How to Avoid Common Sales Mistakes for Growth

Founders, avoid these 5 common sales team blunders! Having built sales teams from scratch at 3 companies, here are key pitfalls to steer clear of: 1️⃣ 𝗧𝗵𝗶𝗻𝗸𝗶𝗻𝗴 𝘆𝗼𝘂 𝗰𝗮𝗻 “𝗼𝘂𝘁𝘀𝗼𝘂𝗿𝗰𝗲” 𝘀𝗮𝗹𝗲𝘀 𝗳𝗿𝗼𝗺 𝗱𝗮𝘆 𝗼𝗻𝗲 Early-stage sales require founder involvement. You need to understand your market, refine your pitch, and develop the playbook. No hired gun can replace your passion and product knowledge. 2️⃣ 𝗛𝗶𝗿𝗶𝗻𝗴 "𝗽𝗿𝗼𝘃𝗲𝗻" 𝘀𝗮𝗹𝗲𝘀 𝗿𝗲𝗽𝘀 𝗳𝗿𝗼𝗺 𝗯𝗶𝗴 𝗰𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀 Startup sales in the initial days are hard, especially B2B sales. Why would a business want to take a chance buying from an unknown company? Sales reps from big companies had it relatively easy selling a well-established product. Instead, hire scrappy self-starters who had to sell more “difficult” products. When they join you, your product would seem easier to sell. 3️⃣ 𝗛𝗶𝗿𝗲 𝚘̲𝚗̲𝚎̲ 𝗳𝗶𝗿𝘀𝘁 𝘀𝗮𝗹𝗲𝘀 𝗿𝗲𝗽 Hiring 1 sales rep to start does not save you money or time. You won’t be able to conduct an A/B test to see what works. If the 1 sales rep you hired did not work out, you’d never know if there was an issue with the sales rep or your sales process. The magic number is 2. Hire 2 of them so you can quickly figure out what is working. 4️⃣ 𝗦𝗲𝘁𝘁𝗶𝗻𝗴 𝗶𝗻𝗰𝗲𝗻𝘁𝗶𝘃𝗲𝘀 𝗮𝘀 𝗮 𝗳𝗹𝗮𝘁 % 𝗼𝗳 𝘀𝗮𝗹𝗲𝘀 There are 2 problems with setting incentives as a flat % of sales - a) it becomes difficult to budget and hold sales reps against targets, b) in the early days, you’re trying to figure out what is a “correct” sales target and may risk giving up too much value. My personal favorite is the OTE (On-Target Earnings) model that is adjusted quarterly. 5️⃣ 𝗕𝗲𝗶𝗻𝗴 "𝗵𝗮𝗻𝗱𝘀-𝗼𝗳𝗳" 𝗮𝗳𝘁𝗲𝗿 𝗵𝗶𝗿𝗶𝗻𝗴 𝗮 𝘀𝗮𝗹𝗲𝘀 𝗹𝗲𝗮𝗱𝗲𝗿 Your involvement remains crucial. As a founder, you are always selling. Conversations with prospects and customers provide you a chance to share your product vision and continuously gather feedback for your product. So, stay connected to the front lines, join key meetings, and continually engage your customers. Every customer loves to speak with the founder of the company ;-) 🔥 Which one surprised you most? Comment below! 👉 Want to dive deeper into building a killer sales team? Let's connect! #Sales #StartupSales #SalesLeadership #FounderTips

