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 😁

“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!

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? 

Most AEs I know want $300K+ W2s. Some dream of $1M. Yet most are stuck under $200K. 7 sales habits that made me 7 figures: 1. Learn your buyer so well you can peer into their soul. I had a VP of sales tell me this once after a pitch: "It's as if you're peering into my soul." That's the key to sales success, marketing success, product success. When you understand your buyer's hopes, dreams, fears, and frustrations like the back of your hand, magic happens. 2. Improve your business acumen, not just sales acumen. Ever notice when your CEO gets in a room with a customer's CEO, deals accelerate? It's not just peer-to-peer dynamics. It's business acumen matching business acumen. Study income statements, cash flow, balance sheets. Become a business professional who happens to know how to sell. 3. Fall like lightning. Money loves speed. Speed of execution, speed of response, speed of decision making. If you respond to customers fast, they mirror your speed. If you take two days to follow up, they'll take two days or more. Get in the habit of moving very fast. 4. Take a leadership position with your buyer. You've sold your product dozens, maybe hundreds of times. Your buyer has bought it zero, once, or twice at most. Who should be leading? Sales is an act of leadership. Always know the WHAT (next step), WHO (involved), and WHY (reasoning). 5. Surround yourself with sellers better than you. I was fortunate to join Gong and learn from Ryan Longfield, Kelly Wright, Justin Geller, and Jameson Young. You become like the five people you spend the most time around. Get around successful people and you'll automatically start to mimic them. 6. Work insanely hard. Hard work is an act of optimism. You believe the effort you put in today will pay off tomorrow. To get extreme results, you have to work extremely hard. Extreme people get extreme results. 7. Become so good they can't ignore you. Over-invest in your skill set. Read for 30-60 minutes every day.  Skills make you rich, theories don't. If you invest in building your skills for five years, I guarantee you'll wake up to a completely different life. 💡 Which of these 7 resonates most with you? P.S. I’m running a live Q4 masterclass for AEs and sellers: How to negotiate and close bigger deals, earn more commission, and avoid end-of-quarter hell. You’ll learn 7 elite negotiation strategies to grow (and protect) contract value and commissions even against savvy procurement pros. Grab a spot here: https://lnkd.in/ekUtg5rw

My best salesperson was struggling because she was selling so much and could not keep up with the paperwork. She sucks at the latter, but paperwork made sure there was follow-through for customers and payments are collected. Conventional wisdom suggests weaknesses offer growth opportunities. But instead of coaching her to eliminate the weakness, I hired an administrator to do the admin stuff. Why? Don’t ask a monkey to swim when they are at their best, swinging in the trees. For her, admin work is demotivating. She dislikes it, and it distracts her from perfecting what she likes best- sell! When we leverage our strengths, it feels natural. Marcus Buckingham advises employees to identify and cultivate their natural skills and advantages. “If you want to win, if you want to excel, if you want to stand out, you’re going to have to take the few unique things about you that are beautiful and powerful, and take them seriously, and turn them into contributions.” Here are some ways to operationalise Buckingham's advice. 1. Use self-reflection and feedback to identify your strengths. Then name them, and find ways to leverage these optimally for others and for yourself. 2. Learn from people who are great at leveraging their strengths. 3. Find ways of applying and adapting your strengths to new situations and in different circumstances. 4. Manage your weaknesses by eliminating them, and if not possible, minimising their impact so they are not derailers. # 4 resonates with me. A LinkedIn friend, Andy, messaged me about an error on my LinkedIn profile. It was a highly visible mistake, but I missed it! I told Andy my carelessness was what got me into trouble early in my career. In my first job, many were vying to join the Planning Division. I got it. But I did not realise my weakness would show up big time as the work involved writing policy papers that are discussed at the Board level. Every letter, word and punctuation mark must be in order. Not getting every fact on point is a career breaker. I can’t ignore my weakness. I must manage it. I tried many ways to overcome it, but nothing worked. My manager coached, but I was beyond help. I am surprised I did not have a breakdown! Finally, I realise I could not change myself. So I changed jobs. Instantly, because of different job requirements, my weakness was not a derailer, just an irritant. I leverage my strengths, gain confidence, and eventually, recognition. Back to the salesperson who dislikes admin work. She still dislikes it. She also got promoted and is leading a team, helping them sell, sell, sell. And she is still getting bonuses for doing something she loves - selling. And how is the admin staff doing? Very well! Every salesperson appreciates that he helps them shine. And he gets a share of the team's bonus. When people leverage their strengths, they look forward to work instead of worrying about mistakes they will make. Agree?

