Sales Success Methods

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 😁

Gong just announced last week they blew past $300M in ARR. WOW. In 2016, I started at Gong as the 2nd US employee at $200k ARR. 20 SaaS sales tips I learned during my time in that storybook growth journey: 1. Money follows pain. Stop selling benefits. Start selling pain relief. You'll close more. 2. WHO matters more than WHAT. If you're talking to the right person: But you have bad sales technique? You can still win. If you're talking to the wrong person: And have great sales technique? You lose. 3. Don't multi-thread. Single-thread with multiple people. Break people out into 1:1 meetings. Stole this from Krysten Conner. 4. Don't multi-thread too much. Looping in the wrong people can kill your deal. Get the blend of people just right. No, IT doesn't always need to be involved. 5. Great cold emails don't talk about your product. They talk about pain. They look like a page from your buyer's diary. 6. Follow up. Fast. Some sellers take days to follow up. They don't want to seem desperate. Stop it. This isn't dating. Speed sells. 7. The secret to enterprise deals: Pick the deals you can win; then win the deals you pick. 8. Build your business acumen. It makes your sales techniques 2x as effective. Without acumen, you're hollow. 9. Don't seek approval. Seek to solve problems. Big difference. Don't grovel. 10. Buyers don't buy because of ROI. ROI doesn't drive purchases. Emotion does. They simply need ROI to justify the purchase. 11. There are two winners in each deal: The seller who won. The seller who ejected from the deal early and didn't waste time. 12. "Continuity of power" is the ultimate metric. Getting access to power is one thing. Getting a 2nd or 3rd meeting with power is entirely different. Only sellers with sharp acumen get the latter. 13. Great sales calls start with planning. Don't wing it. 14. Voice tone matters. Stop inflecting up. Inflect down. It sets an equal tone. 15. Become a master wordsmith. Words trigger mental pictures. Mental pictures trigger emotions. Emotions trigger actions. Actions close deals. 16. Don't negotiate price too early. It should be the last thing you do before the deal closes. Anything else is too early. 17. Talk about money like it's nothing. Quote a $600,000 proposal with a straight face. That's a super power. The best salespeople have a casual attitude about money. The worst salespeople freak out when they talk numbers. 18. Selling is a set of skills. Not a personality trait. 19. Use the same words your buyer uses. Stop paraphrasing. Stop putting your own twist on things. Use their words. 20. Always know the next step. Bad news: If you don't know what next step you'll suggest? You're wasting that sales call. Selling is an act of leadership. So lead. P.S. Master every aspect of SaaS sales with a FREE trial of pclub.io here: https://lnkd.in/gzF2YwKt

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

I watched a company lose a $1.2M deal last quarter because they were still running MEDDPICC like it's 1996. They identified a Champion and an Economic Buyer. They documented Pain points. They were textbook perfect. The problem in 2025 is that no single Champion can get a deal done. Sales methodologies from the 90s weren't built for today's buying committees, consensus-driven decisions, and distributed authority. The modern sale requires a complete methodology upgrade. No more obsessing over a Champion. You need relationships with the entire team. No more chasing generic Pain points. You need Numerical Priorities linked to business outcomes. No more vague "Compelling Event". You need documented, financially-validated trigger points. No more hoping for Decision Criteria. You need to shape it with objective benchmarks. The best sellers still run a methodology, but it's evolved. They're identifying group priorities, mapping out competing initiatives, and anchoring everything in provable ROI. Try this on your next deal…instead of asking "What's keeping you up at night?" ask "What are the top 3 numerical priorities for your department this quarter?" Watch how quickly you can separate real deals from wishful thinking.

