Leadership In Sales Teams

Sales leaders need to put an end to this MADNESS. Here's a strategic seller who was put on a PIP after hitting 166% of his $1.2M quota because he didn't hit the required "activity metrics.” There’s a better way to lead: It's simple... Stop treating knowledge professionals like factory workers. Specialized knowledge, building networks, and embracing tech innovation are more important growth levers than measuring activity inputs. This is especially true for strategic sellers. If you're leading sellers who have to engage with multiple executives at large companies and you're scrutinizing their "activity metrics,” I suggest you do an audit of your management style. Here are 3 great places to start: 1. WHO DO YOU WORK FOR? The average tenure of a VP of Sales is 17 months (down from 26 mos in 2010, per Gong). You’re in a high-pressure position, so it’s a good time to think about who you *truly* work for if this trend has any chance to reverse. Instead of thinking of your board and C-Suite as your bosses, what if you flipped the model on its head? This is known as Inversion Thinking. Instead of: “What do I need to show people at the top to keep my job?” Ask: “What can I do to help the people below me reach their full potential?” 2. WHAT IS THE MEASURE OF SUCCESS? Is the team you lead given a revenue quota or something else? Businesses need revenue to survive and grow… Not more meetings on the calendar. So why over-index on activity inputs if the important outcomes are being surpassed? This is known as Linearity Bias, the assumption that a change in one quantity produces a proportional change in another. More calls, emails, and meetings ≠ more revenue. Instead of chastising reps who are over quota but under activity, try deconstructing their unique approach and giving them a platform to share it with the rest of the team. Viewing sellers like this as “lucky” will limit your growth and tenure. 3. HOW MUCH TRUST DO YOU HAVE? “We had 2 reps put in their notice this week, and I know 2 more who are about to resign.” This was verbatim from a Strategic Account AE I spoke with last week at a Series D startup. Why? Because their senior sales team must participate in 2 cold call blitzes each week in addition to 80 outbound outreaches. “We feel like glorified SDRs. 1,000 calls have produced 10 meetings, a 1% return.” They’re fed up and burned out…so they’re leaving. If a tenured seller leaves tomorrow, what’s the cost of finding, vetting, onboarding, and training a new seller? What's the cost of lost momentum with existing pipeline? If you’re leading with activity and not strategy, I guarantee you don’t have trust in your sales team. As we enter 2024, I encourage you to think differently. The era of 17 months tenure, <40% quota attainment, and 63% of sellers experiencing burnout doesn’t have to continue. You can be the change. 🐝 P.S. Strategic sellers seeking a better way, subscribe: https://buff.ly/3noPjbn

One salesperson had brought in 20 of the company’s 23 customers. That wasn’t only a success story. It was a warning. The person was clearly talented. They had strong relationships. They understood the market. They knew how to create trust and move conversations forward. But the number exposed something else. The company had not built a sales capability. It had built a dependency. There is nothing wrong with having exceptional performers. Every company wants them. The risk begins when customer trust, account knowledge, sales judgment, and revenue creation remain concentrated in one or two people. That creates vulnerabilities many CEOs do not see until something changes. The top seller leaves. They burn out. They reach their capacity. A key contact moves to another company. Their existing network stops producing at the same rate. Then leadership realizes the rest of the team was never truly developed. A strong sales organization is not defined only by how much its best person can produce. It is also defined by how well the company transfers what works. Can managers develop sound judgment in other sellers? Can multiple people build executive relationships? Can customer knowledge survive a transition? Can the team create pipeline without relying on one person’s reputation? Can the company continue growing when the hero is no longer available to carry it? Your top performers should be an advantage. They should not be the infrastructure. How much of your revenue confidence still lives with the same one or two people?