Career Acceleration in IT Services (2025) Stop selling hours. Start proving outcomes: A North American client asks, “What’s your day rate?” You answer, “$38/hr blended.” Then comes the new question: “Will you price on outcomes?” That’s the market telling you how to grow ... or get squeezed. - Hours are a commodity. - Outcomes are the currency. - Evidence is the new margin. What this means for your career (not just your firm) 1. Your comp will track outcomes, not effort. Rate cards are flattening. People who prove impact get paid more, faster. 2. AI shifts the bar. Run-work deflates; transformation gets the money. Learn to move KPIs, not tickets. 3. “Full-stack thinking” wins. Build + guide + manage in one flow. Tools help. Judgment differentiates. 30-Day Acceleration Plan (simple, measurable) 1. Pick one KPI you can move. Examples: cut incident time-to-resolve by 30%, raise conversion by 10%, reduce cloud cost by 15%. Done when: you have a Day-0 baseline and a 30-day target. 2. Design a tiny outcome offer. One KPI delta. One timeline. One fee/bonus at risk. Done when: your proposal fits on one page. 3. Instrument truth. Set up weekly value snapshots (before/after chart + 3-line note). Done when: a shared doc auto-updates every Friday. 4. Ship a thin slice with AI assist. Use AI for speed (scripts, summaries, evals). Keep humans on judgment. Done when: one shipped change is live and measured. 5. Publish your Outcome CV. Replace “responsibilities” with “before → after → time.” Done when: you have 3 entries with numbers your manager/client can verify. Role examples (steal one) BA: “Reduced handoff cycle from 5 days to 2 by AI-drafted specs + review checklist.” QA: “Cut escaped bugs 40% using risk-based tests + AI log triage.” Designer: “Onboarding redesign lifted Day-7 retention from 22% → 31%. Built with AI copy drafts, human fix.” DevOps: “Cloud cost −18% via right-sizing + spot strategy.” Data/ML: “Re-ranker raised trial-to-paid by 9% in 21 days. GPU hours tied to uplift.” Avoid the traps - AI-noise: copied prompts without understanding. - Sunk-tool fallacy: using a tool because you bought it. - Vanity latency: microsecond wins no one feels. Negotiation script (use it) "Rather than $38/hr, let’s run a 30-day pilot tied to [KPI]. If we hit [target], you pay [fee] + [at-risk bonus]. If we miss, you pay [lower floor]. Weekly snapshots, pre-agreed dispute resolver." Are you still quoting hours in 2025 - or are you proving outcomes? Comment “OUTCOME CV” and I’ll send a 1-page template (baseline, snapshots, before/after bullets, proof line). #DhandheKaFunda: Your degree won’t save you. Your AI-accelerated craft may. In a deflationary services market, evidence is the new margin.

I am wrapping up our hiring process for our first two sales roles at Lawfully. We had over 700 applicants apply—standing out isn’t easy. For these roles I was the recruiter, hiring manager, and executive sponsor. Here’s my advice on how to stand out: Getting Through to the First Stage— 1. Reach out directly to the recruiter, hiring manager, or executive sponsor I gave priority to candidates who reached out personally. Some sent LinkedIn DMs, while others crafted thoughtful cold emails. Two memorable examples: one email had the subject line “Matt, I’m skiing my way into your inbox,” and another featured a personalized video introducing herself and addressing common interview questions. Make sure your outreach is thoughtful, creative, and mindful of people’s time. Done right, it sets you apart Done poorly, it can backfire. 2. Make your Linkedin look professional Many applicants had unprofessional profile photos, large employment gaps, or short stints at companies. While you shouldn’t judge a book by its cover, with 700 applicants to review, these things can quickly lead to being passed over. You control your LinkedIn narrative and the professional story it tells. Demonstrate to recruiters that you can commit and follow through. 3. Use the right professional jargon. For this SDR role, candidates with SDR experience were fast-tracked to interviews. Ensure your job titles and descriptions align with industry standards to avoid being missed. Make it clear what you do, especially if your role mirrors the position you’re applying for. Getting Through the Interview Stage— 1. Research the company before your interview. Out of 60 people I interviewed, only one could identify our competitors, and few provided detailed responses about our products and services. One candidate couldn’t name a single thing about Lawfully, while another was clearly reading straight off our homepage. Take the time to learn about the company. It shows genuine interest and sets you apart. 2. Answer all the questions. I evaluated candidates on several criteria, including experience, passion, coach-ability, and their ability to learn. To gauge learning, I asked their favorite books—professional or otherwise. If someone admitted they didn’t read, it was a quick signal to move on. 3. Answer positively and tie it back to the role and your strengths. Strike the right balance between positivity and authenticity. Candidates who dwelled on negative experiences sent a clear sign they weren’t the right fit. 4. Align your answers with company & hiring manager goals When candidates nailed this, they were an automatic pass. One standout example was a candidate who asked about our goals right at the start of the interview. Throughout the conversation, he consistently explained how he would help us reach our milestone. I’ve got 20 more tips to share—including what it takes to crush the final round. Drop a comment, and I’ll send them your way!

