Understanding Sales Cycles

I was at Starbucks in an airport. Packed. Long line. Only two baristas. After I ordered I said, “Busy day?” She shrugged. “Eh.” So I tried again. “Normal day?” She smiled. “Exactly. Every day all day.” Then I added, “There’s no way I could keep up with all these orders.” And she lit up. That’s called eliciting. I learned it from Chris Voss. You’re not making small talk. You’re not interrogating. You’re making a thoughtful guess about how someone feels. First guess? Miss. Second guess? Hit. And when you hit, they think: “Finally. Somebody gets me.” Same thing happens in sales. Prospect: “I don’t think a tool can handle our commission rules.“ Typical seller: “I understand how you feel. Many people felt the same way. But what they found was that our platform is flexible enough to manage any rules.” Prospect hears: pitch and pull away. Better elicitation: “So you’ve got layers of exceptions, different rates for roles, territories, and special spiffs stacked on top.” Now they lean in: “Exactly. That’s our mess.” Or they correct you. Either way, you’ve opened the door. Because trust doesn’t start with a pitch. It starts when someone thinks: “Finally. Somebody who gets me.” Trust before transaction.

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

In sales, we obsess over KPIs like time-to-close, win rates, and pipeline velocity. But there’s one metric almost no one is tracking, and it might just be the most important one: time-to-trust. Time-to-trust measures how quickly a sales rep can move a prospect from skepticism to belief. From "I’m not sure about this" to "I see how this can solve my problem." Why is this so critical? Because trust accelerates everything else. When trust is established, objections shrink, decision cycles shorten, and deals become about solving problems, not defending price tags. So how do you measure and accelerate trust-building? 📊 Leverage credibility markers Start every interaction with proof. Case studies, data points, and even a concise narrative about your company’s mission create instant authority. 📊 Make testimonial-driven introductions A warm handoff from a satisfied client or a shared connection carries exponentially more trust than any cold outreach. 📊 Be radically transparent Share both the upside and potential limitations of your solution. People trust honesty, not perfection. Great sellers already know this intuitively: deals are won or lost at the trust level. But imagine what could happen if you measured, optimised, and made trust the centrepiece of your strategy. What’s your take? Are you tracking trust-building in your sales process? If so, how? Share in the comments below! 👇 #salesstrategy #trustinsales #saleskpi #buildingtrust #salesleadership #businessgrowth #salesinsights #customertrust #salesprocess #b2bsales #salestips #salesperformance #relationshipselling #salesprofessionals #salescoaching

Discounts aren’t killing your profit margins. They’re killing your brand. Bold? Maybe! But after working with high level e-commerce clients, I’ve seen this pattern repeat far too often. Here’s why discounting is a trap and what you should do instead: One client of mine was stuck in a "discount or die" cycle Offering 20-30% off constantly. Their sales were decent, but: - Profit margins? Shrinking. - Customers? Loyal only to the discounts, not the brand. So, what did we do? We threw the discounts out the window and Implemented this no-discount blueprint: 1️⃣ Stack the Value →Instead of cutting prices, we built bundles with exclusive perks: Premium products + personalized add-ons. ↳ Result: 45% higher average order value – no discounts needed. 2️⃣ Scarcity That Matters → We launched limited-edition products Based on actual customer demand. No fake urgency, just genuine exclusivity. ↳ Impact: A 167% increase in full-price purchases. 3️⃣ Reward Loyalty, Not Bargain Hunters → We created a loyalty program focused on engagement: Early access, exclusive content, priority service. ↳ Result: 78% higher customer lifetime value. 4️⃣ Premium is a Mindset → Redesigned their brand story to scream exclusivity: - Behind-the-scenes storytelling - Expert-led masterclasses - Premium unboxing experiences ↳ Outcome in 6 months: ✅ Profit margins: +34% ✅ Customer retention: +56% ✅ Brand perception: +89% Discounts train customers to wait for sales. Value trains them to stay for the brand. P.S. - Want to escape the discount spiral? Let’s build a strategy that scales your profits and positions your brand as the premium choice. Drop a “Yes” in my DMs if you’re ready to level up. (And no, this doesn’t include a 20% off strategy.) But you can Follow me to learn more things about SEO. #EcommerceStrategy #MarketingStrategy #BrandPerception

Want to be the go-to leader in your Climate Tech category? Most founders on LinkedIn get this wrong: → They write aimlessly, without a clear strategy. → They follow advice meant for coaches & consultants. Your business isn’t the same. Your sales cycles are 6-12 months. Chasing LinkedIn likes won’t cut it. Here’s the #1 shift top Climate Tech founders are making right now: Think beyond LinkedIn. Most of the advice you hear on this platform comes from people who: a) Have never worked in tech space b) Only know how to help coaches & consultants But you're different. You're running a Climate Tech company, whether it's the latest alt protein solution or a climate risk assessment tool. Your sales cycles are 6-12 months. Fundraising timelines are just as long. You need a system that keeps your company top of mind — beyond LinkedIn. "Ok, Roman, get to the point." You need a LinkedIn → Email pipeline. 83% of B2B buyers prefer email over social media for business communication (Source: HubSpot). This means you can use LinkedIn to attract high-intent prospects to your brand. Then move them to email where you can nurture 90% and convert 10% over time. THAT is what will make you stand out in 2025. Not chasing likes and virality. PS. With sales cycles that can take 6+ months, you can’t afford to let prospects forget about you. Email keeps them engaged until they’re ready to move.

