Sales Series: The Last Day – Where Deals Are Won or Lost Today is an important day if you're a CRO, Sales Leader, or Enterprise Rep at Fortune 1000 or SMB companies. It’s the last day of the month and the last day of Q3, 2024. I still remember my early days managing NetCom Learning's sales directors (our CRO, Christiaan Filoon, now manages the team along with the Sales Directors)—those nail-biting, heart-pounding last days of the month where every call, every email mattered. One month, an Enterprise Rep in the DC Metro area closed a deal just minutes before midnight, and it made all the difference. That deal taught me that the last day is where the magic happens—but only if you're willing to put in that extra effort. As Vince Lombardi said, "It’s not whether you get knocked down; it’s whether you get up." I know the last day of the month or quarter can feel like a sprint. It's that high-stakes game where every interaction could tip the scales in your favor. But here’s the thing—the last day isn’t just about pressure; it’s an opportunity. Did you know that, according to LinkedIn Sales Solutions, 60% of sales professionals are more likely to close deals at the end of the month? This is your chance to get creative with offers, revisit old leads, and find those win-win deals. Here are five of the best tactics you can use today: 1. Revisit Q3 deals and dormant opportunities that need a final nudge. 2. Reach out with personal messages to hesitant prospects. 3. Align with your internal team for cross-selling opportunities. 4. Use strategic incentives to create urgency without compromising value. 5. Leverage executive presence for key deals to reinforce commitment and trust. And remember, today’s efforts aren’t just about hitting targets—they’re about building relationships, learning what works, and setting yourself up for success in the next quarter. According to Salesforce, 30% of annual sales happen in Q4, so finishing Q3 strong is key. So, let’s make the most of this day! The finish line is where champions are made. Let’s give it our best shot. #EnterpriseSales #SalesStrategy #EndOfMonth #EndOfQuarter #SalesGoals #SalesTeam #CRO #CEO #SalesMindset #OpportunityMindset
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Ahhh, glory days. Interesting conversation yesterday with a colleague who lamented that today’s sales SaaS reps aren’t as effective as we were. I was more optimistic based on the reps I’m coaching, but his words stuck with me. What I see is a generational phenomenon, that extends beyond the sales profession. My experience centers on competitive, enterprise software sales that began in the ‘80s with the database wars. The world’s greatest sales leaders taught a generation of sellers to compete - and win- like Sun Tzu. Many moved to selling ERP and other enterprise platforms, as our clients transitioned from mainframes to distributed systems. Multimillion dollar sales that required us to increase business insights that would pass muster with a CFO. We Rainmakers further honed our consultative sales skills, helping clients buy next-generation tools for app development, industry apps, security, integration, CRM, mobility, and more to increase efficiencies, productivity and profitability. It also generated trillions in revenue and personal wealth. Throughout this period, we received insightful, in-person, strategic sales training and read every sales book published. Many of us continue to read them regularly, with the same voracity as ever. We routinely built relationships thanks to face-to-face events and meals, establishing lifelong friendships with client sponsors who often rose within their organizations due to our collaboration to improve their businesses. Most of us who benefited from this extensive training are now either retired, CEOs, CROs, or investors. And the Rainmakers who continue to sell are, rightly, the rarest and highest paid sellers in the market. This includes many younger sellers, but the pandemic made it much harder for most, significantly impacting the socialization skills of all college graduates, particularly those entering sales roles. With remote learning and limited in-person interactions, many reps today lack essential communication and networking skills. Many of these reps are charismatic and smart but, to achieve sustainable growth, they need the same training we received plus ‘live’ deal coaching to help them win immediate deals. If you know me, you know this is my ‘why’. Today’s reps also need their companies to participate in as many face-to-face events as possible (like CAMP IT Conferences and Plug and Play Tech Center) to build the relationships needed to help clients truly improve their businesses. Too many reps are indeed struggling today but I think the future is bright. I’m optimistic that future Rainmakers - those fortunate enough to work for companies investing in sales training and deal coaching - will generate even more revenue and wealth than their predecessors.
