of the buying committee. Here's how it would work. As an example, let's say we sell large cybersecurity deals ($100k+ ACV) into the enterprise / Fortune 1000. Our economic buyer is the CISO, but other relevant stakeholders, influencers and blockers include the CTO, CFO, CIO, the procurement and legal team, maybe the CEO because it's strategic, and all kinds of VPs and Directors within the security team. Let's say we build a list of 500 target accounts. Most companies will already have cybersecurity-related content going out, that's table stakes. But let's say we now take our own CFO and create thought leadership content from her perspective and publish it on her Linkedin. It's not content that a CISO will find interesting, but other CFOs will. Now we do the same thing for our own CTO, CIO, CEO, Head of Procurement, Head of Legal, VP SecOps, Director of GRC, etc. Our CTO creates content that's relevant for other CTOs Our CIO creates content that's relevant for other CIOs Our Head of Procurement creates content that's relevant for other Procurement leaders They're each creating their own content, sharing their own lessons from their own world, posting it through their own Linkedin profile, which would be relevant to THEIR peers Now we come back to our 500 target accounts. We connect our CTO with the 500 CTOs at those target accounts. We connect our Head of Legal with the 500 Heads of Legal at those target accounts. We connect our VP SecOps with the 500 SecOps leaders at our target accounts. As they're each sharing insights, they're building trust within that specific stakeholder of the buying committee. We can then use Linkedin's relatively new Thought Leader ads to GUARANTEE distribution to the right, individual decision makers at our target accounts. The nice thing about the Linkedin ad manager is that it TELLS you which companies are most engaged with our ads, so we know where we're resonating and can forward it to the sales team. How do we get our CTO, CIO, Head of Legal etc to actually post regular content? By interviewing each of them once every 2 weeks for 1 hour, host an "internal podcast" with them, ask them about their lessons and insights, and pull video clips and text posts that we prepare into almost-done Linkedin posts for them. All they need to do is look over the posts, make a couple changes, and publish. 1h/week All the rest (ads, connecting, scoring, outreach) can be done by someone else. How much faster are we building trust? How much easier will it be to overcome all the hurdles and blockers on our deals? How much better are we penetrating our target accounts than our competitors? To me it seems like a no-brainer. No large B2B company is actually doing this. Happy to help if someone actually wants to try - project33.io

Last month, we won a deal at $120K when our closest competitor quoted $31K. Here are the 3 strategies we use to win 90% of our head-to-head deals in enterprise (even when we're 4x the cost): 1. Make Discovery Valuable for the Prospect Most discovery calls are filled with endless checklist questions that only benefit the vendor. Discovery should be buyer-focused and help the prospect to understand if you are a good fit for THEM. Questions should only be asked if the answer helps you provide value to them. Good discovery is literally a differentiator because most AEs run through a checklist given to them by leadership. The questions all benefit the seller, not the buyer. If you truly understand the prospect’s problem and have enough market/product knowledge to get them to their solution, you’re already ahead of 95% of sellers. In this deal, the prospect literally said “Oh my god. Vendor X just kept asking questions and we couldn’t get a glimpse of the product. They didn’t understand our problem and were more worried about our timeline and if we had budget. I feel like you all truly understood our problem and were helping us solve it as if you were a part of our team.” Don’t be the sales rep that prospects hate because you waste their time on calls. The bar is insanely low here. 2. Secure Executive Buy-In Early and Build Multiple Champions From the start, we involved key stakeholders from four different teams and their CMO. I was close with everyone, was on text with 4 people (including procurement), and had separate Slack threads with different teams who were involved. To the point where we felt like friends and conversations were casual and enjoyable. Everyone was bought in except one person. But all the champions let me know this, what the concerns were, and we worked together to get them on board because we all had a common goal. This could easily been blocked behind the scenes if this was not the case. 3. Show them what it is like to work with your team BEFORE the Contract is Signed The prospect mentioned that they learned a lot during the sales process. They refined some of their processes even before the contract was signed. We helped them understand what was possible with the product and helped them with strategies that improved their processes whether they went with us or not. We brainstormed ideas, experiments, and growth channels. They knew partnering with us meant not only a premium tool, but a premium team that was fully invested in their success. They kept having us meet more and more people on the team to talk through ideas, which also built stronger and stronger consensus. TAKEAWAY: DO NOT COMPETE ON PRICE. It will only get you so far. Price, free trial, POC, etc. are not real differentiators for enterprise. Differentiate in product, support, sales process, speed of innovation, level of partnership and UX. Not in price. What are the best strategies you’ve seen success with in enterprise?

