Understanding Sales Cycles

My client fired their entire SDR team on Tuesday By Friday, their pipeline had grown by 60% This sounds impossible It's not After auditing 50 B2B sales organizations over 10 years, I've uncovered the most expensive myth in modern selling: → The belief that MORE activity at the TOP of your funnel will fix conversion problems at the BOTTOM Let me share what actually happened: This mid-market software company was spending $350,000 annually on their 4-person SDR team - 100+ cold calls per rep daily - 17 meetings booked weekly - "Incredible metrics" according to leadership - But their close rate? A devastating 1.2% The VP of Sales was convinced they needed MORE outreach, MORE automation, MORE top-of-funnel I suggested something different: pause all prospecting for 7 days Instead, we had their account executives do something radical - engage with the 215 prospects already in their pipeline who'd gone cold after initial meetings Using a framework we developed: - 65 prospects responded within 24 hours - 41 booked follow-up meetings - 23 re-entered active buying cycles - 6 closed within 14 days (total value: $212K) The shocking revelation? - Their pipeline wasn't empty - It was overflowing with neglected opportunity. This company didn't have a lead generation problem. They had a lead nurturing catastrophe. By reallocating resources from mindless prospecting to strategic engagement, they've now: - Reduced CAC by 60% - Shortened sales cycles by 30% - 2x their close rate The counterintuitive truth: Sometimes the fastest path to growth is to stop chasing new opportunities and start converting the ones you've already earned. What percentage of your marketing and sales budget is focused on prospects who've already shown interest vs those who haven't? That ratio reveals everything about your future growth trajectory P.S. If you need help with your sales, send me a message

Every sales leader I talk to at the moment is struggling with some version of the same issue. The symptoms are different, but the underlying cause is the same. - Sales cycles elongating - Deal slippage - Prospects not showing up to meetings - An uptick in ghosting - Poor forecast accuracy - A drop in deal volumes - A drop in conversion rates What's actually happening out there in Buyer land? I've been delivering win-loss reviews for B2B companies around the world since 2011 and I'm seeing buyer behaviours I've never observed before... Let me break down some of them quickly for you and share some guidance on how to use these lessons to your advantage: Trend #1: Risk has jumped up the decision tree in order of importance, to the very top of the list for many clients, even more so when it's a new vendor. Action: Go deeper on risk in your discovery conversations, recognise that risk is both organisational and personal...find ways to better manage, mitigate and share risk with your clients...Be the low risk option. Trend #2: Value for Money, Responsiveness and Cost are consistently selected as the most important decision criteria by many clients. Action: Responsiveness should be an easy one to get right, but many sellers are stretched too thin right now...do less, but do it better. Trend #3: Change in Strategic Direction is the most frequently cited reason for customers coming to market for a new solution at the moment. Action: Try to reverse engineer this reason, to understanding what caused this change in direction and what it actually means for the business. These are your keys to the kingdom, when building a rock solid business case. Trend #4: Feedback from Peers and Colleagues has emerged as the most trusted information source for almost all respondents. Action: Case studies and customer references are losing their luster...find ways to tap into the trust which prospective clients have in their own peer network, as a way to unlock deeper connections and build trust. Trend #5: Customers are demanding more detail in the proposal documents, tender responses and business cases which they are receiving. Action: Put in the work, avoid the cookie-cutter responses, find your win themes and weave them in, share the detail they need to make an informed decision. I haven't got a crystal ball, so I can't tell you if/when the pendulum will swing back the other way, from a buyer behaviour perspective. What I can tell you with a high degree of certainty is that prospective customers have raised the bar, in terms of their expectations from their vendor partners. It's our job now to to elevate the preparation, patience and professionalism of B2B sellers everywhere, to meet these changing needs and maintain our relevance to the customers we serve.