In today’s competitive job market, great candidates get overlooked all the time—not because they lack skills, but because they don’t know how to stand out. If you want recruiters and hiring managers to notice you, remember you, and hire you, focus on these three game-changers: 1️⃣ Go Beyond Job Applications ❌ Mistake: Submitting applications and waiting for a response. ✅ Strategy: Leverage networking, referrals, and direct outreach to bypass the black hole of online applications. 💡 Tip: Instead of applying cold, find someone inside the company (a hiring manager, recruiter, or peer) and send a thoughtful message: 📩 “Hi [Name], I’m really interested in [Role] at [Company]. I’d love to hear your perspective on what makes someone successful in this team. Would you be open to a quick chat?” This humanizes your application and makes it easier to land an interview. 2️⃣ Position Yourself as the Best Fit ❌ Mistake: Listing responsibilities instead of results. ✅ Strategy: Make your resume and LinkedIn profile a magnet for opportunities by showcasing impact. 💡 Example: ❌ “Managed customer accounts and improved retention.” ✅ “Led customer success efforts for 50+ clients, increasing retention by 30% and driving $1.2M in revenue.” Your resume should answer: Why should they hire YOU? 3️⃣ Interview with Confidence & Clarity ❌ Mistake: Rambling or underselling yourself. ✅ Strategy: Use the STAR method to tell compelling stories and practice speaking with impact. 💡 Example: Instead of vaguely saying “I helped launch a new product,” try: 🎤 “I led the launch of [Product], managing a cross-functional team and driving a 40% increase in adoption within 6 months.” ➡ The clearer your value, the easier it is to hire you. 🔥 Bottom Line: 📌 Stop relying on job boards—network strategically. 📌 Show impact, not just experience. 📌 Nail your interview with strong, structured answers. 🚀 The right approach makes you the candidate they can’t ignore. 👉 Found this helpful? Reshare to help others in their job search!

Success in sales isn’t about luck or timing—it’s about ownership, discipline, and consistency. I see it all the time: salespeople wait for the “perfect moment” to reach out, or they think too much instead of taking action. Here’s the truth—the only bad call is the one you never make. Prospecting isn’t something you do “when you have time.” It’s a daily habit, like a muscle that gets stronger the more you work it. The more consistent you are, the more momentum you build, and the more confidence you gain. Planning ahead matters too. End your day by mapping out tomorrow—who you’ll reach, what your message will be, and what the next step looks like. Preparation removes hesitation and keeps you moving forward. Every interaction should bring value. Don’t just sell features—help your prospects think differently about their business. Follow up, bring insights, and show them you understand their challenges. And above all, check your attitude. Focus on helping others succeed, and your results will follow. Success in sales isn’t given—it’s earned by showing up, taking action, and creating momentum every single day.

Are your salespeople covered in Band Aids? Too often, sales leaders are on the hunt for the quick fix. The “Band Aid” solution. We study harder. We memorize scripts. We push product knowledge into our reps until they can recite it backwards and forwards. And for a while, it works. But here is the problem: Band Aids always fall off. They cover the wound, they buy us time, but eventually, we need another one. In sales, that means temporary bumps in performance but not real transformation. Here is the truth. If your sellers only learn to regurgitate product details, you are training them to compete in the most transactional game possible. And in today’s world, transaction alone will not win. Buyers expect more. They need more. Imagine this instead. What if your sellers not only knew the product inside and out, but also knew how to truly communicate? I mean really communicate, in a way that makes the person on the other side of the conversation feel seen, heard, and connected. That is not a Band Aid. That is a root solution. That is the kind of capability that does not peel away with the next quota cycle. When sellers learn to connect at the human level and deliver the product knowledge with clarity and confidence, the outcome is predictable: Stronger trust Shorter sales cycles Deeper relationships Sustainable growth No more Band Aids. Just real sales transformation. If you are a sales leader, ask yourself: are you training your people for the quick fix or equipping them for lasting change?