Strategies for Selling to Enterprises

"We're disrupting the industry!” The CTO checked his watch. $4M deal dead in 5 words. The CTO's eyes glazed over. Fifth time this week. My client froze. His billion-dollar product roadmap reduced to a startup cliché. I've sat through 1,000+ enterprise sales meetings. Here's what nobody tells founders about selling to big companies: Your "innovation" is their "risk." Your "disruption" is their "danger." Your "revolution" is their "rebellion." Truth is, there are only 3 types of enterprise buyers: The Veterans (80%): - Want stability above all - Need proof, not promises - Buy from safety signals The Climbers (15%): - Chase calculated wins - Need evidence, not excitement - Buy from success stories The Visionaries (5%): - Build the future quietly - Need substance, not show - Buy from deep insight Last week, a founder pitched "groundbreaking AI" to a Fortune 500 buyer. The buyer's real thought? "Who wants to be the first penguin in the water?" After $100M+ in enterprise deals, here's the secret: Don't sell transformation. Sell risk reduction. Don't pitch revolution. Pitch results. Don't promise the future. Prove the present. Because in enterprise sales, the most dangerous word isn't "no." It's "maybe." And "maybe" is what you get when you speak Silicon Valley to Wall Street. Want to close enterprise deals? Learn to translate innovation into insurance. That's worth more than any pitch deck.

Here’s the proposal template that helped me close over $100 million in enterprise sales: It’s also helped my clients close more than 50% of their deals when they use it. And until now, I’ve never shared it publicly. Most sellers are great at pitching features. But the ones who consistently win big deals? They know how to tell a great story. The truth is, executives don’t buy products - they buy confidence. They buy vision. They buy a story they want to be part of. If you want to sell like a top 1% seller, you need a proposal that doesn’t just inform… it moves people. Here’s how I do it 👇 The Story Mountain Framework for Sales Proposals: 1. Exposition – Introduce the characters and setting. Start with them: → “You’re trying to expand into new markets… to grow revenue… to unify your tech stack…” Set the vision. Make them the hero. 2. Rising Action – Lay out the challenges and obstacles. → “But growth stalled. Competitors moved faster. Customer churn increased.” Quote discovery calls. Surface real pain. Build emotional tension. 3. Climax – Introduce your solution. → “Then you found a better way…” Now show how your solution helps them overcome the exact obstacles you outlined. 4. Falling Action – Ease the tension. → “Here’s our implementation plan. Here’s the ROI. Here’s how others in your industry succeeded.” Give them confidence that this won’t just work—it will work for them. 5. Resolution – End with clarity. → “Here’s our mutual action plan. Let’s get started.” Lock in buy-in, next steps, and forward momentum. This structure has helped me close some of the biggest deals of my career—including an $8-figure enterprise deal at Salesforce where I used this exact approach. I broke it all down in this week’s training—and for the first time ever, I show you the actual proposal I used AND tell you how to access my Killer Proposal Template for free. 👀 Watch the full training here: https://lnkd.in/gPY_cvv5 No more boring product pitches. No more ghosting after the readout. Just proposals that close.

Long sales cycles really frustrate founders in the early days especially. One thing to understand is that there are 2 types of purchases in bigger enterprises: budgeted, and non-budgeted / discretionary. Bigger deals are almost always budgeted -- on a yearly / annual basis. And that means that are part of an annual planning process, often one that gets locked down in the fall, a few months before the close of the fiscal year.  In many cases, you can work on a deal before budget is approved, but you just can't get the deal signed.  You gotta ask and listen here. You can often get a pilot going, and even a draft deal put together. But you usually can't get it signed and approved until it's formally budgeted -- for >next< year. Smaller deals can come out of an extra, discretionary budget all departments have -- but that budget isn't huge. When I was a VP in the Fortune 500, mine was about $400k a year. My boss' was probably $2m all-in. But that's to cover 1,000+ employees in one department. It's not that much really, especially these days when we all are already paying for 100+ SaaS apps.  But, these deals can close anytime. So expect big deals in some cases to take what feels like a loooong time.  Especially in Years 1 and 2. And also note this is why it's totally OK and in fact best practice to ask enterprise prospects on even the first call if the potential purchase is "budgeted". It tells you how they are thinking about the space -- and also, both how big a deal you might get, and how long it might take. If it's not budgeted, try to get a fast deal in just one group, get your foot in the door. If it's budgeted? Aim for the prize, but understand it likely will take longer.  You'll get really frustrated with long sales cycles in the early days, when you are just trying to put points on the board quickly. But later, you'll see once you have 5, 10, 20+ longer sales cycle deals in the pipeline ... they'll close with regularity, every quarter. Even if any individual deal is a bit ... sloooow.

