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

What’s Really Happening in Enterprise Sales (2024–2025) Enterprise sales didn't collapse, but they’ve quietly reshaped themselves while most teams keep selling like it’s still 2019. The rules have changed. If your team hasn’t adapted, you’re probably already feeling it: slower cycles, ghosting buyers, unpredictable quarters, and frustrated reps. Here’s what I’m seeing across every enterprise org I advise: 1. Sales Cycles Got Longer - The average cycle for large deals is now 6 to 12 months, often longer. - Budgets are tighter, and approvals are more layered. - Pilots and proof-of-concepts are now expected in most deals. 2. Stakeholders Multiplied - Deals now involve 5 to 10 or more decision-makers. - You’re not selling to a champion; you’re selling to finance, IT, legal, security, and operations. - Any one of them can stall, derail, or block a deal. 3. Buyers Are Overloaded and Guarded - Attention spans are shrinking while inboxes overflow. - Every “quick intro” feels like another task to manage. - Buyers now expect clear value upfront before they take a meeting. 4. Reps Must Become Strategic Advisors - No one wants a pitch; they want a navigation partner. - Enterprise sales now mean consulting on internal change, building business cases, and multi-threading effectively. - Top reps spend 60% - 70% of their time mapping influence and removing blockers, not demoing the product. 5. Internal Pressure Is Sky-High - Sales leaders must hit aggressive quotas with leaner teams. - One stalled deal can derail an entire quarter. - Forecast accuracy and pipeline quality now matter more than raw volume. - The spotlight is on deal progression, not activity dashboards. If you’re still running a 90-day playbook in a 9-month sales world, it’s not your reps. It’s the model. #EnterpriseSales #SalesLeadership #GTMStrategy

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 😁

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.

"We're moving forward with another vendor." Every rep's nightmare sentence. I pressed for details. "Their approach felt more open. We actually knew what we were buying into." That stung. I'd shared: ••• Exhaustive feature documentation ••• Dozens of success stories   ••• Complete pricing breakdowns Where'd I go wrong? Days later, I got access to our competitor's sales process. The difference hit instantly: They didn't preach transparency. They lived it. Their follow-up wasn't an email avalanche. It was one collaborative hub where buyers could: ••• Monitor which stakeholders engaged with what ••• See their exact position in the evaluation journey ••• Find materials curated for their unique pain points ••• Manage internal distribution seamlessly My revelation: I was buried in PDFs. They were cultivating partnership. Next prospect, new approach: I built a shared workspace exposing EVERYTHING: → Which team members on our side viewed their data → Critical docs they'd missed → Realistic implementation expectations → Where we excel AND where we don't The buyer's response: "Finally, someone not playing games." Ink on paper in 10 days. Here's what's real: Today's buyers aren't starved for data. They're starved for authenticity. Yesterday's strategy: Bombard with polished assets that sidestep weaknesses. Tomorrow's strategy: Build transparent environments that tackle doubts directly. Your buyers know when something's off. Even when nothing is. Quit running sales like a shell game. Start running it like a glass house. You with me?

Long before Google, I had a student job at the biggest toy store in Europe, Hamleys of London. Specifically, the one in Regent Street. I was 24, working mostly on commission, selling the Puzzle Car – an interactive jigsaw puzzle. At first, I found it challenging to get out of my comfort zone to stop people so I could pitch the toy. I’d do the demonstration, explain what it does, and watch people smile, nod—and walk away. No sale. But I paid attention. I started noticing patterns. Some people were drawn in by the movement of the toy itself. Others needed a push—a story about how their kids would love it, or how it was the perfect gift. And then there was the biggest sales driver of all: crowds. When one person bought, suddenly, three more wanted one too. If a crowd gathered, more people stopped to watch. And the more people watched, the more people bought. It was my first lesson in FOMO and social proof—and it wouldn’t be my last. But beyond that, selling toys at Hamleys turned out to be a crash course in business, leadership, and startups. Here are 5 lessons that still stick with me today: 1 – Storytelling sells People don’t buy products; they buy emotions, experiences, and stories. The best pitches aren’t about features—they’re about making people feel something. 2 – Rejection is part of the process For every ten people who watched my demo, only one would buy. Sound familiar? Founders hear "no" way more than "yes." The trick is to keep going and not take it personally. 3 – Know your audience Parents wanted to hear how educational and safe the toy was for their kids. Kids just wanted to see it move. The message mattered as much as the product. 4 – Energy matters If I looked bored or unmotivated, people kept walking. But when I was excited, when I believed in what I was selling, people stopped to listen. Whether you’re leading a team, pitching investors, or selling a product, your energy is contagious. 5 – You eat what you kill Working on commission meant no guaranteed paycheck. If I didn’t sell, I didn’t earn. It was a powerful lesson in accountability—something every founder understands. No one is coming to save you. You have to make it happen. Looking back, I didn’t know this job would teach me so much about business, startups, and leadership. But the fundamentals are the same, whether you’re selling a toy or building a company. What was your first job, and what did it teach you?

