Sales Career Development

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 😁

Last week, we closed a deal with a $10 billion (revenue) company. No click bait. Just a story that marks a new era. Here's what their SVP told me: “A few years ago, our sellers didn’t need real skills. Tailwinds and great product-market fit carried us. We had nothing more than order-taking skills.” He went on: “But today? Sales cycles are complex. Buying committees are more educated & skeptical. The ZIRP era won’t come back for another generation. We need to maximize revenue per rep. That starts with skill capacity.” We’re no longer in the ZIRP era. We’re in the Skill Capacity Era. I asked him what skills matter most now. Here’s what he said: 1. Disruptive Insight Selling. Great sellers don’t pitch. They reframe the problem. They introduce a unique insight that shifts the buyer’s thinking. In a way that favors a purchase. Most AEs can’t do this. They offer thinly veiled product pitches. No insight. No acumen. Top sellers reframe the buyer’s mind. They communicate, without saying it: “I know your business — and I understand this problem better than anyone else.” 2. Developing and Quantifying Value. Open your CRM. Look at the notes in the ‘pain’ field.' Now ask yourself: Are these the problems C-level execs care about? Or mid-level frustrations? Most AEs stop at surface pain. The best go deeper — and quantify what they find. They uncover the need behind the need. That’s where the deal lives. 3. Frictionless Multi-Threading. Buying committees are larger. Buying committees are more risk averse. Buying committees are prone to “do nothing.” Yet sellers have the same multi-threading habits they did two years ago: Work with one, MAYBE two people. Stick with the most comfortable contact. Avoid the skeptics. The best salespeople don't just multi-thread. They drive consensus. 4. CFO-Level Business Cases You don’t need to be a spreadsheet wizard. But you do need to speak CFO. If your ROI pitch sounds like a sales deck? At best, they’ll roll their eyes. If it sounds like a financial case with scenarios? You’ll get to “yes” faster. 5. Taking Control. The Challenger Sale gave sellers a game-changing framework: Teach. Tailor. Take Control. Most AEs don’t know how to do that without sounding tone-deaf to buying dynamics. They defer. They wait. They follow the buyer’s process and hope for the best. But in this market? Hope is not a strategy. AI can’t lead a room. It can’t challenge a buyer’s process. It can’t manage power dynamics. That’s your job. The best AEs define the pace and tone of every deal they touch. ZIRP is gone. The order-taker economy is dead. Welcome to the Skill Capacity Era. The CRO flex isn’t bloated headcount anymore. It’s skill density × revenue per rep. P.S. Start transforming your revenue team with these 24 skill transformation tips: https://lnkd.in/g_JF-ytC

In the high-stakes arena of #B2BSales, particularly when engaging the C-suite and Boards, "back of napkin math" is more than just a display of acumen – it's a potent catalyst for building #trust. Imagine a conversation where a senior leader articulates a critical business challenge, perhaps around CAC payback or share of wallet. The seller who can immediately and fluently grasp the underlying financial equation and articulate the potential impact of their solution, without missing a beat, speaks a language that resonates deeply. This isn't about complex modeling done offline; it's the agility to understand core drivers of their success and perform quick, insightful calculations within the flow of the conversation. For instance, if a Chief Revenue Officer (#CRO) mentions a goal of reducing customer churn, a seller with this skill can instantly frame the value of their solution in terms of retained revenue and lifetime customer value, demonstrating a tangible understanding of the CRO's priorities. This competence signals the seller not only listened - but also deeply comprehends which levers to use to solve the client problem. Why is this so crucial for building trust? Because it showcases several key elements that senior leaders value: Deep Understanding: The ability to perform this kind of rapid analysis demonstrates you've done your homework and truly understand their business model, challenges, and objectives. It moves you beyond being a mere vendor to a knowledge partner. #CustomerUnderstanding Intellectual Horsepower: It signals a sharp mind and the capacity to think strategically about their business. This builds confidence in your ability to deliver real value. #StrategicThinking Efficiency and Respect for Time: Senior executives are time-constrained. A seller who quickly gets to the heart of the financial implications respects this constraint and demonstrates a focus on outcomes. #TimeEfficiency Transparency: By engaging in these on-the-spot calculations, you reveal your underlying assumptions and logic, fostering a more transparent discussion. #TransparentCommunication Credibility: It elevates your status from a product peddler to a trusted advisor who speaks the language of business results. #TrustedAdvisor Think about it: when a seller can seamlessly weave in relevant financial implications – the potential ROI, payback period, impact on key KPIs – it’s not just data; it demonstrates commitment to the customer's success. It shows you're thinking beyond the product/service features and instead - are focusing on their strategic outcomes. To be clear - "Back of napkin math" isn't about being precisely accurate in real-time. It's about demonstrating a strong intuitive grasp of financial levers that matter to the customer and the ability to articulate value in their terms, instantly. This fluency builds a bridge of trust, making conversations more meaningful and impactful. #Gartner

