Strategies for Selling to Enterprises

MBA schools get one thing right. Frameworks. Consultants swear by them. And here's what most CSMs miss: Your job? It's consulting in disguise. Every customer meeting. Every QBR. Every escalation. You're solving problems. But where do you start? That's where frameworks come in. Your secret weapon. Your north star. Your problem-solving toolkit. Let me break down the top 10 that'll transform your CS game in 2025: 1. MECE Not just for consultants anymore. Mutually Exclusive, Collectively Exhaustive. Perfect for segmenting your customers. Enterprise vs. Mid-market vs. SMB. No customer falls through the cracks. Every account has a home. 2. SWOT Your QBR's best friend. Analyze each account's: Strengths (feature adoption) Weaknesses (unused modules) Opportunities (upsell potential) Threats (competitor presence) Make every review strategic. 3. PESTLE Because your enterprise customers are complex. Political (stakeholder mapping) Economic (budget cycles) Social (team dynamics) Technical (integration needs) Legal (compliance requirements) Environmental (remote work impact) Miss one? Risk renewal. 4. 5 Whys Low product adoption? Ask why. Poor engagement? Ask why. High churn risk? Keep asking why. Root cause analysis saves accounts. 5. BCG Matrix Your portfolio management tool: Stars: Growth accounts Cash Cows: Stable enterprises Question Marks: New logos Dogs: Churn risks Prioritize your time accordingly. 6. Porter's Five Forces Not just for market analysis. Use it for customer health: User adoption strength Executive buy-in Alternative solutions Integration stickiness Budget competition The complete health score. 7. OKR Because "increase retention" isn't enough. Objective: 95% renewal rate Key Results: - 100% QBR completion - 90% feature adoption - 48hr response time 8. RACI Map your customer's journey: Who's Responsible for success? Who's Accountable for renewal? Who needs to be Consulted? Who stays Informed? Clear ownership = Clear success 9. SMART Goals Make every success plan count: Specific feature adoption targets Measurable usage metrics Achievable timelines Relevant to business goals Time-bound implementation 10. 3Cs Customer (their needs) Company (your solution) Competition (their alternatives) The triangle of customer retention. Here's what most CSMs miss: Frameworks aren't rigid rules. They're power tools. For discovering value. For driving adoption. For ensuring renewal. Master these. Apply them to your accounts. Watch your renewal rates soar. Because great CSMs? They're framework ninjas. ------------------ ▶️ Want to see more content like this and also connect with other CS & SaaS enthusiasts? You should join Tidbits. We do short round-ups a few times a week to help you learn what it takes to be a top-notch customer success professional. Join 1999+ community members! 💥 [link in the comments section]