Retention Isn’t Sexy - Until You’re Broke Brands chase growth. But when the faucet turns off and the market tightens, email becomes your backbone. So why do we treat it as a short-term fix rather than a long-term asset? I hear this conversation replayed to me all the time from CRM and Brand Managers: Their Manager: Targets are down. Budget’s gone. Just send more emails. CRM: We already sent one this week with a promo. Manager: Send another. Bigger discount. CRM: Unsubscribes were high last time… Manager: Send to everyone — even non-engagers. Add urgency. And so it begins. 📉 Deliverability drops. 📉 Clicks tank. 📉 Unsubscribes rise. 📉 The database - your only owned audience - starts eroding. But the revenue target stays the same. This is what happens when you treat email like a faucet you can turn on and off — instead of a system you build and respect. 💡 Want to break the cycle? Here’s how smart brands avoid the spiral: 1. Build an acquisition engine, even when times are good. Don’t just chase sales. Chase subscribers, on all channels, not just site pop-ups. If 2% of traffic buys, aim for 20% to subscribe. That’s your future revenue. 2. Agree on discounting guardrails. Not every campaign needs a percentage off, even if times are tough. Consider other conversion tools like: - loyalty perks - free gifts - tiered basket incentives - competitions - outlet-style categories 3. Treat non-converters as humans, not dead weight. Reduce frequency, but stay visible. Try to understand why they’re lapsing e.g gift buyers? Promo-only? Seasonal? 4. Use peak trading to re-acquire, not just sell. Black Friday can re-engage lapsed customers. But the follow-up can’t be more noise. Build a new journey. Reset the relationship. 5. Track long-term metrics. Not just revenue-per-send. Show your management week on week how these are growing: -LTV - Repeat purchase rate - AOV - Site visit frequency from consumers on your database 6. Invest in content, not just campaigns. Nurture a community. Give them reasons to stay subscribed. Boost engagement before you ask for a sale. Remember nobkdy going to buy daily and weekly, you need more to keep them engage. Think weekly style tips, news Roundup, podcast drops, games, polls etc Email can be your safety net — but only if you protect the list, grow it intentionally, and stop burning it out with knee-jerk sends. Want to find out our playbook for growing your subscriber base rapidly. (like how we grew out base to 17m). DM me. Build it right. Because when things get tough, it’s your email list that keeps the lights on.

Every time I see a brand send “15% off ends tonight!” for the third time in a week, I cringe... Because I know what’s happening behind the scenes. The margins are bleeding. The customer is being trained to never pay full price. And the brand is losing long-term trust for short-term cash. Here’s the hard truth: → Discounting is easy. → It makes you feel busy. → It gives you a spike. But it’s lazy marketing. And worse, it's unsustainable. You don't need to stop sending emails. You just need to send better ones. Here are 5 emails that build trust and drive revenue, without a discount in sight: → Founder Story Email Tell the story of why you started. Real photos. Real problems. Real mission. This builds connection and repeat customers. → Customer Spotlight Email Show off someone who loves your product. Add a quote. Add a photo. Make your customer the hero. → FAQ Email List the top 5 objections you hear before people buy, and answer them. Every one of those is a chance to convert someone sitting on the fence. → Behind-the-Scenes Email Show how your product is made. Or how your team works. Transparency builds loyalty. → Results Email Before-and-after photos. Screenshots. Metrics. Show your product actually works. That sells more than a discount ever will. If you keep hitting the discount button, your brand dies a slow death. If you build trust, the revenue takes care of itself.

