Sales

Most sellers misuse discounts. They drop them too late. Talk to the wrong person. Add pressure. Miss their number. I’ve taught 1,000s of reps how to do it right. Here are 7 ways to use incentives without looking desperate: I’m not anti-incentives. I’m anti-commission breath. And that’s exactly what shows up when sellers drop a 30% discount on the 29th of the month…only to find out their champion still needs two more approvals and a legal review. It doesn’t close the deal. It just creates pressure. On you and your buyer. Here’s a better way. 1. Incentives are not discounts Don’t pitch 30% off like a used car dealer. Offer something valuable with a story behind it: → A month free → Preferred pricing → Bonus feature access It has to be legit—and tied to a reason (like quarter-end, new logo program, etc). 2. Talk to the decision maker If your buyer can’t actually sign, an incentive won’t help. You need someone who can say yes—or who can push it through. 3. Ask about their process first “What’s your timeline for getting this done?” If it’s next quarter, ask if an incentive would help them pull it forward. If they say yes, you might have a deal to accelerate. 4. Don’t offer anything if the timing isn’t natural You’re not trying to force urgency. So say: “I don’t want to show you this if it’s not something that’s realistic for you.” Let them opt in. 5. Always qualify timing “If we were able to offer something strong, do you think you’d be able to move forward this month?” You want buy-in before they see price. Not after. 6. Map the path to signature Lay out the mutual action plan: - Who needs to review the proposal? - When does legal need it? - How long does procurement take? If it’s not doable, don’t offer it yet. 7. Bring it up early in the month Waiting until the end will kill the deal. Even motivated buyers run out of time. So if you’re going to offer an incentive—do it with 2–3 weeks to spare. Not 2–3 days. TAKEAWAY Discounts don’t create urgency. Timing does. Know their process. Earn the yes. Stay out of panic mode. Close without pressure. Sell with trust.

One way I help my clients sell more, faster: Remove friction from the sales process. Most B2B service companies have a horrible sales experience. → booking multiple calls to figure out what a prospect needs → filling out a form and waiting days to book a sales call → custom proposals that take weeks to create → 100's of iterations on that proposal It makes it hard for prospects to choose them. There is an easier way to sell. Yes, even for custom deliverables. Like websites, equipment manufacturing, Salesforce fixes, patent and trademark applications, IOT remote monitoring systems, and the like. It's simple. Turn your discovery process into a paid offer. → systematize it → create a templated deliverable → provide calls to get the information you need → include your proposal at the end of the deliverable → do one final call to present your report and your proposal → make it low-cost enough to feel like an impulse buy One of our clients has achieved a 100% upsell rate to their custom offer. Think about that for a minute. - sell a $1k-$5k offer - that sells your $50k-$500k offer Every. Damn. Time. This tactic has worked for multiple B2B industries: - manufacturing - industrial services - professional services - equipment sales - commodity sales The trick: you need to have the right initial offer. One people want. Priced for an easy sale. Want a product that creates a 100% upsell to your main offer? Shoot me a DM. I've done this for multiple B2B industries. And my clients who implement it make a sh*t ton of money. You could, too. ✌🏼 #shftyourbrand

