Common Sales Mistakes

I’ve managed 100+ AEs and run probably 100,000 deal reviews. If I got $1 every time we crowned our Main Contact our ‘Champion’, I could've bought a Tesla Model X by now (the meme Will Aitken made for Aligned nails it👇). Here are the 8 biggest mistakes AEs make when selling with champions—and the fix: 1. Main Contact ≠ Champion I admit, it feels good having someone update you on every detail of a deal and doesn’t give you a hard time. But that doesn’t necessarily make them a champion. Can they truly influence execs? Are they willing to fight politics and budget? Motivation is great, knowledge is great—but not enough to close a deal. 2. Settling for One Champion While having a real champion is great, you shouldn't stop there. Latest stats show deals involve 11 stakeholders—That’s a lot of opinions… When two more people make the case together, decision risk drops, and they’re far more likely to get everyone on board. Also, champions can leave or lose political battles—If you can, don't settle on one. 3. Thinking Execs Will Care Executives are busy, stay high-level, and rarely have time for your 25-slide pitch. They need to hear a concise, compelling case—fast. If you don’t help your champion distill it down to a crisp 1-pager or bullet-proof 10-minute deck, the exec will pass or default to “Let’s hold off.” 4. Overestimating Champion Motivation More often than not, reps send champions 5 decks, 4 white papers, and 7 case studies, overestimating their motivation. And if they do have that level of time, are they even real champions? Keep resources minimal, targeted, and easy to share internally. Less confusion = more clarity = faster decisions. 5. ‘Blue Bird’ Champion? Not a Strategy Letting your champion 'work their magic' while you watch from the sidelines is wishful thinking. Co-sell with them: schedule joint calls, get their feedback on internal pushback, and arm them with tight value narratives. 6. Zero Internal Coaching Building on #5, your champion will present your solution in front of their team—have you coached them on your solution’s top 3 outcomes? Do they know how to handle “We have no budget” or “We tried a similar tool before”? Don’t let them wing it. 7. No Mutual Plan, Just Hope Feeling good about your champion being strong enough to lead the way? That’s how deals die. Yes, they know their internal politics, but you know how to buy in your category. Combine both skills. A mutual plan > following hope. 8. ‘Decision Maker’ Myth It’s 2025, and committees rule. There’s rarely a single all-powerful Decision-Maker. Identify both ATL (exec-level) and BTL (manager-level) stakeholders. Use your champion to bring them into the conversation early and build consensus from the ground up. First on the problem, then on the solution. —— Buying decisions happen when you're not in the room. You either influence them by building Champions right, or dance around in circles with a Main Contact. Choose which salesperson you want to be.

🚨 The Alcohol Industry Has a Customer Problem—And It’s Costing Them. 🚨 Who is drinking—and what they’re drinking—is changing. Fast. Women drive 60% of wine sales in the U.S. Younger generations are drinking less but spending more on quality. The future of alcohol? More diverse, more experience-driven, and less interested in tradition for tradition’s sake. Some categories are keeping up. Spirits are adapting. Beer is innovating. Even non-alcoholic brands are exploding. And wine? It’s stuck in time. 📉 Outdated Branding – Alcohol marketing still clings to masculine imagery, prestige cues, and legacy appeal instead of reflecting who’s actually buying—or who they need to attract. 🍷 Mismatch in Production – Women overwhelmingly prefer sparkling, rosé, and acid-driven whites, yet wineries still push heavy, high-alcohol reds as if the 90s never ended. 💰 Leadership Gaps – The industry decision-makers are out of sync with the next generation of consumers, creating a disconnect the wine industry can't afford to ignore. If wine wants to survive, it needs to change. What’s the Fix? ✨ Marketing that reflects reality – Swap the slow-motion Cabernet pour for a fun, lo-fi lifestyle video featuring young (or middle-aged) women actually enjoying the product in real life. 🍷 Wines people want – Stop forcing a product fit and start listening to data and consumers. 💼 More women & diverse leadership – If the industry wants to stay relevant, it needs decision-makers who understand its next generation of buyers. The industry talks about tradition, craftsmanship, and heritage. But none of that matters if you’re losing your customers. 👉 Will wine evolve—or keep losing relevance with the next generation of drinkers?