When I was CRO of a $200M SaaS, doing POCs almost destroyed us—months wasted, team exhausted, buyers constantly delaying. Until my VP Sales said, “Kill the POC. We’ll validate value clearly in 3 hours flat”. Here's exactly how we rebuilt our sales process and cut our sales cycle by 50%: BACKGROUND: We were selling 100% enterprise. POCs were the automatic default: Heavy, technical validation lasting 1-3 months. It was painful… - Sales Engineers were overloaded - Buyers kept delaying due to resource issues - Buyers kept wanting more “just one more test” Initially, I thought: It’s Enterprise, that’s the game right? Until our VP Sales, Idan Arealy, joined. Two weeks in, he tells me: “No offense—but these POCs are total overkill.” “Buyers don’t need these endless tests.” “They’re not doubting the tech.” “They’re doubting the value.” “And we don’t need this complexity to prove value.” So he suggested a simpler, smarter alternative: The 'Use Case Workshop'—and it changed everything. Here’s the step-by-step: —— 1. Kickoff (45 min) - AE positions the workshop immediately post-demo: “Here’s what we typically do next to help validate real-world scenarios in just hours—no heavy lift needed. Shall we set it up?" - SE runs deeper disco into problem root causes in a kickoff call - AE sets clear Mutual Action Plan (MAP) 2. Internal Alignment (60 min) - SE & AE clearly define and build initial use-case solutions - Output: Slides outlining impactful solutions & open questions 3. Use Case Co-Design (45 min) - Live session with buyers walking through scenarios - Collaboratively refine solutions LIVE (e.g. Miro, slides): “Walk me through this problem in more detail—we’ll map exactly how solving it looks." 4. Prioritization & Wrap Up (30 min) - Jointly prioritize top 3 impactful use cases clearly: "Which scenarios, solved, would immediately solve [Problem]?" - Lock down committed next steps ↳ Result? - 3 focused hours (instead of months) - Clear, confident buyers ready to champion - 100% faster sales cycles & higher win rates —— POCs are NOT mandatory. Buyers don't want endless tests. Don’t default to what most buyers ask. Design what will solve what they need— With as little friction as possible. That's: Sales Process Design 101. P.S. We built Aligned to help manage the chaos of Complex Sales. 100% FREE Deal Room used by 40K AEs to run POCs, MAPs, etc. Try it https://lnkd.in/d_49kHZE

Buyers rarely choose the objectively best option. They choose the one they recognize. In many B2B decisions, familiarity plays a greater role than features or pricing. Teams may evaluate multiple vendors, but preference often leans toward the one they have consistently seen, heard, and understood over time. The reason is simple. Recognition signals safety. When a brand shows up repeatedly with clear, consistent messaging, it reduces perceived risk. Buyers feel more confident choosing what already feels familiar, even if alternatives may appear stronger on paper. This is where many marketing strategies lose effectiveness. In the pursuit of novelty, teams constantly change angles, campaigns, and positioning. But without consistency, recognition never compounds. Messaging resets instead of reinforcing, and trust takes longer to build. Repetition, when done well, is not redundancy. It is reinforcement. Each consistent touchpoint strengthens recall. Each repeated idea builds confidence. Over time, familiarity becomes preference, especially in longer B2B buying cycles. This week’s newsletter explores the psychology behind recognition, why repetition drives trust, and how to build consistency without losing relevance. For teams focused on sustainable growth, this is a shift worth understanding.

Your product isn’t failing…it’s grown up. Every successful Indian brand eventually hits a point where sales slow down. That’s the maturity stage of the product life cycle. The brands that survive don’t panic. They play smarter. Here’s how you can also do : 1️⃣ Find New Users When your current audience is saturated, growth comes from people who have never tried you. • New Markets: Move beyond metros. Tier-II and Tier-III cities are hungry for quality products. • Competitor Switchers: Offer loyalty points or “exchange offers” to tempt rival customers. 👉 Think of how Zomato started targeting small towns once metros were crowded. 2️⃣ Increase Usage Among Current Customers Sometimes you don’t need more customers you need more moments of use. • Show fresh ways to enjoy the same product. • Encourage higher frequency: “twice a day,” “every weekend,” etc. 👉 Amul promotes butter not just for toast, but for parathas, desserts, even baking. 3️⃣ Refresh the Product People love the familiar, but they notice when you keep it exciting. • Quality Upgrade: Better ingredients, more durability. • Feature Upgrade: New flavours, limited-edition festive packs, eco-friendly packaging. 👉 Parle-G introduced premium “Platina” cookies while keeping the classic biscuit alive. 4️⃣ Adjust the Marketing Mix Sometimes a smart tweak beats a big reinvention. • Price: Create a ₹10 entry pack for reach or launch a premium version for status. • Place: Sell on quick-commerce apps, WhatsApp, or local kirana tie-ups. • Promotion: Regional festivals + local influencers = instant attention. 👉 Tata Tea nails this with hyper-local ads for every state. 5️⃣ Build the Next Big Thing While you stretch today’s hero product, quietly invest in what’s next. 👉 Reliance didn’t stop at Jio; it’s already deep into retail and AI. Example Product: South Indian Filter Coffee Goal: Make people drink it more often. Visual: A lively Bengaluru co-working space. Copy: “Morning ritual? Now your 4 p.m. brainstorm booster. Ready-to-pour filter coffee packs, anytime energy.” A single new habit = more sales. The maturity stage isn’t the end it’s the test. Brands that educate, refresh, and adapt turn maturity into long-term dominance. Which Indian brand do you think is stuck in maturity but ready for a comeback? Drop your idea in the commentslet’s share strategies that could spark its next growth wave. #linkedin

