Sales Discovery Tips

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

Most sales calls fail… in the first 2 minutes. Not because of: • Poor pitching • Weak closing • Bad pricing The real mistake? Rushing to give solutions before understanding the problem. That's why: • Quick solutions get ghosted • Fast proposals get stuck • Rapid responses get ignored The best closers know— Deep understanding wins more deals. ← Read this again. Go slow if you want to go fast. You need to earn trust before a sale can happen. All clients want: • To be seen • To be heard • To be understood So when you prescribe solutions or jump to conclusions without understanding where they've been, what they've tried, where they're going, what their fears are, what an ideal partner experience might be like, your solutions might be falling on deaf ears. Duh! Doesn't everyone already know this? Knowing and doing are two different things. Sad to say, I've witnessed too many people in sales scenarios: ask "checklist questions" (the kind where you go down a list and the answer doesn't seem to matter), ignore obvious signs of "I'm not ready to move forward" and bulldoze ahead, and not listen with empathy or understanding of what the prospect is going through. The sales call winds up being just a lead-up to asking for the sale. If this is what you're doing, why go through the charade of feigning like you care? Just ask for the sale up front. What's the alternative? The answer is the question. Get good at asking questions. Big. Beautiful. Questions. Next. Learn how to listen. What is the client saying? What aren't they saying? What else could this mean? Then, ask good follow up questions. It's how you demonstrate, what they say matters. Say: "I'd like to loop back and ask you to unpack what you said about (x). I want to know more." What is one of your favorite, beautiful questions that you love to ask in the sales/discovery conversation with prospects? How do they respond? Let's build a list for everyone to benefit. Don't forget to save and share this post for later reference. #salestraining #smallbusinessadvice #smallbusinesstips #getmoreclients

This is the winning B2B Marketing playbook for 2026. Let me break it down for you with 5 pillars: 1. Create content for passive buyers Some businesses are not ready to buy (for various reasons) and don't want to be in your linear sales sequence. The best scenario is to build top of mind awareness for these types of buyers through content marketing. - Develop clear content pillars - Publish consistently across time - Vary formats and channels 2. Build a solid intent signals gathering system For long we thought attribution was the key, but with the new B2B marketing playbook, intent signals are more important. You need to constantly identify a list of prospects that have higher intent than average. - Track content engagement across channels - Score prospects based on signals and frequency - Centralize signals in one CRM or system 3. Use ads to amplify what already works Ads will not create demand out of the blue but it will expand your reach and reinforce awareness with repetition. - Promote top-performing content - Retarget engaged and high-intent audiences - Focus on repetition, not aggressive messages 4. Get ready to capture demand from active buyers When they're ready, businesses want a fast response across channels. If you take 48 hours to reply to an inquiry, you'll lose (especially in red ocean markets). Build an efficient inbound sales system to capture and manage demand. - Optimized social media profiles - Dynamic forms to segment leads - Soft captures like webinars or guides 5. Run warm outreach for potentially active buyers Some ready-to-buy prospects who like your brand may not contact you. They may be busy, forget, or assume you’ll reach out. Acknowledge this reality and contact them directly. - Build a social selling routine - Create warm email sequences - ABM for larger accounts And AI is an enabler across the playbook. *** We are looking to help 3 more B2B businesses to install and run this playbook in Q1 2026, tell me if you're interested.

