Sales Leadership Techniques

I always get in trouble for these types of posts, but age or arrogance, I do not care anymore. I have interviewed 100 of the best sales leaders over the past 5 years. None has impressed me as much as Carles Reina at ElevenLabs. He scaled their GTM from $0 to $330M in ARR in just 3 years. Today I released our episode with him and have gone over it to condense my biggest lessons from the discussion. 🚀 8 Lessons on Building a $330M+ Revenue Machine 1. The "20x" Quota Rule Forget the standard SaaS 6x–8x multiple. At ElevenLabs, the rule is simple: you must bring in 20 times your base salary in revenue. If your base is $100k, your quota is $2M. It sounds aggressive, but it sets a high-performance bar where over 80% of the team hits their targets. 2. Hire "Hunters," Not Just Product Experts A common mistake is hiring for product knowledge and hoping to "train" the sales muscle. Carles learned the hard way: you need people with a natural "hunter" mentality who are hungry, driven, and passionate. You can teach the tech, but you can’t teach the hustle. 3. Be "Ruthless" with Pipeline Reviews Carles holds monthly pipeline reviews where he drills into every detail in front of the entire team. If you aren’t doing your job, you get called out publicly. This transparency ensures everyone learns from each other's mistakes and keeps the team on their toes. 4. Salespeople Belong on the Road If the sales team is in the office for multiple days, Carles starts getting worried. A remote culture works if it’s a "road" culture. Sellers need to be out talking to customers face-to-face, not just hiding behind virtual meetings. 5. Land Small, Expand Fast Don't get bogged down waiting months for a six-figure enterprise deal. Land with a $12k contract to bypass layers of approval. Once the MSA is signed, the "land" is over, and the "outbound" mission begins to capture every other team in the organization. 6. Forecast with Brutal Negativity Optimism kills sales organizations. Carles advises being as negative as possible when forecasting. If a deal is worth $500k, forecast it at $24k. This prevents "inflated" pipelines and forces the team to work twice as hard to ensure the real targets are hit. 7. The 72-Hour "First Contract" Goal Onboarding at ElevenLabs isn't about weeks of reading manuals. New hires join calls immediately. The target? Sign your first contract within your first two weeks. Some have even closed enterprise deals within 72 hours of joining. 8. Treat Customers as a Community, Not a Transaction Transactional selling leads to churn. Building a community—where you give customers your WhatsApp, interact constantly, and do what's right for them even if it costs you money—is how you retain them forever. Huge thanks to Mati Staniszewski and Luke Harries for helping to make this one happen. (link in comments) #founder #funding #business #investing #vc #venturecapital #entrepreneur #startup

For my first 16 years in tech sales, I averaged 240K/year. In my last 4 years, I averaged 720K/year. I did this by using an approach I call Yo-yo selling: 🪀 It’s how you win large, complex enterprise deals by building credibility with senior executives at the beginning of a sales cycle. This will save you months of spending time with mid or lower level Directors on a deal cycle, only to have your deal stall because it's not a priority for Executives. Here’s the concept: You start at the top, get senior level sponsorship for a deep discovery, drop down into the business, then bounce back up with a report of findings. This is the process I've used for nearly every 7-figure deal I've ever closed. Step 0: Research before outreach Before asking for time, I do deep strategic research. Earnings calls. Investor decks. Press releases. Executive interviews. I also spend time talking to their team to see if the problem that I solve exists in their company. Using that research, I build a Point of View that connects their top business goals to real execution gaps. This earns executive time. Today, AI tools like ChatGPT make this easier than ever. What used to take hours now takes minutes. If you skip this step, you lose your edge. Step 1: Prospect to the top and gain their sponsorship to engage Lead with your POV. The key is to teach them something new about their business which they aren't already aware of, and show them how it's putting their highest level goals at risk. If they lean in, offer up a deep discovery with your team and their team. Lock in a date to come back for a readout. Have them assign a project manager to help you coordinate Step 2: Drop down Once you have executive sponsorship, meet with their team. The key is to have the Exec sponsor send out a note to their team explaining what it's for. This will keep the assessment moving forward. Study workflows. Capture friction. Collect quotes. Do not pitch. Just listen. Step 3: Bounce back up Bring it all together in an executive summary. Show how their vision connects directly to what’s broken below. Present a focused business case. Build a custom demo. Create a roadmap and implementation plan. That’s where deals close. Real example from my career At Berkshire Hathaway HomeServices, we were told “no” on a point solution. Instead of walking away, I stepped back and asked what the company really needed. After deep research, I re-engaged the COO with a transformation POV centered on the experience of 50,000+ agents. The result was one of the largest new logo deals in Salesforce history. But Yo-yo selling alone isn’t enough. Because it's hard to execute and takes patience. Top performers also master their mindset, habits, and discipline. That’s why I put together a free masterclass for sellers who want to break into the top 1 percent. 👉 Watch the free training here: https://lnkd.in/eWD8mTqH If you’re serious about enterprise sales, this will change how you sell.

