Sales Success Methods

Last week, I heard from a super impressive customer who has cracked the code on how to give salespeople something they’ve always wanted: more selling time. Here’s how he transformed their process. This customer runs the full B2B sales motion at an awesome printing business based in the U.S. For years, his team divided their time across six key areas: 1. Task prioritization 2. Meeting prep 3. Customer responses 4. Prospecting 5. Closing deals 6. Sales strategy Like every sales leader I know, he wants his team to spend most of their time on #5 and #6 — closing deals and sales strategy. But together, those only made up about 30% of their week. (Hearing this gave me flashbacks to my time in sales…and all that admin tasks 😱) Now, his team uses AI across the sales process to compress the amount of time spent on #1-4: 1. Task prioritization → AI scores leads and organizes daily tasks 2. Meeting prep → AI surfaces insights from calls and contact records before meetings 3. Customer responses → Breeze Customer Agent instantly answers customer questions 4. Prospecting → Breeze Prospecting Agent automatically researches accounts and books meetings The result? Higher quantity of AI-powered work: More prospecting. More pipeline.  Higher quality of human-led work: More thoughtful conversations. Sharper strategy. This COO's story made my week. It's a reminder of just how big a shift we're going through – and why it’s such an exciting time to be in go-to-market right now.

I analyzed 12 months of ABM campaigns that actually worked. Here's the data: Most Account-Based Marketing fails before it starts. After analyzing 12 months of successful ABM campaigns (and plenty of failures), I've identified the patterns that consistently drive pipeline. Here's what the data shows: 1. Timing matters just as much as content Accounts that received 3+ touches within 48 hours of showing buying intent converted 4x better than those that received the same content a week later. 2. The magic number is 6.2 (for this brand at least) The average closed-won deal had 6.2 stakeholders involved. Yet most ABM campaigns only target 1-2 personas per account. Expand your reach. 3. The "champion experience" is everything The accounts where we delivered a memorable experience to a single champion (personalized video, custom research, direct exec outreach) had 3x higher conversion rates. 4. Sales and marketing misalignment kills ABM Our most successful campaigns had sales activity within 24 hours of marketing touches. When this alignment slipped to 72+ hours, conversion rates dropped by 48%. 5. Personalization at scale actually works But not how most people do it. We tested 4 levels of personalization: - Generic (18% engagement) - Industry-specific (27% engagement) - Company-specific (42% engagement) - Individual + company-specific (63% engagement) 6. Direct mail isn't dead But swag is worthless (or at least it didn’t work for this audience 🤷♀️). Our highest ROI direct mail: Personalized research reports addressing the account's specific challenges. $250 spend → $45K in pipeline (average). 7. The "Double-Down Effect" When an account engages with ANY marketing touch, immediately increasing the frequency and personalization level produces a 3.5x lift in conversion rates. The companies getting ABM right understand it's not a campaign—it's a complete go-to-market strategy. P.S. I'm working on a new episodic ABM show in collaboration with Clay, so stay tuned 🤗

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 😁

If you close $50k+ deals, I have news: Sales is not a numbers game. Sales is a skills game. 7 skills that grow your income without burning out on the volume game: 1. Finding 'the need behind the need.' Great salespeople dig under the surface. When buyers share their problems, they listen. But then they follow up with: "What's going on in your business that's driving that to be a priority?" THAT gets to the true priority. 2. Quantifying customer pain. No measurement, no money. Quantifying pain does three things: a) justifies the spend b) creates urgency c) helps your customer appreciate the magnitude of the problem. Try asking: "What metric is suffering as a result of these challenges?" 3. Creating champions. A great champion runs through brick walls to get the deal done. They sell your product internally when you're not in the room. Indeed: Salespeople don't close deals. Champions do. A league of champions is like a magnetic force for closing deals. 4. Business acumen. The best sellers in the world are actually businesspeople that happen to know how to sell. Don't just improve your SALES acumen. Improve your BUSINESS acumen. Senior execs will respect you 10x more than reps who only know the latest sales techniques. 5. Executive conversations You can close five-figure deals without this skill. But if you want to close six, seven, and eight figure deals? You better have gravitas when it comes to 'facing off' with senior execs. They're direct. They use plain language. They're efficient. 6. Negotiation. Negotiation is a 'threshold' skill. That means it makes almost all of your other skills more valuable. Becoming a great negotiator will pay dividends the rest of your life. Dig in and master it. 7. Writing. Clear writing indicates clear thinking. Sloppy writing indicates sloppy thinking. Your job as a seller is to persuade and communicate. Become a master of every medium that involves: - sales calls - written word - group presentations What skills would you add?