Handle objections like a six-figure salesperson It’s not about talent—it’s about preparation. Here’s how to tackle objections effectively: → Anticipate common objections, plan your responses. → Reframe objections into opportunities to add value. → Practice these strategies until they become second nature. 👉 Get more cheat sheets like this: sign up for SalesDaily Premium: salesdaily.co/upgrade Here are 12 common sales objections and how to respond to them: 1.) We’re already working with another vendor. ⇢ Acknowledge their loyalty and ask what they value most. ⇢ Differentiate by emphasizing areas where you outperform competitors. ⇢ Ask: “What’s one thing you wish they did better?” 2.) This isn’t a priority. ⇢ Show understanding and suggest exploring how you can prevent a specific problem later. ⇢ Ask: “Would a quick chat now help for when it does become a priority?” 3.) We don’t have the budget. ⇢ Use humor or empathy to acknowledge their constraints. ⇢ Offer a preview so they can assess if it should be on their radar for next year. ⇢ Ask: “Would that work for you?” 4.) I need to think about it. ⇢ Respect their hesitation and offer to schedule a follow-up. ⇢ Ask: “What specific questions are still on your mind?” 5.) Send me an email. ⇢ Agree but provide context to ensure relevance. ⇢ Ask: “Would these outcomes align with what you’re focused on now?” 6.) I’m not interested. ⇢ Subtly acknowledge their position while offering value. ⇢ Ask: “Would exploring this together make sense before deciding further?” 7.) Where did you have my number from? ⇢ Clarify politely and explain where you found their contact information. ⇢ Reassure them by tying your outreach to their goals. 8.) Your price is too high. ⇢ Acknowledge their concern and reframe the conversation to focus on value. ⇢ Ask: “Do you feel confident our solution would help you achieve your goals?” 9.) We’re happy with what we have. ⇢ Validate their satisfaction but share examples of clients who improved despite being content initially. ⇢ Ask: “Would you be open to exploring potential gains on your end?” 10.) Call me back in 4 months. ⇢ Agree and ask what’s expected to change in that timeframe. ⇢ Probe lightly to uncover urgency: “Would anything make it worth discussing sooner?” 11.) I’m not interested. ⇢ Acknowledge their decision and highlight how their role impacts outcomes. ⇢ Ask indirectly: “Would it make sense to explore other perspectives before deciding?” 12.) We tried something similar before, and it didn’t work. ⇢ Avoid sounding defensive and reframe the conversation by emphasizing how you’re different. ⇢ Transition back to the pitch confidently: “Let’s dive in, and I think you’ll be pleasantly surprised.” Preparation is the key to handling objections confidently. Save this guide, adapt these responses to fit your style, and turn challenges into opportunities. Want a high-res version of this cheat sheet? 👉 Sign up for salesdaily.co

I’ve been in sales for 17 years and managed 100s of AEs. This profession is so full of bad advice and it took me ages to find my mentors. Here are 9 things I wish someone had told me years ago… 1. Buyers Close Deals, Not You It’s easy to obsess over sales meetings. But the real magic happens in buyers' internal meetings—those you’re not invited to. Align your actions with the critical steps THEY need to build consensus. Don't sell. Enable them to buy. 2. Your Sales Process is Meant to Be Broken On that note, your role is not just to execute your process but to offer ‘Project Management Services’ to your buyers’ process. Your process is there to offer a good foundation to build on, but it only covers 5-17% of your buyers’ process. 3. Calendar Overload = Illusion of Control Weekly champion syncs feel great, but the truth is—you’re probably not moving the needle much. If you fail to equip buyers between calls with the right tools or content, you’ll discover your “champion” isn’t championing. Help them build momentum internally—24/7. 4. Budget is Almost Never the Deal-Breaker Stop asking about budget on the first call. It is rarely a reason to qualify out. No buyer only spends on pre-allocated line items. “No budget” simply means “No Justification” to create one for the value you’ve been able to convey. 5. Accessing Stakeholders is NOT Enough Multithreading is not about having many people on your calls/emails. That’s a vanity metric. It’s about building separate relationships to support their specific needs/requirements/concerns. That’s what truly moves the needle. 6. Executives Hate Deep Discovery on Calls Structured deep discovery doesn’t work well in executive calls. You must lead with stories, teach them something new, and let a conversation develop. They have zero patience. If you try to have long conversations first, they’ll tune off. 7. You’ll Fail 99% of Outbound Intro Calls if You Treat Them Like Inbound You lead with discovery on Inbound but lead with insights on Outbound—It’s OK to use slides if they serve the discovery. It’s even OK to demo before you have all the pain points figured out. As long as it all serves the discovery. 8. Drop the ‘Perfect Discovery’ Fantasy A perfect disco only works in a role-play. Try it in real life and you'll end up with no next steps. Worry less about your framework, and more about having a meaningful conversation around ‘why do anything’, ‘why now’, and ‘why you’. The rest only helps you and can come later. 9. Speed is Your Biggest Easy ‘Hack’ to Drive Urgency Nothing cuts down deal cycles like dictating a fast rhythm of communication. Received an email? Answer from your phone right away. Talking next steps? Offer a call tomorrow. Discussed timeline/MAP? Recap that on every follow-up. —— Don’t make it harder than it has to be. Make mistakes. Learn from them. But always learn from other people’s mistakes first. P.S. Check out Aligned-the tech I wish I had https://lnkd.in/dwX_Zizk