The hardest part about selling to legal is that you’ve got to persuade a skeptical audience that’s professionally trained to poke holes in whatever you say. Here are a few thoughts about how to do it effectively, based on my personal experience: 1. Be up front about your weaknesses. Your buyer has a natural tendency to poke holes, so tell them *everything* about your offering. Even the bad stuff. I realize this advice may go against what some sales trainers say. But seriously, in this market, doing that will earn you credibility. Plus, the most argumentative lawyers (I’m looking at you, litigators) will try to debate you on it, saying that your “weakness” is actually a strength. 2. The little things matter. If you use a phrase the wrong way, if you have typos in emails, if you show up to the meeting late/don’t end on time—it will for sure be held against you. Lawyers see a careless error and immediately assume that you have absolutely no idea what you’re talking about. If that seems a bit unfair, just be aware that it’s the same standard they have when dealing with other lawyers too. 3. Your background will be scrutinized more than you think. Lawyers judge their peers based on how well they did in school decades ago. Credentials go very far in this world. That doesn’t mean you necessarily have to have the best schools on your resume. But your background and track record will be weighed more heavily than it would be elsewhere. Lawyers will also quickly size up your company based on awards/rankings, too--for better or worse. Some of you might say “Hey, not all lawyers are like this! There are so many exceptions.” And you would be absolutely right. But lawyers are also extremely guarded and polished. So don’t just assume that if they smile and nod while you’re delivering your pitch, that they fully agree with what you’re saying. They’re probably holding a lot back. Just to be polite. Lawyers: Did I miss anything? Or am I completely off base here? 