61% of sales reps say selling is HARDER than it was 5 years ago. And that stat came BEFORE the recent tech layoffs, budget freezes and buying committee chaos. According to Salesmate, the top sales challenges of 2024 include longer deal cycles, budget freezes, and decision maker ghosting. Sound familiar? Most reps are panicking. But I’ve seen this before. I sold through the Great Recession. Got promoted 12 times in 8 years. Closed over $700 million in contract value. Hit President’s Club almost every year. Managed a team of 110 before I turned 31 (I’m 41 now). Now I train reps at Google, Zoom, Salesforce, and more on how to thrive in ANY environment… not just when the pipeline’s hot. If you want to be the AE who earns $250K–$500K while everyone else just survives, you have to master this: 👉 How to handle objections without triggering defense mechanisms 👈 (We are in a LOW trust environment in 2025. Layoffs, inflation, interest rate whiplash. People are cautious. Buyers are nervous. Budgets are tighter. That creates friction and with it, skepticism.) Because objections are higher now. Resistance is higher. And if you show up with commission breath, it’s game over. Instead, use this: The HEART Framework This is how top reps turn objections into opportunities. (H) Heard Don’t rush. Don’t rebut. First, make your buyer feel safe. Acknowledge their concern without trying to “solve” it immediately. Example: “I totally appreciate that. Thanks for being honest.” (E) Elaborate Go deeper. Ask questions to surface the root issue, not just the symptom. Use soft tone and pacing to create psychological safety. Try: “Can you tell me more about that?” or “What’s behind that concern for you?” (A) Aside from that Isolate the objection. You want clarity, not confusion. Ask: “Aside from [X], is there anything else holding you back from feeling 100% confident?” (R) Reclarify Value Shift focus. Bring them back to what they liked about your solution. Ask: “Before we dive back into that concern, what stood out to you the most about what we’ve discussed so far?” (T) Transition Now you address the root objection with context. Pull from earlier discovery. Reference past failed solutions. Let them convince themselves. “You mentioned trying X for 6 months with no results. What do you think would change if you kept going down that path?” This isn’t persuasion. It’s precision. Done right, your buyer talks themselves into the close. But here’s the deeper point: If you can stay calm, curious, and service driven when everyone else is pushing discounts, you win. And not just this quarter. You win for life. — Hey Sales Leaders… want to get your team through this TOUGH market? We should talk. I can train your team with our proven repeatable sales systems: https://lnkd.in/eaibeK8q

I was asked today a very simple question, How can I #prospect better on #LinkedIn? This simple question does not have a simple answer. So I did what I always do and made my list, went to #askSSL.ai and used my” Brynne Avatar” who is already trained in my voice, with my content, and my prohibitions oand spent about 20 minutes crafting and editing the following: ⸻ How to Prospect Better on LinkedIn Without Sounding Like a Sales Pitch Prospecting on LinkedIn isn’t about sending more messages. It’s about starting the right conversations with the right people in the right way. The professionals who succeed treat LinkedIn as a relationship platform, not a cold-calling tool. Here’s how to shift from pitch-based outreach to conversation-driven social selling. 1. Transform Your Profile from a resume to a Resource If you are in a revenue-driven role, your LinkedIn profile should not be a resume. It should speak directly to the challenges and goals of your ideal buyer. Lead to your solution by offering insight and value that not just shows how you help but actually helps, earning you the right to get the conversion. 2. Engage Before You Reach Out Engagement builds visibility and credibility. Thoughtful comments on the right posts open doors. The more value you bring in public conversations, the more permission you earn to move to private messaging. 3. Reconnect with Existing Relationships Take inventory of your network. Revisit clients, prospects, and referral partners. Share something relevant. Ask a thoughtful question. Start conversations around topics that are meaningful to them. 4. Map Paths to Referrals Use LinkedIn and Sales Navigator to find mutual connections. Ask for introductions. Warm referrals often outperform any cold outreach. Most professionals want to help. You just need to ask the right way. 5. Write Like You Speak Skip the templates and formal language. Your message should feel like it belongs in a real conversation. The goal is not to sell. The goal is to earn a response. Bonus: use the native voice messaging or video messaging in the LinkedIn app to humanize the connections even more. 6. Use AI to Prepare Smarter Tools like askSSL or ChatGPT can help you write better outreach messages, create personalized content, and research your prospects. Use AI to support strategy, not replace it. Prospecting on LinkedIn is about earning the right to a conversation. That can come through valuable content, a warm referral, or thoughtful engagement. The key is to start trust-based conversations that feel helpful, not salesy. When you make them matter, you matter. How do you prospect better on LinkedIn? #sslinsights