Life insurance is often described as a business of rejection. In a profession where the success rate may be as low as 5%, the reality is that 95% of conversations may end in a “no,” a postponement, or a rejection. For many advisors and even employees entering the industry, this constant rejection can be emotionally draining. The biggest mistake people make is taking professional rejection personally. Over the last 25 years, I have observed that success in life insurance is rarely determined by intelligence, education, or communication skills alone. Instead, it is determined by an individual’s ability to handle setbacks, remain positive, and continue moving forward despite disappointments. When I look back at some of the most successful agency leaders and advisors I have met, a few common qualities stand out. These lessons are not only relevant to insurance but to any profession that demands perseverance and human interaction. Key Lessons from 25 Years in Insurance Sales 1. Resilience is the ultimate differentiator. The ability to bounce back after rejection is often more important than talent. 2. Success is built on daily habits. We often call them “BBC” — Boring But Critical. Consistent prospecting, follow-ups, and relationship-building create extraordinary results over time. 3. Never confuse professional rejection with personal rejection. A prospect rejecting a policy is not rejecting you as a person. 4. Practice creates mastery. Repeated conversations, presentations, and objection handling eventually develop exceptional competence and confidence. 5. Temperament matters more than potential. Many unlikely individuals have built remarkable insurance businesses, while highly qualified people have struggled because they could not cope with rejection and uncertainty. 6. Long-term success belongs to those who stay in the game. Persistence often beats brilliance in a profession where consistency compounds over time. After 25 years, my biggest learning is that life insurance is not merely a business of selling policies; it is a school of character. It teaches resilience, discipline, emotional maturity, and the ability to keep going when results are not immediately visible. Those lessons have proven valuable far beyond the insurance industry itself. P.S. The picture is from my first year in Insurance industry. #LifeInsurance #Sales #Lessons #Learnings

I closed $2M in founder-led sales in under a year. No sales background. No formal training. Just a mindset shift that changed everything: Stop trying to qualify prospects. Instead, focus on disqualifying them. Here’s what that looks like: 1/ Ask the tough questions that most people avoid. - Why don’t existing solutions like X, Y, and Z work for you? - Why are you taking time out of your day to talk to me? - Is this something you truly need right now, or are you just exploring? 2/ Listen. Really listen. These conversations aren’t about closing deals. They’re about learning why people buy or why they don’t. 3/ Be okay with prospects walking away. If the pain isn’t strong enough, they’re not the right customer. And that’s okay. Don’t fear disqualifying prospects. It’s better to lose a few now than to waste time chasing customers who don’t need you. If the pain is strong enough, they’ll stay. What’s one question you ask during discovery that’s made all the difference?

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!

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.

