Sales Quota Achievement

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

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

Why Your Sales Team Isn't Hitting Targets and HOW TO FIX IT 📊Today many businesses struggle with declining sales performance, and one of my clients - a mid-sized tech firm, faced this very issue. Despite having a talented team, they consistently missed their sales targets, leading to frustration and dwindling morale. They started sales coaching with me, and here's how we started and turned things around. Conducting Diagnosis: Understanding the Core Issues through a sales audit, and after an initial assessment, it became evident that several factors contributed to the poor performance. These are listed broadly as follows: 🚫Lack of Clear Goals: The sales team didn’t have well-defined, achievable targets. They were chasing numbers without a strategic plan. 🌀Inadequate Training: Despite their talent, the team lacked training in the latest sales techniques and tools. There was also an inefficient sales process at play. 🗯Poor Communication: There was a significant disconnect between the sales team and other departments, leading to missed opportunities and misunderstandings. 📌Low Motivation: Constant failure to meet targets had demoralized the team, impacting their productivity and drive. To address these issues, we implemented a comprehensive coaching and facilitation program focusing on well executed strategies: 🎯 Setting SMART Goals - to give the team clear direction and purpose. Fine tuning the sales process also contributed to efficiency. 💪Enhanced Training - on advanced sales techniques, product knowledge, and customer engagement strategies. 🧲Optimizing the Sales Process - by identify the bottlenecks and making necessary adjustments, we ensure that the process is customer-focused and aligns with their buying journey. 🎎Improving Communication - by establishing regular cross-departmental meetings and open communication channels to ensure everyone was on the same page. 👊Motivation and Incentives - by introducing a reward system to recognize and celebrate achievements, boosting morale and encouraging a healthy competitive spirit. Within three months, there was a complete transformation - the team had a high morale and camaraderie. Soon, they not only met but also exceeded their sales targets, achieving a 30% increase in sales. The clear goals, enhanced skills, and improved communication fostered a collaborative and motivated environment. The client’s sales performance skyrocketed, and the once-struggling team became a powerhouse of productivity and success. ✨✨ Need help identifying and fixing the issues in your sales team? Contact me for expert guidance and tailored solutions! 📌https://lnkd.in/dGGM5vCK #sonniasingh #sonniasinghleadershipcoach #salescoaching #salesoptimization #businessresults #SalesPerformance #SalesTargets #TeamMotivation #SalesTraining #SalesProcess #SalesLeadership

After 7 years of navigating sales and leading teams in price-sensitive markets across Southeast Asia, I've broken down my experience into these 10 lessons: 1. Leverage real-world examples: When addressing prospects' questions, anchor your responses in actual experiences with other clients. This illustrates social proof without sounding boastful. 2. Showcase intimate understanding: While discussing your product, be tactical, not theoretical; see #1. Display an in-depth understanding of the problem and the client's workflow. 3. Demonstrate first, ask second: Highlight the efficacy of your solution without pushing clients into an immediate commitment. Consider giving consultations, hosting workshops, delivering event talks, or writing articles. 4. Engage, don't oversell on LinkedIn: Stay active on LinkedIn, but refrain from frequent direct selling. Instead, genuinely engage with prospects' content and assist them. Ideally, they shall approach you first. 5. Outbound sales done right: If reaching out, ensure you a) contact 3 to 4 individuals within target organizations, b) A/B test email content and subjects, and c) follow up 3 to 4 times. Rinse and repeat. 6. Emphasize social proof: Populate your digital channels with client testimonials. Create a prominent “Wall of Love” on your website to host all testimonials and case studies, then distribute these across emails, ads, website, social media, blogs, and onboarding materials. 7. Build a lot of social proof: Consider the following to gather more testimonials: a) Offer to draft them for your client, b) Provide services at a reduced/no cost initially, and c) Incentivize the sales team not just for closing deals but also for acquiring testimonials/case studies. 8. Experience on the ground matters: Invest time in your target markets. Begin pitches by sharing personal anecdotes and what you cherish about that particular country. 9. Optimize commission structures: Continually refine your commission structures. Experiment until you find the sweet spot where the team is incentivized optimally for maximum output. 10. Streamline your deck: All supplementary slides should be in an appendix, displayed only if required. The deck structure I like follows this: a) introduce you and your company b) the as-is state c) why existing solutions are not effective d) requirements for the new world e) your solution f) demo g) social proof h) next steps What have I missed?