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Consistent SaaS Sales: managing your partnerships might be as important as managing your time... The best sales reps know that their most valuable resource is their time, so there's always an emphasis on how you're using the 8-10 hours you have each day. But with all this focus on yourself and how your time is spent, you can miss the gold in the relationships you hold: your partners. Make sure to build outreach to your partners during your workdays and not just to ask for introductions or information. I've found that the more I give to others in business; the more I receive. One of my first closing roles was providing solutions for SMB owners in the Atlanta area, so a great deal of my job was meeting with business owners to determine if there was a way we could help them. And many times either the fit was off, or the timing was, so I ended up making connections for the people I met with others I had met from the days before. This ended up being a big part of my week from a prospecting standpoint; connecting new partners I had created with others. And I was rewarded with P-Club, Fast Start Award, etc. Build partner outreach into your weekly prospecting cadence with a focus on how you can help them, and watch the law of reciprocity work its magic. #sales #selling #saasSales #b2bsaas
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The unhappy path to quota: ⛔️ Work account list from top to bottom ⛔️ Work a ton of smaller deals ⛔️ Waste a lot of time chasing unqualified deals The happy path to quota: ✅ Work accounts most likely to engage ✅ Work a balance of large and small deals ✅ Invest all your energy into qualified deals This starts with territory planning. Play the odds and invest energy in accounts with the highest likelihood of closing. Sales leaders, provide guidance for reps so they spend time on the right accounts. Here's a 3-part strategy you can use for QBRs later this month and next: 1/ Analyze every deal worked in the last 6 months: ↳ What are the top two industries where you win the most? ↳ For the closed/won deals, what persona(s) was the first meeting with? ↳ What personas mobilized the deal internally? ↳ What use cases/solutions did you sell the most of? ↳ For the closed/lost deals, what made them a bad fit? ↳ What size were these companies? ↳ Were there patterns in specific department headcount or growth? ↳ What triggers did they have in common? 2/ Make a list of closed/lost deals to re-approach: ↳ Timing was bad ↳ Contract renewal dates are coming up ↳ Missing features or capabilities ↳ Didn’t get access to power ↳ Lost to a competitor ↳ Lost to no-decision 3/ Add your accounts into Sales Navigator, and run these searches: ↳ Accounts with prospects who are past employees of current clients ↳ Accounts within industries where you have the most success stories ↳ Accounts with newly hired executives that match your personas ↳ Accounts with good emails/phone numbers of your ideal personas ↳ Accounts with ideal triggers (hiring, etc.) ↳ Accounts where you have intro opportunities through teamlink ↳ Accounts where your leadership has connections ↳ Accounts where you have 1st-degree connections ↳ Accounts with contacts in your local geography ↳ Contacts who follow your company on LinkedIn ↳ Contacts you’ve had past interactions with on LinkedIn ↳ Contacts who are newly promoted into a leadership position ~~~ A proper territory strategy goes narrow and deep—not wide and shallow. Future efforts should be informed by your org's past successes. Use this list as a cheat for your next QBR. What would you add to the list? #Sales #Prospecting #Outbound
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When I was VP of Sales, my top AE closed $4.8M in 2 years (200%/Quota) and bought his first house. I will NEVER forget the feeling when I heard that. You gotta love Enterprise Sales! Here are the 5 bad habits mid-market AEs need to fix if they want to make the jump to Enterprise: 1. Running a 5-figure Problem Discovery Most AEs sell Product-Level problems. AKA the Root Causes their product solves for. Aligned Example: Spreadsheet MAP adoption issue. Enterprise sales is about selling a Transformation. Product Pain = 5 fig ACV Transformation = 6-7 fig ACV Aligned Example: [company] must go upmarket to win its strategic battle against [competitor]. Stock price is suffering. Sales competitive win rate in large deals is poor due to lack of POC control. When MAPs are used, it goes up 50%. Standardization is a must. 2. Not Thinking About What It’s Like To Buy Most AEs are taught to FAKE buyer empathy: “I NEED to do discovery” “I NEED to personalize my follow up” The next level of sales is unlocked when buyer empathy is a HABIT. “Did my buyer get enough in disco to build a compelling business case?” “What is my buyer doing now in their buying process I can support?” 