The worst cold email I received this month started with: "I'd love 15 minutes to introduce myself and show you what we do." Nobody cares about your introduction. Nobody has time for a generic pitch. After analyzing thousands of outreach sequences, I've discovered a psychological shift that's doubling meeting rates for innovative sellers. The best performers aren't focusing on their product. They're focusing on buyer psychology. Here's what's actually working in 2025: 1. The Curiosity Gap When you write "Other VPs in your space are seeing X trend" instead of "We help companies do Y," you create an information gap buyers want to fill. Our brains hate incomplete information. Use this. 2. Relevance Triggers Generic outreach gets generic results. When you mention a buyer's LinkedIn post or recent initiative, you're bypassing their "sales defense system." Relevance is required. 3. Specificity Signals "This could help you grow revenue" gets ignored. "Companies like yours are seeing 22% reduction in CAC" gets attention. Specific numbers signal you actually know what you're talking about. 4. Miniature Commitments Don't ask for 30 minutes. Ask for feedback on one specific insight. Small asks lead to bigger conversations. 5. Value-First Mindset Position yourself as a resource, not a vendor. Share insights without expecting anything in return. Reciprocity is powerful. The old playbook of "smile and dial" is dead. Meeting quotas in 2025 requires understanding human psychology. What psychological principle has worked best in your outreach?

"We have budget for $199,000," the procurement manager spat at me. I had a $325,000 deal forecasted, and we had 7 days left to close it. That was June, 2020. End of quarter. Egg about to be smeared all over my face. I paced around my house while my family swam at the pool. Cursing under my breath. Back then, I knew every negotiation tactic in the book. But that was the problem: My negotiation "strategy" was actually what I now call "random acts of tactics." A question here. A label there. Throw in a 'give to get.' There was no system. No process. Just grasping. Since then, I now follow a step by step process for every negotiation. Here's the first 4: 1. Summarize and Pass the Torch. Key negotiation mistake. Letting your buyer negotiate with nothing but price on their mind. Instead: Start the negotiation with this: “As we get started, I thought I’d spend the first few minutes summarizing the key elements of our partnership so we’re all on the same page. Fair?” Then spend the next 3-4 min summarizing: - the customer's problem - your (unique) solution - the proposal That cements the business value. Reminds your counterpart what's at stake. They might not admit it: But it's now twice as hard for them to be price sensitive. After summarizing, pass the torch: "How do you think we land this plane from here?" Asking questions puts you in control. Now the onus is on them. But you know what they're going to say next. 2. Get ALL Their Asks On the Table Do this before RESPONDING to any "ask" individually. When you 'summarize and pass the torch,' usually they're going to make an ask. "Discount 20% more and we land this plane!" Some asks, you might want to agree to immediately. Don't. Get EVERY one of their asks on the table: You need to see the forest for the trees. “Let’s say we [found a way to resolve that]. In addition to that, what else is still standing in our way of moving forward?” Repeat until their answer is: "Nothing. We'd sign." Then confirm: “So if we found a way to [agree on X, Y, Z], there is nothing else stopping us from moving forward together?" 3. Stack Rank They probably just threw 3-4 asks at you. Now say: "How would you stack rank these from most important to least important?” Force them to prioritize. Now for the killer: 4. Uncover the Underlying Need(s) Ignore what they're asking for. Uncover WHY they're asking for it. If you don't, you can't NEGOTIATE. You can only BARTER. You might be able to address the UNDERLYING need in a different, better way than what they're asking for. After summarizing all of their 'requests,' say this: “What’s going on in your world that’s driving you to need that?” Do that for each one. Problem-solve from there. P.S. These 7 sales skills will help you add an extra $53K to your income in the next 6 months (or less) without working more hours, more stress, or outdated “high-pressure” tactics. Go here: https://lnkd.in/ggYuTdtf

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?