A rep on my client's team hit his annual quota in 4 months. $1.5M on a $438K quota. Same market. Same product. Same comp plan as every rep who missed. The difference was 5 strategies the top 1% use and almost no one else does. #1 Stop chasing titles. Chase the “little” Domino. The economic buyer isn't always the highest title in the room. They're the one person who can say yes when everyone else says no, and no when everyone else says yes. Miss them and you lose deals you thought were locked. #2 Run your discovery like a litigator. A lawyer doesn't take every case. They build the case first, then decide if it's worth pursuing. Your first call should do the same. If you can't build a business case, disqualify early and protect your time. #3 Convert latent pain into active pain. Most prospects don't feel urgency because their pain is a scratch, not a wound. Your job is to ask questions that help them realize it's actually gushing. When they feel level 10 pain, they take level 10 action. #4 Coach your champion like they're going into a boardroom. If your champion can't sell internally, you lose. Coach them on every objection their boss will raise. How they explain it to you is exactly how they'll explain it to the decision maker. Fix it before that meeting happens. #5 Audit your deals before they go sideways. Happy ears kill pipelines. Rate every active deal across 8 categories: pain, opportunity cost, desired outcomes, executive influence, resources, fear of failure, trust, and buying criteria. Whatever scores low is your next call. Most reps grind harder when deals stall. The top 1% diagnose faster. P.S. If you're a sales leader reading this thinking "I need to forward this to my reps". Pause for a second. The reason only your top 1-2 reps execute these strategies consistently isn't a talent problem. It's a system problem. The goal isn't to find more reps who naturally do this. The goal is to build a system where every rep on your team does this. If you want to see exactly where that gap lives on your team, grab the free Revenue Leak Diagnostic Playbook: https://lnkd.in/g8DFrh7J

People are often shocked when I tell them that at Enjay, my sales team has ZERO financial incentives. No commissions. No "deal closing" bonuses. "Limesh, how does the team function? What drives them?" सच बात ये है, I used to think incentives were the only fuel. But over 20+ years, I realised something uncomfortable. 👉 When business owners rely solely on financial incentives to drive sales, they are being lazy. It is their way of saying: "I don't want to teach you.  I don't want to build a process.  I don't want to create sales material.  Just take this money and bring me results." It is a shortcut. And shortcuts kill "Dhandha" in the long run. 👉 Here is the reality of our office:  We hire freshers.  If I dangle a carrot in front of a fresher who doesn't know how to sell, it’s not motivation.  It’s cruelty.  They need training, not pressure. 👉 Also, heavy incentives often breed "Toxic High Performers"—people who hit targets but destroy the company culture. 👍 So, how do we hit our numbers without the greed factor? 1. We Plan Together. Marketing, Support, Dev, and Sales sit together. We decide the goal. It is not dictated from the top; it is agreed upon mutually by the team members. 2. We Predict the Roadblocks. We ask, "What will stop us from hitting this goal?" We identify the bottlenecks before they happen. 3. We Monitor Execution, Not Just Results. We don't wait for the 30th of the month to scream at people. We watch the daily inputs. 4. We Focus on Potential. Incentives reward performance. Systems nurture potential. 👍 Business is an Infinite Game.  We aren't running a sprint to hit a quarter-end number.  We are running a marathon to stay relevant for decades. 🌹 Stop trying to bribe your team to work.  Build a system that makes their success inevitable. Thoughts?

