Michael Dame

It’s time to think about WIN rate differently. While there are various ways of calculating most look at what is in the pipe over a period of time. Some add deals that push out of the quarter. Some just calculate win/loss and don’t in deals still open. Here’s what’s missing… Few people track: How did we do when a decision was made to switch from incumbent? This is valuable information for two reasons: 1) Current economic climate reduces number of companies willing to switch. The incumbent will often reduce price to keep your business so your solution has to be even more differentiated. Since everyone is using same AI that can be more challenging than ever. 2) Beating the competitor to rip from incumbent is critical. It’s a different approach to beat someone who is painting a vision (whether real or not doesn’t matter because customer has never experienced). As you assess your WIN rate make sure you understand which competitor is giving you more challenge and build a strategy accordingly. EXAMPLE: Perhaps you win against do nothing (incumbent) by reducing the friction of implementation. EXAMPLE: Perhaps you win against a competitor by offering a trial or more flexibility in something important to them. EXAMPLE: Perhaps you look at your pipeline differently. How many of deals in my pipe are committed to a decision? The better you understand the WHY behind your results the easier it is to fix. Agree?

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Hey Salespeople: My first big commission check dropped for $45K in 2008. That was a huge influx of cash for a single guy in his mid-twenties. I still remember the thrill when it hit my bank account. At the same time, I also remember having a little bit of a panic attack. What was I supposed to do with a single lump sum that's equivalent to most peoples' annual salary? My anxiety only got worse in the coming years as I closed more deals and even bigger checks came in. Then I started leading major account teams for Gartner and my OTE doubled. Don't get me wrong. I was incredibly lucky to have the financial opportunity I did at such a young age. But I had no clue how to effectively manage it. And I know I wasn't the only emerging sales professional wrestling with this dynamic. Money / earnings has always been weirdly taboo in our culture. I see it all the time. Reps start finding success. They close a couple of big deals. The commission drops. And they immediately get analysis paralysis. The ones that muster up the courage to ask for help mostly get outdated feedback: - Invest in real estate >> In this market? Interest rates are through the roof - Buy crypto >> You sure about that? The market could crash at any moment - Invest in meme stocks >> Is that really the best move? There's other ways to drive faster ROI To be clear, I don't have anything against these more traditional investment methods: - I own a home - I have some crypto - I invest in common stocks to hedge against inflation My point is that there are other more exciting & dependable ways for protecting wealth for top salespeople.  Here are a couple of stats from BCG: - From 2018 to 2023, luxury watch values grew annually by 20% - This is close to 3x the S&P 500 which only grew 8% The right luxury watches have always out-performed broader markets. I wasn't smart enough to know this research back in the day. I honestly just bought nice watches as a statement piece. As a way to legitimize my pole position in the stack rankings and take a seat at the grownups table. But all these years later, my love for this unique category has grown. I've been more intentional about showing other sales professionals that there are more creative & exciting ways to leverage their earnings. More to come every Thursday on this passion project I've been working on related to this. P.S. Drop a comment for a luxury watch that's on your wishlist.

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117 Comments

Key takeaways from Wilson360 TLR this week in Denver! Business should be simple: 1. Growth and retention of employees 2. Pipeline of new talent 3. Growth and retention of customers 4. Pipeline of new customers There’s thousands of books, speakers, and beyond on business and success. Those are the core four. Simplicity, focus, and prioritization around the core four = growth + profit. SHAWN PRINCE Attentive.ai

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💸Best advice I have for all Sales Humans out there 💸 Master your commission plan inside out. Create a detailed spreadsheet from day one of your role, ensuring you know precisely what you’ll earn with each deal closure. While managers strive to double-check calculations, no one will safeguard your earnings like you will. In my experience across various companies, discrepancies in payments have arisen multiple times – because mistakes happen. Without my vigilance, I would have missed out on significant earnings! If you’re unsure about your compensation plan, don’t hesitate to ask questions. A good manager will not only explain it but also assist you in calculating it accurately! And most importantly if it is wrong don’t be afraid to STICK UP FOR YOURSELF!! #commission #salesadvice #topperformers #sales

