Key Enterprise Sales Practices

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

Most sellers only uncover ONE level of impact in discovery. That’s why their deals stall, ROI slides don’t land, and their champions can’t sell internally. The truth? There are 4 levels of impact (and if you miss even one, you’re selling half-blind): Selling is helping. But helping means going deeper than “company KPIs.” Here’s the framework I coach every AE on when they’re trying to win enterprise SaaS deals: 1. Company Impact This is where 90% of reps stop. “What’s the cost savings? What’s the revenue upside?” That’s table stakes. If you don’t tie your software to actual numbers—lost revenue, margin impact, labor cost—your ROI story collapses in front of a CFO. Example: A Service Cloud rep I coached quantified millions lost in unbooked hospital referrals because of missed scheduling calls. That turned a “$500K tool is too expensive” into “8X ROI, no-brainer.” 2. Buyer Impact Your champion has skin in the game. They left a stable job. Their reputation, career trajectory, even their family’s well-being are tied to this project. If you can show them how your solution makes them the hero internally, you create unstoppable personal buy-in. 3. User Impact These are the people who log in every day. If they hate the tool, adoption dies. If they love it, productivity soars, morale improves, turnover drops. Shadow them. Ask what frustrates them. Show them a better day in the life. 4. Customer Impact The most overlooked layer. How does your product improve the end customer experience? Faster service, better outcomes, less stress? For a hospital, it’s not about “efficiency.” It’s about a patient getting a life-saving scan booked in hours instead of days. Stop selling features. Stop selling “savings.” Start selling IMPACT. - Company. - Buyer. - User. - Customer. Miss one—and you’ll miss the deal. Hit all four—and you’ll never sell the same way again. Selling is helping. Always.

In 6 years, I was promoted 3 times to become the youngest L7 Sales Leader at AWS, leading a team that hit 119% attainment on >$150M yearly quota. Here are 5 hard lessons I learned about enterprise sales: 1. Enterprise Sales = Team sport Winning big deals means selling internally as much as externally. I spent almost as much time getting internal resources, securing executive buy-in, and aligning product teams as I did in front of the customer. 2. Trust Beats Price Every Time I’ve seen won deals where we weren't the cheapest option. Why? Trust. Building relationships where the client believes in your long-term partnership is the single biggest lever you can pull in enterprise sales. 3. FOFU > FOMO The buyer doesn’t care about FOMO as much as they care about FOFU: fear of fucking up.The biggest question they’re asking themselves is, “Will this decision get me fired?” Your job is to make the deal as risk-free as possible. 4. Always Build a Business Case Enterprise buyers need justification for spending big. If you’re not building a clear, data-backed business case, you’re asking your champion to sell for you—and they won’t. The stronger the ROI/COI (cost of inaction) argument, the easier the sale. 5. You’re Not the Hero, You’re the Guide Perhaps the most important thing to internalize. Your role shifts from salesperson to strategist. EMPOWER. Don't OVERPOWER. Guide your champion on how to sell internally. Set a clear, step-by-step strategy with them. Orchestrate the entire process—internally and externally—and ensure all the pieces are aligned and moving in the same direction. TAKEAWAY: In enterprise sales, you’re the quarterback. not the one carrying the ball to the endzone. Your job is to: orchestrate the play, guide your champions, and set your team up for success. It's not about doing it all yourself; But leading the right people in the right direction at the right time.

🔥 The most dangerous phrase in enterprise sales? "Our inbound is strong." If your pipeline depends on inbound, you're already behind. By the time an RFP hits your inbox, the customer has already mapped the problem, compared options, and decided what "value" looks like. You're not influencing anymore. You're reacting. I've analyzed thousands of enterprise deals: • Inbound deals close at 18% • Outbound deals close at 42% • Inbound discounts 3x more Why? Inbound feels safe. Dashboards light up. Activity rises. It feels like progress. But activity ≠ control. When you rely on inbound, you're stepping into a deal defined by someone else. Real control happens before the prospect calls. It happens when you shape how they think about the problem itself. 🎯 See what others miss The best sellers uncover pain before it's visible. They don't wait for interest. They create awareness through discovery. That positions you as advisor, not vendor. 💡 Lead before problems are defined Selling starts when you help buyers make sense of confusion. Name the problem. Quantify impact. Do this before discussing solutions, and you own the narrative. 🔥 Build urgency through understanding Don't push timelines. Reveal what's at stake. Pain without consequence = complaining Consequence without action = worrying Connect all three = deals move To every seller told to "wait for marketing leads" — stop waiting. Your quota doesn't care. Prospecting isn't old-fashioned. It's strategic. When you engage before the buying process begins, you're not filling the pipeline. You're shaping demand. If your growth depends on inbound, you're scaling luck, not leadership. - Be early. - Build trust. - Create intent. - Define success. That's how enterprise sellers win. Too harsh? Or the wake-up call we need? Follow for more B2B sales reality checks. #EnterpriseSales #B2BSales #Sandler #OutboundSales #SalesLeadership

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.