Lots of VPs of Sales talk about CAC like it’s a single number. But CAC isn’t a number. It’s a portfolio. And every segment you sell into - SMB, MM, ENT - has its own CAC profile. If you’re burning $12K to land a $6K SMB customer, but $30K to land a $300K enterprise deal, your CAC isn’t broken. Your allocation strategy is. And if you’re still only measuring CAC at the company level? You’re flying blind. This is where leaders can separate themselves. You shouldn't just measure CAC. You should segment it, analyze it, and build around it. Here’s how to operate: 1. Stop treating CAC as a blended metric. Break it down by: - Segment: SMB vs MM vs ENT - Channel: Outbound vs Inbound vs Partner - Geography: Especially when global expansion is on the roadmap Because “our CAC is $17K” means nothing. But “our CAC in enterprise is $28K with a 9 month payback” is a decision making asset. 2. Act on what you learn. Once CAC is segmented, shift resources toward efficiency: - Reallocate reps to higher leverage segments. - Focus enablement on where ramp time is shortest. - Adjust comp plans and funnel targets to optimize payback. Basically, stop managing by gut and start optimizing by unit economics. 3. Simplify how CAC gets modeled. No 12 tab spreadsheet. No MBA required. Just start with this: - Take total S&M spend for the quarter (headcount, tech, programs, all in). - Map each cost center to the segment it supports. - Divide by new ARR closed per segment. That’s your directional CAC by segment. Clean enough to inform strategy. Tight enough to move fast. Example: Let’s say you spent $1.2M in sales & marketing last quarter. You break it down like this: - $400K was tied to your SMB motion (BDR team, paid media, onboarding). - $300K went toward mid-market (AEs, webinars, tool spend). - $500K supported enterprise (field reps, events, solutions consultants). Now, you look at new ARR: - SMB closed $150K - MM closed $600K - ENT closed $1.2M Your directional CAC per segment: -SMB = $400K / $150K = 2.67x CAC - MM = $300K / $600K = 0.5x CAC - ENT = $500K / $1.2M = 0.42x CAC On the surface, SMB looks like it’s growing. But holy moly it’s killing your efficiency. This back of the ol napkin CAC view is clean, fast, and tells you exactly where to scale or pull back. 4. Pair CAC with LTV and look for leverage. Don’t just ask, “Can we afford this rep?” Instead ask: - “Is the LTV in this segment big enough to justify our spend?” - “Are we acquiring customers we can actually retain and expand?” - “Where are we getting 4:1 returns...and where are we burning cash?” Find the segments where CAC gives you leverage anbd build everything around those. If your CAC model ends in one number, it’s not a model. It’s a guess. You don’t scale by chasing total pipeline. You scale by doubling down on efficient segments. The best revenue leaders I've known don’t ask for more leads. They ask for better economics. And they know exactly where to find them.

Want to know why top performers close 2-3x more deals than average reps? It's not that they're smarter. It's that they've mastered deep work. After studying hundreds of high-performing sellers, I've found one consistent pattern: They protect their prime selling hours like their life depends on it. Most reps are drowning in shallow work, constantly switching between email, Slack, CRM updates, and social media. Each task switch costs you 23 minutes of focused energy. The result is a day filled with activity but empty of results. Here's how innovative sellers are implementing deep work: 1️⃣ Power Blocks They schedule 90-minute uninterrupted blocks for their most important selling activities. No email. No Slack. No phone. Just focused execution on revenue-generating work. 2️⃣ Energy Management They align their most important tasks with their peak energy hours. For most, that's 9-11 AM, not 3 PM after back-to-back meetings. 3️⃣ AI-Powered Prep They leverage AI to prepare for sales calls in half the time. "I feed the AI my call notes, recent news, and past objections. It gives me a hyper-focused prep document in 5 minutes instead of 45." 4️⃣ Elimination Before Optimization Before trying to get faster at tasks, they ask: "Does this task even need to exist?" You can't optimize what should be eliminated. 5️⃣ Digital Minimalism They turn off all notifications during selling hours. No Slack pings. No email popups. No LinkedIn alerts. The sellers implementing these practices aren't working more hours. They're just getting 3x more value from the hours they work. Most sales organizations obsess over activity metrics while ignoring the quality of focus behind them. What would happen if you protected just one 90-minute deep work block every day?