"I'll just wing it. I'm good on my feet." A Managing Director said this before walking into a $50M budget approval meeting. He walked out empty-handed. After 25+ years watching high potential executives crash and burn in "the room where it happens," I've learned something most people miss: 𝗧𝗵𝗲 𝗿𝗲𝗮𝗹 𝘄𝗼𝗿𝗸 𝗵𝗮𝗽𝗽𝗲𝗻𝘀 𝗯𝗲𝗳𝗼𝗿𝗲 𝘆𝗼𝘂 𝘄𝗮𝗹𝗸 𝗶𝗻 𝘁𝗵𝗮𝘁 𝗿𝗼𝗼𝗺. Influence isn't about charm. It's about preparation. Here's an approach you can put into practice today to immediately up your influencing impact. 𝗧𝗵𝗲 𝗔𝗱𝘃𝗮𝗻𝗰𝗲 𝗪𝗼𝗿𝗸 𝗙𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸: 𝟭. 𝗠𝗮𝗽 𝘁𝗵𝗲 𝗣𝗼𝘄𝗲𝗿 (𝗡𝗼𝘁 𝗝𝘂𝘀𝘁 𝘁𝗵𝗲 𝗢𝗿𝗴 𝗖𝗵𝗮𝗿𝘁) • Who really makes the decision? (Hint: Not always who you think) • What keeps them up at night? • Who do they trust for input? One client discovered the "junior" person in the room was the CEO's former chief of staff. Guess whose opinion mattered most? 𝟮. 𝗕𝘂𝗶𝗹𝗱 𝗬𝗼𝘂𝗿 𝗖𝗼𝗮𝗹𝗶𝘁𝗶𝗼𝗻 𝗕𝗲𝗳𝗼𝗿𝗲 𝗬𝗼𝘂 𝗡𝗲𝗲𝗱 𝗜𝘁 The worst time to make allies? When you need them. Smart executives plant seeds months before the harvest: • Coffee with the skeptics • Informal temperature checks • Strategic information sharing By the time you're pitching, you already know who's with you. 𝟯. 𝗞𝗻𝗼𝘄 𝗧𝗵𝗲𝗶𝗿 𝗟𝗮𝗻𝗴𝘂𝗮𝗴𝗲, 𝗡𝗼𝘁 𝗝𝘂𝘀𝘁 𝗬𝗼𝘂𝗿 𝗠𝗲𝘀𝘀𝗮𝗴𝗲 Match your message to their metrics: • Revenue-focused? Show growth • Cost-conscious? Show savings • Risk-averse? Show mitigation Same idea. Different frame. Completely different outcome. 𝟰. 𝗣𝗿𝗲-𝗦𝗲𝗹𝗹 𝗘𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗧𝗵𝗮𝘁 𝗠𝗮𝘁𝘁𝗲𝗿𝘀 The meeting isn't where you sell. It's where you confirm. If you're introducing new information in the room, you've already lost. The best executives I know follow this rule: 𝗡𝗼 𝘀𝘂𝗿𝗽𝗿𝗶𝘀𝗲𝘀 𝗶𝗻 𝗯𝗶𝗴 𝗺𝗲𝗲𝘁𝗶𝗻𝗴𝘀. 𝗘𝘃𝗲𝗿. That person who always seems to "get lucky" with approvals? They're not lucky. They're doing 10x the advance work you are. While you're perfecting your slides, they're having strategic hallway conversations. While you're rehearsing your pitch, they're addressing objections before they're raised. 𝗧𝗵𝗲 𝗕𝗼𝘁𝘁𝗼𝗺 𝗟𝗶𝗻𝗲: Your ability to influence has very little to do with your charisma in the moment. It has everything to do with the relationships you've built, the intelligence you've gathered, and the groundwork you've laid. Stop counting on spontaneous charm. Start investing in strategic preparation. Because in the C-suite, there are no successful surprise attacks. 🎯 When was the last time you walked into a crucial conversation truly prepared—not just with data, but with deep insight into every person in that room? Be honest. Your next promotion might depend on it. ------------ ♻️ Share with someone who needs to stop winging it and start winning it ➕ Follow Courtney Intersimone for more truth about what really drives executive success

I was Wrong about Influence. Early in my career, I believed influence in a decision-making meeting was the direct outcome of a strong artifact presented and the ensuing discussion. However, with more leadership experience, I have come to realize that while these are important, there is something far more important at play. Influence, for a given decision, largely happens outside of and before decision-making meetings. Here's my 3 step approach you can follow to maximize your influence: (#3 is often missed yet most important) 1. Obsess over Knowing your Audience Why: Understanding your audience in-depth allows you to tailor your communication, approach and positioning. How: ↳ Research their backgrounds, how they think, what their goals are etc. ↳ Attend other meetings where they are present to learn about their priorities, how they think and what questions they ask. Take note of the topics that energize them or cause concern. ↳ Engage with others who frequently interact with them to gain additional insights. Ask about their preferences, hot buttons, and any subtle cues that could be useful in understanding their perspective. 2. Tailor your Communication Why: This ensures that your message is not just heard but also understood and valued. How: ↳ Seek inspiration from existing artifacts and pickup queues on terminologies, context and background on the give topic. ↳ Reflect on their goals and priorities, and integrate these elements into your communication. For instance, if they prioritize efficiency, highlight how your proposal enhances productivity. ↳Ask yourself "So what?" or "Why should they care" as a litmus test for relatability of your proposal. 3. Pre-socialize for support Why: It allows you to refine your approach, address potential objections, and build a coalition of support (ahead of and during the meeting). How: ↳ Schedule informal discussions or small group meetings with key stakeholders or their team members to discuss your idea(s). A casual coffee or a brief virtual call can be effective. Lead with curiosity vs. an intent to respond. ↳ Ask targeted questions to gather feedback and gauge reactions to your ideas. Examples: What are your initial thoughts on this draft proposal? What challenges do you foresee with this approach? How does this align with our current priorities? ↳ Acknowledge, incorporate and highlight the insights from these pre-meetings into the main meeting, treating them as an integral part of the decision-making process. What would you add? PS: BONUS - Following these steps also expands your understanding of the business and your internal network - both of which make you more effective. --- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