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!

Your deals are stalling because you're tracking the wrong things. I just watched another rep lose a "sure thing" deal. Had budget, authority, need, timeline... all the BANT boxes checked. Still lost. Here's the problem: BANT tells you if someone CAN buy. It doesn't tell you if they WILL buy. Same with MEDDIC. Better than BANT, but it's still focused on what WE need to qualify them, not how THEY actually make buying decisions. So I created something different. The ADVANCED method that was inspired by Nate Nasralla. A - Acknowledged Problem  D - Documented Issue V - Validated by Team  A - Authorized by Executive  N - Narrowed to External  C - Chosen as Vendor  E - Established Timeline  D - Deal Terms Finalized This isn't another qualification framework. This is how complex B2B buyers actually progress through their decision making process. I break down all 8 stages in the carousel below, but here's why this works: Each stage has predictable win rates. Stage 0-1 deals close at 10-20%. Stage 6-7 deals close at 80-90%. Unlike other frameworks, ADVANCED tracks buyer behavior, not seller activities. It shows you exactly how deep you are in THEIR process. I even updated my entire pipeline to match this framework. Now I know the real probability of every deal closing... not just my gut feeling. Most importantly? It tells you what needs to happen next. No more guessing. If you're tired of "sure thing" deals that never close, maybe it's time to track what actually matters. Stop measuring what's convenient for you. Start measuring how your buyers actually buy. BTW. Can you honestly say where each of your deals stands using these 8 stages? If not, you're flying blind. The best reps know exactly where they stand. Now you can too. — Want to progress through these stages faster? Master multithreading with this free 100-min masterclass: https://lnkd.in/gYbk_Y2v

Your free POC is quietly killing your best deals. I’ve seen too many 7-figure opportunities die in pilot purgatory—not because the product failed, but because the seller hesitated to ask for real commitment upfront. Here’s what executive buyers are really saying when they ask for a free POC: “We’d like you to take all the risk while we decide if we might pay you later.” That’s not a partnership. That’s deferral dressed up as due diligence. There are only two times a POC should be free: 1. Testing a beta feature that needs real-world validation 2. Exploring a completely new use case that’s never been done Even then, get a signed commitment for a press release or case study in return. Free access for them should mean visibility and positioning for you. Now, when they ask for a POC, here's what you do: Don't call it that. Call it what it really is: A “strategic bridge investment.” This isn’t a trial—it’s the first phase of their transformation. The structure is simple: • Fixed scope with clear success metrics • A contractual trigger: full rollout signed by a specific date • Investment counts as credit toward the larger deal • No follow-through? They still pay full price Why this approach works better than traditional POCs: • It eliminates pilot purgatory • It creates shared timelines and alignment • It shifts the frame from transaction to transformation • It positions you as a strategic guide—not a vendor auditioning The mindset shift is everything: Start big. Stay big. Lead with the full vision of what’s possible. Then show them what they risk losing when they force you to think small. Real talk: Most sellers avoid this approach because they think it's "too aggressive." But here’s what I learned: This is how you stop shrinking 7-figure potential into 5-figure tests and start landing transformational enterprise partnerships that build lasting, compounding value. Curious to hear from others: What’s the biggest POC trap you’ve witnessed? Let's learn from our collective experience. 🐝

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!