Last week, we closed a deal with a $10 billion (revenue) company. No click bait. Just a story that marks a new era. Here's what their SVP told me: “A few years ago, our sellers didn’t need real skills. Tailwinds and great product-market fit carried us. We had nothing more than order-taking skills.” He went on: “But today? Sales cycles are complex. Buying committees are more educated & skeptical. The ZIRP era won’t come back for another generation. We need to maximize revenue per rep. That starts with skill capacity.” We’re no longer in the ZIRP era. We’re in the Skill Capacity Era. I asked him what skills matter most now. Here’s what he said: 1. Disruptive Insight Selling. Great sellers don’t pitch. They reframe the problem. They introduce a unique insight that shifts the buyer’s thinking. In a way that favors a purchase. Most AEs can’t do this. They offer thinly veiled product pitches. No insight. No acumen. Top sellers reframe the buyer’s mind. They communicate, without saying it: “I know your business — and I understand this problem better than anyone else.” 2. Developing and Quantifying Value. Open your CRM. Look at the notes in the ‘pain’ field.' Now ask yourself: Are these the problems C-level execs care about? Or mid-level frustrations? Most AEs stop at surface pain. The best go deeper — and quantify what they find. They uncover the need behind the need. That’s where the deal lives. 3. Frictionless Multi-Threading. Buying committees are larger. Buying committees are more risk averse. Buying committees are prone to “do nothing.” Yet sellers have the same multi-threading habits they did two years ago: Work with one, MAYBE two people. Stick with the most comfortable contact. Avoid the skeptics. The best salespeople don't just multi-thread. They drive consensus. 4. CFO-Level Business Cases You don’t need to be a spreadsheet wizard. But you do need to speak CFO. If your ROI pitch sounds like a sales deck? At best, they’ll roll their eyes. If it sounds like a financial case with scenarios? You’ll get to “yes” faster. 5. Taking Control. The Challenger Sale gave sellers a game-changing framework: Teach. Tailor. Take Control. Most AEs don’t know how to do that without sounding tone-deaf to buying dynamics. They defer. They wait. They follow the buyer’s process and hope for the best. But in this market? Hope is not a strategy. AI can’t lead a room. It can’t challenge a buyer’s process. It can’t manage power dynamics. That’s your job. The best AEs define the pace and tone of every deal they touch. ZIRP is gone. The order-taker economy is dead. Welcome to the Skill Capacity Era. The CRO flex isn’t bloated headcount anymore. It’s skill density × revenue per rep. P.S. Start transforming your revenue team with these 24 skill transformation tips: https://lnkd.in/g_JF-ytC

They promoted me because I could close. They almost fired me because I couldn't forecast. Nobody tells you this about sales leadership. You get promoted for being great at ONE thing. Then suddenly need to master FIFTY things nobody taught you. I've been a leader for 15 years. Built 3 teams over 100 people. And ya'll, I had to learn these skills the hard way. 5 Skills They Expect But Never Teach: Pipeline Math Wizardry Your CEO asks: "What's our path to $10M next quarter?" You better know: - Coverage ratios by stage - Conversion decay rates - Rep capacity calculations - Territory math that actually works I spent my first 6 months as a manager using "gut feel" for forecasts. Nearly got canned. Now I can build a revenue model in my sleep. 2️⃣Board Presentation Translation Board: "Why is CAC up 47%?" What they hear: Excuses What they want: Solutions with data You need to speak three languages: Board speak (ROI, LTV, efficiency) Rep speak (activity, skills, motivation) Customer speak (value, outcomes, success) Miss the translation? Miss your job. 3️⃣ Managing Up While Protecting Down Your CEO wants 50% growth. Your team is burnt out. Your CFO cut the budget. This is the dance nobody teaches: - Push back with data, not emotion - Shield your team from corporate chaos - Negotiate realistic targets - Take bullets meant for your reps I've seen too many leaders throw their team under the bus to save face. That's not leadership. That's cowardice. 4️⃣ The Therapy License You Didn't Know You Needed - Monday: Sarah's getting divorced - Tuesday: Mike's parent is sick - Wednesday: Jennifer thinks she's getting fired - Thursday: Tom actually IS getting fired - Friday: You're having a breakdown But guess what? You show up smiling. Every. Single. Day. Half your job is managing emotions. Theirs AND yours. 5️⃣ The Context Switch Olympics 8:00 AM - QBR prep 8:30 AM - Rep crying about quota 9:00 AM - Strategic planning 9:30 AM - Deal rescue mission 10:00 AM - Team meeting (be inspirational!) 10:30 AM - Termination conversation 11:00 AM - Board deck review Seven different mindsets. Seven different energies. Zero transition time. The Brutal Truth: These aren't "nice to have" skills. They're survival skills. And nobody's teaching them. That's exactly why I built the Sales Leadership Accelerator Tired of leaders learning through failure instead of frameworks. Inside SLA, we cover ALL of this and then some. 14 hrs of leadership topics. Tactical not theory 12 hrs of sales training topics. Proven in the trenches 12 proven templates. AND COMING SOON AI Sales Leadership Coach in your pocket. Proactively working with you. If you’re a manager drowning… If you're a director who can't crack the board code... If you're a VP tired of winging it... You need this. Because the difference between leaders who survive and leaders who thrive? It's not talent. It's training.