Gong just announced last week they blew past $300M in ARR. WOW. In 2016, I started at Gong as the 2nd US employee at $200k ARR. 20 SaaS sales tips I learned during my time in that storybook growth journey: 1. Money follows pain. Stop selling benefits. Start selling pain relief. You'll close more. 2. WHO matters more than WHAT. If you're talking to the right person: But you have bad sales technique? You can still win. If you're talking to the wrong person: And have great sales technique? You lose. 3. Don't multi-thread. Single-thread with multiple people. Break people out into 1:1 meetings. Stole this from Krysten Conner. 4. Don't multi-thread too much. Looping in the wrong people can kill your deal. Get the blend of people just right. No, IT doesn't always need to be involved. 5. Great cold emails don't talk about your product. They talk about pain. They look like a page from your buyer's diary. 6. Follow up. Fast. Some sellers take days to follow up. They don't want to seem desperate. Stop it. This isn't dating. Speed sells. 7. The secret to enterprise deals: Pick the deals you can win; then win the deals you pick. 8. Build your business acumen. It makes your sales techniques 2x as effective. Without acumen, you're hollow. 9. Don't seek approval. Seek to solve problems. Big difference. Don't grovel. 10. Buyers don't buy because of ROI. ROI doesn't drive purchases. Emotion does. They simply need ROI to justify the purchase. 11. There are two winners in each deal: The seller who won. The seller who ejected from the deal early and didn't waste time. 12. "Continuity of power" is the ultimate metric. Getting access to power is one thing. Getting a 2nd or 3rd meeting with power is entirely different. Only sellers with sharp acumen get the latter. 13. Great sales calls start with planning. Don't wing it. 14. Voice tone matters. Stop inflecting up. Inflect down. It sets an equal tone. 15. Become a master wordsmith. Words trigger mental pictures. Mental pictures trigger emotions. Emotions trigger actions. Actions close deals. 16. Don't negotiate price too early. It should be the last thing you do before the deal closes. Anything else is too early. 17. Talk about money like it's nothing. Quote a $600,000 proposal with a straight face. That's a super power. The best salespeople have a casual attitude about money. The worst salespeople freak out when they talk numbers. 18. Selling is a set of skills. Not a personality trait. 19. Use the same words your buyer uses. Stop paraphrasing. Stop putting your own twist on things. Use their words. 20. Always know the next step. Bad news: If you don't know what next step you'll suggest? You're wasting that sales call. Selling is an act of leadership. So lead. P.S. Master every aspect of SaaS sales with a FREE trial of pclub.io here: https://lnkd.in/gzF2YwKt

6Sense CEO - out. GainSight CEO - out. Outreach CEO - out (last year). Clari - just sold. These were supposed to be the big winners; the very best B2B salestech companies. Now, with IPO dreams dashed, the whole crop of early/mid 2010s unicorns seems to be stagnating. What changed? The SaaS market itself. Here are the 3 biggest shifts GTM leaders need to know: 1. Tool overload 2 years ago, every CMO I talked to used 6Sense. A few months ago at a conference, just 1 CMO of 30 was still using it. I’ve heard similar from CROs ditching Outreach, Gong and Clari. Are the tools bad? Have they failed to deliver? Not necessarily. But there there are only so many $60K–$100K tools a company can justify when deals are harder, budgets are tighter, and adoption is painful. For those sales tech leaders, going public suddenly looks hard if they are bleeding subscriptions – likely much faster than they can replace them. 2. The playbook is tired When SaaS took off in the late 2000s, the playbook was fresh. Hire sharp young BDRs. Load them up with a bevy of tools - Outreach, Zoominfo, etc. But we overused the playbook. One BDR might get 10 meetings per month. But that doesn’t mean 100 BDRs will get 1,000 meetings. At least not 1,000 GOOD meetings. More is better, until it’s not. With too many BDRs chasing too few buyers, Outreach became a spam cannon. Buyers are fatigued. Response rates are continuously dropping as a result. Think 6Sense solves it? Create inbound? The problem is, there just isn’t enough inbound to fill most sales funnels. The playbook is broken. The former salestech leaders are doubly impacted: their customers are canceling subscriptions even as their own sales motions suffer from the diminishing returns. 3. The competition has changed For the past decade, the cost of SaaS development was dropping. AI is making software development even cheaper. Competitive moats are drying up. For the big guys - our prior winners - it means competing with new startups even while their established competitors copy their best features. They can bundle in more functionality to try to prop up their renewals - fight fire with fire. Gong has done this best, adding engagement and forecasting solutions. Clari’s sale is effectively doing similar by merging into SalesLoft. But there is no guarantee that it works for any of them, when their core features are now available elsewhere. Usually cheaper. Make no mistake, these changes are here to stay. If Outreach was a spam cannon, Clay + AI SDRs are spam Weapons of Mass Disengagement. What’s true for 6Sense and Clari and the rest, is doubly true for new, smaller point solutions. Getting attention is harder than ever. And a product feature advantage isn’t what it used to be. Especially when customers are trying to cut you from the day you sign them. You can still win in this market. It takes a focused value proposition and incredibly sharp targeting. Serve where you are strongest.

