Mistakes to Avoid as a Sales Development Representative

It took me 6 years as a commission-only sales rep to make my first $1M in commissions in a single year. If I could go back in time and help my younger self get there faster… I’d tell him to NEVER do these 7 mistakes: 1. Stop being a product pusher You’re not selling the thing You’re selling the results of what your thing does Don’t focus on your product’s features and benefits Focus on the person’s/company's problems and where they want to be. That’s what prospects care about. 2. Sounding needy Sounding desperate will just drive prospects away You don’t want to say things like: “Just tell me what it’s gonna take for you to buy today” (Lowers your status) “If you buy today, we can offer a 20% discount” Etc… 3. Being assumptive too early You don’t want to say things like this too early in a conversation: “When we onboard you, we’ll do XYZ” It will trigger sales resistance with many prospects and cause them to emotionally shut down and throw objections at you. 4. Lowering your status Most salespeople lower their status to “please” the prospect. They build “fake rapport”, say “yes” to everything, and let the prospect have all the “power” You want to do the opposite to come across as the trusted authority, the expert who can solve their problems and get them the results they want. 5. Sounding overly-excited Ever heard “If you’re not excited about what you’re selling, your prospect won’t buy”? That’s a big myth. In fact, there's no data that supports this assertion at all. If you come across as overly-excited and biased, you’ll just trigger sales resistance with many prospects. You want to come across as more neutral, unbiased, collective and detached. 6. Sounding scripted Great salespeople are like great actors/actresses. They know their lines, but they sound natural. You should 100% have a framework/script so you don’t wing it. But you want to understand it so well that everything you say sounds natural. 7. Asking surface-level questions Surface level questions aren’t enough to get your prospect to emotionally open up to you. Don’t ask: “What are your top 3 challenges right now?” Ask: “Off the record, what’s really going on over here that’s caused you to look at possibly changing companies/vendors?” (curious tone)

Last month we closed a deal with a $1B company that gave 50% of the decision committee voting power to frontline end users. Yet, most AEs obsess with ONLY selling to executives. Here are 15 multithreading mistakes costing you quota: 1. Ignoring the BTL (Below The Line) of power might mean you’re losing some of the biggest potential deal influencers. Give them the respect they deserve. 2. Sticking to a ‘main contact’ and thinking that entitles them to the title.‘Champion’.  Not everyone can be a Champion. Don’t stop until you find one. 3. Neglecting a potential 2nd champion. Yes, you need a focal point for project management, but having multiple people pushing? Even better. 4. Settling for access over influence. The fact you had 10 people on Zoom does not mean you have multiple threads. Work to turn access into evangelists. 5. Trying to have everyone on every call. The only way to maximize influence is by building separate threads. That’s how you listen, create intimacy and impact. 6. Not using multi-channel to maximize influence. Switching between Text, LinkedIn DMs, Email, and Deal Rooms is a great way to build multiple threads. 7. Not recommending who to involve. Many buyers don’t know and end up looping in the wrong people, or miss key ones. Be their expert buying guide! 8. Not asking. Fear of breaking rapport prevents you from advancing the deal. You think that meeting X will help? Explain why and ask for that meeting. 9. Not doing additional outreach. Fear of burning bridges is justified, but the fear of being stuck with someone who can’t get anything done but give info is worse. 10. Overdoing the outreach. If you’re sending cold emails all day in active deals, you are probably burning bridges. Try your champion first. Work WITH them. 11. Doing the outreach alone. I’ve never sent a ghostwritten email as CEO/VP that wasn’t well accepted. Make it part of your process. 12. Not using title matching. Your champion, or their CXO, are far more likely to say yes to a meeting when you loop in your CXO. Be smart, not a ‘Hero’. 13. Not multithreading internally. Working on a complex deal? Lone wolves don’t get far in sales. Build a deal team to help with strategy, complex requests, etc. 14. Multithreading with ‘commission breath’, making it about wanting to get to power; Make it about backwind support to your champion and buying process. 15. Thinking it’s about getting to power. Sometimes you’re speaking with power, but they’re too busy to be champions. Don’t only obsess over execs, loop their teams in. —— Multithreading is not about getting 10 people on a call. It’s not sending cold outreach all day to new people. And it’s not only about getting to executives. It’s a set of actions you take throughout the deal. To DERISK your buyers’ process (and thus yours). By maximizing *access* to people who can offer guidance. And maximizing *influence* over the people who have it. Obsess about the right things.