The Sequoia pitch template is BS: Use it at your own peril! This week we're hosting the private party for the finalists of The Deeptech Demo Day Back during the competition, 250+ super cool companies showcased. And some really slick presenters! Well done to all participants to have the nerve to go on stage and pitch. But! Most startups out there still follow this outdated principle of "problem -> solution -> market... blah blah blah" Total BS! Because they made it really hard for people to get their uniqueness. Or rather: Don't mistake a template for a blueprint. It should be a starting point if you don't know where to start. Yet all businesses are different. Focus on your top strengths: on what makes you stand out. 3 examples: 1️⃣ If you have strong revenue or booked orders: ❌ Don't leave this until the end, after spending slide after slide talking about "how big the market will be". ✅ Instead: Do bring it right at the start and hit investors in their face with it. Then explain how you're doing it. Unless the market itself is not obvious (unlikely in many cases), there is no need to remember investors that "Quantum will be big" or "AI will be in most software". NO ONE GIVES A 💩 - because it's obvious! You're underselling yourself if you don't bring your exceptional traction upfront. 2️⃣ If you're a pre-seed or early seed your team is your make-it-or-break-it: ❌ Don't bury your team at the back! ✅ We will back you and your team. So tell us WHY you are exceptional and uniquely positioned to tackle a huge problem. Sometimes less is more. Especially if the background and story make sense. Which brings me to... 3️⃣ YOUR story is more important than any template: ❌ Don't forget to check the flow and making sure you're hitting investors with your best punch early on. ✅ Many times interesting founders lost themselves in the flow of the template "this is the problem, this is the market, here is KPMG giving us data on the market..." Boring! And also mostly useless. A template is useful to make sure you answer all the key questions. Once you have done that, scatter the slides/points, and bring it back with the RIGHT FLOW for YOUR story! 😎 Then go and smash the stage! Or the inbox 💪 🎤 💻 By the way: I made all these mistakes myself raising my 1st #deeptech VC. My pitch was also not perfect. It never will be. But when I closed the fund it was a lot better than it was at the start thanks to feedback and by keeping similar principles in mind. - Lead with your best punch - Don't bury yourself and your team - Bring it all together with YOUR storytelling flow --- Happy raise!

A VP just called me about a rep who's been working a "hot lead" for 6 months with zero progress. Here's how our diagnostic conversation went: Me: "Do they have confirmed budget?" VP: "Well, the rep says not exactly confirmed..." Me: "What's their timeline for making a decision?" VP: "They said maybe this year, maybe next..." Me: "What's their decision process?" VP: "Uh, I think the VP has to approve it..." Then I asked the question that exposes every fake deal: "What would have to happen for them to say no?" Complete silence. That's when I knew this "opportunity" was a complete waste of time. Here's the hard truth for sales leaders: If your reps can't answer these basic qualification questions, they're not working real opportunities. They're chasing ghosts. The signs your team has a qualification problem: → Sales cycles that drag on for months with no progress → Forecasts full of "thinks," "maybes," and "hopefullys" → Reps who can't explain why a prospect would reject them → Pipeline inflation with terrible conversion rates Real opportunities have: ✓ Identified budget and clear decision authority ✓ Timeline driven by genuine business need ✓ Defined process with known stakeholders ✓ Specific criteria that could disqualify you The best sales teams I work with qualify aggressively and early. They'd rather have a smaller pipeline of real deals than a bloated forecast of fantasies. Your reps' time is your most expensive resource. Stop letting them waste it on deals that were never real in the first place. — Sales Leaders, want to be a world class sales manager and get your team crushing quota? Go here: https://lnkd.in/ghh8VCaf

So many deals do not work out for agency recruiters, many of them which could've been saved had they done this: - Assess risk at the outset AND continuously When you look at an agency recruiter with a higher than normal amount of droppers or rejected offers, it comes down to their lack of repetition. If they asked a key question on the first vetting call, that would already be a huge improvement from so many who don't even manage to do that. But on top of that, so many recruiters just stop asking questions for the rest of the process! They just assume it's all good. So they neglect to ask: Where else is the candidate interviewing at? How is work going for the candidate? What are their travel schedules coming up? How are they feeling about their initial desire to leave? What's going on at work that could be different for the candidate? How are their financial expectations going? What number works for them now in light of things? So many recruiters get lazy in the middle of the process and forget to ask about these things! They just stop asking. So they're completely blindsided when: - Stock prices drastically change which makes the candidate question if they should leave. - Work got much better mid process which gets rid of their RFL (reason for leaving). - Some painpoint that wasn't given to them is now given to them. A LOT can change mid to late process. As they say, the game ain't over til it's over. It's YOUR job to stay on top of everything and make sure no ball gets dropped. So just remember: REPETITION IS YOUR BEST FRIEND. #r2r #rec2rec #recruitmenttraining #headhunter #recruiters #recruiter