“It’s not enough to just win,” an old boss of mine used to explain. “The other side has to lose, badly.” Nothing gave him more satisfaction than eating his rivals’ lunch - and his competitive nature was contagious. When I started my first business I adopted his approach. But I soon also learned that I had to ally that competitive spirit with a more nuanced approach if I was to retain clients rather than just churn through them. Unlike winning deals, retention isn't just about having the best product — it's about creating value and a level of reliability that rivals can't match. 1. Retain on value, not price: Competitors will use price to try and attract your customers. It’s tempting to drop your yield accordingly, but that’s a race to the bottom. Instead take time to make sure your client can see how much they get for every pound or dollar they invest. Adding extra value will always be more profitable than reducing your fee. 2. Add features before you’re asked to: Write a customer engagement strategy that involves adding useful new services or features for your existing customers at least once or twice a year. Use these to upsell, build loyalty and increase their pain of moving suppliers. 3. Build trust through relentless delivery: Unreliability is one of the top reasons clients will look elsewhere. Meet key clients on a regular basis to understand how their needs are evolving and pivot your offering accordingly. And always keep your promises. 4. Outmanoeuvre your competitors: Never underestimate how determined your competitors will be to knock you off your perch. Devote adequate time to learning from their approach so you know the threat you face. Match your instinct to win new business with an equal determination to retain customers. Crack that and not only will you eat your competitors’ lunch today but you’ll have it every day.

I've watched 1,000+ sales pitches fail for the exact same reason. After coaching some of the best AEs in tech, I discovered the real problem isn't what you're saying—it's the entire framework you're using. Most companies create pitch decks that brag about themselves. This NEVER works. Customers don't care about your products. They care about their problems. For years, I've taught my private coaching clients a framework that's completely transformed their close rates. I call it the 5 P's of Pitching: 1/ PROBLEM What high-level business problem do you solve? This must matter to executives—not technical teams. If you sell CRM, your problem isn't "manual data entry." It's "rep underperformance" or "missed forecasts." 2/ PRIMARY REASON Why does the problem exist? Nail the root cause. "Leadership has poor visibility to pipeline and no accurate way to predict which deals will close." Articulating this builds immediate credibility. You speak their language. 3/ PAIN What metrics are suffering because of this problem? Missed forecasts lead to plummeting stock prices, revenue shortfalls, and sales layoffs. This is where you make it personal for the decision maker. 4/ PROMISE How does your solution address the PRIMARY REASON for the problem? "Our AI-driven forecasting prevents inaccurate manual forecasting and low deal visibility." Don't list features. Focus on solving their specific challenge. 5/ PAYOFF What metrics will improve when you solve their problem? For CRM: improved quota attainment, rep productivity, and accurate forecasting—all driving revenue and profitability. The 5 P's framework works because it's centered on the customer, not on your product. The best part? It takes 15 minutes to build and dramatically increases your close rate. If you want a copy of the 5P's template I use with my clients, comment TEMPLATE below.

I used to say the right recommendation in meetings and watch it get ignored until someone else repeated it, and suddenly it moved forward. I thought they missed it, but they heard me clearly the first time. I had no power in that room, and my framing made it easy to dismiss. This is what changes as you move closer to executive roles. You will sit in rooms where your title does not carry weight yet. You will still be expected to influence decisions that impact revenue, risk, and direction. Influence is not reserved for people with authority, it is built through how you position ideas. I learned that influence is a system you can apply even with low formal power. Here are 12 ways to do it in practice. Make them think it was their idea by planting logic early and letting them carry it forward. Start with the business problem so leaders engage before forming resistance to your recommendation. Tie your recommendation to revenue, risk, retention, or customer impact so it feels relevant. Bring proof before you speak so your point lands with credibility and not opinion. Present a clear decision with tradeoffs so the room moves toward action faster. Align privately before meetings so public conversations feel like confirmation, not persuasion. Mirror the language leaders already use so your idea feels familiar and easier to accept. Show the cost of inaction so staying the same feels like a risk. Make the first step easy so momentum builds without resistance from the group. Identify who actually influences decisions and build alignment with them early. Ask better questions to surface pressure points leaders are already trying to solve. Close by connecting your idea directly to what leadership already said matters most. This is the work most people miss when they say they are ready for executive roles. Execution gets you in the room, but influence decides if you stay there.