This week, GM, Snap, and Stellantis all pulled their earnings guidance. Why? Because they don’t know what’s coming next. Tariffs. Supply chain volatility. Budget pullbacks. Policy shifts. It’s not just a turbulent quarter—it’s a systemic fog. When even the most sophisticated operators can’t see clearly, trust becomes the deciding factor in every deal. So, the question becomes: What can your business do to build trust faster? Here’s the insight: When uncertainty rises, clarity becomes the most persuasive asset you have. Buyers are cautious. Legal teams are conservative. Everyone is scanning for hidden risk. A certified contract is a fast, effective way to say: “We’re not hiding anything. These terms are fair, and independently verified.” This isn’t just legal hygiene—it’s a leadership move. It signals that you’re serious about doing business the right way. If you’re a business leader, here are four things you can do now: Use contracts that are objectively rated as Balanced or Customer Favorable Eliminate known deal-breakers before negotiations begin Publish transparent terms to accelerate buyer trust Show your work—let the data back up your fairness claims The economy may be uncertain, but how you show up in deals doesn’t have to be. I recorded a short take on why this matters now more than ever. If your team is navigating long sales cycles or facing legal delays, take a minute to watch this. Contracts shouldn’t be a barrier. They should be a signal of trust. -------- 🚀 Olga V. Mack 🔹 Building trust in commerce, contracts & products 🔹 Sales acceleration advocate 🔹 Keynote Speaker | AI & Business Strategist 📩 Let’s connect & collaborate 📰 Subscribe to Notes to My (Legal) Self

Sales calls feel exhausting because you're doing two jobs at once. Building trust AND solving their problem. Only one of those should happen on the call. When someone hears about you for the first time on a sales call, they're not fully listening. They're half-evaluating. "Is this person credible? Do they actually get my problem?" You can feel it too. So you start over-explaining. Listing achievements. Justifying pricing. By the time you get to the actual solution, you're both tired. Here's the T.R.U.S.T framework we use to make sure trust is built before the call even starts. 1. Thought clarity → Share how you actually think.  → Your decision-making process. The frameworks you use.  → People stop questioning if you can help them once they see how you think in public. 2. Relevance signals → Talk about what keeps your buyers awake at 2 AM. → When your content speaks to their active pain, they feel understood before they even meet you. 3. Unforced results  → Don't make proof the hero of your content. make it context. → Example- "Last quarter, while fixing X for a fintech client" 4. Strategic familiarity-  → Be consistent in what you talk about and how you talk about it. 5. Timely entry  → Track when shifts happen in your industry: funding rounds, new hires, product pivots.  → That's when budgets open and problems get prioritized. You can't fix a trust problem during the pitch. You fix it before the call is even booked. #SalesStrategy #TrustBuilding #PreSales #ContentMarketing #SalesTips

Most companies don't need more content. They need better, more strategic, value-driven content. 🚀 👉 Copying your competitors? It only adds to the noise — it doesn’t differentiate you, and it definitely doesn’t drive pipeline. Here’s what to do instead if you're serious about scaling content the smart way: → Audit your existing content — identify what's driving outcomes (not just traffic). → Align your strategy with your Sales, Product, Success, and Support teams — integrate real customer feedback into your content plan. → Map your content to the full buyer journey — awareness → consideration → decision → expansion. → Focus on intent over volume — not every high-volume keyword matters to your funnel. → Identify opportunity gaps where you can genuinely add value, not just "rank." → Build content clusters around your core solutions to strengthen topical authority. → Refresh and optimize existing content regularly to keep it aligned with evolving customer needs. → Treat SEO as a distribution channel, not a content strategy. → Prioritize formats that match intent — blogs, webinars, guides, comparison pages, customer stories. → Measure what matters: influenced pipeline, sales velocity impact, time-to-value reduction — not vanity metrics. Content marketing isn’t about churning out more. It’s about building a real growth engine — one piece of strategic content at a time. Need help turning your content into a revenue-generating machine? Drop me a DM and let's get talking! 👋 #contentmarketing #b2bsaas #b2bmarketing #saasmarketing #seostrategy #b2bcontent

I've built dashboards for 100+ companies. This is the one CEOs actually open every week. Not because it's fancy. Because it answers the question they actually care about: are we growing or is it just seasonality? Let me explain. Monthly sales numbers lie to you. December always looks great. January always looks terrible. Compare them and you'll panic for no reason. I've seen it happen. Finance teams running around thinking the sky is falling when really it's just... January. The fix is simple. Stop comparing month to month. Start comparing this December to last December. This Q4 to last Q4. Apples to apples. That's what trailing 12 months does. Smooths the noise. Shows you what's actually happening. Here's what this dashboard gives you. Total sales at the top with prior period comparison. You see the number and whether it's up or down in one glance. No digging. A 12-month trend chart in the middle. Not 47 charts. One chart. Clean. You can actually see where you're heading instead of squinting at a rainbow of lines. Quarterly breakdowns below that. Each quarter compared to the same quarter last year. This is where seasonality gets exposed. Q1 up 32%. Q2 up 56%. Q3 up 76%. Q4 up 95%. That's not a lucky December. That's real momentum. And at the bottom, monthly detail. Side by side with prior period. For the people who want to dig deeper. You know who you are. When your CEO asks "are we actually growing?" you don't guess. You don't fumble through five tabs while everyone waits. You pull this up and the answer is sitting right there. That's what a good dashboard does. Makes the answer obvious before anyone finishes asking the question. That's exactly why I built Model Wiz. It's a free Excel add-in that connects to your QuickBooks, pulls your data, and builds dashboards like this one automatically. No formulas to write. No manual updates every month. Just connect your data and it's yours. What's your system for separating real growth from seasonal noise?