5 things I wish I knew early in sales that would've helped me crush quota faster and stop waking up in a panic at 3 a.m. When I started selling, I chased every lead and had bad case of "happy ears." Every lead. Every maybe. Every “just checking in” email. Nobody told me I was doing it all wrong. Here’s what I wish someone hammered into me on day one: 1. Stop selling your product. Start selling the pain-free future. Nobody gives a damn about your roadmap. They care about how you make their problem go away for good. Early me sold features. P club me sold freedom. 2. Discovery isn’t about checking boxes. It’s about earning the truth. I used to treat discovery like a qualification script. Now I treat it like a therapy session. If they don’t trust you with the real pain, you’ll never sell the real solution. 3. Urgency doesn’t come from discounts. It comes from consequences. I dropped prices to close faster. It didn’t work. You know what does? Making them feel the cost of doing nothing. Time kills all deals sure, but fear of regret keeps deals alive. Introduce a problem they haven’t even named yet. 4. “Just following up” is a guaranteed delete. I used to send weak follow-ups and wonder why I got ghosted. You want replies? Drop the routine get weird and off the wall. Subject line creativity. Sharing new insights or a new pov only matters if they open the damn thing. Be unique or be ignored. 5. The best reps don’t chase. They disqualify. Fast. They build new pipeline daily. Fast. Rookie me chased every maybe. Veteran me kills bad deals in minutes. Top reps win not by doing more, but by doing less of the wrong sh*t. Your time is your most valuable close rate lever. So stop wasting it with the mistakes beginner me made.

99% of sales reps still make this fatal mistake. It’s not weak pitches. It’s not pricing. It’s this: They make the meeting about themselves. Reps walk in with 25-slide decks: ➡ “We’re in 80+ countries.” ➡ “We have 22 billion-dollar brands.” But here’s the truth: No one cares. Your customer is thinking about one thing: “Can you solve my problem?” If the answer isn’t obvious in the first few minutes… They’re just waiting for you to leave. Great salespeople flip the script: ✅ Lead with the customer’s world — not yours ✅ Show you understand their pain ✅ Co-create solutions, not pitch products Because when you stop trying to impress… You start becoming a trusted partner. And trusted partners get: ✔ More meetings ✔ Longer conversations ✔ Bigger deals 💡 Sales leaders: How do you train your teams to make it about the customer - not themselves?

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.

You don’t need to “sell harder” to grow. You just need to stop doing these 8 things... You’re great at what you do. Your Clients trust you. You focus more on helping than “selling” So why does growth still feel so slow? It’s rarely one big mistake. It’s usually tiny habits getting in the way. Here are 8 of the most common business development slip-ups (and how to fix them fast): 1. Talking Too Much ↳ More words ≠ more trust. ↳ Overexplaining crowds out the client’s voice. → Switch gears, listen more than you talk. 2. Pitching Too Soon ↳ Early pitches often feel like pressure. ↳ Trust hasn’t earned you the right—yet. → Lead with a question, not a solution. 3. Only Reaching Out When You Need Something ↳ Going quiet between asks erodes trust. → Reach out when it’s about them, not you. 4. Waiting Until You’re “Ready” ↳ Perfect timing is a myth. ↳ Momentum beats planning every time. → Take imperfect action. Start now. 5. Skipping the Follow-Up ↳ That amazing call? ↳ It fades fast without a next step. → Nudge the ball forward before the moment cools. 6. Over-Explaining ↳ More detail isn’t more helpful. ↳ It often overwhelms and muddies the message. → Let their priorities set the agenda. 7. Perfecting Messages You Never Send ↳ Rewriting is often just fear in disguise. ↳ Your help doesn’t count if it stays in drafts. → Progress starts the moment you press send. 8. Making It About You ↳ Leading with your résumé misses the mark. ↳ Clients don’t want a hero—they want a guide. → Frame your work through their lens. You don’t need to sell harder. You just need to show up better. Less pressure. More presence. Less pitching. More listening. Less perfection. More momentum. 💡 Small shifts. Big impact. Which one’s your priority this week? Let me know 👇 📌Follow Mo Bunnell for BD strategies that put relationships first and actually work.