The best AEs break the buyer / seller dynamic early and continually throughout a sales cycle. They provide value, serve as a trusted advisor, and foster constructive tension to drive action. The rubber band analogy always stuck with me, the best reps stretch the rubber band and create that healthy tension, just before the point where it snaps. It’s in that healthy tension where value is created and action is taken. You will be uncomfortable, and that’s a good thing. A few of my favorite ways to do this- 📊 Bring Insights: Share something they don’t know about their own business, reframing their problem in a way that makes them think differently. This positions you as an expert and shifts the dynamic from seller to advisor. You need to be able to add actual value to their business, beyond product promises. —“Most companies in your space think their biggest challenge is [X], but what they’re missing is how [hidden challenge / insight] is actually driving those inefficiencies. Here’s what top performers are doing differently to stay ahead…”— 💵 Reframe Value: Stop talking price - focus on the business impact. Show them the cost of doing nothing and tie your solution directly to the outcomes they care about. Make it impossible for them to ignore the value. —“Right now, you’re spending [X amount of time/resources] to address this, but it’s costing you [specific business impact]. If we can fix this, you’re looking at [clear business outcome]. What would that kind of impact mean for you this quarter?”— 🤝 Create Constructive Tension: Push them out of their comfort zone. Use data and smart questions to show why sticking with the status quo is risky. The goal is to make staying the same feel more uncomfortable than making a change. —“If nothing changes, how long can you sustain [current situation] before it starts affecting [key business priority]? Based on what I’ve learned, and other companies I’ve spoken to in your situation, it sounds like this isn’t something sustainable, would you agree?”— 🎯 Tailor to the Buyer: Know your audience. Speak to what matters most to each stakeholder - ROI for the economic buyer, seamless integration for the technical team, and real results for the end users. The more personal, the more effective. —“For you as the [economic buyer/technical lead/end user], I know [specific priority] is critical. Here’s how we’ve helped companies in similar roles solve [specific pain point] and achieve [measurable outcome]—does that align with what you’re trying to accomplish?”— Shed the bad habits from the ZIRP era, and start selling!

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 helped scale Outreach to $250M and discovered enterprise sales is just House of Cards with contracts. After 1000s of deals, here are 7 political plays that close deals (while your competition plays checkers): 1. **Your Deal Has a Deep State** The official buying committee? That's theater. The real decision happens in Slack DMs and parking lot conversations. Found the Shadow Cabinet or die wondering why you lost. 2. **Champions Are Campaign Managers, Not Fans** Stop looking for people who "love your product." Find someone who wants to WIN INTERNALLY. They'll push your deal because it makes them look like a freaking hero. 3. **Every Exec Meeting is a Debate Stage** Never present alone. Set up your champion to introduce you like: "I brought in the team that helped Uber cut sales cycles by 50%." You just became the incumbent. 4. **Opposition Research > Discovery Calls** Spent 3 hours stalking a prospect's LinkedIn. Found their CFO complaining about tech stack costs. Opened with: "Saw your CFO's post about burning $2M on unused licenses..." Deal closed wayyyyyy faster. 5. **Plant Stories, Not Slides** Killed a competitor by having 3 different stakeholders "randomly" mention how that vendor fumbled a similar rollout. Never said their name once in my pitch. 6. **The October Surprise is ALWAYS Coming** Legal, Security, CFO—someone will emerge last minute. Have your "break glass" plays ready. I keep 5 pre-written emails for every deal-killer scenario. 7. **Vote Counting Starts Day One** Track your votes like a campaign pollster: - Strong Yes: 3 - Lean Yes: 2 - Undecided: 4 - Opposition: 1 If you can't move the undecideds by week 3, you're toast. —— Enterprise sales isn't about product. It's about power. Master the politics or stay stuck at $5k deals.

Want to know why top performers close 2-3x more deals than average reps? It's not that they're smarter. It's that they've mastered deep work. After studying hundreds of high-performing sellers, I've found one consistent pattern: They protect their prime selling hours like their life depends on it. Most reps are drowning in shallow work, constantly switching between email, Slack, CRM updates, and social media. Each task switch costs you 23 minutes of focused energy. The result is a day filled with activity but empty of results. Here's how innovative sellers are implementing deep work: 1️⃣ Power Blocks They schedule 90-minute uninterrupted blocks for their most important selling activities. No email. No Slack. No phone. Just focused execution on revenue-generating work. 2️⃣ Energy Management They align their most important tasks with their peak energy hours. For most, that's 9-11 AM, not 3 PM after back-to-back meetings. 3️⃣ AI-Powered Prep They leverage AI to prepare for sales calls in half the time. "I feed the AI my call notes, recent news, and past objections. It gives me a hyper-focused prep document in 5 minutes instead of 45." 4️⃣ Elimination Before Optimization Before trying to get faster at tasks, they ask: "Does this task even need to exist?" You can't optimize what should be eliminated. 5️⃣ Digital Minimalism They turn off all notifications during selling hours. No Slack pings. No email popups. No LinkedIn alerts. The sellers implementing these practices aren't working more hours. They're just getting 3x more value from the hours they work. Most sales organizations obsess over activity metrics while ignoring the quality of focus behind them. What would happen if you protected just one 90-minute deep work block every day?

After 25 years in enterprise tech, I've learned these 5 truths the hard way. Most sales leaders won't tell you this: 1. The deal isn't won in the demo. It's won in discovery. If you don't understand their pain better than they do, your demo is just a product tour. 2. Your champion is NOT your buyer. Champions recommend. Economic buyers sign checks. If you can't map both, you don't have a deal—you have a conversation. 3. Long sales cycles aren't the problem. Unpredictable ones are. A 9-month cycle you can plan for? That's enterprise. A deal "closing next month" for 6 months? That's broken qualification. 4. Procurement is not your enemy. Help them do their job well, and they become your ally. Fight them, and every deal becomes a war. 5. The close is not an event. It's the natural outcome of a well-run process. If you're "closing hard," something already went wrong. I've closed deals from $50K to $50M. These lessons took me a decade to learn. Save this for your next deal review. What's the enterprise sales truth you learned the hard way? ↓ Swipe through the carousel for the full breakdown.