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 😁

I used to count every "no" in sales like they were failures. Big mistake. After thousands of rejections, here's what I've learned: Each "no" isn't pushing you further from success. It's pulling you closer to your next "yes." Think about it... My worst sales day ever? 47 straight rejections. My best sales day ever? The very next day. Why? Because those 47 "no's" taught me EXACTLY what wasn't working. Here are 5 truths about rejection every salesperson needs to hear: 👇 1. It's NEVER personal (even when it feels like it is) They're not rejecting YOU. They're rejecting the timing, the budget, the priority. I once had a prospect tell me to "never call again." 6 months later? They became my biggest client. Their situation changed. Not me. 2. Most people don't know they need help Your job isn't to convince everyone. Your job is to help people realize their problems. ↳ They think their process is "fine" ↳ They don't see the inefficiencies ↳ They're comfortable with mediocre Sometimes a "no" is just "I don't understand yet." 3. Motivation can't depend on outcomes Lost a deal? Your energy stays HIGH. Got ghosted? Your enthusiasm stays STRONG. Faced rejection? Your optimism stays INTACT. Because here's the truth: The prospect who needs you most might be your next call. Don't let the last "no" rob them of your best effort. 4. Your perfect customers are out there Not everyone needs what you sell. But someone desperately does. While you're wasting energy on the wrong prospects, Your ideal customer is struggling without your solution. Every "no" gets you closer to finding them. 5. Remember your wins For every rejection, someone said "yes." For every slammed door, another opened. For every lost deal, you've transformed a business. Keep a "wins folder." Screenshots of thank you emails. Messages from happy customers. Success stories you've created. Open it after tough days. Here's what changed everything for me: I stopped seeing "no" as failure. I started seeing it as data. No budget? Note it. Move on. Wrong timing? Calendar it. Follow up. Not interested? Perfect. Next. Because rejection in sales isn't a wall. It's a filter. It filters out the wrong fits. It filters out the bad timing. It filters out the mismatched needs. Until all that's left... Are the people you can actually help. So the next time you hear "no"? Don't slump your shoulders. Square them. You're not failing. You're filtering. And your next "yes" just got closer.

Your title doesn’t make you a leader. Your actions do. And no actions speak louder than how you treat your team. The wrong ones cut them down.  The right ones lift the up. Here’s how great leaders ALWAYS say the right things:  (and 10 phrases that backfire) 1. ❌ "Let me know if you need anything." ↳ Puts the burden on them to ask for help. ✅ "I'll check in with you Thursday on [specific challenge]." ↳ Makes support proactive and actionable. 2. ❌ "Who dropped the ball here?" ↳ Sparks blame instead of solutions. ✅ "Walk me through what happened so we can prevent this next time." ↳ Encourages learning and accountability. 3. ❌ "We've always done it this way." ↳ Shuts down innovation. ✅ "Help me understand what you're seeing" ↳ Invites fresh ideas and perspectives. 4. ❌ "That's not your job." ↳ Stifles initiative. ✅ "I appreciate you spotting that. Let’s discuss how to handle it." ↳ Encourages ownership and collaboration. 5. ❌ "You should have..." ↳ Creates shame and defensiveness. ✅ "Next time, what if we try...?" ↳ Keeps feedback future-focused and constructive. 6. ❌ "I don’t have time right now." ↳ Makes people feel unimportant. ✅ "I want to give this the attention it deserves." ↳ Shows you care while setting clear expectations. 7. ❌ "Just figure it out." ↳ Creates stress and isolation. ✅ "What part are you stuck on? Let’s break it down together." ↳ Supports problem-solving without micromanaging. 8. ❌ "That’s a bad idea." ↳ Shuts down creativity. ✅ "What problem are you trying to solve?" ↳ Encourages discussion instead of dismissal. 9. ❌ "I'm disappointed in you." ↳ Triggers shame and damages trust. ✅ "I know you can do better. What do you need?" ↳ Maintains high standards while offering support. 10. ❌ "Because I said so." ↳ Kills buy-in and motivation. ✅ "Let me share my thinking on this." ↳ Builds trust through transparency. The best leaders know: It’s not just what you say, it’s how you say it. What’s your take? ♻️ Repost to help others  🔔 Follow Dave Kline for more.