What if your biggest competitive advantage is hiding in plain sight in your competitors' customer complaints? While most B2B executives chase the latest growth tactics, strategic leaders are systematically mining competitor trust gaps to win enterprise deals. In today's procurement environment, trust isn't just a vendor evaluation criterion—it's become the decisive factor in contract decisions worth millions. The reality of enterprise buying is stark: procurement teams have stopped believing vendor promises. They demand transparency in pricing models, proof of service delivery capabilities, and verification of product claims. Most vendors fake this transparency with polished sales decks and case study theater. The winners convert their competitors' credibility deficits into contract wins. Here's how B2B growth leaders are operationalizing trust to capture enterprise market share: Audit Competitor Credibility Gaps. Deploy systematic analysis of competitor RFP losses, customer churn patterns, and service delivery failures. Every trust breakdown in their client base represents a qualified prospect for your pipeline. Engineer transparency into your sales process. Move beyond vendor presentations. Provide independent verification of ROI claims. Offer transparent pricing with no hidden implementation costs. Make radical honesty your competitive differentiation in the procurement process. Align revenue operations around building trust. Tie sales comp, customer success KPIs, and product delivery SLAs directly to trust-building behaviors. When trust becomes measurable in your CRM and tied to quota attainment, it becomes operationalized. Build enterprise trust intelligence. Create account-level dashboards tracking trust indicators across your target prospect base. Monitor competitor service failures, contract disputes, and client satisfaction scores to time your outreach perfectly. The enterprise opportunity is massive: procurement teams are actively seeking vendors they can trust with mission-critical initiatives. While competitors struggle with credibility issues, you capture their displaced enterprise accounts. Ready to transform competitor weaknesses into enterprise wins? Start with a systematic audit of trust vulnerabilities among your top 50 target accounts. The pipeline impact could be transformational. Read more: https://lnkd.in/eRV9sWAK __________ For more on growth and building trust, check out my previous posts. Join me on my journey, and let's build a more trustworthy world together. Christine Alemany #Fintech #Strategy #Growth

"We've been working this deal for 8 months and it just went dark." (Ouch!) Last week, I had three different sales leaders tell me versions of this same story. Big enterprise deals that seemed "sure things" suddenly stalling or disappearing completely. Here's what's really happening: You're selling like it's 2015, but buyers have fundamentally changed how they make decisions. Seriously, the old playbook is dead: → Build relationship with one champion → Demo your product extensively → Negotiate on price to close → Wait for their "decision timeline" Why this fails in modern enterprise selling? #1 Committee-based buying Average enterprise deal now involves 6-8 decision makers. Your single champion can't drive consensus alone, no matter how much they love your solution. #2 Risk-averse buyers Post-2008, post-COVID, buyers are terrified of making bad decisions. They'd rather stick with status quo than risk their careers on your "game-changing" solution. #3 Budget complexity Money exists, but it's trapped across departments. Your champion in IT loves you, but the budget owner in Finance has different priorities. Here’s how elite enterprise sellers win these days: A. Multi-thread from Day One Map the entire buying committee before you pitch anything. Identify the economic buyer, technical evaluator, user champions, and potential blockers. Build relationships with each. B. Sell business outcomes, not features Stop talking about what your product does. Start quantifying the business impact of not solving their problem. Make the cost of inaction higher than the risk of action. C. De-risk the decision Provide case studies from similar companies. Offer pilot programs. Create implementation roadmaps. Give them ammunition to defend the decision internally. D. Control the process Don't ask "What's your timeline?" Tell them "Based on your goals, here's the optimal implementation schedule." You drive urgency, they don't. Here’s a real life example: One client was stuck on a $400K deal for 6 months. We mapped 8 stakeholders they'd never engaged. Built business cases for each department. Deal closed in 45 days at $650K. The difference? They stopped selling a product and started orchestrating a business transformation. Enterprise deals aren't won in demo rooms. They're won in boardrooms, budget meetings, and implementation planning sessions. Sales leaders, how are you implementing this across ALL your reps? Want to talk about how we could help? Go here: https://lnkd.in/ghh8VCaf