"We have a margin problem." When was the last time you heard that statement? To be fair, the external environment for many businesses is intense today: diminished spending power of consumers, increased attention to inflation, currency impacts, growing costs, battle for talent, and greater competitive activity are all combining. It can certainly feel like a margin problem! Here are a few steps I recommend right away when looking at margins and taking decisions to improve your Competitive Positioning: 1) Start by re-segmenting your customers, markets, and products/services- consider what may have changed, and how you can best segment to understand the purchasing decisions of each key group. What criteria are you using to determine your priorities for the future? 2) Understand and re-evaluate your competitive advantage. Why are customers choosing you relative to all the other alternatives? 3) Challenge your value proposition for your highest priority customer segments, and rebalance where necessary- why are your customers loyal to you and sticking with you even as price increases may be necessary? Revisit your pricing initiatives and programmes, and understand where they can be improved on and what can be tested/experimented with. 4) Consider how new business models may be able to assist you in better servicing your current customer needs, or in attracting an entirely new segment of users with a different willingness to pay. What is your ideal portfolio of Core, Growth, and Explore business models? 5) Determine where you can better serve your highest priority customer segments through building, developing, and adapting entirely new capabilities Your customers are not static, and your Strategy cannot be reviewed just once a year in updating to the dynamic environment we are all in. Fire, Aim, Ready is not a winning approach. What are you finding most effective in addressing the "margin challenge" of 2025 and beyond? Strategy is Mastery. Let's build the future together.

🚨 𝗦𝗲𝗹𝗳-𝗮𝘄𝗮𝗿𝗲𝗻𝗲𝘀𝘀 𝗶𝗻 𝗦𝗮𝗹𝗲𝘀? Most teams think they have it. I know.. The word 'Self-awareness' has been tossed around like a chew toy - too worn out to grab, too overused to notice. But here's the thing: Old doesn't mean it's not classic gold. After 10 years of working in sales orgs & another 12 working with sales teams, I've watched this pink elephant stomp on more deals than a poor pipeline ever could. Here's the expensive reality when sales pros lack self-awareness in their: 🔹 𝗪𝗼𝗿𝗹𝗱𝘃𝗶𝗲𝘄 → The lens they unconsciously use to assess prospects. Eg: They instinctively prioritise prospects who ‘look’ successful or come with swanky brand names - assuming they’re the only high-value leads. 🔴 Potential Fall: Missing golden opportunities because they're too busy judging prospects through personal biases. ✅ Move: Coach the team to challenge their own surface-level assumptions. The right prospect isn’t always the most obvious one. 🔹 𝗧𝗵𝗼𝘂𝗴𝗵𝘁 𝗣𝗮𝘁𝘁𝗲𝗿𝗻 → The internal narratives shaping their approach. Eg: “Let’s get this done in the shortest, most efficient way.” 🔴 Potential Fall: Rushing the process—jumping into selling mode before fully understanding the prospect’s real needs, leading to shallow conversations & lost deals. ✅ Move: Efficiency isn’t just speed—it’s outcome. Train reps to be empathic listeners - not just to gather information, but to connect with emotions. 🔹 𝗘𝗺𝗼𝘁𝗶𝗼𝗻𝗮𝗹 𝗣𝗮𝘁𝘁𝗲𝗿𝗻 → The underlying emotions shaping their behaviour. Eg: “If they say no, they’re rejecting me.” 🔴 Potential Fall: A ‘No’ to the product feels like a ‘No’ to them. Instead of detaching, they spiral—dwelling in shame, overanalysing the loss, or get hijacked into a mode of desperation for a quick win. ✅ Move: Detach identity from the deal. Coach teams to build intrinsic self-regard. The best salespeople study the ‘No,’ refine it, & move forward—without dragging their self-worth into it. 🔹 𝗛𝗮𝗯𝗶𝘁𝘂𝗮𝗹 𝗔𝗰𝘁𝗶𝗼𝗻 → The behaviours shaping how they’re perceived. Eg: “Clients matter. Everyone else? Not my problem.” 🔴 Potential Fall: Transactional over relational. They chase deals but neglect non-clients, peers & strategic relationships—making them forgettable, unlikable, and unreferrable. ✅ Move: Likeability is leverage. Train reps to build genuine connections, not just close deals. Being great at sales means people want to work with you again, & send others your way. Case in point? I work with massive sales teams but would only refer clients to the ones I trust & like. Sorry, not sorry. Self-awareness in sales isn’t just about knowing your strengths & weaknesses. It’s about knowing your blind spots before they cost you business. The best sales pros I've met are connectors, listeners, & self-correcting individuals who don’t let their own ego, assumptions, or habits get in the way of a deal. Which point resonates? Share below! 👇🏼 #SalesEQ #Resilience