🚀 Dive into the evolution of sales: From hard-selling to consultative expertise! 🌟 🔍 Sales Stereotypes: Outdated Views Remember the aggressive sales tactics of the 70s and 80s? That era is long gone! 📚 Today's sales landscape rejects pushy, self-oriented strategies. It's all about understanding and empathy. 🤝 🌐 Consultative Selling: The New Norm Modern sales demand a consultative approach, where understanding client needs is key. 🎯 It's not just about closing deals; it's about being a knowledgeable advisor to clients. 🧠 📈 Expertise Matters Successful salespeople are experts in their client's journey and challenges. 🚀 They provide tailored solutions, not just products. This expertise is crucial for impactful sales. 💡 🤔 Real-World Scenario: CEO's Dilemma Imagine a CEO struggling with a problem. Two salespeople approach with different tactics. 🏢 The first lacks advice and insight, while the second offers specific, researched solutions. 🕵️♀️ 🔥 Consultative Selling in Action The effective salesperson dives into the CEO's issue, offering concrete advice and options. 🛠️ This approach demonstrates deep understanding and readiness to solve real problems. 👍 🏆 Why Consultative Selling Wins Clients seek salespeople who offer more than a product – they want expertise and solutions. 🌟 Being a consultative sales professional means being the go-to person for solutions. 🥇 📌 Pushiness Redefined True pushiness is about pressure and manipulation, not about offering valuable advice. 🚫 Leading clients with knowledge and guidance is the essence of modern sales. ✨ Embrace this shift towards consultative selling to truly connect with and assist your clients. It's not just about selling; it's about being a trusted advisor in their journey to success. 🚀💼

Stop hiring salespeople with sales experience That's the advice I gave a CEO who'd missed targets for 5 straight quarters His board nearly fired him for implementing it 6 months later: → Revenue: Up 110% → Sales cycle: Reduced by 40% → Customer retention: Improved from 60% to 80% Here's what most companies fundamentally misunderstand about sales performance: Experience in sales is often your biggest liability, not your biggest asset When we analyzed their team's performance: - Veterans with 10+ years experience had the lowest close rates - Reps with the most training relied on outdated techniques Those with the most "sales knowledge" asked the fewest questions Industry experience correlated with assumption-based selling So we rebuilt their team with what I call "Blank Slate Methodology": - We hired curious people from non-sales backgrounds - We recruited from customer service, teaching, and research roles - We prioritized inquiry skills over persuasion tactics - We eliminated commission-only structures The transformation was remarkable: - First meetings-to-opportunity ratio: Increased 100% - Price objections: Decreased 40% - Win rate against competitors: Up from 23% to 35% - Post-sale NPS scores: Jumped from 32 to 50 The uncomfortable truth about modern B2B sales: Traditional sales experience has become a predictable pattern that sophisticated buyers recognize and resist Your competitors are fighting over the same recycled sales talent Meanwhile, successful businesses are building sales forces from entirely different talent pools – people whose natural curiosity and problem-solving instincts haven't been corrupted by years of traditional sales conditioning What if you stopped hiring sales experience and started hiring learning capacity instead? The companies making this shift are quietly revolutionizing their industries while others wonder why their experienced teams keep underperforming. The path is clear The question is: Are you bold enough to take it? Have to mention that this approach DOESN'T APPLY to every business P.S. If you need help with your sales, send me a message

If your sales strategy is still built on “Always Be Closing,” you’re stuck in the past. The old-school “ABC” sales mantra was great in the 90s, but in today’s market, it just doesn’t cut it anymore. Customers are smarter, more informed, and want genuine partnerships—not pushy sales tactics. So, what’s working now? Here’s what modern sales looks like: ⤵️ 1) Always Be Connecting: Build genuine relationships, not just transactions. Focus on long-term value, not short-term gains. Customer retention and loyalty are more profitable than chasing new leads. Use social selling to establish trust before the pitch. 2) Always Be Curious: Ask probing questions to uncover real pain points. Listen more than you speak (aim for 80/20 ratio). Continuously educate yourself on your client's industry. 3) Always Be Consulting: Position yourself as a trusted advisor, not just a vendor. Offer strategic insights that go beyond your product. Sometimes, the best sale is telling a client they don't need you (yet). 4) Always Be Customizing: Customize your approach to each prospect's unique needs. Use data and AI to personalize at scale. Adapt your offering to provide bespoke solutions. 5) Always Be Collaborative: Work with prospects to co-create solutions. Involve multiple stakeholders in the buying process. Encourage internal partnerships to deliver comprehensive value. 💡 In today’s sales world, the rule is simple: "Always Be Valuable." Your worth isn't measured by closes, but by the positive impact you make on your clients' businesses. #SalesStrategy #BusinessGrowth #ModernSales #SalesEvolution  #SalesTips #ThoughtLeadership