11 Red flags in your sales pipeline that are costing you deals (And how to fix them before it’s too late) You think your pipeline is healthy? A full list of leads, promising conversations, and you’re already counting the wins. But what looks good on the surface might be hiding major problems that are killing your close rate. Here are 11 red flags to catch before they cost you deals: Leads That Ghost After the First Call ↳ If they vanish, they were never serious buyers. Too Many Stuck Deals ↳ If deals aren’t moving, your pipeline is clogged, not growing. No Clear Decision-Maker in Sight ↳ Talking to the wrong person? You’re wasting time. Pricing Objections Keep Coming Up ↳ If prospects always push back on price, you haven’t built enough value. Prospects Who “Just Want to Learn” ↳ Interest without urgency means they’re not ready to buy. Lack of a Next Step After Every Call ↳ If there’s no clear action item, momentum dies. Relying on One or Two Big Deals to Hit Quota ↳ Pipeline health = multiple strong opportunities, not one make-or-break deal. Competitors Keep Winning Your Deals ↳ If you’re losing to the same competitors, something needs to change. Deals Dragging Beyond the Expected Sales Cycle ↳ A slow close usually means a weak commitment. Too Many Unqualified Leads in Your Funnel ↳ More leads ≠ better pipeline. Quality > Quantity. Your Pipeline Is All About You, Not the Buyer ↳ If your sales process doesn’t align with how buyers buy, expect friction. These aren’t just small issues—they’re silent deal killers. A pipeline full of bad opportunities isn’t a pipeline. It’s a false sense of progress. Fix these, and you’ll stop chasing dead leads and start closing real deals. Did I miss any major red flags? Drop them in the comments! ⬇️

I stopped asking "What are your priorities?" in sales calls. I'd get generic, unhelpful answers each time. I ask these instead: 1. What are the top 3 metrics you're measured on this quarter? ↳Knowing their key performance indicators reveals what truly matters. 2. What's keeping you up at night about hitting those goals? ↳Their biggest fears and challenges point to where you can create value. 3. Where are you currently losing revenue or leaving money on the table? ↳Quantifying the cost of inaction builds urgency for change. 4. Have you explored other solutions before? What didn't work? ↳Understanding past failures helps you differentiate and avoid the same pitfalls. 5. What would a successful outcome look like for you in 6 months? ↳Aligning on their definition of success guides your solution positioning. 6. Who else is impacted by this issue across the company? ↳Identifying all stakeholders ensures you bring the right people into the process. 7. What's your budget range for addressing this? ↳Getting a sense of investment appetite upfront avoids wasted time. 8. What's your decision-making process and timeline? ↳Mapping the path to a decision keeps the momentum going. 9. What concerns do you have about moving forward? ↳Surfacing objections early allows you to directly address them. 10. How will you measure ROI if we're successful? ↳Defining ROI metrics upfront justifies your pricing and business case. Vague, open-ended questions lead to vague, unhelpful answers. Get specific, and you'll uncover the insights to truly understand the buyer's situation. --- Repost ♻ to help your network with this important skill Comment “SEQUENCE” below if you want me to send you 13 email sequences that sell like crazy. 

When I was in sales, the hardest question was: “Which accounts are actually worth my time?” We had CRMs full of companies and contacts, but no real way to know who was in-market. So we spent hours digging through filings, news, and social posts – hoping to find a signal. Even the best reps could only cover 30 to 40% of the accounts they were assigned. The rest was just wasted opportunity. That’s changing with AI. I have been talking to our customers and even our own reps at HubSpot about how they are using intent data to drive better prospecting. And it is dramatically different. Here is what I am seeing great reps do: Spot demand before it’s obvious. They are using AI to scan job postings, funding announcements, press coverage, even community chatter, to flag the accounts most likely to buy. Qualification is completely different with intent data. Make conversations personal and relevant. Reps are using AI to get alerts the second an account shows intent, like visiting a pricing page right after a funding round. And they are using sequences to send out relevant emails that feel personal. This is what intent-based qualification and prospecting looks like. Salespeople can not only cover more accounts, they can connect with each account in a deeper way. One sales leader we connected with told me: “What used to take 20 hours a week in research now takes one. And we’re seeing better responses than ever.” Prospecting used to be guesswork. With AI, it’s precision.

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