Salespeople at firms with more flexible working policies grew sales 4 times more than those without.  The biggest challenge of assessing flexible working is the nebulous task of measuring productivity.  That’s why a huge piece of new research from Boston Consulting Group is so valuable. The study took data from 554 large companies (employing a total of 26.7 million people). It found that “fully flexible” firms — increased sales four times faster than those with more rigid policies. Flexible firms grew sales 21% between 2020 and 2022 compared with 5% growth for companies with rigid hybrid or fully onsite workforces.  The firms that only did a few office days a week grew sales at x2 the rate of those in the office full-time. More than anything this demonstrates the more workers feel trusted to do their work in the way that suits them best the better the results. If only every job role was as measurable as sales. https://lnkd.in/gSZtnMgf

Confession time: As a leader, I often get asked if I'm more intuitive or calculative in my decision-making. The truth is, it's a bit of both. Recently, we were in the middle of expanding our vendor partnerships at Falabella, and an opportunity came up with a key supplier. The catch? We had only 72 hours to decide before a competitor could swoop in. My gut told me this partnership was the right move—it aligned with our long-term goals, and the supplier's reputation was solid. But I couldn’t just go off instinct. I called an emergency meeting with my team. We reviewed everything—from the supplier’s past performance to our budget forecasts and potential market shifts. I knew we had to move fast, but I wanted to make sure every angle was covered. In the end, the numbers confirmed what my instinct was already telling me—I made the call to sign the deal. Looking back, it wasn’t just about moving quickly—it was about being decisive with the right balance of instinct and analysis. In moments like this, I make sure to keep a few things in mind: > First, while my decisions are based on facts, I never forget the human side—how my choices impact my team, my partners, and the people around me. > Second, I’m constantly aware that leadership is as much about people as it is about strategy. > Finally, it's important to act swiftly but thoughtfully, blending instinct with calculated risks. What about you? Do you lean more toward intuition or calculation when making decisions?

Last week I spoke to a CRO who's team hit 225% of quota in Q3 ($74M - 80% of which came from his enterprise team) and won two new logos from Fortune 100 companies. Here are the 8 strategies he implemented to help get them there: 1. Hired senior sellers and directors who know the complex sale and pay them aggressively. He bought years of experience instead of trying to figure out true enterprise selling on the fly. This led to more near term success with large enterprises. 2. Got his internal executives on board to play cameo roles in strategic parts of important sales cycles. 3. Attracted board of advisor members who are mega-connected in the industries his team sells to. Their role is 100% to open doors at the executive level. 4. Gave sellers controlled access to board of directors / board of advisors to coordinate executive introductions. 5. Created multiple paths to executive engagement: - Produced serious, data driven thought leadership content. (Ungated industry surveys and benchmark studies). This kind of thought leadership is how to “sell without selling” at the highest level. - Convinced his CEO to become prolific on LinkedIn and Twitter. To see this play in action, watch CEO’s like Jason M. Lemkin and Sam Jacobs as they speak to their audiences every day (multiple times a day). And for a masterclass in gaining a followership, follow the queen of mindshare, Arianna Huffington. - Sponsors quarterly executive roundtables (execs only, no sellers involved - they engage later) 6. Built out a high-quality internal Value Engineering team. Solid business cases built on customer-derived assumptions are the currency your champions need to get buy-in for big purchases. 7. Built a Key Account program which gives marquee accounts special access to resources and (some) influence on product roadmap. The more special your big accounts feel, the stickier the relationship and the more TAM you can earn across their organizations. 8. Implemented governance structures with large customers. A good governance structure is a series of pre-agreed meetings throughout the year at different levels in the organization to care for and feed the relationship. The CRO told me, “Having a governance structure in place saves my sellers from having to chase meetings all the time and brings customer executives to the table for more strategic conversations.” It is these strategies (and more) which I teach in the Mega Deal Secrets Masterclass. If you are a sales leader looking to build a leaner, more efficient ENT selling capability, DM me to discuss. #sales #enterprisesales