I’ve built 4 sales orgs and led sales going from $1M-100M in ARR. I made every mistake in the book. If I had to do it all over again, here are the 5 biggest landmines I’d make sure to avoid: 1. YOU CAN’T FIX A BAD FIT; YOU CAN RUIN A GOOD ONE: Hire right, and you can tweak and adjust with leadership and process; hire wrong, and no amount of leadership or process will save you. However, even the best AEs fail without clear processes, coaching, and a collaborative culture. Hiring right builds a good team; leadership and process make it world-class. Do both—or fail. 2. DON’T BE FOOLED BY ‘CLOSERS’: “Closer” is not a skill—it’s an outcome. Struggling to close isn’t about needing smooth talkers; it’s a full-deal execution problem. Top AEs set deals up to close themselves with curiosity, empathy, project management, grit, and problem-solving. Avoid aggression, excessive confidence, or pressure tactics; Hire AEs who make buying feel easy. 3. SCALING GETS MESSY; EXPECT IT: Growth breaks things—reps lose coaching, playbooks dilute, morale dips and leads become less effective. Plan for buffers, build resilience and expect things to go wrong. Chaos is inevitable; embrace it and prepare. 4. DIMINISHING RETURNS WILL HAUNT YOU: What works at Series A won’t at Series B+. The bar rises—bigger accounts, multi-year deals, no discounts, and quality must stay high. Scaling means sprinting while running a marathon. Evolve your sales motion—or fall behind. 5. CULTURE WILL MAKE OR BREAK YOU: At 5 people, culture is organic; at 50, it’s intentional. Avoid silos, lone wolves, and toxic “sales bro” culture. Build collaboration-first environments with trust, learning, and team success. Culture isn’t “Friday beers”; it’s where teams thrive. Build it—or lose them. —— Building an elite sales team is tough. Feels like sprinting a marathon. We all make a TON of mistakes. I know I have. Just don’t stop. And never beat yourself up. Innovate. Learn. Improve. Keep pushing forward. Adopt this mindset for 2025, and you’ll be just fine. 🤟

Most salespeople lose deals. Not because of the competition. Because of these 6 mistakes. I've watched it happen for 35 years. The same 6 mistakes. Over and over again. Here are the mistakes salespeople make. 𝟭. 𝗧𝗵𝗲𝘆 𝘁𝗮𝗹𝗸 𝗮𝗯𝗼𝘂𝘁 𝘁𝗵𝗲𝗺𝘀𝗲𝗹𝘃𝗲𝘀. The buyer doesn't care about your product, your company or your quota. They care about their problems. The moment you make the conversation about you — you've lost them. 𝟮. 𝗧𝗵𝗲𝘆 𝘁𝗮𝗹𝗸 𝘁𝗼𝗼 𝗺𝘂𝗰𝗵. The best information in that room is sitting across the table from you. But you'll never hear it if you never stop talking. Ask. Then listen. Really listen. 𝟯. 𝗧𝗵𝗲𝘆 𝗱𝗼𝗻'𝘁 𝗺𝗼𝗻𝗲𝘁𝗶𝘇𝗲 𝘁𝗵𝗲𝗶𝗿 𝘃𝗮𝗹𝘂𝗲. Customers don't buy ideas. They buy outcomes. If you can't connect your solution to their revenue, their costs, or their profit — you're just noise. Show them the money. 𝟰. 𝗧𝗵𝗲𝘆 𝗮𝗿𝗲𝗻'𝘁 𝗽𝗿𝗲𝗽𝗮𝗿𝗲𝗱. Nothing signals "I don't respect your time" faster than showing up without doing your homework. Know their business. Know their market. Know their challenges. Before you walk in the door. 𝟱. 𝗧𝗵𝗲𝘆 𝗱𝗼𝗻'𝘁 𝗳𝗼𝗹𝗹𝗼𝘄 𝘂𝗽. The deal doesn't go cold because the customer lost interest. It goes cold because you disappeared. Follow up is your job; not theirs. A written recap with clear next steps — within 24 hours. Every time. 𝟲. 𝗧𝗵𝗲𝘆 𝗻𝗲𝘃𝗲𝗿 𝗳𝗶𝗻𝗱 𝘁𝗵𝗲 𝗿𝗲𝗮𝗹 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗺𝗮𝗸𝗲𝗿. You can have the perfect solution and still lose. If the person saying yes can't really say yes — your deal is already stuck. Ask the uncomfortable questions early. It's always easier before the stakes get high. 35 years. Thousands of deals. Same mistakes. The good news? Every single one is fixable. 💬 Which of these have cost you the most deals?    