Some of the best product strategy sessions don't happen in a boardroom. They happen during a customer call that unexpectedly turns into a deep-dive on reality. Just had one of those conversations that perfectly crystallized the challenges facing sales leaders today. The insights were too good not to share: ↳ On Market Positioning: Companies generating $5M-$100M almost universally reject the "mid-market" label, self-identifying as "enterprise." This isn't just semantics; it's a core messaging challenge. ↳ On Scaling: The default strategy for hitting higher targets is still to "throw more bodies at the problem", hiring more reps instead of unlocking the full potential of existing teams. ↳ On Management: The most valuable activity, personalized coaching and role-playing, is impossible to scale effectively with human managers alone. It's the biggest bottleneck to growth. ↳ On Risk: A 6-9 month sales ramp time is still accepted, meaning companies invest hundreds of thousands of dollars before knowing if a new hire will truly work out. ↳ On Feedback: Even well-intentioned coaching from a new manager is often met with friction. Trust must be built before feedback is fully accepted. ↳ On Process: For modern, process-driven teams, how you achieve your number (activity, methodology) can be just as important as hitting the quota itself. Outcomes alone don't tell the whole story. ↳ On Tools: Despite the proliferation of CRM platforms, many teams still rely on manual spreadsheets to track daily rep activity, creating data chaos. This is why we're building SalesTable – AI Sales Enablement for Modern Teams. This is the problem space. The future of sales leadership isn't about more managers; it's about augmenting them with intelligence that scales. What's the most resonant insight on your team? #Sales #GTM #B2B #AI #RevenueOperations #Founder

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

Navigating Pitfalls: Common Sales Leadership Strategies That Can Derail Success As sales leaders, the path to success is complex and filled with potential pitfalls. By categorizing these challenges, we can better understand and address them. Here's how these insights break down into four key categories: 🚀 Strategy Missteps: Balancing Act: Avoid over-emphasizing new customer acquisition at the expense of existing ones. Growth requires a balanced approach. ⚖️ Evolving Strategies: In a rapidly changing B2B landscape, sales strategies must evolve to meet new buyer needs. 🌱 Chart Your Own Path: Don’t follow the crowd; tailor strategies to what's proven effective for your organization. 🛤️ Embrace Change: Be ready to adapt and make necessary changes if current strategies falter. 🔄 Operational Oversights: Quality Over Quantity: Prioritize high-quality leads over a high volume of low-quality ones. 🎯 Meaningful Metrics: Focus on outcomes, not just activity, for genuine insights into success. 📈 Pipeline Reality Check: Maintain a realistic view of your pipeline to improve win rates. 🔍 Developmental Dilemmas: Continuous Learning: Ongoing B2B sales training and development are crucial for keeping your team competitive. 📚 Simplify to Amplify: Simplify over-complicated sales processes to empower your team. 🔄 Customer-Centric Concerns: Customer Voices: Valuing customer feedback is essential for avoiding loss to competitors. 👂 Patience Pays: Prioritize the customer’s readiness over pushing for quicker deal closures. ⏳ Realistic Targets: Set achievable sales targets to prevent stress and burnout, ensuring a modern approach that values relationships. 🎖️ Reflective Realizations: Achieving Goals: Remember, success is strategically winning the right deals, not just hitting numbers. 🏆 Best Practices: Lean on reliable best practices to enhance effectiveness, rather than fleeting trends. 🌟 By understanding these categories, you can steer clear of common pitfalls and guide our teams toward more effective and successful sales strategies. How do these categories resonate with your experiences? Let’s share insights and grow together! 👇

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.