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In sales, it’s important to have transparent—and sometimes tough—budget conversations early and often. In custom software development, it doesn’t help the buyer to hold their budget cards close to the vest. Costs can increase quickly if we don’t understand the most impactful requirements and determine an MVP that fits within a realistic budget. "Realistic budget" varies by buyer. We need to talk about it...even when it's tough. Here’s how to approach them confidently (without breaking a sweat): Know Your Stuff Get the Numbers Right: Be clear on both your budget and the client’s. Break down where the money will go and why that allocation makes sense. Show the Data: Back up your recommendations with data—how past investments led to growth or how future spend will deliver returns. Spell Out ROI: Be specific about how each dollar spent contributes to the overall outcome. The math will sell the value. Keep It Real Manage Expectations: Be upfront about what’s possible within the budget. No one likes surprises, so it’s better to be candid than face frustration later. Explain Trade-Offs: If certain features need to be cut to stay within budget, explain what will be impacted, helping the client see the trade-offs. Be a Problem Solver Offer Flexible Options: If budget is tight, suggest scalable solutions. Start with essentials and add more features over time. Help Prioritize: Collaborate to figure out what’s most important so you can focus resources on what matters and get more out of the budget. Tie the Budget to Big Picture Goals Link It to Strategy: Show how the budget ties into broader goals—sales targets, efficiency, or growth. People are more likely to approve when they see the bigger picture. Highlight Long-Term Benefits: Remind them the budget is an investment, not just an expense. Focus on things like customer retention, productivity, or gaining a competitive edge. Listen, Empathize, and Be Patient Hear Them Out: Understand their concerns. The more you listen, the easier it is to address pain points. Stay Calm and Respectful: Budget talks can be tense. Stay patient and respectful. Focus on Building a Partnership Be a Partner, Not Just a Vendor: Frame the conversation as a team effort. Work together to find the best solution for everyone. Stay Flexible: Be willing to adjust to meet their needs without compromising quality or results. Know When to Hold Your Ground Stick to Your Bottom Line: If the budget becomes too tight to deliver value, don’t be afraid to speak up. Don’t Overpromise: Avoid overpromising things that could hurt quality or cause issues down the road. In closing, having effective and meaningful budget conversations will build trust with the buyer and certainly increase your close rate. #sales, #budget, #toughconversations, #customsoftwaredevelopment, #baytechconsulting, #roi, #sellwithconfidence

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Sorry Sales Managers and VP's of Sales... You might be competing, and losing, against higher priority projects, that are more critical to running the business. Still wondering why your sales reps aren't selling? Take a look at your product - market fit.

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Things top salespeople do: - Understand prospect problems - Control what they can control - Are ruthless with qualifying - Lose more than they win Things top salespeople don’t do: - Make excuses ----- P.S. If you're free 𝗮𝘁 𝟭𝟮 𝗽.𝗺. 𝗘𝗦𝗧 𝘁𝗼𝗱𝗮𝘆, join SellBetter's daily show to hear how top sellers get their prospects' attention with 𝘂𝗻𝗶𝗾𝘂𝗲 & 𝗰𝗿𝗲𝗮𝘁𝗶𝘃𝗲 𝗼𝘂𝘁𝗿𝗲𝗮𝗰𝗵. I'll drop the sign-up in the comments.

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28 Comments

If you decide your sales team needs to help with renewals make sure they are incentivized correctly (I usually see a 70% new bookings goal and a 30% renewal / upsell goal). If you don't incentivize hunting, sales tend to farm too much and your growth will slow.

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AE: “It sounds like you're not sure if we are your vendor of choice just yet. Not a problem. I unfortunately can't get a lower price point approved is this scenario. Can I ask what is missing for you so we can manage expectations?” Any way you slice it, if your prospect does not yet know if you are the vendor of choice, there is no reason to negotiate. Being a vendor of choice, knowing the timeline, the start date, as well as the decision making process are four ingredients to have in order to begin negotiation. So ask what is missing for them. Stay curious.