I’ve made every one of these mistakes myself. The difference between those who plateau and those who win consistently comes down to one thing: They recognize the mistake, correct it, and keep sharpening. Here are the biggest traps I see sellers fall into (including me) and what to do differently: ⏳ Treating all deals the same I used to chase everything with the same intensity. A $1K deal got the same effort as a $1M strategic relationship. That is not strategy. Prioritize the mountain-moving opportunities. Scale or eliminate everything else. 📩 Weak follow-up A great meeting means nothing without momentum. After every call: Follow up fast Recap decisions Identify the next step and owner If you wait, interest fades and doors close. 🗓️ Living in meetings that don’t matter I’ve sat in weekly syncs that added zero value. Take a balcony-view of your calendar and ask: Does this move pipeline, relationships, or revenue? If not, remove it. 📢 Sounding like every other seller Your prospects are drowning in noise. Show up with something useful, not generic. Ask yourself: Does my message teach them something new? Am I bringing a unique point of view? Sales is not persuasion. Sales is leadership. 🗣️ Talking more than you listen The customer should be talking more. Always. Ask real questions and sit in the silence. They will tell you what they care about if you let them. 💰 Selling on price instead of value If value is clear, price is secondary. Focus on the pain, the cost of doing nothing, and the measurable change you create. 🚀 Trying to win alone Sales looks individual on paper, but the best deals are won by a team. If you need help, ask. If you learn something, share. No heroes. Just collaboration. 📚 Standing still The moment you stop learning is the moment someone else passes you. Study the people who are winning. Copy nothing. Learn everything. The game is simple. Control your time. Communicate with clarity. Stand out. Get better every single day. What’s the biggest sales mistake you see most often — and how do you fix it?

Nobody talks about the deals they lost. So I will. Here are 3 sales mistakes I made that cost me 7 figures in revenue:   1. I chased every lead the same way. I didn’t qualify hard enough. I treated “interested” as “ready.” Result: bloated pipeline. Wasted time. No close. 2. I pitched too soon. I wanted to impress, not understand. So I skipped discovery — and built solutions for problems that didn’t exist. 3. I followed up like a rep, not a partner. I checked boxes. Sent templates. No value. Follow-up should feel like strategy, not spam.   Each one of these cost me big time. But here’s the upside: I learned, adapted, and now teach others how to avoid the same. Don’t let ego block evolution. Learn from the misses. That’s where the real growth lives.

Here are 6 of my biggest sales mistakes. (After 17 years in sales I’ve made a ton) Here are the ones I learned the most from: 1. 𝗧𝗿𝗲𝗮𝘁𝗶𝗻𝗴 𝗮𝗹𝗹 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁𝘀 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 At the beginning of my career, my prospecting process was: Get a list of prospects → use the same script for every call → rip calls No ICP, no research, no strategy. I wasted a ton of time & cost me and the company $$$. Quantity matters, but not at the expense of quality. ----- 2. 𝗖𝘂𝘁𝘁𝗶𝗻𝗴 𝗰𝗼𝗿𝗻𝗲𝗿𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗽𝗿𝗼𝗰𝗲𝘀𝘀 I learned my company’s sales process, but in my mind, it was way too many steps. I was hired to close deals, and the process added friction. I wanted to go fast. So I started to cut out steps Allowed the prospect to dictate the next move Which resulted in every evaluation being different. Doing so had the opposite outcome I was going for. Process exists for a reason. ----- 3. 𝗦𝗲𝗹𝗹𝗶𝗻𝗴 𝘃𝘀. 𝗦𝗼𝗹𝘃𝗶𝗻𝗴 My early thoughts on selling were that I needed to “convince” prospects why they needed our product. I spent years thinking this defined great sellers. But the more I tried to “convince” the worse my results. It wasn’t until I changed my focus to “solving” problems that the tide turned. ----- 4. 𝗧𝗵𝗲𝗺 > 𝗬𝗼𝘂 I would spend hours prepping for meetings. Memorizing my talk tracks. My talk track: 30-45 min PPT monologue about my company & awards Looking back, I wish I could apologize to everyone who had to sit through one. Spend hours prepping. But make the conversation about them not you. ----- 5. 𝗕𝗮𝘁𝘁𝗹𝗲 𝗚𝗿𝗼𝘂𝗻𝗱. 𝗡𝗼𝘁. 𝗖𝗼𝗺𝗺𝗼𝗻 𝗚𝗿𝗼𝘂𝗻𝗱 For the longest time, I would get pissed anytime someone asked for a discount or tried to negotiate. I would go into every negotiation thinking I needed to: Hold my ground Defend our product’s value Believing that I needed to win That mindset cost me a ton of deals early in my career. Negotiating shouldn’t be adversarial - it should be collaborative. ----- 6. 𝗕𝗲𝗹𝗶𝗲𝘃𝗶𝗻𝗴 𝗘𝗢𝗤 𝘄𝗮𝘀 𝗟𝗶𝗳𝗲 𝗼𝗿 𝗗𝗲𝗮𝘁𝗵 Now I still struggle with this occasionally, but have gotten way better as I’ve gotten older. The EOQ can bring a lot of stress. I would prioritize it over everything: Missed family vacations Missed kid's sporting events Was absent during Holiday gatherings It’s by far my biggest career regret. EOQ is important. Balance is vital. Family is everything. Hope this helps someone. What mistakes have you made during your career?