If I were 27 and wanted to become a VP of Sales by 31, here’s exactly what I’d do: This isn’t theoretical. It’s based on me doing nearly all of these things and watching the people who actually got promoted...and the ones who didn’t. Let’s go 👇 1/ Meet with 1-2 VPs or CROs outside your company every week. Talk with them. Ask real questions. Don’t just send cold connection requests. Most people love helping someone who's curious and serious 2/ Say YES to helping your peers. Jump on a call. Listen to their calls. Share a few things that helped you. If you say, “Let me know how I can help,” and never do anything... don’t bother 3/ Learn to read a company’s financial statements. I loved monthly exec finance reviews because I understood them and could ask smart questions. Most sellers have no clue. Be the one who does 4/ Master SaaS metrics. Know CAC, LTV, CAC Ratio, burn rate. Understand why these matter before you're managing a $20M sales team quota 5/ Learn how to interview. I read 5+ books on it early in my leadership career and wished I had done it years earlier. Want my top 5 recs? Drop a comment and I’ll share 6/ Ask to be part of hiring. Volunteer to sit in on interviews. Share what you’re learning. This shows initiative and earns trust with leadership 7/ Make sure your boss and their boss KNOW you want to lead. Don’t assume they can read your mind. Say it clearly. Then go earn it, don't wait for it to drop into your lap 8/ Get ridiculously good at spreadsheets. If you don’t know VLOOKUP, SUMIF, or pivot tables, fix that fast. You’ll use these almost daily in sales leadership esp at startups 9/ Get certified in your CRM. Learn how to create reports and dashboards. Most reps don’t do this. That’s why they stay reps 10/ Track your own funnel metrics, primarily conversion rates. Find weak spots. Write up a Google Doc with your own plan to improve them. Then… go do it 11/ Meet people in Marketing, CS, Legal. Learn how they work with (or against) Sales. Future VPs know how to navigate cross-functional bull$h|+ 12/ Practice clear, succinct writing. Execs don’t read 5-paragraph essays. Send the TLDR version. Rambling, bloated messages won’t cut it 13/ Read 12 business or leadership books a year. Apply just 5% from each. You’ll lap most people who "are too busy" to read. Ask me for recs in the comments 😡 There's nothing I hate more than a rep that asks to be promoted to sales leadership, sticks their hand out but then does nothing proactively on their own. Yes, these can be hard and take extra time esp when you're tired. But most salespeople won't even do 3 things on the list above & then wonder why they're not getting promoted. What's 1 other thing people should do to increase their chances of getting into sales leadership?

The sales leaders of the future won't be hired for their ability to close deals. They'll be hired for their ability to build systems that close deals at scale. This shift is already happening. The VPs and CROs getting hired right now aren't the ones with the best Rolodex or the smoothest demo skills. They're the ones who can answer: → What does good look like here? → Why does it work? → How do we replicate it across the team? They're system builders. Process architects. Pattern recognizers. And here's why this matters more than ever: You can't deploy AI into your org if you don't know what works. AI needs context. It needs logic. It needs the "why" behind the "what." If you can't explain why your top rep wins, you can't train AI to do it. If you can't document your sales process, you can't automate it. If you don't have an operating system, AI just amplifies chaos. The sales leaders of the future are context experts. They don't need to be engineers. But they need to know what's possible. They need to understand what Claude, GPT, and Gemini can actually do — so they can direct their teams and rev ops on how to build things the right way. This isn't coming. It's here. And if you're a current VP or CRO who still thinks your job is to "be in the room" for big deals... You're about to get lapped by leaders who've built machines that work without them. If you're an aspiring sales leader wondering what skills to develop... Stop obsessing over your pitch. Start obsessing over your systems. Learn how to document what works. Learn how to build repeatable processes. Learn what AI can do — and how to deploy it. That's the new job description. The leaders who figure this out will scale. Everyone else will wonder why they got passed over. PS - This is exactly what I teach in the Sales Leadership Accelerator with the Sales LeadershipOS — how to build the systems, processes, and operating rhythm that separates good leaders from great ones. https://lnkd.in/ejPDhZw4