I analyzed 100+ loyalty programs in the last 30 days. Most brands still run loyalty like it’s 2009: Earn points, get a discount, repeat. The top 10%? They’re using loyalty to change behavior- not just reward it. If I were Head of Loyalty at a $10B+ brand today, here’s exactly what I’d do to build a program that drives LTV, repeat purchases, and real retention: 1. Stop Giving Away Loyalty - Make Them Pay for It Costco, RH, Barnes & Noble. When customers pay upfront, they buy in - literally and psychologically. Forget free points. Paid memberships = commitment, retention, higher LTV and emotional sunk cost. 2. Make Loyalty Required, Not Optional - Integrate Directly into Payments Starbucks preloads!!! When rewards are embedded in how people pay, behavior shifts faster, and for longer. This is probably the biggest opportunity in loyalty right now. 3. Forget Delayed Points - Instant Gratification is More Important Immediate dopamine beats theoretical future savings. Slow accumulation = slow engagement. Instant offers = repeat behavior. The 2nd purchase matters more than the 10th. 4. Make Loyalty Emotional, Not Transactional REI, North Face, Sephora. Customers want to belong, not just save. Identity, community, and shared values are outperforming cashbacks and discounts in driving long-term loyalty. Loyalty isn’t just a discount strategy, it’s a brand strategy. 5. Invest in Status + Experiences, not Generic Perks This isn't just theory – with companies like Rapha and Lululemon offering loyalty members exclusive product drops, community events and behind-the-scenes experiences. Lean into waitlists and exclusive product drops. Less financial. More status + psychological “being in the club.” 6. Reward Engagement, Not Just Transactions MoxieLash, Pacifica, Lucy & Yak. UGC. Reviews. Referrals. Loyalty now means participation. The modern flywheel starts before checkout - and lasts far beyond it. ~~ Bottom line? If your loyalty program is still playing a game from 15 years ago, your customers are going to find better options. Today, the best brands in 2025 aren’t just rewarding loyalty- they're engineering it. PS: We analyzed 100+ programs across QSR, retail, travel, and fintech. Next week I’ll share the Top 30 loyalty programs leading the way. Stay tuned🙏

Your product’s biggest strength? Might be the reason you're losing. Stop me if you've seen this before: A rep walks into a demo, guns blazing with the flagship feature. Patented AI. Endless integrations. Dashboards so pretty you want to frame them. The problem? None of that matters if the buyer doesn’t care. It’s like offering a juice cleanse to someone who just asked for a steak. This is the trap: we confuse differentiation with default positioning. Just because something is unique doesn’t mean it’s useful. Just because something is premium doesn’t mean it’s priority aligned. I’ve lost deals this way. You probably have too. Brian LaManna broke this down during a Sales Assembly course last week. His thesis is that the game isn’t about showing what makes you great...it’s about showing why you’re exactly right for them. Here’s how to make the shift: 1. Start with strategic fit, NOT product strength Before you drop into demo mode, answer this: What strategic priority does this prospect actually care about? - Reduce CAC by 15% - Launch in Europe by Q3 - Retain 95% of enterprise accounts - Improve onboarding velocity for ramping reps If your feature doesn’t map to one of those? It’s window dressing. No matter how powerful it is. 2. Quantify the cost of staying put Sellers love to sell the future. Buyers make decisions based on the cost of the present. If your differentiation doesn’t help them: - Close the gap between current and ideal state - Avoid a known risk - Or capitalize on an urgent opportunity... …it’s irrelevant. Build the business case around urgency, not just capability. 3. Use differentiation to de-risk the decision Great sellers use differentiation to reduce perceived risk. Bad sellers use it to inflate perceived value. “We’re the only vendor with XYZ” Only matters if: That feature ties to a must have outcome AND you make it feel safer to choose you than to stall or default to the status quo Otherwise? You sound like every other overengineered solution they don’t need. 4. Tailor the pitch by segment and stage Early stage startup? They care about velocity, not sophistication. MM? Probably looking for plug and play solutions with high ROI. ENT? Stability, compliance, scale...and political cover. Same feature, totally different framing. Differentiation that doesn’t flex by buyer type fails. Differentiation isn’t about being better. It’s about being the right answer to their very specific problem - right now. You’re not selling a Ferrari. You’re selling a way out of whatever corner they’re currently stuck in.