7 worst sales call mistakes I saw in 2023: 1. Complicated "upfront contracts" There's nothing wrong with a good UFC. But some reps take a 180 seconds to get through them. Rule of thumb: If you can't set the objective and agenda in 30 seconds? Trim it. Don't make it complicated. 2. No business acumen. Come on, sellers. If you're asking your buyer for $50,000 or more? And you don't know the difference between an asset vs. liability? Or cash flow vs. profit? Why should they look to you? Clean this up. I once heard a seller say to a buyer (after the buyer said the word "P&L"): "P&L? Oh jeeze don't take me back to my college days. What does that mean again?" He was trying to be funny. It wasn't though. 3. Out of the box demos. Here's a question to think about: If your demo doesn't change based on what you learned in discovery... What was the point of discovery? Tailor your solution. I know. It's hard. But that's why we make the big bucks in this profession. 4. "Penciling in" next steps Many reps schedule pointless next steps. They just want a calendar event on the books. But they give the buyer no reason to show up. Have a point of view. What should be the next step? Why that? Who should be involved? What's the agenda? You don't have to overdo it. Just put some purpose behind it. 5. "Let me see what I can do"-style negotiations This tight economy has many of us selling scared. A slight HINT of price resistance? We cave. "Let me see what I can do..." There goes 40% of your ACV. Do yourself (and your company) a big favor. Instead of capitulating immediately... Ask a question. "What's driving you to need that concession?" "What constraints are you dealing with?" Negotiating is problem-solving. Cutting your contract value in half is lazy problem-solving. 6. Not earning the right to do discovery. Sometimes, you don't have to do this. Many buyers are roaring and ready to go. But some buyers? Some buyers are cold. You need to warm them up before you ask your questions. In these situations, give value before you get it. Walk them through a pain-deck, Get them up to speed on what you solve. Then pass the torch: "Anyway, enough about us and what we typically solve. Tell me about your biggest challenges when it comes to _______." 7. Too many questions in a row without a change of pace. If you ask six or seven questions in a row? One right after the other? At best, you come across as robotic. At worst, you come across as interrogating. Rule of thumb: Every 3-4 questions, stop. Summarize what you heard. Vibe with your buyer for a minute. Offer a new perspective. Then get back to your questions. You'll buy time. You'll give a better experience. You'll close more deals. - What did I miss? P.S. If you're a head of sales (or enablement) and you want to transform your SaaS sales team's skills with a "night and day" difference, go here: https://lnkd.in/g2CkE295

10 Things Mediocre Sales Reps Do. That Make You Close ... A Lot Less. 1️⃣ Immediate Discounting Reps who jump to offering discounts often lack confidence in their product or don’t know how to create urgency. It’s a sign they’re relying on price as their only lever, which devalues the product and sets a bad precedent for future deals. A strategic discount can help push a deal to close faster, or get it over the line.  But it doesn’t make someone want to buy in SaaS. Almost never. 2️⃣ Not Understanding the Product This is way, way, way too common. If a salesperson doesn’t deeply understand the product they’re selling, they can’t effectively address customer needs or objections. Worse, they might overpromise features that don’t exist, which destroys trust and leads to churn . 3️⃣ Fear of Competition Great salespeople respect their competitors and use them as a benchmark to improve. Weak salespeople, on the other hand, either avoid discussing competitors or badmouth them, which makes them look insecure and unprofessional. In general, don’t hire folks into a highly competitive sales environment that have only worked at a market leader. 4️⃣ Blaming Others Reps who constantly blame marketing, leads, or lack of support for their failures are avoiding accountability. While external factors can impact sales, great reps find ways to adapt and succeed regardless of the challenges . 5️⃣ Lack of Updates or Progress A weak salesperson often has no meaningful updates to share. They’ll either ghost their manager or repeat the same vague status reports, which signals they’re not actively working their pipeline or moving deals forward . 6️⃣ Not Knowing the Buyer If a rep doesn’t understand who the key decision-makers are, what their pain points are, or where the deal stands, they’re flying blind. This lack of preparation is a major red flag and often leads to lost deals . 7️⃣ Not Believing in the Product Selling something you don’t believe in is nearly impossible. If a rep doesn’t genuinely think their product solves a problem, it shows —and customers can sense it . 8️⃣ Over-Reliance on Scripts While scripts are helpful, reps who stick to them rigidly often fail to adapt to the unique needs of each prospect. Sales is about listening and tailoring your approach, not just reciting lines. 9️⃣ Poor Time Management Weak salespeople often spend too much time on low-priority tasks or chasing unqualified leads. Great salespeople know how to prioritize their time and focus on high-value opportunities. 🔟 Lack of Follow-Up Many deals are lost simply because the rep didn’t follow up. Weak salespeople either forget or assume the prospect isn’t interested after one or two attempts, while great reps stay persistent without being pushy. 👬 The good news is that some of these weaknesses can be addressed with training, coaching, and self-awareness. But if you see too many of these traits in one rep, it’s often a sign they’re not the right fit for the role. 