3. Trying to Close Deals Most AEs chase quota by trying to optimize the END of the sales process. Being on top of it, applying creativity, resilience, and moves. Don’t get me wrong, Grit is a top-performer skill. However, top sellers close due to a well-executed FULL sales process. They get their deals so ready they practically close themselves: Compelling business case, highly committed champion, and consensus built. No Enterprise seller survives on grit. 4. Thinking You Can Be A ‘Hero’ Most AEs think they’ll get praise by proving *they* can manage a large strategic deal end-to-end. They won’t let others ‘steal their thunder’! But there are no lone wolves in the 7-figure deal range. Top sellers multi-thread internally as much as externally: - They know the CPO will talk about the product best - Execs will get buyer exec involvement and buy-in best - The Founder/CEO will talk about the vision best High-stakes deals require the best *your company* can offer. 5. Poor Organization and Attention to Detail Most AEs are so used to running the volume game, that when they go upmarket they don’t understand why they lose. Enterprise is different. You might have 10 opps in your pipe. If you don’t execute every step at OCD level, you’re toast. The best AEs are obsessed with structure and process: - They know no deal is the same; they tailor every move - They strategize internally to build the best possible plan - They collaborate with champions to create that plan - They orchestrate decision materials and build MAPs - They see their value as Buying Process as a Service —— P.S. We built Aligned to help manage the deal complexity of Enterprise Sales; Champion Enablement, Multithreading, and more. 100% FREE Deal Room. You can try here: https://lnkd.in/dwX_Zizk
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Unleashing Your Sales Potential: Lessons from a 380k ARR Deal As sales professionals, we’re always striving to close more deals. With October here, it’s the perfect time to drive results and finish the year strong. Here are key insights that helped me secure a 380k ARR deal with a win rate over 25%, focusing on delivering value in enterprise sales. 1.) Unwavering Belief Your belief in your product is your secret weapon. When you truly understand and trust what you’re selling, it shows in every interaction. This conviction inspires confidence in your prospects. 2.) Relentless Inquisitiveness Let your curiosity guide conversations. Understand your prospect’s business, challenges, and goals. Ask questions that foster dialogue and demonstrate that you care about their success. 3.) Value-Based Selling Focus on the tangible ROI your solution delivers. Quantify impacts in terms of time saved or revenue generated, shifting the conversation from price to value. 4.) Pursuing Decisions, Not Just 'Yes' Aim for clarity over agreement. If a prospect says no, dig deeper to understand their reasoning. Use effective questioning techniques to uncover their needs. 5.) Quality Over Quantity Be selective with demos; prioritize qualified prospects. Quality interactions lead to higher close rates—I've achieved rates of 40%, 54%, and even 60% by focusing on the right opportunities. 6.) Strategic Account Planning For key accounts, develop plans outlining business objectives, stakeholders, and opportunities for growth. This proactive approach aligns your solutions with their goals. 7.) Empower Clients Instead of just selling, empower clients with insights and tools to overcome challenges. Position yourself as a partner in their success. 8.) Continuous Improvement Seek client feedback to refine your approach. Show commitment by evolving to meet their needs. 9.) Effective Communication Build relationships with multiple stakeholders within an organization to navigate decision-making effectively. As we enter October—a critical month for driving results—let’s implement these strategies aggressively. Sales is a growth journey filled with opportunities to refine your skills while providing genuine value. Now, go out there and crush it! #SalesSuccess #SaaS #GrowthMindset #TechSales #CloseMoreDeals #AE #EnterpriseSales #ClosedWon
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At 26, I became a VP of sales for a fast growing SMB SaaS company. I trained our AEs to close 50-80+% of our demos (50% was considered bad). Many of those AEs were making $175K-$200K (for SMB that's really good). Here are 4 more techniques that worked (that would also help MM and ENT): 1. FOLLOWED UP UNTIL THEY TOLD US TO STOP: We couldn't afford to give up on leads after just 7 attempts. Selling at an early stage startup means you have to ride the bull for a long time (without harassing and getting on their bad side). Unless the prospect told us to stop, we would continue following up. Activities for 1 lead would show we followed up over 36 times just via phone. I had some AEs following up with a LEAD for a year (we didn't have lifecycle marketing back then). Eventually, we reeled them back and they went with us. When we lost deals, we'd follow up to find out why they didn't choose us, we were relentless. 