Fortune 500 vs bootstrapped startup. David still beats Goliath. The giants had the budget. The brand. The buyer's default. But we won. Not by being louder. By believing deeper and leading bolder. #ForwardFriday reflection: True giants don't just win deals. They build paths for others to follow. Here's how underdogs win high-stakes deals: Not with size. With behavior, EQ, and calculated courage. 🔥 1. Start with conviction → Know why this matters to you and them → Connect solution to user, business, and mission → Belief drives clarity. Clarity drives conversion. 📌 "Here's why this matters to me, and to the people you serve." 🔍 2. Get radically relevant → Use their language. Mirror priorities. → Don't pitch, diagnose. → Personalized insight beats polished decks. 📌 "What's something people usually miss about what you're solving for?" ⚖️ 3. De-risk the decision → Reduce cognitive load → Make "yes" feel safe → Offer pilots that build belief 📌 "What would make this a no brainer for you and your team?" ⚡ 4. Win the emotional moment → People decide emotionally, justify logically → Let them see themselves winning 📌 "What would make this decision feel like a win for you personally?" 🎯 5. Pivot with cognitive flexibility → Don't freeze. Don't force. Reframe. → Guide through uncertainty, not around it 📌 "If we looked at this from a 'cost of delay' angle, what shifts?" 🧘♀️ 6. Regulate high stakes emotion → EQ builds trust. Calm cuts chaos. → Mirror emotion, not just logic. 📌 "Sounds like there's pressure here; want to talk it through?" 🔁 7. Build anti fragile trust → Don't vanish. Add value. → Every "no" deepens relevance 📌 "Thanks for the candor. That helps us get sharper. Here's one idea..." 🏆 This is how underdogs win. Not with scale. With science. With self awareness. With better buyer experiences. Living our values daily. — #ForwardFriday: Tag a leader who's winning by redesigning the game, not just playing it. ♻️ Repost to remind every underdog what's possible. ➕ Follow Holly Moe for sales strategy rooted in buyer psychology + peak performance. P.S. It's Forward Friday! Each week, I turn our engagement into real-world impact. It's my weekly tradition of ensuring our conversations create ripples of good - providing meals, water, and business support to people worldwide. 🌊

The moment after conversion is when most companies stop optimizing. It's also precisely when the most valuable customer relationship building begins. I've watched countless enterprises pour millions into acquisition, only to neglect the critical post-purchase journey that determines whether that customer ever returns. It's a costly psychological blind spot. After helping companies like Adobe and Nike optimize their digital experiences for over a decade, I've seen this pattern repeatedly: ↳ Companies celebrate the conversion, then immediately shift focus back to acquiring the next customer But the "recency effect" means your customer's last impression of your company is the one that sticks. A seamless checkout experience followed by a confusing onboarding process or silence creates cognitive dissonance that erodes trust. One SaaS client we worked with was losing 42% of new users within the first week after conversion. By implementing a structured onboarding process with progressive revelation of features, we reduced that to under 15%. There are three post-purchase communication strategies that consistently drive retention: ↳ Proactive communication about both positive AND negative situations (address potential issues before customers experience them) ↳ Structured onboarding that guides users to their first "win" with your product as quickly as possible ↳ Strategically framed review requests that set the right expectations (the difference between "Tell us what you love" vs. "Give us your feedback" is massive) The companies that master the post-purchase experience don't just retain customers... they create advocates who drive acquisition more effectively than your marketing ever could. Does your optimization effort stop short?