Cold Calling Is Dying. Here’s What’s Replacing It. The numbers don’t lie: • Cold call success rates have dropped to 2.3% in 2025, down from 4.8% last year (Cognism). • 72% of sales calls never reach a person, and it takes 8+ dials to connect with just one prospect. • Only 28% of reps still view cold calling as effective. Meanwhile, high-performing teams are doing something different. Research-Driven, Insight-Led Outreach Wins: • Reps who thoroughly research their prospects are 3x more likely to succeed (Clevenio). • Prospect-specific research can lift conversions by ~30%. • Insight-led outreach builds trust before a call is ever placed. Email and Social Are Outpacing Phone-First Approaches: • Personalized cold emails outperform generic ones by 32%; average reply rates are 8–9%. • 78% of social sellers outsell peers, and social-enabled teams hit quota 66% more often. Takeaway: 1. The call is no longer the first touchpoint. It’s the third or maybe the fourth; it’s only viable once you have demonstrable engagement via other channels. 2. Buyers start with research—so should you. Start with research. Deliver value. Leverage email and social. Then—and only then—call with context. You’re no longer the teacher like when you were knocking on doors. 3. This is how modern sales works. And this is how trust is built at scale. Welcome to the future, my friends. 🙌🏾 #NervousSystemsStrategist #SalesLeadership #ModernSelling #ColdCalling #SalesDevelopment #InsightSelling #SalesStrategy #SalesEnablement

Stop "letting the data speak for itself"—it's a dangerous illusion. Data doesn't speak. Humans do. Here’s the paradox of modern analytics: more data often means less certainty. When we had basic metrics, life was simple. Now, richer datasets reveal complexities that challenge assumptions. Every new variable introduces hidden correlations and interdependencies to untangle. Fun fact: All data carries a human fingerprint. Yes, even your super-objective sensor data! A human designed the sensor, chose its placement, and calibrated it. There's a web of human decisions behind every number. Want proof? Ask your favorite marketer how many "customers" you have—then see if sales agrees. What we choose to measure (and how) matters. Our dashboards aren't neutral observers; they reflect human choices. The metrics we track shape company behavior, creating feedback loops that amplify small biases into systemic effects. The riskiest datasets are often not the messy ones—but the "clear" ones masking hidden complexity. Consider this simple example of three products: ▪ Product 1: 355 ratings, 345 with 4-5 stars, average 4.6 ▪ Product 2: 4501 ratings, 4311 with 4-5 stars, average 4.7 ▪ Product 3: 19 ratings, 14 with 4-5 stars, average 4.8 Which one is "best"? Product 3 leads in average rating but has only 19 reviews. Product 2 has volume backing its strong score. Product 1 claims the highest percentage of positive ratings. Each could legitimately be called "the best"—all supported by the same data. Great analysis isn’t just about finding answers. It’s about understanding why we’re measuring something and how it shapes decisions. That's why tomorrow belongs to analysts who deeply understand their business domain. The superpower isn’t running fancy models—it’s knowing which assumptions are baked into the data and identifying unasked questions. That’s the beautiful irony of data: the more we have, the more we must rely on human judgment and expertise. Unless you’ve run a tightly controlled experiment, data only reveals its truth when paired with our uniquely human ability to grasp context, spot patterns, and question the numbers.

ROI presentations are deal killers. Gong's data shows a 27% drop in close rates when reps present ROI at any point in the sales process. Think about it from the buyer's perspective: "The ROI of our solution is 300%" sounds like every other vendor pitch they've heard this month. Executives tune out because they've been burned by inflated ROI promises before. Smart reps skip the ROI theater entirely. Instead, they build business cases that executives actually care about. Here's the blueprint: #1 Assess their current state. Document what's happening now based on actual stakeholder conversations. Their goals, obstacles, and challenges. Make it specific to their situation, not generic industry problems. #2 Run a problem cost analysis Quantify the real financial impact. Which metrics are suffering? Direct costs, indirect costs, opportunity costs. What's the monthly burn rate of doing nothing? Get specific numbers, not ballpark estimates. #3 Identify the root cause Identify why problems exist, not just what problems exist. Show the underlying issues that need addressing. This separates consultants from vendors. #4 Give them multiple outcome scenarios Present three paths: status quo, conservative improvement, and optimistic improvement. Ranges feel realistic. Single "guaranteed" outcomes feel like sales BS. #5 Give them an implementation reality check Be honest about what success requires. Time investment, resource allocation, change management challenges. Transparency builds credibility. The shift is subtle but powerful: ROI presentations = "Here's why our product is great" Business cases = "Here's why your current situation is unsustainable" One focuses on your solution. The other focuses on their problem. When you help executives understand the true cost of inaction, price becomes secondary. Stop selling ROI. Start selling necessity. — Want to see a real coaching call walking through price objections? Go here: https://lnkd.in/gbBjgxxS Sales Leaders: Want to install systems to get your reps crushing quota? DM me.