One thing that your sales team is not doing - and it’s costing you millions!! What if your sales team operated like a micro-VC firm? Instead of chasing every lead that shows interest, they’d evaluate opportunities with the same rigor a VC applies to startups: looking for long-term fit, growth potential, and alignment with your company’s “investment thesis” (aka your Ideal Customer Profile). Here’s how this mindset could transform your team: 🔎 Evaluate leads like potential investments. VCs don’t throw money at every startup with a flashy pitch deck. They dig deep, looking at market potential, the team’s capabilities, product market fit and how well the startup aligns with their portfolio strategy. Your sales team can apply the same logic by scoring leads against key criteria: budget, authority, need, timing, and, most importantly, how well they fit your ICP.    📈 Prioritize growth potential over short-term wins. Venture capital is not about quick returns; it is about compounding growth. In sales, this means focusing on accounts that offer repeat business, long-term loyalty, or opportunities to expand within the organization, even if they require more nurturing upfront. 💰 Allocate resources with precision. VCs deploy their capital strategically, focusing on startups with the highest potential ROI. Your team can do the same by aligning SDR time, marketing resources, and account executive focus on leads with the highest likelihood of becoming not just customers, but valuable customers. Instead of chasing every deal, this approach ensures your team spends time and resources on what truly drives results. A clear focus on high-value opportunities means less time wasted and more wins that make an impact. Does your sales team have an “investment thesis”? If not, now is the time to create one. It could be the most strategic move you make this year. #salesstrategy #leadgeneration #salesgrowth #salesoptimization #businessdevelopment #leadquality #b2bsales #salesleadership #salesperformance #revenuegrowth #salesmanagement #salespipeline #scalingsales #icp #salesinnovation

Probing: The Art that Transforms Sales Conversations Monologue To Dialogue In today’s competitive landscape, sales is no longer about telling—it’s about understanding. The real shift happens when we move from monologue to meaningful dialogue. Research and industry surveys consistently indicate that sales effectiveness can improve by nearly 40% when conversations are driven by dialogue rather than one-sided pitching. So, what makes the difference? ✅ Probing with Purpose Great sales professionals don’t just ask questions—they ask the right questions. Thoughtful probing helps uncover: Customer needs beyond the obvious Hidden concerns and decision triggers The real “why” behind the buying intent ✅ Dialogue Builds Trust When customers feel heard, they engage more openly. A dialogue creates a sense of partnership rather than a transaction, leading to stronger relationships and higher conversion rates. ✅ Listening is the New Selling Active listening is as powerful as asking questions. It enables you to respond with relevance, empathy, and precision. Here are 5 Most effective techniques 1. Open-Ended Questioning Move beyond yes/no questions. Encourage the customer to share context and perspective. Example: “Can you walk me through your current process?” 👉 This uncovers deeper insights and keeps the conversation flowing. 2. The 5 Whys Technique Don’t stop at the first answer—dig deeper to find the real problem. Example: Customer: “We want to reduce costs.” You: “Why is that a priority right now?” 👉 Helps uncover root causes rather than surface-level needs. 3. SPIN Probing (Situation–Problem–Implication–Need Payoff) A structured way to guide conversations: Situation: Understand context Problem: Identify pain points Implication: Explore impact Need Payoff: Highlight value 👉 This turns conversations into consultative selling. 4. Reflective Questioning Paraphrase and confirm what the customer said. Example: “So if I understand correctly, delays in delivery are impacting your client satisfaction?” 👉 Builds trust and shows active listening. 5. Future-Focused Probing Shift the discussion toward outcomes and aspirations. Example: “What would success look like for you in the next 6 months?” 👉 Helps position your solution as a bridge to their goals. 💡 Key Takeaway: If you want to elevate your sales impact, shift your focus from presenting solutions to exploring problems. The quality of your questions will define the quality of your outcomes. #SalesExcellence #ConsultativeSelling #CustomerExperience #Leadership #LearningAndDevelopment #BusinessGrowth