Your POC process is probably why you're not closing enterprise deals.   After analyzing POC outcomes across our portfolio, the data is clear: Companies with structured and priced POCs close 3x more deals than those running free pilots.   Why charge? Price signals seriousness. Even nominal fees filter serious buyers from tire-kickers. Frame your pilots as fixed-fee engagements: Say "we structure this as a 4-week, fixed-fee engagement to quantify value and build your business case."   Be sure to clarify pricing expectations in the process: If your pilot costs $5K but commercial deals are $100K-$300K based on the value unlocked, state this explicitly to avoid anchoring.   Here are 5 best POC best practices we see:   1. Define success criteria, not scope Align on specific KPIs, business outcomes, and who signs off before writing a line of code.   2. Time-box ruthlessly with weekly checkpoints POCs should run 30-90 days max. Set weekly or bi-weekly checkpoints to maintain urgency.   3. Pre-commit the path to commercial discussions Before starting any pilot, confirm that hitting the success metrics will trigger stakeholder presentations and commercial negotiations.   4. Demand access to the full buying center Technical users alone can't close deals. Ensure you meet decision-makers and budget holders during the POC, not after.   5. Document like a contract Formalize scope, terms, and deliverables in the agreement. Include specific responsibilities for both sides, data access requirements, success metrics, timelines, and post-POC commitments.   --   POCs are where your enterprise motion gets built. Treat them that way.   I wrote a guide to AI pricing with Madhavan Ramanujam and Joshua Bloom that discusses these ideas in more detail. If you're curious to dive deeper, I'll leave that link below. Also, Madhavan just released a new book called Scaling Innovation that also explores these topics. Highly recommend!

Years ago, I watched one of the best enterprise salespeople I've ever known lose a million-dollar deal simply because "𝗜 𝗱𝗼𝗻'𝘁 𝘄𝗮𝗻𝘁 𝘁𝗼 𝗯𝗲 𝗽𝘂𝘀𝗵𝘆". This brilliant, capable professional was letting million-dollar opportunities slip away because she was afraid of seeming aggressive. Sound familiar? Here's the reality I've found after analyzing thousands of sales interactions: The average B2B purchase requires 8+ touches before a response, but most salespeople give up after 2-3. 𝗧𝗵𝗲 𝘀𝗼𝗹𝘂𝘁𝗶𝗼𝗻 𝗶𝘀𝗻'𝘁 𝗳𝗲𝘄𝗲𝗿 𝗳𝗼𝗹𝗹𝗼𝘄-𝘂𝗽𝘀—𝗶𝘁'𝘀 𝗯𝗲𝘁𝘁𝗲𝗿 𝗼𝗻𝗲𝘀. Working with clients across industries, I've developed what some have called the "Goldilocks Sequence" – not too aggressive, not too passive, but just right for maximizing response rates without alienating prospects. It starts with how we view follow-ups. Stop thinking of them as "checking in" and start seeing them as opportunities to deliver additional value. For each client, we build what I call a "Follow-Up Content Library" with 5-10 genuinely valuable resources for each buyer persona – a mix of their content and third-party research addressing likely challenges. Having this ready means follow-ups can pull the most relevant resource based on the specific situation. The sequence itself has a rhythm designed to respect the prospect's time while staying on their radar: 𝗗𝗮𝘆 𝟭 is the initial value-focused outreach with a specific insight (never generic "I'd like to connect" language). Around 𝗗𝗮𝘆 𝟯, we send a gentle bump, forwarding the original email with: "I wanted to make sure this reached you. Any thoughts on the [specific insight]?" It's brief and assumes positive intent. By 𝗗𝗮𝘆 𝟱, we shift to an alternative channel like LinkedIn, with a personalized note referencing the insight, but still no meeting request. Around 𝗗𝗮𝘆 𝟴 comes the pure value-add – sharing a relevant resource with no ask attached: "Came across this [article/case study] that addresses the [challenge] we discussed. Thought you might find it valuable regardless of our conversation." 𝗗𝗮𝘆 𝟭𝟮 brings what I call the "pattern interrupt" – a brief email with an unexpected subject line and single-question format that's easy to respond to. Then, around Day 18, we send the "permission to close" message: "I'm sensing this might not be a priority right now. If that's the case, could you let me know if I should check back in the future? Happy to remove you from my follow-up list otherwise." This sequence generated a 34% response rate for an enterprise software client compared to their previous 11% using traditional methods. The key difference? Every touch adds legitimate value rather than just asking for time. And because it's systematic, it removes the emotional weight of deciding when and how to follow up. What's your most effective follow-up technique? I'm always collecting new approaches to share with clients. #SalesFollowUp #OutreachStrategy #PipelineGeneration