The Strategic Seller: Moving Beyond Product to Partner in the C-Suite B2B sales success hinges on strategic alignment, not just product specs. The shift from vendor to C-suite partner demands a mindset revolution—one grounded in value hypothesis and multi-dimensional frameworks 💡 The Value Hypothesis: Your North Star Start with a simple question: “What does success look like for your customer?” This dynamic hypothesis evolves through financial analysis, stakeholder dialogues, and market insights, ensuring solutions tie directly to executive priorities like ROI and market share 🔍 The 4 Dimensions of Value 1. Business Value : Quantify ROI, efficiency gains, and growth 2. Individual Value : Align with stakeholders’ career goals and pain points 3. Solution Value : Technical excellence framed by strategic impact. 4. Provider Value : Trust and partnership as differentiators . 🚪 Elevate Conversations to the C-Suite Break free from technical silos. Engage leaders on their terms: Discuss efficiency with the COO. Highlight customer engagement for the CMO. Link solutions to growth for the CEO. 🛠 Navigating Challenges Resistance from technical gatekeepers? Use Multiple Equal Offers (MEO) to de-risk decisions Competitor noise? Differentiate through relentless value refinement and agility 📚 Continuous Evolution Small tweaks—like pre-meeting “priming” emails—compound into strategic credibility. 🌟 The Bottom Line Strategic selling isn’t a tactic—it’s a transformation. By mastering value hypotheses, embracing agility, and partnering at the top, you become indispensable. Are you ready to rethink your sales playbook? 🔍💼 #StrategicSelling #C suite #ValueHypothesis #SalesLeadership #B2BSuccess

In today’s complex enterprise landscape, getting a deal across the finish line is more than selling a solution; it’s about navigating a labyrinth of internal processes and proving real value. Rainmakers know they must go beyond selling and develop a deep empathy for the challenges their champions face internally. Here’s how they do it: 1️⃣ Understand the Journey: Your client champion isn’t just buying a solution - they’re guiding it through committees for risk mitigation, security audits, business justifications, legal reviews and often dealing with risk-averse gatekeepers who fear yet another unused platform on the shelf. 2️⃣ Tailor Proposals with Clarity: Craft proposals that go beyond pricing and vague promises. Show immediate ROI and connect the dots to measurable business outcomes and ensure the path to success is obvious to those new to your offering. 3️⃣ Empower Change Champions: Equip champions to lead change confidently within their org. Identify where past solutions stalled and provide insights to drive adoption and maximize impact. Rainmakers collaborate with their champions on a mutual action plan - a treasure map - to help them improve the business. YOU are a Rainmaker. Let’s make it rain.

Sellers often mistake connections for relationships. Here are 5 ways you can build high-impact relationships, whether they’re specific to an opportunity, or they’re part of your greater network. ✅ Map out the relationships you have for a specific opportunity. I do an exercise with clients where we build out their relationship ecosystems and buying roles in an opportunity. This will give you a picture of strengths and gaps. Mapping your relationships doesn’t need to be time-consuming; it will pay off by helping you accelerate progress and reduce risks in your opportunities. ✅ Assess for gaps and get beyond the typical silos. You might be building relationships only where you’re most comfortable. Your success will be in getting beyond your comfort level; you can do that by assessing and filling in relationship gaps. In mapping your relationships you’ll see patterns. For example, you may see a pattern where you’re selling only one product or solution to one type of role. You’re siloed and likely missing many other relationships. This is especially important if your growth strategy includes expanding different products or services within your client base. ✅ Build your strategic alliances. This one strategy has made a significant difference in both the quality of my relationships and the quality of the opportunities I’m able to create. Do you have alliances outside of your organization, with other providers serving like clients? A way to begin is by creating a list of the tangential providers who sell non-competitive products or solutions to your clients and verticals. From there you can assess which ones are the most promising and begin building those relationships. ✅ Focus on deepening relationships with current clients. In the quest to always earn net-new clients, deepening relationships with current clients is often forgotten. But this can be the best source of continual, high-quality opportunities. One strategy is to create a list of your top ten clients and then create a relationship map for each one. See where you can uncover new relationships and new ways to serve that client. You’ll amplify your success with a client where you already have trust and credibility. ✅ Aim higher in the organization. You might be used to working in the middle of an organization, and in many cases that may be where your decision-makers are. But you can (and should) build awareness and relationships at the higher levels of an organization. Ways you might start this process include introductions on LinkedIn, sharing of research and insights that can improve their business, or a request for a higher-level leader to join your next account review or project meeting. To get started, choose one of your top clients and begin working through at least one or two of these strategies with that client in mind. It will undoubtedly open more relationships and also opportunities to serve your client and win high-value business. #ModernSeller #Sales #Relationships