You don’t remember what a brand said. You remember what it showed you.    “Show, don’t tell” works because people remember what they see and experience, not just what they’re told.  It’s why the best campaigns rely on proof, not promises. When brands demonstrate their value, they create connections that standard advertising simply cannot match. Here 3 three perfect examples: 📍 Volvo Cars (worth $62.3B) (Statista, 2023) They turned a boring safety feature into internet gold when they filmed Jean-Claude Van Damme doing the splits between two moving trucks.  Over 100 million people watched a commercial about truck stability.  Think about that. They didn't bore us with technical specs—they created something people actually wanted to share. 📍 ROLEX ($10.7B in annual revenue) (Morgan Stanley & LuxeConsult, 2022)  They don't just tell you their watches are durable—they put them on the wrists of people climbing Mount Everest or exploring ocean depths.  Instead of clinical lab tests, they show their products survive the harshest conditions on earth. Real people, real challenges, real proof. 📍 Dyson (valued at $14.5B) (Forbes, 2021) They completely changed how we think about vacuum cleaners when they made those clear collection chambers. Suddenly, you could actually see all the dirt you were picking up.  They transformed cleaning from an invisible chore into visible evidence of success. That's so much more powerful than just claiming "powerful suction" in an ad. To apply this in your own business: Start by identifying your core value proposition. Then ask: How can we demonstrate this visually rather than just claiming it? What tangible proof can we show? What experience can we create that makes customers see our value firsthand? The most convincing argument isn't what you say about your product—it's what your customer sees for themselves. What product demonstration changed your perception of a brand more than their advertisements did? #BrandStorytelling #MarketingStrategy #ShowDontTell

Your Competitor Isn’t Another Sales Organization In modern B2B sales, your biggest competitor isn’t a rival company. It’s your client’s fear of being wrong. Most decision-makers aren’t comparing your solution to someone else’s. They’re comparing action versus inaction. The risk of change feels greater than the pain of staying the same. Deals die quietly — not because your product failed, but because buyers lack the certainty to sign. Sales leaders often misread this. They push for more follow-ups, bigger pipelines, and better decks. But none of that fixes the real problem: your buyer doesn’t feel safe making a decision to change. Here’s how to fix it: 1️⃣ Lead with Insight — Start with a non-obvious idea that reframes the buyer’s world. 2️⃣ Reframe the Risk — Move from “What if this fails?” to “What if you don’t act?” 3️⃣ Transfer Confidence — Prove you understand their problem better than they do. 4️⃣ Build Consensus — Find the “CEO of the problem,” the one responsible for results. 5️⃣ Teach, Don’t Pitch — They buy rarely; you sell daily. Be their guide, not a vendor. Expertise is the new currency. Modern buyers don’t need pressure — they need confidence. #SalesLeadership #B2BSales #ModernSelling #OneUp #SalesStrategy

A few weeks ago, I made a mistake. I analyzed a dataset and thought I had the answers. So I recommended a change. And it failed. Not because the data was wrong… But because I forgot about the humans behind the numbers. Here’s the thing: While data shows what is happening. People explain why it is happening. A dashboard might tell you sales dropped 20% last month. But it will not tell you that; Your top salesperson just went on maternity leave. or, Your biggest client's head office moved to a different city. Numbers whisper. Behavior speaks. Combining them, tell stories that drive successful actions. If you want your recommendation to be successful, Don't stop at analysis, Investigate the human story behind the dataset as well. Because the most important part of your data, It is what your data is not showing you.