Why B2B companies lose big clients (and how to fix it) 3 Questions with Shawn Chan 1️⃣ What’s a surprisingly effective strategy you’ve used recently? Account-Based Marketing (ABM). Here’s the playbook: ✅ Deep research – Go beyond the usual LinkedIn stalking. Dive into annual reports, press releases, and earnings calls. Find out what keeps stakeholders up at night. ✅ Multi-stakeholder engagement – Don’t just talk to the decision-maker. The CFO, CIO, CMO, and Head of E-Commerce all have different priorities. You need to understand them all. ✅ Personalized interactions – Use a centralized database (CDP/CRM) to track insights and tailor outreach. No more generic messaging. The results? ✅ Higher engagement rates. ✅ Shorter sales cycles. ✅ Bigger deals closed. ABM works when you stop selling and start solving. 2️⃣ What’s a project that didn’t go as planned, and what did you learn? Losing a key enterprise client in the Philippines. The mistake? ❌ We focused too much on features. The client cared about AI-driven automation, not just a better dashboard. ❌ We ignored the CFO’s influence. Our competitor positioned a lower-cost solution, and we weren’t in the conversation early enough. The fix? ✅ Expand stakeholder engagement – Don’t rely on a single champion. ✅ Build relationships across finance, IT, and operations. ✅ Shift to value-based selling – Highlight business impact, not just features. ✅ Start renewal discussions early – Don’t wait until contracts are up. Stay ahead of procurement. Losing the deal hurt. But it forced us to refine our retention strategy. And that made all the difference. 3️⃣ What key lesson have you learned from a peer or influencer? From Piyush Goel, I learned the power of leading with intent. His approach to leadership? ✅ Understand individual aspirations – Every team member has different motivations. He took the time to figure them out. ✅ Prioritize mentorship and coaching – Regular 1:1s weren’t just status updates. They were opportunities to help people grow. ✅ Follow up relentlessly – He didn’t just offer advice and move on. He made sure you executed. Beyond work, he emphasized personal development. He recommended books like Atomic Habits and advocated continuous improvement. Lesson learned: Great leaders don’t just manage. They invest in people. And that investment always pays off.

How do you grow a $600M business to $5B, report directly to Satya Nadella, and close a $600M+ deal while your customer’s company is collapsing? This week on the pod: Hayden E. Stafford (Microsoft → Seismic) shares the enterprise playbook - and what you can borrow, even if you're a startup just getting to $1M. Let's just say, I ran out of ink on this one 😅 My top takeaways from the conversation: 1️⃣ Sellers don’t just close deals, they should own retention too. Align comp plans across AEs and CSMs around net revenue retention (NRR) to keep everyone accountable for long-term customer success. 2️⃣ The best partners don’t just co-sell, they co-build. Transactional channel programs have short-term upside. Strategic partnerships, like Seismic’s product-level integrations with Salesforce, create durable GTM advantage. Prioritize partners who will build with you, not just sell for you. 3️⃣ Vertical GTM is a durable competitive moat. Seismic’s dominance in financial services (42% of revenue) wasn’t accidental, it was by design. Deep domain expertise + tailored messaging + compliant workflows made the company a no-brainer for regulated buyers. Start narrow, win deep. 4️⃣ Sales methodology ≠ win formula. A flashy sales methodology means nothing if you don’t know what actually moves deals. Instrument every stage of your funnel with non-negotiables. Know your conversion drivers and hold reps accountable to executing against them.  5️⃣ The best sellers think like consultants. Top enterprise reps don’t just run sales cycles, they orchestrate change management. That means multi-threading early, co-creating value narratives with the buyer, and staying involved post-sale to ensure outcomes land. 6️⃣ Your GTM team structure should mirror how customers buy. Seismic maps sales, CS, and services to the same segments. That way, there’s no disconnect when ownership changes hands. If your post-sale team is playing catch-up, you’ve already lost.  7️⃣ You can’t scale enterprise without rethinking incentives. At Microsoft, Hayden reallocated partner dollars to build a direct field team. He tied seller comp to outcomes and changed partner incentives to drive strategic behaviors, not just transactions.  8️⃣ Treat your comp model like a product. Seismic optimized pay curves so reps could still win big, but only if they delivered both expansion and retention. Treat your comp model like a product: design it, test it, and iterate for efficiency and growth. Revenue growth is math, not magic.  More on moving SMB to enterprise from Hayden in the full episode, available on the GTMnow website or wherever you get your podcasts by searching "The GTM Podcast" 🎧 #gtm #saas #enterprise