✨Just wrapped up a coaching engagement that I can't stop smiling about 😄 When this sales rep first reached out to me, she was on a performance improvement plan 📉 and genuinely questioning whether she was cut out for sales. A veteran who'd been a top performer at previous companies, she was now missing quota for consecutive quarters at her new organization. "I'm doing everything the same way I always have," she told me during our first session. "But it's just not working here." That phrase – "the same way I always have" – was our first clue. After analyzing her approach, the pattern became clear. Her strengths had always been relationship-building and thorough discovery. Her previous companies sold complex solutions with long sales cycles where these skills shone 🌟. But her new company had a transactional offering with a shorter cycle, and her approach was creating friction rather than momentum. Instead of completely overhauling her style (which never works long-term), we identified specific micro-adjustments that would preserve her natural strengths while adapting to the new environment. 𝗪𝗲 𝗰𝗿𝗲𝗮𝘁𝗲𝗱 𝘄𝗵𝗮𝘁 𝗜 𝗰𝗮𝗹𝗹 "𝗣𝗮𝗰𝗲 𝗠𝗮𝘁𝗰𝗵𝗶𝗻𝗴" 𝘁𝗲𝗰𝗵𝗻𝗶𝗾𝘂𝗲𝘀  – ways to maintain her thorough approach but calibrate it to her prospect's buying velocity. For instance, instead of a comprehensive discovery, we designed a "Quick Discovery" framework focused on just three critical questions  with optional deep-dive paths depending on the prospect's engagement signals 𝗪𝗲 𝗮𝗹𝘀𝗼 𝗱𝗲𝘃𝗲𝗹𝗼𝗽𝗲𝗱 𝗮 "𝗩𝗮𝗹𝘂𝗲 𝗖𝗼𝗺𝗽𝗿𝗲𝘀𝘀𝗶𝗼𝗻" 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆  – ways to articulate complex value propositions in simpler, quicker formats without losing impact. This preserved her consultative approach while respecting the faster decision timelines. 𝙏𝙝𝙚 𝙢𝙤𝙨𝙩 𝙥𝙤𝙬𝙚𝙧𝙛𝙪𝙡 𝙘𝙝𝙖𝙣𝙜𝙚 𝙘𝙖𝙢𝙚 𝙬𝙝𝙚𝙣 𝙬𝙚 𝙢𝙖𝙥𝙥𝙚𝙙 𝙝𝙚𝙧 𝙣𝙖𝙩𝙪𝙧𝙖𝙡 𝙥𝙚𝙧𝙨𝙤𝙣𝙖𝙡𝙞𝙩𝙮 𝙨𝙩𝙧𝙚𝙣𝙜𝙩𝙝𝙨 𝙩𝙤 𝙨𝙥𝙚𝙘𝙞𝙛𝙞𝙘 𝙢𝙤𝙢𝙚𝙣𝙩𝙨 𝙞𝙣 𝙝𝙚𝙧 𝙣𝙚𝙬 𝙘𝙤𝙢𝙥𝙖𝙣𝙮’𝙨 𝙨𝙖𝙡𝙚𝙨 𝙥𝙧𝙤𝙘𝙚𝙨𝙨 —𝙬𝙝𝙚𝙧𝙚 𝙩𝙝𝙚𝙮 𝙘𝙤𝙪𝙡𝙙 𝙗𝙚𝙘𝙤𝙢𝙚 𝙨𝙪𝙥𝙚𝙧𝙥𝙤𝙬𝙚𝙧𝙨 𝙧𝙖𝙩𝙝𝙚𝙧 𝙩𝙝𝙖𝙣 𝙤𝙗𝙨𝙩𝙖𝙘𝙡𝙚𝙨. She quickly turned things around, exceeding her targets and regaining her confidence. The lesson that keeps proving itself true: Sustainable sales success rarely comes from completely changing who you are. It comes from strategically adapting your natural style to the specific environment you're selling in. Have you ever found yourself in a new role or company where your tried-and-true approaches suddenly stopped working? How did you adapt? 🤔 #SalesCoaching #PerformanceImprovement #SalesSuccess