The answer to your outbound problems isn't: ⛔️ AI ⛔️ More volume ⛔️ SDR agents ⛔️ More relevance ⛔️ Dialers It's your OFFER. Let me explain... Most reps reach out with something like: “Just want to introduce myself and our company…” “Let’s do a quick call so you know your options when budgeting season comes around...” The problem? You have NOTHING to offer. If there’s no immediate need, there's zero reason to take a meeting with you. So you need a way to entice buyers to meet when they have a problem, but are not actively shopping. Here are three types of offers you can use to entice buyers to meet with you: ✅ Offer #1: Good - Pitch The Blind Date Position who the buyer will be meeting with. Hype up the AE, sales engineer, or yourself. Show them that meeting with you will be worth their while. Example: A client of ours sells an automated welding solution. The manufacturing industry is facing a massive shortage of welding talent. Their SDRs pitched it like this: “I’d love to introduce you to Eric. He’s worked with a dozen manufacturers like Caterpillar, Karavan, and more, who are all facing similar challenges. He’ll walk you through how they’re automating the most difficult welds and dealing with the labor shortage. Even if nothing comes of it, you’ll walk away with a better understanding of how the industry is solving this.” Even if the buyer isn’t shopping, they gain value from the conversation itself. ✅ Offer #2: Better - 1:Many Offers These are high-quality, reusable insights that still feel tailored. Think: competitive benchmarks, industry research, or best practice guides. Example: We have a client that sells to ecomm brands. They conducted a mystery shop of 400 competitors to analyze response times, customer service channels, etc. Their reps used those insights to open cold calls with: “Hey Katie, I submitted a ticket on your site, and it took about 48 hours to get a response. It was about 3x longer than folks like Patagonia and the North Face. Again, it’s Jason. Mind if I share more about why I’m calling?” That’s an offer that feels immediately relevant and valuable. It gets a conversation started immediately. ✅ Offer #3: Best - 1:1 Offers These are custom-tailored experiences or resources created specifically for the prospect. It’s you and your organization putting in serious effort to customize the offer. This works best at the enterprise & strategic levels. Examples: - A cyber risk analysis - A benchmarking analysis - A workshop - A personalized audit of a website checkout flow. - Visiting and experiencing the brand firsthand, then sharing insights. - Offering free data, licenses, or pilots. These take more work, but they convert like crazy. ~~~ Which one's most applicable for you?

We closed enterprise customers like Airbnb, DocuSign, and the NBA without a sales team. Instead, we used one unconventional strategy: founder-led content. Here's why storytelling beats selling every time - and how any B2B founder can use it. If you haven’t noticed, the old growth channels don’t work anymore: - Paid ads are saturated and expensive - Hiring a sales team with AEs and SDRs doesn't work if they don't have a playbook to follow - Cold email open rates are down 25% With minimal funding early on, we had to find creative ways to get in front of our customers for Chezie. Eventually, we figured out that webinars + LinkedIn was the best setup: 1. We hosted webinars that our ICP (ERG owners at 1000+ person companies) cared about and got 250-500 registrations 2. We shared every webinar on our personal LinkedIns 3. We started every webinar with our founder story and why we cared so much about ERGs (Dumebi Egbuna and I used to lead ERGs when we worked in corporate) The result? 60% of our early pipeline is INBOUND; they came to us. Most founders overcomplicate content. Creating content doesn’t have to be creating a newsletter and posting 5x/week on LinkedIn and launching a customer community and replying to messages in relevant Reddit communities and publishing case studies and writing blog articles to get a presence on SEO and… You get it. My advice? Pick ONE channel: - LinkedIn (my personal recommendation) - Webinars - An email newsletter - SEO-optimized articles/blogs/case studies/templates - TIkTok/YouTube videos Go with the channel where the largest percentage of your customers spend their time. Use their interactions as fuel for future content. Lead with your personality and why you felt compelled to start your company. In the age of AI, there is only ONE thing that your competition can't copy: you, the founder. Everything else (product, design, team experience, etc.) can be replicated in a month. Every day you wait, another founder in your space is building an audience. Pick your channel. Share your story. Do it today. Your future customers are already scrolling. Will they find you or your competitor?