2. CO-DEMOED: Most AES are demoing their product 100% of the time. But we knew that the only way to convert prospects was to turn the demo into an experience, not a classroom lesson they had to sit through. One way we did this really well was give mouse control during the demo. Example: "Earlier I said this was going to be easy to use, which is something you stressed would be a deal breaker, but do not trust me. I want you to experience this first hand. I'm going to give you mouse control to [do function/feature]...let me know what you think.." 3. GUT CHECK PROSPECTS: How many times have you heard a prospect say, "we need this yesterday" or "ASAP" This happens everyday for SMB AEs So during discovery/demo, if a prospect said that and we knew there was nobody else involved in the deal, we'd do what I call a "gut check." We would call them out and see if they were serious. Example: "So if at the end of this call you see that we can solve your top 3 challenges [repeat challenges], would be ready to move forward with us today?" If they were, it was a 1-call close. If they weren't, they would bring up reasons and objections we could now handle moving forward. 4. QUIT OBJECTION HANDLING: Old school objection handling teaches you to use logic to "corner" your prospect. But that stuff doesn't work anymore. We realized that although we sounded cool and clever (classic Wolf of Wallstreet), it wasn't effective. So instead, we got more curious and empathetic. Instead, we treated objections like Concerns. And the only way to understand concerns is to ask questions. So whenever we heard an objection (AKA Concern), we stopped and did more discovery. Example: → Prospect: "Our current solution allows us to do X, and it doesn't seem like you can do it with yours." → AE: "Curious, would you say that's more critical for you than [other problems we can solve that competitor cannot]?" Our goal was to understand, not rebuttal. P.s. 6,000+ AEs are mastering their disco with these questions (free): https://lnkd.in/eR69raD4
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At 26, I became a VP of sales for a fast growing SMB SaaS company that got acquired in just 4 years. I trained our AEs to close 50-80+% of our demos (50% was considered bad). Many of those AEs were making $175K-$200K (for SMB that's really good). Here are 4 more techniques that worked (that would also help MM and ENT): 1. FOLLOWED UP UNTIL THEY TOLD US TO STOP: We couldn't afford to give up on leads after just 7 attempts. Selling at an early stage startup means you have to ride the bull for a long time (without harassing and getting on their bad side). Unless the prospect told us to stop, we would continue following up. Activities for 1 lead would show we followed up over 36 times just via phone. I had some AEs following up with a LEAD for a year (we didn't have lifecycle marketing back then). Eventually, we reeled them back and they went with us. When we lost deals, we'd follow up to find out why they didn't choose us, we were relentless. 2. CO-DEMOED: Most AES are demoing their product 100% of the time. But we knew that the only way to convert prospects was to turn the demo into an experience, not a classroom lesson they had to sit through. One way we did this really well was give mouse control during the demo. Example: "Earlier I said this was going to be easy to use, which is something you stressed would be a deal breaker, but do not trust me. I want you to experience this first hand. I'm going to give you mouse control to [do function/feature]...let me know what you think.." 3. GUT CHECK PROSPECTS: How many times have you heard a prospect say, "we need this yesterday" or "ASAP" This happens everyday for SMB AEs So during discovery/demo, if a prospect said that and we knew there was nobody else involved in the deal, we'd do what I call a "gut check." We would call them out and see if they were serious. Example: "So if at the end of this call you see that we can solve your top 3 challenges [repeat challenges], would be ready to move forward with us today?" If they were, it was a 1-call close. If they weren't, they would bring up reasons and objections we could now handle moving forward. 4. QUIT OBJECTION HANDLING: Old school objection handling teaches you to use logic to "corner" your prospect. But that stuff doesn't work anymore. We realized that although we sounded cool and clever (classic Wolf of Wallstreet), it wasn't effective. So instead, we got more curious and empathetic. Instead, we treated objections like Concerns. And the only way to understand concerns is to ask questions. So whenever we heard an objection (AKA Concern), we stopped and did more discovery. Example: → Prospect: "Our current solution allows us to do X, and it doesn't seem like you can do it with yours." → AE: "Curious, would you say that's more critical for you than [other problems we can solve that competitor cannot]?" Our goal was to understand, not rebuttal.