My client just had her first $100K month. Same offer she's been selling for two years. Nothing about the transformation changed. Nothing about the deliverables changed. What changed? She stopped customizing everything. Here's the uncomfortable truth most business coaches won't tell you: Your offers aren't the problem. The way you've designed them is. I spent the last year obsessed with one thing: offer architecture. Not because my clients weren't getting results. They were crushing it. Not because revenue was struggling. We had our best year ever. But because I kept watching talented educators hit revenue ceilings they couldn't break, and the culprit was always the same three mistakes: MISTAKE #1: Making every offer customized Customization feels like premium service. It's actually a full-time job you just created for yourself. You cannot scale customization. You cannot automate it. You cannot easily delegate it. Scalable offers solve common problems in repeatable ways, with room for personalization in delivery, not design. MISTAKE #2: Staying in experiment mode too long There's a season for throwing things at the wall to see what sticks. But too many entrepreneurs camp there for years. At some point, you have to stop saying yes to every opportunity and start saying no to things that don't align with where you're going. Yes, that means turning down money today to create space for bigger growth tomorrow. MISTAKE #3: Building high-ticket offers with no client journey Your $10K offer doesn't exist in a vacuum. If you don't design a clear path that helps clients ascend from where they are into your highest transformation, you'll always struggle to fill premium seats. Strong offer suites don't just sell to today's clients. They grow with them over time. When I restructured our offers last year, I didn't add more services. I refined what we had. Created clear pathways. Eliminated custom work that was draining the team. Made it obvious what clients needed and when. Revenue didn't just grow. It became predictable. If you're working hard but not seeing corresponding growth, your problem probably isn't marketing. It's offer architecture. The structure matters more than the strategy. What's one offer you know you need to refine or retire?

I’m sick of LinkedIn being a highlight reel. Growth is messy. Especially your first year. Here are 5 big mistakes I made in my 12 months as Head of Sales at Aligned (don’t tell Gal): 1. Believing process would self-correct behavior Assuming that once the right process, tooling, or framework was in place, execution would naturally follow. Revamping the process didn’t magically fix misalignment. Reps first need to fully understand the why, followed by regular reinforcement. 2. Letting “Clean enough” data drive decisions Trusting CRM reports, dashboards, and signals that looked ‘fine’ instead of questioning each layer. A system of record is NOT a system of truth. Decisions built on sh*t data compounded quietly. 3. Over-indexing on permission instead of ownership. Not because I lacked confidence. But because I respected collaboration, buy-in, and alignment. Ironically, that slowed everything down. I spent too much verifying, instead of just doing it. The moment I started making calculated calls and rolling them out, everything moved 10x faster. 4. Not being direct enough Raise your hand if you’ve ever worked for a Sales Leader who instructed you to ‘Be Direct’ and then when you were, they either took it personally or never looked at you the same? I was scarred from previous experiences, and afraid to say what I really meant. Gal regularly encourages me to “be more Israeli,” so I’m now working on bringing 2016-2020 Meredith back! 5. Underestimating context switching. Head of Sales is a hard F*ng job. Deal reviews. Customer calls. Hiring Interviews. Forecast. Cross-Functional Strategy. Executive alignment. Slack pinging every 12 seconds. I tried to be available for everything. The constant switching fried my decision-making. Now I context block: Mornings = AEs + customers only Midday = Strategy Afternoon = reporting + ops Interviews stacked back-to-back Less switching for better thinking. —--------------------------------------------- None of these were explosive. No big blowups. No major disasters. Just small gaps. But in sales, small gaps become big misses. So in year 2, we’re closing the gap. P.S. Because you can’t spell mistake without steak, here we are at at Peter Luger in Las Vegas

