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 😁

When a 6-figure deal is on the line,  what you say next matters. Most CEOs lose deals they could’ve won. Not because the price was too high.  Not because the product was wrong. But because they said the wrong thing (or nothing at all). Negotiation isn’t just a skill. It’s a leadership tool.  And every word matters. So I built a negotiation cheat sheet for leaders who can’t afford to lose the room. 14 high-impact negotiation phrases.  Plus, exactly what to say when you hear them used on you. Here’s the list: 1. “We’re ready to move fast if the terms are right.”  → “Let’s define ‘right.’ What’s most important to you?” 2. “What does success look like to you?”  → “Great question. Let me walk you through our goals.” 3. “We’re exploring a few options right now.”  → “What would it take to move us to the top of your list?” 4. “Can you walk me through how you got to that number?”  → “Sure. Happy to explain our value step by step.” 5. “That number just doesn’t work for us.”  → “Help me understand what you need to make this work.” 6. “Let’s make sure we’re solving the right problem first.”  → “Totally agree. Let’s align on the real goal here.” 7. “That’s outside the scope of this agreement.”  → “Would you like a separate proposal for that?” 8. “We’d need a little more flexibility here.”  → “What kind of flexibility are you hoping for?” 9. “We’re looking for a long-term partner, not a short-term fix.”  → “So are we. What would that look like to you?” 10. “We’re happy to move forward if X is included.”  → “If we do that, can we close today?” 11. “We’ll need internal sign-off before we commit.”  → “Of course. What concerns do they usually raise?” 12. “That’s a great point. Let’s talk about how we could meet in the middle.”  → “I’m open. What would that look like to you?” 13. “That feels like a win-win to me.”  → “Agreed. Let’s write it up.” 14. “We’ll need that in writing before moving forward.”  → “Of course. I’ll send it over now.” Save this.  Share it with your team.  Refer back before your next big conversation. It'll help you: Stay calm. Gain leverage. Lead with confidence. ♻ Repost to help a CEO in your network. Follow Eric Partaker for more on business strategy.

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?

17 years in tech sales taught me 17 truths nobody talks about at SKO: 1. Your biggest deals will come from the relationships you build when you have nothing to sell. 2. The top 1% don't work harder. They work at a higher altitude. 3. Every seller earning $1M+ has a side project. It's called investing 70% of their commissions. 4. Your manager's job is to hit their number, not develop your career. Take ownership of your growth. 5. The best time to negotiate your comp plan is after you've crushed your number, not before. 6. Panic attacks don't disqualify you from success. I had one in my first role. Still got nervous when I was making $1.5M. 7. Your personal brand is worth more than your President's Club awards. 8. If you're still still asked to meet activity metrics as a strategic seller, you're in the wrong company. 9. The sellers who retire early treat commissions like venture capital, not lifestyle upgrades. 10. Your introversion isn't a weakness. It's a $50M superpower waiting to be optimized. 11. Design thinking beats sales process every time. Whiteboards and narrative-driven business cases close more deals than PowerPoints. 12. The moment you stop checking your bank balance on Friday is when you've actually "made it." 13. Your quota isn't your goal. It's your baseline. Think 3x, not 1.2x. 14. Every company promising "uncapped earnings" has a secret cap. It's called territory reduction or account favoritism. 15. The future of sales isn't AI-proof. But strategic thinking is. 16. Your next role should optimize for learning, not earning. The money follows mastery. 17. Tech sales isn't a career. It's a 10-year wealth accelerator. Plan your exit from day one. Bonus truth they really won't tell you: The sellers who win long-term aren't playing the same game as everyone else. They're using sales to build something bigger. What game are you playing? 🐝 P.S. If these truths make you uncomfortable, good. Comfort is the enemy of the extraordinary career and life you can build.

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?

After 25yrs in sales here's 25 lessons i wish i'd learned sooner →Selling is simple. Not easy. →Deals die in vague next steps. →Stop pitching. Start diagnosing. →Mindset beats talent. Every time. →Pipe gen is THE most important skill. →If you’re single-threaded, you’re toast. →Emotion drives motion in deals →A ‘maybe’ is more dangerous than a ‘no’. →Multithreading isn’t optional. It’s insurance. →The person asking questions controls the call. →It’s not about your product. It’s about 𝘵𝘩𝘦𝘪𝘳 pain. →You can’t coach someone you don’t understand. →Selling to power is a different language. Learn it. →The first call matters. The follow-up matters more. →Buyers aren’t ignoring you. They’re overwhelmed. →Top reps do deep work: research, prep, reflection. →“Just checking in” is code for “I have nothing to say.” →If they say “we’re interested,” you’ve learned nothing. →Forecasting is mostly fiction without real qualification. →Internal selling is just as important as external selling. →The first-line sales manager job? Hardest in the game. →You don’t close deals. Customers do. You just guide them. →Most onboarding focuses on product. It should focus on buyers. →Champions can’t win you deals. But you can’t win without them. →You won’t lose a deal for asking a tough question — only for avoiding it. Some of these took years (and a few scars) to learn. If you’re new to sales — steal them. If you’ve been around the block — which ones resonate most? 👇 Add yours in the comments.