Last week, I was asked "What are the top 5-10 skills of $1M income salespeople?" 90% of salespeople can't answer this. They usually stop at 3-4. Here's the top 10: 1. VALUE-CREATING Discovery. I'm not talking about the "typical" discovery most salespeople do (the kind every buyer hates). I'm talking about the kind that actively creates value for your buyer. The kind where you leave them off better than how they entered the disco call. 2. Business Acumen. Business acumen makes all your other sales skills twice as valuable. That's what we call a "threshold skills." When you improve your business acumen, you automatically get better at discovery, negotiation, prospecting, and more. 3. Negotiation. The richest people in the world are deal-makers. That's not a coincidence. Likewise, the highest paid salespeople are deal-makers. They can negotiate with or without their boss in the room with them. 4. Stakeholder Management. This includes finding (and creating champions). Strategic (rather than random) multi-threading. And accessing Power. In short, this is intentionally managing the "blend of people" involved on the buyer's side. 5. Pipeline Generation. Goes without saying. The person who can feed their own top of funnel control their destiny. They can write their own check. You're not truly in control of your destiny until you can do this. 6. Insightfulness. Great salespeople know their space. They use that knowledge to teach their buyers to think differently about the problem at-hand. This dramatically improves their credibility. It also "rigs" the deal in your favor. 7. Storytelling That Creates Epiphanies. Not just any old storytelling. Storytelling that changes how people think and feel about their situation. Storytelling that leads to epiphanies. You can't convince someone into an epiphany. Because you can tell a story that they can see themselves in. 8. Mastery Over Your Market. When you know your buyers so well you can write a page from their journal, you're golden. What are their hopes, dreams, desires, fears, frustrations? What are the conversations they have going on in their heads? Learn this. Pays huge dividends. 9. Ability to Learn, Un-Learn, Re-Learn. Market conditions change faster than most of our skills evolve to meet them. The top producer of tomorrow is learning the new and different skills that tomorrow will demand. 10. Social and Emotional Intelligence. Obviously, if you have all of the above skills, but you cannot interact with another human to save your life, they aren't worth much. The good news is you can learn emotional intelligence. The bad news is it takes SOME emotional intelligence to learn it. What would you add to the list? P.S. Take the first step and turn discovery calls into paying customers with these 10 discovery scripts: https://lnkd.in/dSPMU5SM

“Sales is not relevant to me, I am in [Function other than sales].” Raise your hand if you've ever thought this way. I would be the first one to raise my hand - dismissing sales as irrelevant to my role in tech. Early in my career, the very word 'sales' conjured images of a sleazy car salesman trying to sell me unnecessary options for my new vehicle. As my career progressed, however, my perspective started to shift. I realized that sales is far more than just transactions and numbers. It's about building relationships, understanding deep-seated needs, adding value and offering meaningful solutions. Sales acumen, I discovered, is like financial literacy – a universal, indispensable skill that transcends job titles, experience levels and functions. To demystify sales and showcase its broad relevance, I reached out to my friend Aaron Norris, a former Principal Account Exec at Amazon Web Services. He is now dedicated to advancing the careers of Account Execs, focusing on long-term happiness, health, and wealth. Here are 5 invaluable tips he shared with me on how sales skills can benefit any role: 1. Discovery: Identifying and understanding your customer's top priority challenges and designing unique value-adding solutions is critical in sales. This is not a one-time effort rather an ongoing process of research, obtaining insights, collaborating and establishing feedback loops to deliver the right solutions and delight customers. 2. Stakeholder Engagement: Adapting the narrative, style, channel and frequency of messaging enables sellers to effectively engage with and obtain buy-in from internal and external executives, technical, and business stakeholders at various levels. 3. Influence: Effective influence in sales hinges on clear, honest communication and a deep understanding of customer needs and team dynamics. It's about building trust by consistently delivering on promises and showing commitment to customers’ and colleagues' success. This approach not only drives decision-making but also strengthens team collaboration, accounting for their unique skills, needs and interests. 4. Resilience: Navigating a high-pressure and target-driven environment, sales professionals often face rejection and must rebound after losses. To remain composed and resilient during challenging times, they prioritize customer focus, engage the executive team early, and make decisions with a long-term perspective. 5. Relationship Building: Building authentic relationships in sales requires prioritizing your customers' success over closing a deal. It involves becoming their most trusted advisor by investing time in building the partnership, understanding their goals and strategy, providing value at every opportunity, and celebrating their wins. Looking for additional insights on the topic? Follow Aaron. He posts daily on the topics of enterprise sales, personal development and leadership. PS: Just for a bit of fun, share a ‘sales horror story’ below!