𝐈 𝐰𝐚𝐬 𝐬𝐩𝐞𝐚𝐤𝐢𝐧𝐠 𝐭𝐨 𝐚 𝐝𝐞𝐚𝐥𝐞𝐫𝐬𝐡𝐢𝐩 𝐨𝐰𝐧𝐞𝐫 𝐥𝐚𝐬𝐭 𝐦𝐨𝐧𝐭𝐡  𝐇𝐞 𝐡𝐚𝐬 𝐚𝐧 𝐢𝐧𝐜𝐫𝐞𝐝𝐢𝐛𝐥𝐲 𝐥𝐨𝐰 𝐭𝐞𝐜𝐡𝐧𝐢𝐜𝐢𝐚𝐧 𝐭𝐮𝐫𝐧𝐨𝐯𝐞𝐫 𝐫𝐚𝐭𝐞 𝐈 𝐚𝐬𝐤𝐞𝐝 𝐡𝐢𝐦 𝐟𝐨𝐫 𝐡𝐢𝐬 𝐬𝐞𝐜𝐫𝐞𝐭… He told me, “I don’t manage from the P&L statement. I manage from the service bay.” Every morning, before he looks at a single report, he walks the shop floor with two cups of coffee, one for him, one for the first tech he sees. He doesn’t ask about deadlines or billable hours. He asks about their lives. He asks what’s frustrating them. He asks what tool would make their job 10% easier. Last month, a tech mentioned they were wasting 30 minutes every time they had to track down a specific diagnostic tablet because they were all shared. The next day, every technician had their own. His leadership team thought he was crazy. It was a $30,000 unbudgeted expense. But he knew the real cost was in the lost time, the mounting frustration, and the risk of a great tech walking away over a simple tool. That one-time expense has already paid for itself in reclaimed billable hours and improved morale. The most profitable dealerships I see aren't run by the best accountants. They're run by leaders who understand their most valuable asset isn't the equipment in the yard, it's the people in the bays.

I am officially exhausted by sales leaders' obsession with the top 1% and President's Club reps. To be clear: I am not against the top 1%. What they achieve is brilliant, and every revenue engine needs them. But I am exhausted by the culture some sales leaders create when they put those reps on an exclusive pedestal and repeat the same tired advice. These sales panel pushes the exact same playbook: hire A-players, fire the bottom 10%, and grind your middle-tier reps until they become 200% unicorns. We have built a "Superstar Economy" in B2B sales. And it is structurally breaking our sales team. When you build a culture and more importantly, a compensation plan, that only worships the outlier, you financially starve the actual foundation of your business: the middle 60%. I call them the Load-Bearing Core. These are the reps who aren't ringing the loudest gongs or posting 250% blowouts. But they show up and quietly deliver 85% to 100% of their number, every single quarter. They are the steel framing that keeps your forecast intact. The architectural flaw in most B2B companies is that we treat a 92% finish like a failure. Leaders lock all the meaningful money, the steep accelerators and the real payouts, behind a 115% or 120% attainment cliff. We tell the Load-Bearing Core that consistent, predictable execution isn't good enough to earn a great living. So, they leave. And the moment your middle 60% walks out the door, your predictability vanishes. You cannot run a B2B revenue engine on the backs of three superstars while you constantly churn and retrain the rest of the sales team. The operational shock of replacing that consistent core destroys pipeline velocity for quarters at a time. The top 5% provide your upside. But the middle 60% keep the lights on. Your compensation architecture needs to offer a clear path for the people doing exactly the job you hired them to do: hitting the number, consistently. But If your plan only rewards the lottery tickets, you are going to lose the foundation.