After 15 years and countless 7-figure deals, here are the **3 things nobody tells you to do FIRST** when you start in Enterprise: I know because I stepped into my first ENT AE role and immediately felt like I'd been dropped in a foreign country without a map. There I was, week 4, staring at my account list (2 giant insurance companies, 2 "household name" banks) with my heart pounding. I kept hoping there was a guide somewhere on how to land deals with these large accounts. Yeah, ENT doesn't work like that. So here are 3 things to do first: 1/ Map the Buying Maze (It's Not a Funnel, It's Spaghetti) Enterprise buying looks like someone threw pasta at the wall. Your champion says "I'll check with Legal." Legal loops in Security. Security wants Procurement. Then someone's CEO quits. Start over. Do this: → Book time with a top performer to map typical buying stages → For each stage, document: Customer options | Your actions | Common roadblocks → Include when to get IT/Legal/Security/Procurement involved Why it matters: ENT buyers juggle 10-15 stakeholders. When you ask "What's next?" they freeze. But when you say "At this point, teams typically bring in IT, set meetings with Legal, and polish the business case for the CFO. What makes sense for you?" - now you're guiding, not guessing. 2/ The CSM = Your Secret Weapon That CSM managing Apple? They've been there 5 yrs. They know everything. And customers tell them what they'd NEVER tell sales. Do this ASAP: → Set up weekly syncs with your CSM → Ask in 1st meeting: "What do AEs here typically miss?" "What's one thing I should I ask customers that doesn't usually get asked?" → Share everything - notes, recordings, concerns CSMs get burned by AEs who overpromise & disappear. Show them you're different. They'll tell you: "Your champion at Netflix is about to get reorg'd" or "Apple's procurement is backed up 90 days." Intel you can't buy. 3/ Memorize 6 Enterprise Stories (Yes, With Note Cards) ENT buyers only care about ENT examples. Period. The system: → Find 6-8 stories from TRUE enterprise accounts → Write each on a note card using STAR: • Situation: Sarah, CISO at 5,000-person firm • Trouble: Security audits taking 3 weeks, blocking launches • Action: Implemented platform with phased rollout • Result: Cut audit time to 3 days, saved $2M → Practice OUT LOUD for 10 min every morning until automatic Note cards hit visual + auditory + kinesthetic learning. Triple threat. When a buyer mentions security concerns, you instantly respond: "That's exactly what Sarah at [similar company] faced..." Instant credibility. ___ Here's the uncomfy thing about that big ENT promotion: Most AEs waste 6+ mo figuring this out through painful trial & error. (I sure did.) You can compress the learning curve: *Map the chaos. *Partner with CSMs. *Master your stories. Everything else is noise. What's the ONE thing you wish someone had told you before your first Enterprise role? 👇

The Challenger Advantage in Enterprise Sales Enterprise markets reward incumbents. Until they don’t. Incumbents benefit from familiarity. Embedded contracts. Operational inertia. Procurement comfort. Challengers win when they expose complacency. When I joined Spectrum Business a decade ago to help build a national enterprise sales organization designed to compete in complex, incumbent-dominated accounts, we were stepping into entrenched environments every day. That journey taught me something fundamental: You cannot out-incumbent the incumbent. You have to out-execute them. That means: 1️⃣ Preparation beyond the RFP We study operating models, executive priorities, and risk exposure — not just product fit. 2️⃣ Strategic intensity Outworking isn’t more activity. It’s tighter feedback loops, sharper discovery, faster executive alignment. 3️⃣ Multi-threaded precision Enterprise deals are won in the white space between stakeholders — not in the demo. 4️⃣ Business outcome fluency If you can’t quantify impact in growth, margin, risk, or velocity, you’re not ready for the C-suite. 