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Overcoming the Chaos of Untracked Sales Activities Wrapping up the day, it’s clear that untracked sales activities create chaos. When deals slip through the cracks and follow-ups are missed, the impact isn’t just lost revenue—it’s damaged relationships and eroded trust within your team. To move from chaos to clarity, start by identifying the key activities that drive your sales pipeline—calls, emails, meetings—and ensure they’re tracked consistently. Implementing automated tracking through a CRM isn’t just about recording data; it’s about creating a reliable system that keeps your team accountable and informed. Here’s how you can turn this chaos around: Automate Activity Logging: Use CRM tools that automatically log every interaction. This reduces manual entry and ensures that nothing is missed. Set Up Alerts and Reminders: Automated alerts for follow-ups can help your team stay on top of their tasks and never miss an opportunity. Analyze and Adjust: Use the data from your tracked activities to identify bottlenecks and optimize your process. What’s working? What’s not? Let the data guide your decisions. Tomorrow, we’ll explore specific tools and techniques to help streamline your sales activities, ensuring your team is always one step ahead. It’s time to take control and eliminate the chaos. #BusinessGrowth #SalesLeadership #LeadershipDevelopment #CustomerSuccess #B2BSales #IndustryInsights #SalesTips #MarketingStrategy #LeadershipTips #BusinessStrategy #SalesExcellence #Entrepreneurship #GrowthHacking #SalesManagement #RevenueGrowth #CustomerExperience #HubSpotLife

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Hot take - The end of the quarter is THE BEST time to prospect. Timing and planning your prospecting is key to pipeline management. When the new quarter starts, you already have the advantage, since others will just be starting. The messaging you communicate the month prior puts your product story in the middle of its sales cycle. Everyone is always worried about closing the quarter strong, but remember, when the next quarter rolls around, it's the beginning all over again.

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Outbound not working? Strip it all back. You need a 15 step sequence. A complicated clay table. 27 inboxes in rotation. Just focus on having conversations with prospects and if they're not interested, ask them why? If you can;t get into conversations. Well that's the first problem you need to solve. Find the problem, apply a solution and repeat.

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Tired of poor pipeline hygiene? Create a Dirty Opps board and review it live with your team multiple times a week. Set clear rules for hygiene and make dirty opps public, and you’ll see hygiene improve quickly. Characteristics of opps that enter this report at QuotaPath: 1. Close dates in the past 2. No recent next steps 3. Deeper funnel stages missing key info (BANT, primary contact, etc)

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Potential customers will often ask about your company's financial situation. If they are relying on you for a critical biz function, they want to make sure you aren't going out of business any time soon. Fair enough. One of the things I highlight in my response is that the amount of money a company has raised does not fully reflect their financial viability. Clazar has raised around $15 million from our Seed and Series A rounds. One of our primary competitors has raised about 10x of that. But I wouldn't trade financial positions with them in a million years. They went through two rounds of layoffs last year and laid off almost half of their staff. They are hemorrhaging customers. On the other hand, we are steadily adding employees and growing at a very fast but sustainable pace. When I have this conversation with prospective customers, 95% of them appreciate this approach. A handful still lean towards big name recognition and the glitz of having raised a unicorn valuation round- guess you can't win them all. But we've found that we are able to take what might initially be perceived as a weakness into a real strength by digging deeper and adding context. #salestip #sellingbliss

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Property Managers/CAMs have lost all faith in Yelp & Google's reviews. If you're a commercial/HOA vendor in SoCal - we have the solution for this: discovervendors.com The 'Vendors' platform is built to protect good companies from unwarranted/fake reviews while making it easy for Managers to find the best vendor partners in their area. Only verified managers on our platform can leave reviews for companies they've worked. They can also easily send RFPs for any service they need in their properties/communities. Make the switch to the only review platform built for our industry, by our industry 🤙🏼

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Every SDR aspires to be an AE. Every AE dreams of becoming a Manager. Every Manager aims to be a Director. Every Director desires to be a VP. Every VP strives to be a CRO. Every CRO wants to be a CEO. Every CEO aims for Billionaire status. Every Billionaire simply seeks to be happy. —— In the end, at the end of the rainbow 🌈, the ultimate goal is true happiness. Ensure you're prioritizing what truly matters.

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