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The unhappy path to quota: ⛔️ Work account list from top to bottom ⛔️ Work a ton of smaller deals ⛔️ Waste a lot of time chasing unqualified deals The happy path to quota: ✅ Work accounts most likely to engage ✅ Work a balance of large and small deals ✅ Invest all your energy into qualified deals This starts with territory planning. Play the odds and invest energy in accounts with the highest likelihood of closing. Sales leaders, provide guidance for reps so they spend time on the right accounts. Here's a 3-part strategy you can use for QBRs later this month and next: 1/ Analyze every deal worked in the last 6 months: ↳ What are the top two industries where you win the most? ↳ For the closed/won deals, what persona(s) was the first meeting with? ↳ What personas mobilized the deal internally? ↳ What use cases/solutions did you sell the most of? ↳ For the closed/lost deals, what made them a bad fit? ↳ What size were these companies? ↳ Were there patterns in specific department headcount or growth? ↳ What triggers did they have in common? 2/ Make a list of closed/lost deals to re-approach: ↳ Timing was bad ↳ Contract renewal dates are coming up ↳ Missing features or capabilities ↳ Didn’t get access to power ↳ Lost to a competitor ↳ Lost to no-decision 3/ Add your accounts into Sales Navigator, and run these searches: ↳ Accounts with prospects who are past employees of current clients ↳ Accounts within industries where you have the most success stories ↳ Accounts with newly hired executives that match your personas ↳ Accounts with good emails/phone numbers of your ideal personas ↳ Accounts with ideal triggers (hiring, etc.) ↳ Accounts where you have intro opportunities through teamlink ↳ Accounts where your leadership has connections ↳ Accounts where you have 1st-degree connections ↳ Accounts with contacts in your local geography ↳ Contacts who follow your company on LinkedIn ↳ Contacts you’ve had past interactions with on LinkedIn ↳ Contacts who are newly promoted into a leadership position ~~~ A proper territory strategy goes narrow and deep—not wide and shallow. Future efforts should be informed by your org's past successes. Use this list as a cheat for your next QBR. #Sales #Prospecting #Outbound
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“Just stop,” spat the COO 4 minutes into my sales call. “I don’t have time for this generic line of questioning.” I was two years into my first account executive job. Thinking I was doing everything right. I asked open ended questions to uncover pain. Just like every sales book told me to do. Yet this COO kicked my teeth in. Leaving me and his ops manager twiddling our thumbs. “I’m as confused as you,” the ops manager said. “We teach our reps to ask the exact same questions.” Years later I figured out what went wrong. According to the data below, there is a negative (yes negative) correlation between asking questions to c-suite executives, and your likelihood of winning the deal. After about four questions, you win rates drop like an anchor to the sea floor. But what conclusion should you draw from that? That it’s a bad idea to ask c-suite execs questions? No. Here’s the conclusion to draw: As far as I can tell, 90% of salespeople ask c-suite execs sophomoric questions that make execs roll their eyes. “What keeps you up at night?” “What are you and your team struggling with?” “What are the biggest challenges in your department?” THOSE questions DO have a negative impact on winning. Asking lots of questions does not equate to success. Why? Because c-suite execs expect you to show up having done your homework. You can get away with limitless questions to a c-suite exec. As long as one thing is true: Your questions provide insight. Your questions stimulate thought. Your questions *don’t just gather information.* Bad example: “What keeps you up at night?” Good example: “I talked to a few people in your org and discovered that you’re focused on increasing ASP and you seem to be stuck at around $50k despite selling to large enterprise accounts. When I hear that issue in other companies, they’re usually struggle with net retention rates – smaller deployments lead to less sticky customers. To what extent is that a conversation among your executive leadership team?” That shows them "you know what's up." That communicates business acumen. That gets them thinking and talking (if you do it right). Start with an observation. Lead into an insight. Transition to a question. That’s how you ‘do discovery’ with senior executives. Keep the generic questions for the underlings. P.S. I created a list of the top 39 questions that sell, which I tested over a 10 year period. If you want that list for free, you can get them here: https://go.pclub.io/list