5️⃣ Service as a competitive lever In large enterprises, the delivery experience becomes part of the buying decision. Responsiveness. Accountability. Operational simplicity. That’s not support — that’s strategy. High-performing challenger teams don’t wait for deals to develop. They engineer momentum. They reduce friction. They make it easier for executive sponsors to say yes. Over time, that disciplined approach translated into meaningful share gains in accounts long considered locked up. Enterprise buyers don’t switch because you’re cheaper. They switch because you make it easier for them to win. Enterprise sales isn’t about a single bold move. It’s about positioning. Controlling space. Building pressure. Anticipating responses before they happen. The incumbents may start with the board, but disciplined challengers reshape it — one move at a time. And over time, when the positions compound and momentum is engineered, the outcome becomes inevitable.

I closed a $2.5M deal while working at Salesforce, here’s how I would use AI today to double the ACV and find more deals just like it... I spent nearly 5 years at Salesforce - part of the Enterprise Corporate Sales team. Everything was manual. If I were an AE today, here’s how I’d use AI to build pipe smarter and close more ACV: 1) AI = Research on steroids I’d use tools like OpenAI & Gemini for deep research on public companies: – Annual reports – Earnings calls – Strategic priorities – Competitor benchmarks What took days now takes minutes. How it would’ve helped that deal: Back then, I spent hours going through board-level priorities buried in annual reports. Today, AI could extract the key risks/opportunities in 60 seconds and turn that into 3 high-leverage angles for my outreach based on Salesforce solutions and their current use of Salesforce. 2) Upload and upgrade I’d feed past decks, call notes, and email threads into GPT. Then ask: – What messaging is resonating? – What worked for similar personas? – Where are the gaps? AI becomes my deal co-pilot, sharpening discovery, tightening follow-up, and helping me write what actually converts. How it would’ve helped that deal: I had 7 internal stakeholders to keep aligned across a 9-month sales cycle. I manually pulled notes and tried to tailor follow-ups. AI could’ve auto-summarised every call, highlighted misalignments, and even predicted objections based on tone and history. 3) AI-powered account planning Using Clay, I’d layer: – Tech stack data – Firmographics – Buyer job changes – Social signals – Website intent ...to build smart lists and trigger campaigns when timing is right. How it would’ve helped that deal: That $2.5M deal came from catching a company at a pivotal moment — expanding globally. If I had signals set up, I could’ve found 5 more just like them, earlier, and closed with stronger positioning. 4) Personalisation at scale Forget “Congrats on the funding” emails. I’d link their strategic objectives (from the CEO’s podcast or a 10-K report) directly to a product outcome. Then auto-find the owner of that KPI, validate their email, and drop them into a smart sequence. How it would’ve helped that deal: Our winning moment was tying our solution to their “Cost to Serve” reduction goal. AI could’ve helped me find that language faster and deliver that message to more decision-makers earlier in the cycle. 5) Structured playbooks > scattered hustle Every sequence mapped to: – Persona – Buying stage – Signal trigger – Outcome-based CTA Less guessing, more compounding. AI writes, tests, adjusts — and scales what works. How it would’ve helped that deal: I had to build sequences from scratch, manually. AI would’ve given me frameworks, rewritten based on tone/persona, and scaled them across lookalike accounts. Want the playbook on how to roll this out for yourself? Comment 'ACV' and I'll share it directly with you. Connect with me first.