Outbound is dead in cyber. Long live AE-owned prospecting. I will die on the hill of "outbound is dead". But it's been misunderstood when I've brought it up here. In cybersecurity, generic mass outreach is dying or it's a zombie waiting to be whacked. Targeted, value-driven prospecting led by Account Executives is thriving. SDR's have a hard time doing this not because they can't, but because the system is not setup for them to do it (i.e. comp plans, org structures, etc.) We know from research that personalized outreach based on deep account knowledge delivers 3x better engagement than templated SDR approaches. Yet we keep trying to build outbound motions with higher volume and worse conversion rates 🤮 Here's my framework for building a repeatable pipeline development program where AEs actually own the process: 👉 *The Value Hypothesis Approach* 1. Narrow the focus dramatically: Your target account list should be small enough that each account gets hours of dedicated research. 2. Make AEs accountable for contact mapping They need to identify key stakeholders and understand the organizational dynamics before any outreach begins. 3. Develop specific value hypotheses This is the game-changer. Each account gets 2 customized value proposition based on their specific situation. 4. Collaborate on hypothesis refinement The best teams involve SE/PreSales, Product Management, and Sales Leadership in critiquing and improving these hypotheses. 5. Execute with precision With this foundation, outreach becomes a targeted conversation rather than a generic pitch. 6. Close the feedback loop: Sales leaders need to document which value hypotheses resonated and which fell flat - this becomes your competitive advantage. The best-performing enterprise sales teams allocate at least 1/3 of AE time to this process. Yes, it's resource-intensive, but the results speak for themselves. 2 hours a day (minimum) every day, every AE, for 3 months. Then come back and tell me 'thank you' Unexpected benefit: When AEs spend 10+ hours weekly on strategic prospecting, your inbound and partner-led conversion rates automatically improve. Why? No AE will let warm leads slip after experiencing how much work cold prospecting takes. Pro-tip? Spend 'Training Thursdays' evaluating value hypothesis together. Double pro-tip, combine Value Hypotheiss with 'Show me You Know Me' on your messaging (follow Samantha McKenna - She crushes SMYKM content) Anyone here that calls value hypothesis something else? I used to call it my 'angle'. Need something more catchy and less scientific-sounding 😆

Improving 2nd purchase conversion by 5% can boost LTV by 20-35%. But most brands don't focus on this. Some tips to increase re-purchase (#5 is my fav) 👇 I looked at data for 100+ of our retail brands. On average: - First-time buyers have a 15-30% chance of returning - After a second purchase, that jumps to 60-70% Because of this snowball effect, little improvements to 2nd purchase conversion (+5%) can mean significant LTV jumps (+20-35%) Here's a handful of tactical things we've seen work. ----- 1. Focus on a shorter window than you think. Run your retention curves. Chart % of customers making 2nd purchase by month. You want to find where the cumulative repeat rate flattens out. - Most brands will be ~90 days. - Consumable brands (supps, food/bev, beauty) will be shorter (30 days). - Products w/ longer usage cycles may by 180 days or more. It all depends. Many brands make the mistake of using a 12-month window to look at churn. You've almost certainly lost that customer by then. Focus on a shorter window than you think. 2. Cross-category has a higher propensity of longterm retention ----- Cross-category buyers (almost always) have a higher LTV than single-cat buyers. - If they bought jeans, offer tops or accessories - If they bought skincare, suggest adjacent skus, not refills - If they bought a core product, introduce them to your specialty items Ps, you can segment your CRM and split test this. Just remember to tag your customers when measuring long-term LTV performance. ----- 3. Micro-commitments + Add Value! Before asking for a 2nd purchase, squeeze out small/easy commits: - Request product feedback/review (one question) - Offer style or usage guidance (post-purchase series) - Provide value-added content related to their purchase - Solve common problems w/ the products - Show how other customers use it Each small activity builds more engagment (and goodwill) w/ your brand. ----- 4. Implement a "Last Chance" campaign If your 2nd purchase window is 90 days, maybe that's Day 60. Deploy a specialized "almost lost" campaign. - Use language w/ mild urgency (avoid depsparation) - Include an unexpected benefit or small gift/gwp/ The offer MUST be better than what you'd give a first-time customer. ----- 5. Make the product better That's it. Just improve the product quality, and you'll see a natural jump in repurchase. It helps acquisition too (referral/WOM). By shifting a little focus from acquisition to that crucial second-purchase moment. What's your 2nd purchase "window"? 30, 60, 90 days? What are you doing to shrink that window? #ecommerce #customeranalytics #ltv