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The startup landscape is experiencing a shift. In Q1 2024 alone, 254 venture-backed companies went out of business, many of which have previously attained nine figure valuations. In the world 🌍 of SaaS sales that means a successful sales team has never been more exceptional. There are fewer winners among us and I encourage everyone to share what’s working for them. Gal Aga brings up the importance of coaching in his 2nd point. Sales coaching is critical to your sales team’s success. What ai 🤖 tools are you using? Are they helpful? Having the right talent, leadership and coaching are essential. So how can the wrong tools 🛠️ f*ck all this up? In about a million ways. If you can use 1 tool to replace Salesforce (+its accompanying headaches) AND coaching you are ahead of the game. #toolstack #streamline #salesteam6
CEO @ Aligned | Don't Sell, offer Buying Process As A Service | Move the back-and-forth into a customer workspace that drives revenue
90% of companies die trying to go from $1M-$10M ARR. My sales team at Syte hit it in 2-years when I was VP Sales. Here are my top 6 learnings I’m implementing now at Aligned as we move up-market: 1. Pipeline before salespeople You CANNOT hire more AEs before you see your pipeline math working (with a 20% buffer). At some point, we had to let a few AEs go. Guess what happened? We closed MORE. AEs won’t magically fill the gaps. Outbound can take 6mo to start working, so even top AEs who were SDRs will fail unless you have this figured out first. 2. You have to coach, no matter who you hired Lack of coaching is how you screw everything up. It’s how the top 1% AE at [Big Brand Name] misses quota and bails after 2 quarters since it took them too much time to adapt. No coaching also means no progress, and no progress means boredom and decreased performance. Hire coaches or do it yourself. 3. If you’re not in the field, you’re irrelevant I was still running $500K deals while having 20 people on my team. Why? There’s no way to build good foundations for growth if you’re a ‘Dashboard VP’. Don’t get me wrong, I was a data geek. But I knew exactly what my team was experiencing, what to build, what was not working, etc. Plus, you get to build a team-selling culture. It's priceless. 4. Sales methodologies won’t magically fix your Sales Velocity The board ALWAYS wants you to go upmarket and increase ACV. There’s always going to be a drop in Win Rate after the first 2-3 AEs. Sales Velocity is going to be a constant battle, but you can’t just bring in MEDDICC/Sandler and hope for the best. You must dig for the Root Cause. Is it a Discovery issue? POCs dragging? Solve what needs to be solved. 5. Be both process-obsessed and anti-process At $1M-$10M, you don’t need every CRM stage to be tied to ten validations that send alerts to reps about what to do. What you do need is to figure out ‘what good looks like’ and document it so all reps can follow along. If you build for process adherence, you kill creativity, motivation, and speed. If you build to show top workflows, tactics, and frameworks, you actually get adherence. 6. Have extreme buyer-centricity Sales experience is what drives 50%+ of buying decisions. More than value-price ratio, product, or brand. In the race to $10M, this is even more true. You’re still unknown, and your product is shaky. With today’s evolved buyer and how complex buying has become, you CAN’T afford friction in your process. Almost every enablement initiative we ran was Buyer (not Sales) focused. —— You’ll make mistakes and it will be a bumpy ride. Just please, don’t make the same mistakes I have. Join Pavilion, follow SMEs, and find a mentor. Surround yourself with good advice. That's the key. P.S. We built Aligned to drive # 6 and transform from ‘Selling’ to ‘Enabling Buyers’; to end the sales friction that leads to buyer indecision and ghosting. A 100% FREE Deal Room. You can try it here: https://lnkd.in/dwX_Zizk
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