If your team is selling AI like it’s SaaS, you’re in trouble. Since 2020, my company Rev has sold over $50M in AI products and services. Here are the 3 biggest sales mistakes we made (and how to avoid them): BACKGROUND Rev has been selling AI-enabled demand generation & exegraphic signal enrichment for 10 years – long before AI was “cool.” But we've had to work through BIG misconceptions about what AI is and isn’t. AI Sales Mistake #1: Augment, don’t replace Investors and board rooms LOVE the pitch: "AI will replace headcount for a fraction of the cost!" But there are few use cases (so far) where AI is ready to replace people. For day-to-day business activities, like selling, the tech isn't there yet. If you’re selling staff replacement, will you close that deal? Maybe. Will the customer thrive? Not in 2025. Instead, focus on how you enable people to make smarter, faster decisions. AI Sales Mistake #2: The Insight Sale AI produces insights that *can be* groundbreaking. As sellers, we love it in a demo when our customer notices something that they wouldn’t have known before. But BEWARE. What happens on the next query when the answer – which may be no less sophisticated – is already known? What happens when an outcome your champion thinks is insightful is not considered insightful by the economic buyer? “Yes, we knew that already.” AI helps assemble and analyze information better and faster than a human can. It can generate valuable content and accelerate timelines. But “insight” is tough to deliver every time. Focus on speed, quality, and accuracy, and resist the urge to insight sell! Sell automation, not insight. AI Sales Mistake #3: Black box This one is simple: No business will trust a black box. Consider AI that many of us use every day – Google Maps. Would you REALLY use it if it said “make a left” – “make a right” – “go straight” – and DIDN’T show you the full route? Not a chance. You want control (i.e. to decide for yourself if a more complicated route is worth some extra turns). You have preferences (i.e. driving past your old neighborhood). You still know some things the AI doesn’t (i.e. school is out today, it will be faster than it thinks driving that way). Remember that when you’re asking your prospect to trust AI. Your AI needs to show it’s work, and explain answers. It needs to allow customization. Let the user choose. TAKEAWAY The classic bad AI pitch: “Our AI offers incredible insight. Just feed it data and get out of the way. You’ll be so efficient, you’ll need a third of the heads!” Great for a hypey Likedin posts – but terrible for a real buyer who wants speed to answers, control, and smarter people. So, try this AI pitch instead: “Our AI helps your people get answers to complex questions - but also reasons why - to make your smart people even smarter. They will get unprecedented results when they tune the system and use it daily.” That’s a story everyone should be buying.

No-decision outcomes are happening at an alarming rate. This is frustrating and costly for salespeople. Here are four of the most common causes and how to avoid them. 🛑 Lack of Urgency This happens when a prospect doesn't have an emotional connection to your solution. It presents itself with responses like, "It's too big of a change; we're happy with what we have;" or "We don't see the value." People buy based on emotion and use the data to rationalize their purchase. Create an emotional connection to your product or service early in your conversations. ✳ Use feeling words in your qualification conversation. Questions need to be reminders of their pain and compel them to want to get rid of it. Here are some examples: "Tell me about your frustrations with your current process or product." "How do you feel this harms you and the department's overall performance?" "What kind of relief will everyone experience once you've resolved this issue?" 🛑 Lack of Authority You're talking to the wrong person. To prevent this, you must identify and engage the decision-makers early in the sales process. Making sure you are talking to the right person or persons involved in making a decision is a delicate subject. ✳ Position your questions in a manner that ensures you aren't diminishing your POC and encourages them to invite others. Use statements to set the table, like, "Decisions like this have a broad reach." or "If you're like many people I work with, I'm sure you solicit input from others in your organization." Then I ease in the question, "During these internal conversations, more questions than answers usually arise, so how would you feel about inviting me to join that dialog to provide answers in the moment?" 🛑 Lack of Differentiation When the conversations focus on price, this should alert you that you haven't differentiated your product or service from the crowd. You've become commoditized and lack specific value. ✳ To avoid this in your early conversations, focus your questions on the specific issues, the desired outcome, and what success in the acquisition feels like to the prospect. You don't have to have the best product. You only have to have the product best suited to fix your prospect's problems. Understanding that matters. Focus on the specific features of your product that are suited to resolving that problem, and you will stand above the competition. 🛑 Lack of Follow-up Connect regularly enough to keep the process moving without being an annoyance. Sometimes, it is necessary to be in more contact than others. ✳ Open a conversation: "I keep thinking about what you said or asked regarding "X" and want to clarify a couple of things." You can easily transition from this into, "While I've got you, where are we on...?" Make prospecting suck less. ✅ Subscribe to my newsletter 🔔 Ring the bell on my profile to follow me ➡ Connect with me or DM me #sales #makeprospectingsuckless