I went for lunch with a CRO recently and watched them choose a restaurant. They pulled out their phone, compared ratings on three nearby spots, checked menus, read reviews, watched a 30-second video tour of the venue, and made a reservation - all before walking out the door. Later that day, this same exec complained about sales teams "constantly calling" his company instead of "just giving us what we need to decide on our own." Talk about a disconnect. But the way businesses buy has changed dramatically, whilst many sales teams remain stuck in the past. And the data tells a clear story: • 72% of buyers now complete research independently before ever contacting a vendor • Buyers typically spend only 17% of their buying journey meeting with potential vendors • 77% of buyers say their latest purchase was very complex or difficult Yet most sales teams still focus on controlling the process rather than enabling it. Which is why you need to embrace Buyer Enablement. Imagine you're choosing a new restaurant. You want to: ✔️ Research options on your own time ✔️ Compare menus easily ✔️ See honest reviews ✔️ View the space before visiting ✔️ Get help only when you ask for it B2B buyers want the same experience. They don't want more sales calls - they want better tools to make decisions. Especially as buying committees are growing with the average B2B purchase now involving 6-10 decision-makers, each with different priorities. These teams spend enormous time trying to: • Find trustworthy information • Share insights with colleagues • Build consensus • Justify decisions to leadership When you enable this process instead of interrupting it, magic happens. But what does Buyer Enablement look like? It's about helping buyers buy instead of trying to sell them: ✔️ Create transparent comparison tools ✔️ Provide unbiased educational content ✔️ Offer interactive calculators showing real ROI ✔️ Build self-service product demos ✔️ Design simple ways to share information with digital sales rooms Companies that enable their champion by centralising all info into a deal room are seeing their sales cycles reduce by 14% to 29%. When you help people buy the way they want to buy, you earn trust. Companies seen as helpful during the buying process are 3x more likely to win high-value deals. How to embrace Buyer Enablement: ➕ Map your customer's actual buying journey ➕ Identify where they get stuck ➕ Create tools that solve these specific problems ➕ Make information sharing painless ➕ Measure how these changes impact your sales cycle What changes are you making to align your selling process with modern buying behaviour? #BuyerEnablement

Assume your CRM team is never allowed to offer discounts again. What levers do you have left? A couple of years ago, I was in a client workshop to discuss how CRM can help with our user growth. I thought the workshop might follow the usual agenda: how do we drive more purchases, quickly? Then the founder reframed it with one line: 👉 “For today, let’s assume we never want to offer discounts via this channel. How can lifecycle marketing still drive growth?” That single constraint forced us back to first principles. Because once you strip away discounts, you actually have to solve for the gaps & the leaky bucket problem that CRM is best at: 👉 How can we use nudges for new users to experience value faster? Example: Are there specific content, products, features that we know makes the value a no-brainer. How would we communicate? Here we tested going with plain emails signed by the founder vs a promotional marketing email. The plain email with a suggestion on how to start worked better. 👉 Where’s the friction in their journey we can remove? Example: I remember how Voi (an e-scooters and e-bike company) once sent simple “how to ride” instructions to users who abandoned checkout — aiming to reduce uncertainty in the first trip. 👉 Forced to find the “unfinished” or “underused” behaviors that signal intent, then design CRM nudges to close the loop. Example: We started building automations that didn't scale but were impactful and thoughtful. I think with this reframe, we as a group were forced to think about CRM as a value-delivery engine. I thought the ideas became sharper, we started looking for more behavioral data and funnels, ideas were more user-centered, and a very rewarding experience as a CRM professional. P.S: We also eventually also ran discount campaigns - but we promised that it would always be action triggered. We could choose an email open, or activity in the app but it had to be triggered. Discounts often inflate how effective CRM looks. But take them away—even just for a quarter or a brainstorm —and you force the team to build lifecycle marketing that stands on its own That constraint is one of the best growth unlocks I’ve ever worked under & often use in my work. If you removed all your discounts tomorrow, what do you have left? What would you improve? Where would you start? #crm #lifecyclemarketing #discounting

📊 Over the years of auditing thousands of email campaigns across various industries, I've noticed a concerning trend: The perpetual "sale spiral." 🌀 Companies are trapped in an endless cycle of discounting, each trying to outshout the other in increasingly crowded inboxes. Recently, I worked with a DTC brand whose open rates had declined over 30% over six months despite increasing their promotional frequency. Their customer lifetime value was dropping, and unsubscribe rates were climbing. The diagnosis? Discount fatigue. 😫 Here's what we implemented: We introduced what I call the "70/30 Value Rule" - 70% pure value content, 30% promotional. ⚖️ For the value portion, we created: ➜ Industry insight newsletters ➜ Behind-the-scenes glimpses into product development ➜ Customer success stories ➜ Actionable tips related to their product category ➜ Community spotlights The results after 90 days were compelling: ⭐ Open rates increased by 32% ⭐ Customer feedback emails jumped 215% ⭐ When promotional emails were sent, conversion rates improved by 28% ⭐ Unsubscribe rates dropped by 41% Key Learning: The most successful brands understand that email isn't just a sales channel—it's a relationship builder. By giving your audience "breathing room" between promotions, you create anticipation and trust that translates into stronger campaign performance when you do make offers. This approach requires patience and a shift in metrics. While immediate sales might dip initially, the long-term engagement metrics and customer lifetime value typically show significant improvement within 3-4 months. For companies looking to break free from the discount cycle, start small: Replace one promotional email per week with pure value content. Track not just opens and clicks, but also replies, shares, and sentiment. The data will speak for itself. Remember: In a world where everyone is shouting "BUY NOW," sometimes the most powerful message is simply "We're here to help."