I just watched an AE lose a $1.2M deal after running a "successful" product trial that the prospect LOVED. After 8 weeks of work, the CFO killed it with five words: "Let's try our current vendor." After analyzing 200+ enterprise sales cycles at companies including Salesforce, HubSpot, Thomson Reuters, and Workday, I've identified the exact framework that separates 80%+ trial conversion rates from the industry average of 30%. The psychological shift required… Stop treating trials as product demos and start treating them as RISK ELIMINATION EXERCISES. After being promoted 12 times and hitting #1 in every role before leading a 110-person team to $190M+ annually, I've developed a framework that's transformed how top companies run trials. THE 5 POINT TRIAL QUALIFICATION SYSTEM: 1. 𝗣𝗥𝗢𝗕𝗟𝗘𝗠 𝗩𝗔𝗟𝗜𝗗𝗔𝗧𝗜𝗢𝗡 Ask these 3 questions before any trial: → "What happens if you don't solve this in 90 days?" (quantify impact)  → "How have you tried solving this before?" (establishes solution gap)  → "Who else is affected?" (identifies stakeholders) These eliminate 68% of unqualified trials before they start. 2. 𝗦𝗨𝗖𝗖𝗘𝗦𝗦 𝗗𝗘𝗙𝗜𝗡𝗜𝗧𝗜𝗢𝗡 Document these 4 criteria: → Technical requirements (features that must work)  → Business metrics (quantifiable outcomes)  → Timeline requirements (implementation speed)  → User adoption requirements (usage patterns) Get confirmation: "If we demonstrate [criteria], you'd move forward with purchase by [date]. Correct?" 3. 𝗦𝗧𝗔𝗞𝗘𝗛𝗢𝗟𝗗𝗘𝗥 𝗠𝗔𝗣𝗣𝗜𝗡𝗚 Create a "Decision Matrix" for: → Technical buyers (every trial user)  → Economic buyers (CFO/budget holder)  → Political influencers (who can kill it)  → Current solution advocates (status quo beneficiaries) Document each person's personal win/loss if change happens. 4. 𝗣𝗥𝗘-𝗧𝗥𝗜𝗔𝗟 𝗔𝗚𝗥𝗘𝗘𝗠𝗘𝗡𝗧 Have legal review BEFORE starting: "We typically have legal review the agreement structure ahead of time so there are no surprises and to save us both time so we can hit the deadline of December 1st you set. Would you be open to this during the trial?" 5. 𝗖𝗨𝗥𝗥𝗘𝗡𝗧 𝗩𝗘𝗡𝗗𝗢𝗥 𝗦𝗧𝗥𝗔𝗧𝗘𝗚𝗬 Ask: → "Have you discussed these challenges with your current vendor?"  → "What was their response?"  → "What specific capabilities do they lack?" Document these to prevent the "let's try our current vendor" objection. RESULTS from this framework: ✅ Trial conversion: 32% to 83% in 60 days  ✅ Average deal size: +40%  ✅ Sales cycle: -37%  ✅ Forecast accuracy: +92%  ✅ Time on unsuccessful trials: -43% — Hey Sales Leaders! Want to see how we can install these kinds of results into your org? Go here: https://lnkd.in/ghh8VCaf

Your top rep just hit 180% of quota. Finance is panicking. "We can't pay them $400K! That's more than the VP makes!" So you cap commissions at 150% of plan. So essentially, you just told your best performer to stop performing. Commission caps were things devised by CFOs who have no understanding of sales math. They protect budgets while destroying the behavior that actually drives revenue. Finance folks might look at these as cost savings measures, but here's where it bites you in the ass: 1. Top performers leave. A rep who can generate $2M in ARR won't stick around to make $250K when competitors will pay them $350K. Replacing a top 10% rep costs 6-12 months of their annual production. That's $500K-$1M in lost revenue to save $50K in commission. 2. Everyone else mediates to the cap. Why bust through 150% when you don't get paid for it? Your reps will (understandably) spread deals across quarters, manage timing, and optimize for lifestyle over performance. This is one of the big reasons why the term sandbagging was invented. 3. Your culture shifts from growth to limits. This one hurts the most, IMO. High performers don't just hit numbers. They set the pace, mentor others, and create competitive momentum. Cap their upside, and you've told the entire team that excellence has boundaries. 4. The pipeline math gets busted up. Capped reps stop prospecting in Q4. They play Angry Birds rather than working through December, knowing January resets their earning potential. Your Q1 starts with empty pipelines because Q4 ended with artificial constraints. IF (and I do mean if) you want to build in some creative limits, here are some more palatable ideas: 1. Cap total earnings, not commission rates. Example: $500K total earnings cap vs. commission rate reduction at 150%. This maintains incentive structure while controlling outlier risk. 2. Use progressive rates rather than cliff cuts. - 0-100%: 10% commission. - 100-150%: 12% commission. - 150%+: 8% commission (still earning, but slower acceleration). 3. Tie caps to value creation. Cap kicks in only if deals lack proper qualification or have high churn risk. The logic here is that quality gates maintain standards while still rewarding performance. 4. Make caps a company-size conversation. - Startups should have no caps (you need EVERY deal). - Growth companies should cap at 200%+ (protect budget, reward excellence). - Enterprise should focus on quota accuracy vs payment limits. The talent market is super tight right now, and I know for a fact that many, many companies are struggling to find solid AEs. Keep in mind that gangster reps want work for companies that understand simple math: If a rep generates $3M in value and takes home $400K, you just made $2.6M in gross profit. Cap that earning, and next quarter you'll make $0. So it's really your choice. Pay for performance or explain to the board why your top talent works for competitors.