A Japanese candidate was rejected over "Poor English” Then he went and generated $9M for a competitor Here's why this US CRO regretted his decision... The CRO wanted someone who sounded like him - articulate, confident, full of business jargon. Meanwhile, the candidate was brilliant at building relationships, understood the local market deeply, and had an impeccable reputation with customers and his team. But in the interview, he was humble. He didn't brag about his achievements. And his English, while adequate, wasn't polished. The CRO didn’t hold back. "He lacks confidence. He doesn't seem like a leader." What the CRO missed was that in many Asian cultures, the best leaders don't promote themselves - they let their work speak for itself. They prioritize listening over talking. Building consensus over commanding. And most importantly, they know how to navigate the complex cultural nuances that make or break deals in APAC. This CRO isn’t the only leader I know who thinks like this. The sad truth is that many companies lose exceptional talent because they expect leaders in Japan, Korea, China, and Singapore to communicate and present themselves like their counterparts in their home country. So, if you're expanding into APAC, here's my advice: Partner with someone who understands the local landscape. Someone who can help you recognize what "great" looks like in these markets - even when it doesn't match your "normal" expectations. Because the most capable APAC leaders might not be the ones who speak perfect English or dominate the room. They're the ones who can build the teams, drive the revenue, and earn the trust of your customers. And that's what really matters.

Most people fail in sales. Because nobody ever taught them the real skills. → The skills that close deals. → The skills that build trust. → The skills that put food on the table. I’ve mentored reps for years, and I see the same mistake again and again: People chase features, tricks, and hacks, but ignore the fundamentals. Here are 11 sales skills you need if you want to stop losing deals 👇 1. The Prospecting Rule of 10 You give up too early. Great reps push through 10 touches (email, call, LinkedIn, video). Persistence beats talent every time. 2. The Silent Close Ask your question. Then shut up. Silence creates pressure. Pressure forces truth. Truth closes deals. 3. The Value-First Formula Nobody cares about your product. They care about their problem. Teach them something new → you win trust. 4. The No-Fee Boundaries Discounts don’t win. They cheapen. Hold your price = hold your worth. Respect drives revenue. 5. The 30-Second Pitch Reset If they look lost, stop. Simplify. Restart. Confused minds never buy. 6. The Rule of 3 Questions Before pitching, ask 3 open-ended questions. Diagnosis before prescription. Urgency comes from discovery. 7. The Story Sell Humans buy stories, not features. Keep it short. Keep it real. Stories stick. 8. The Champion Method Find the person who will sell for you when you’re not in the room. Champions close deals. Not reps. 9. The Confidence Posture Stand tall. Speak slowly. Breathe deeply. Confidence builds credibility. Credibility builds trust. 10. The Follow-Up Framework Most reps stop too soon. 80% of deals close after 5+ touches. Fortune lives in the follow-up. 11. The Pipeline Truth Stop lying to yourself. Sandbagging kills trust. Healthy pipeline = healthy career. 👉 None of these are taught in school. 👉 All of these decide whether you win or lose. And that’s why so many sales careers stall. If you’re in sales, save this post. If you lead a team, share it with them. Because mastery of these 11 skills = the difference between an average rep and a top 1% earner.

I watched a company lose a $1.2M deal last quarter because they were still running MEDDPICC like it's 1996. They identified a Champion and an Economic Buyer. They documented Pain points. They were textbook perfect. The problem in 2025 is that no single Champion can get a deal done. Sales methodologies from the 90s weren't built for today's buying committees, consensus-driven decisions, and distributed authority. The modern sale requires a complete methodology upgrade. No more obsessing over a Champion. You need relationships with the entire team. No more chasing generic Pain points. You need Numerical Priorities linked to business outcomes. No more vague "Compelling Event". You need documented, financially-validated trigger points. No more hoping for Decision Criteria. You need to shape it with objective benchmarks. The best sellers still run a methodology, but it's evolved. They're identifying group priorities, mapping out competing initiatives, and anchoring everything in provable ROI. Try this on your next deal…instead of asking "What's keeping you up at night?" ask "What are the top 3 numerical priorities for your department this quarter?" Watch how quickly you can separate real deals from wishful thinking.