A rep just told me: "Marcus, I had a perfect discovery call. They loved everything. Then they vanished." I listened to the recording and within 3 minutes I knew exactly why. She asked 47 questions in 45 minutes. The prospect answered every single one. But she never once made them feel the cost of doing nothing. That's when I realized their discovery process was fundamentally broken. Here's the brutal truth about discovery calls that nobody wants to admit: Most reps are trained to extract information, not create buying momentum. "Tell me about your challenges. What's your budget? Who makes decisions?" Those questions make prospects feel interrogated, not understood. They're seller-centric activities disguised as buyer discovery. That's why your prospects ghost you after discovery. That's why deals stall in "interested but not moving forward." That's why your pipeline is full of hope disguised as opportunity. After carrying a bag and leading sales orgs for 14 years and managing $195 million in annual revenue, I discovered something game-changing about discovery calls. The best reps don't ask better questions. They create better experiences. This methodology increased our discovery-to-demo conversion from 23% to 67%. It shortened our sales cycles by 31%. It eliminated 80% of the tire-kickers before they wasted months of our time. Instead of extracting their pain, we started amplifying their vision. Most discovery processes assume prospects know what they want. They don't. They know what's broken, but they can't see what's possible. But there are specific conversation patterns that transform interested prospects into committed buyers. Observable moments that separate real opportunities from casual conversations. When you master these patterns, something magical happens. Prospects start selling themselves. They begin building internal business cases. They volunteer information you never asked for. The 5 discovery mistakes I'm about to show you in the carousel aren't just common problems. They're revenue killers that 73% of sales teams make systematically. Most importantly, I'll give you the exact frameworks to fix them so your next discovery call creates unstoppable buying momentum instead of polite interest. If your prospects aren't eagerly booking next steps at the end of discovery, you're making these mistakes. And hope is not a sales strategy. — Here’s what I’ve learned from running 10,000+ discovery calls: https://lnkd.in/ghJy_9b6

I lost a million dollar deal last year. It hurt WAY more than winning a similar size deal earlier in the year. Learn from my mistakes so you don't have to lose as often. Here is what I did wrong. 1 - Spent too little time building a gap for our solution. This was a popular electronics brand doing a North America relaunch. They did not use a USA based 3PL yet so it was hard building a "current state" vs. "future state" Yet, I focused too much on the future state w/o really learning what their challenges were with their Central america based 3PL. There was no gap - only idealistic thoughts of what could be. I should have spent more time talking about specific challenges that 3PL's face and why our company would be poised to not make them as frequently. 2 - Negotiated too early They wanted a 15% discount right after delivering the pricing proposal. I did not get all the pricing asks out once. They kept coming in seemingly week after week Guess what? We were not the vendor of choice and I found that out too late. Their board of directors were close friends and colleagues w/ executives at large 3PL in America. Should have done more research and called that out early in the process 3 - Not highlighting product & operational gaps When they highlighted certain areas of fulfillment that were important to them I glossed over them without directly saying we needed to make improvements. Pointing out your shortcomings typically gets you to a yes/no answer more quickly. Lose fast, as they say. 4 - Trust & Credibility Our company was well known but I did not leverage testimonials or case studies as frequently as I should have. Typically we were told to do client references at late stages in the sales cycle. I think perhaps, for this account, doing it earlier may have built more credibility earlier on and established somewhat of an authority bias. 5 - Lack of Multi threading I had a strong champion. We had a great relationship and he loved my company. Yet there was an even stronger detractor in their group. This contact loved the other larger 3PL more and I should have actively sought out their opinion earlier. She was not thrilled about our company. Moral of the story is you probably will lose more than you win. Sales, especially 3PL sales, is quite unique. I look at it like baseball. If you hit .300 - you are phenomenal and a silver slugger. If you win 30% in sales, you are most likely going places. Just keep learning from mistakes and you will improve over time. #3PL #ecommerce #sales