“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!

"We're moving forward with another vendor." Every rep's nightmare sentence. I pressed for details. "Their approach felt more open. We actually knew what we were buying into." That stung. I'd shared: ••• Exhaustive feature documentation ••• Dozens of success stories   ••• Complete pricing breakdowns Where'd I go wrong? Days later, I got access to our competitor's sales process. The difference hit instantly: They didn't preach transparency. They lived it. Their follow-up wasn't an email avalanche. It was one collaborative hub where buyers could: ••• Monitor which stakeholders engaged with what ••• See their exact position in the evaluation journey ••• Find materials curated for their unique pain points ••• Manage internal distribution seamlessly My revelation: I was buried in PDFs. They were cultivating partnership. Next prospect, new approach: I built a shared workspace exposing EVERYTHING: → Which team members on our side viewed their data → Critical docs they'd missed → Realistic implementation expectations → Where we excel AND where we don't The buyer's response: "Finally, someone not playing games." Ink on paper in 10 days. Here's what's real: Today's buyers aren't starved for data. They're starved for authenticity. Yesterday's strategy: Bombard with polished assets that sidestep weaknesses. Tomorrow's strategy: Build transparent environments that tackle doubts directly. Your buyers know when something's off. Even when nothing is. Quit running sales like a shell game. Start running it like a glass house. You with me?

Listen up. I’ve coached thousands of sales calls and most reps sabotage their own deals without realizing it. When I started in 2007, I nearly got fired for not understanding how language impacts buyer psychology. Now, after helping teams double revenue in 90 days, I can spot the hidden mistakes instantly. You're probably killing your win rate with these “harmless” phrases. Here are 6 phrases that are absolutely DESTROYING your deals (and what to say instead): 1) "Sorry to bother you..." Starting with an apology tells the prospect, “I’m not worth your time.” You’ve lost before you’ve begun. Top 1% performers NEVER apologize for delivering value. They command attention through absolute certainty. ✅ POWER MOVE: "Hey Alice, Marcus here from Venli. I'm reaching out because we helped Company X increase their pipeline by 37% last quarter, and I noticed your team might be facing similar challenges..." 2) "Just following up..." This lazy phrase screams, “I’ve got nothing to offer, but want your money.” Total momentum killer. Elite reps are wildly precise with their words and always reference specific commitments made in previous conversations. ✅ POWER MOVE: "Alice, you mentioned you were going to discuss our proposal with Charles during your leadership meeting yesterday. I'm curious … what feedback did you receive that we should address?" 3) "I know you're really busy..." Say this, and you’ve just made yourself irrelevant. Game over. Remember: YOUR time matters. Top performers signal status through subtle positioning every time. ✅ POWER MOVE: "I was just wrapping up a strategy session with Lisa, the CEO over at Company X, and wanted to quickly connect about next steps before my afternoon gets packed..." 4) "What are the next steps?" This signals poor process control - no system, no playbook, no real method. The sales machines I build don’t ask for direction - they GIVE it. They own the process. ✅ POWER MOVE: "Based on what we've discussed, here's what typically happens next: First, we'll schedule a technical review with your team for next Tuesday. Then, we'll deliver a customized implementation plan by Friday. How does that sound?" 5) "To be honest..." Wait, Wait... so everything before this wasn’t true? Nothing kills credibility faster. When I turn around failing sales teams, eliminating this phrase is always one of the first habits we break. ✅ POWER MOVE: "That's an excellent question, Alice. Here's exactly how our solution addresses that challenge..." 6) "What do I have to do to get your business?" Is this 1988? This pushy close screams desperation and kills trust instantly. The best reps I've coached understand that closing isn't an event. It's the natural outcome of a well-executed sales process. ✅ POWER MOVE: "It seems like you're hesitating about X. I'm curious … what specific concerns do you have that we haven't fully addressed yet?" Which of these six phrases have YOU been using without realizing it? 

Hey Salespeople: Do you truly understand the Challenger sales methodology (teach, tailor, take control)? It does not mean being aggressive. TEACH – Provide insights that challenge the prospect’s current thinking and help them see an unrecognized problem or opportunity. This approach positions the salesperson as a trusted advisor rather than just a vendor. Example: Instead of just pitching accounting software, show a CFO data revealing they're spending 40% more time on compliance than industry peers, costing them $200K annually in labor inefficiency. TAILOR – Customize the conversation to align with the prospect’s industry, company priorities, and individual stakeholder concerns. Example: When speaking with the IT Director, focus on integration and security features; with the CFO, emphasize ROI and cost reduction; with end-users, highlight ease of use and time savings. TAKE CONTROL – Taking control involves guiding the sales conversation confidently, addressing objections proactively, and steering the prospect towards a decision. This doesn't mean being aggressive, but rather being assertive and value-focused Example: After demonstrating value, saying "Based on what we've discussed, I recommend starting with our enterprise package at $85K annually. To hit your Q3 goals, we should begin implementation within three weeks. Does your team have the authority to move forward, or should we include someone else in our next conversation?"