This is the most underrated problem I've seen when trying to build or expand partnership GTM: Leadership is initially fully behind a new partnership, excited about its potential, but that enthusiasm never makes its way down to the sales teams who are expected to execute. Without alignment, even the best partnership can stall before it has a chance to succeed. Why does this happen? Sales teams are often focused on their core products, and if a partnership doesn’t clearly benefit them or fit into their day-to-day operations, it becomes an afterthought. To turn things around, you need to make sure your partnership incentives, compensation, and training are in lockstep with the teams that will be selling your product. Here’s how to align incentives and drive results: 1. Ensure your incentives are compelling enough for frontline teams. It’s not enough to excite leadership—sales teams need a clear, tangible reason to sell your product. - Introduce a financial incentive or bonus structure that’s competitive with what reps earn on their core products. This could be a one-time bonus for the first sale, or an ongoing commission that rewards consistent effort. -Tie the incentive to their existing sales goals. If your product helps them hit their targets more easily, they’ll naturally prioritize it. 2. Structure partner compensation to motivate co-selling. If your partner compensation doesn’t align with their core goals, they won’t push your product. - Design a compensation plan that aligns with both the partner’s and your business objectives. For instance, if your partner’s core offering is hardware, incentivize bundling your software as part of the sale to create a win-win situation. - Offer performance-based incentives that reward partners for hitting key milestones—whether that’s a certain number of units sold, a specific revenue target, or even customer engagement metrics. Keep it simple and measurable. 3. Provide consistent training and engagement so your product isn’t just another checkbox. Sales teams won’t advocate for your product if they don’t fully understand its value or how to sell it. - Develop ongoing, bite-sized training sessions that fit into their schedules. Instead of overwhelming them with lengthy sessions, focus on 15-minute, high-impact trainings that teach them how to identify the right opportunities. -Pair training with real-time support. Join sales calls, offer one-pagers, and provide direct assistance during key customer engagements. When they feel supported, they’re more likely to feel confident pushing your product. This kind of alignment can make the difference between a stalled partnership and a thriving one. When sales teams are motivated, equipped, and incentivized to sell your product, the partnership stops being just another checkbox—it becomes a key driver of growth.

Don't mistake "Activity" for "Progress" as an AE Activity could be: - Optional non-revenue generating activities - Handling something that's not your job to be a "team player" - Taking on internal tasks cause you don't protect your time - Spending more time than is needed organizing your data or schedule - Making 30 dials JUST to hit a number And I get it "Activity" feels good "Activity" feels busy But "Activity" could also be an excuse to keep you from your real job And "Activity" might even FEEL like you are building and growing But "Activity" is actually crushing you Being busy on the wrong things in your control AND convincing yourself it is a good thing is the killer combination So what can you do? - Be extremely selfish with your time: That junior AE wants to review a call together? Maybe, but they do have a manager for that - Align your time to outcomes: Doing a call blitz? Aim for conversations, not a dials number - Understand internal roles: if you shouldn't be handling billing conversations, pass them off! Your time is too valuable to go above and beyond here This is all about being intentional with the time you control and not taking the easy path presented to you And "Activity" is the easy path Aim for "Progress" #SalesMindset #EmotionalIntelligence #TimeManagement #CorrCompetencies

If your CAC is rising. You're not alone. Many founders attribute increasing customer acquisition costs to market conditions rather than examining their approach. But what worked to get you from £0-1M won't work to get you from £1-10M or £5 to 25M. Different growth stages require different strategies. As you scale, the dynamics shift: The in-market buyers (those actively searching for solutions) become harder to find. You've already captured many of them. Companies often respond by targeting larger accounts, assuming higher contract values will offset increased acquisition costs. This thinking conflates higher value with better fit. When scaling businesses hit this wall, they typically: • Continue with sales outbound despite diminishing returns • Underinvest in awareness & demand generation • Test multiple channels without a coherent strategy • Focus on symptoms rather than root causes The data shows significant inefficiencies: 50-80% of sales reps don't hit quota, marketing produces low-engagement content, and technical overhead increases as you add more systems. Before addressing these issues, proper diagnosis is essential: • Is your value proposition aligned with your target market's pain? • Have you shifted focus from ideal customers to those with larger budgets? • Are your timelines and expectations realistic for demand generation? When your value proposition aligns with your prospect's pain, acquisition costs naturally decrease and sales cycles shorten. The challenge isn't simply throwing more budget at the problem - it's identifying and fixing the underlying inefficiencies in your go-to-market approach. ------ p.s. Want to know why your marketing isn't working? Get my free 6-part email diagnostic series: https://lnkd.in/e-ux6Cjf

In recruitment, time kills deals. It’s a phrase we’ve all heard, but it hits hardest when you lose a strong contractor purely because of silence after an interview. It’s pretty obvious, and everyone must get it, but the reality is: The longer it takes to give feedback, the higher the chance your preferred contractor goes cold, gets snapped up elsewhere, or simply disengages. It’s not just about speed, it’s about communication. When there’s a delay and no explanation, it sends a message (even if unintentional): “We’re not sure,” “We’re not aligned,” or worse, “We’re not that interested.” In any recruitment process, good people don’t sit still. They want clarity, momentum, and a bit of appreciation for the time they put into an interview. So, if internal decision-making takes longer (and it often does), that’s fine, but keep the recruiter and contractor in the loop and provide a bit of context around the delay. A quick update buys goodwill but silence burns trust, shows a lack of respect and can get you a bad reputation. If you're serious about landing the best people, don't let indecision or internal bottlenecks quietly kill your own deal.