Sales Rep Challenges

90% of salespeople can't sell to the C-Suite. It shows: Only 10% of C-Suite executives say sales calls were valuable enough to schedule a follow up. 4 tips to sell to the C-Suite like the top 10% of sellers: 1. Don't make the C-Suite your first meeting. You’ll be tempted to go after the CXO first. Don’t. Unless you already have inside info: Do your homework first. The worst thing you can do? Show up to the C-Suite empty-handed. Do a few “rounds” first. If you sell to CTOs, talk to the engineers. If you sell to CROs, talk to the AEs. If you sell to CHROs, talk to the recruiters. Pay your dues. 2. Start the meeting with a “What I Know” slide. Most CXOs expect sales meetings to be a waste. They rarely agree to them. When they do, they do it reluctantly. But. If you SHOW up like this: “Ok. I’ve talked to three people in your org, read your 10K, and talked to a customer in your industry. Maybe we can start with a summary of what I’ve learned to get your perspective.” INSTANT CREDIBILITY. They will sigh with relief: “Wow, the first time a sales call isn’t a waste,” they’ll think. The rest is yours to lose. 3. RESEARCH-BASED Discovery Only This is not the time for typical discovery. You should have done that by now. That doesn’t mean you can’t ask questions. But. They better be informed. They better be targeted. They better share observations. BAD EXAMPLE: “Tell me about your function's biggest challenges.” *EYE ROLL* GOOD EXAMPLE: “When I talked to John, he mentioned the company was struggling to recruit engineers to get new features to market fast enough. "His concern was hitting deadlines, but I have to imagine you have a broader view of why this issue matters. "Assuming this is a top-of-mind issue, how about we start by getting your take on that?” Do that. That's how you get them listening. 4. Lean on your champion for TACTICAL next steps. This may come as a shock: Don't try to “lock in next steps” with the CXO. They start their day at 7am. They end their day at 7pm. Back to back meetings all day. They are not looking forward to more. Yes, you want to talk again. But use your champion for 'tactical' next steps. Reserve C-Suite next steps for strategic meetings: “I think Lisa and I can take next steps from here. "I’ll keep you in the loop. The one meeting I do think we should have next will be in three weeks from now where we debrief the business case. "Between now and then you’re off the hook, but mind if I go through your EA so that you, me, and Lisa can review this a few weeks out?” “This person gets it,” they’ll think. Ok. That’s four tips. They won't transform your life. But they will level you up a notch. Give 'em a try, and tag a seller who'd like this.

Selling to the C-Suite? Here’s what they actually care about. Most reps blow the meeting before it even starts. Not because their product sucks... but because they show up sounding like a feature brochure with a pulse. When you’re in front of a C-level exec, you’ve got 30 seconds to prove: ✅ You understand their world ✅ You’re not here to waste time ✅ You can move the needle on what matters to them What that looks like, by title: 🧠 CEO – Growth + Risk ✖ Don’t pitch features. ✔ Show how you help them scale faster, cut risk, or hit strategic goals. 💬 “This helps teams like yours enter [X market] 3x faster - with fewer moving parts.” 💰 CFO – Cost + ROI ✖ “This will improve productivity” = fluff. ✔ Quantify ROI. Speak in margins, efficiency, risk reduction. 💬 “We reduced vendor cost 18% and freed 22 hours/month for [role].” 🛠 COO – Efficiency + Execution ✖ Don’t say “streamline.” Prove it. ✔ Show how you simplify ops, reduce friction, and speed up delivery. 💬 “We eliminate 4 handoffs in your process, cutting fulfillment time in half.” 📈 CRO – Pipeline + Predictability ✖ Don’t pitch dashboards. ✔ Show how you help them hit number faster - with fewer surprises. 💬 “We help reps close 12% more deals without changing your CRM.” 📣 CMO – Leads + Attribution ✖ Don’t promise “awareness.” ✔ Show how you help convert demand into real pipeline. 💬 “We cut cost per qualified lead by 38%... and proved it with revenue impact.” 👥 CHRO – Retention + Culture ✖ Don’t pitch “engagement.” ✔ Tie your solution to retention, onboarding, or team performance. 💬 “Your reps ramp 30% faster...and stay longer because the system supports them.” CIO/CTO – Security + Scalability ✖ Don’t ignore technical friction. ✔ Preempt risk and show how your tool fits their stack. 💬 “No extra infrastructure, fully SOC 2 compliant, and deployed in 48 hours.” CPO – Velocity + Adoption ✖ Don’t talk features to a feature owner. ✔ Show how you drive product adoption and roadmap execution. 💬 “Adoption jumped 44% in 3 months - because we removed friction at the edge.” You’re not selling your product. You’re selling outcomes to people with power, pressure, and no patience. 👇 Which C-level convo are you prepping for next? — 📬 Want access to practical sales resources and advice from top sellers every day? Subscribe here: SalesDaily.co

Selling into the C-suite? Harder than ever. One founder cracked the code, selling wholesale nuts 🥜 It might be the shift your team needs (even if you sell software). I coached a business owner named Matthew on a Shark Tank-style show. Great product. No traction with execs. His pitch: “We’ve got the best prices.” Come on, Matthew. No CEO wakes up thinking, “I need a deal on pistachios.” They’re thinking: ⚠️ “We’ve lost our edge.” ⚠️ “My team’s burned out.” ⚠️ “We need to wake people up.” So Matthew made the shift. He stopped pushing product and started selling what execs actually buy: urgency, outcomes, and impact. 🟢 Low retention and engagement became the problems to solve 🟢 Focus and energy replaced “great price” 🟢 A snack became a strategy And just like that, doors cracked open. 🌰 Regardless of what your reps are selling, if they lead with features, they’re making it harder to close. Buyers don’t need more information. They need more confidence. You’ve got just over 4 weeks to close Q3 strong. Take a few minutes today and ask yourself: ➡️ Are we building confidence or just delivering clever pitches? ➡️ Can a distracted buyer instantly tell why we’re the best choice? ➡️ What’s happening in their world that makes inaction risky right now? #Sales #B2BSales #SalesLeadership #BeMoreSellMore

I polled the sales team at one of my clients to see what they actually wanted their Solutions Consultants to get better at. These were their top 5 responses (what they didn’t want was surprising). 1. Storytelling. 100% of sales respondents wanted their SC to get better at storytelling. It’s not surprising because, having been an SC myself, there are two problems we face: 1) We don’t get any training on storytelling, and 2) Many of us are not involved with post-sales, so we rarely hear customer stories firsthand. 2. Picking up on behavioral cues. This is always a challenge for SCs, partly because of our background typically being more technical in nature, but also because of the “one-night stand” nature of our business. It’s not uncommon for an SC to enter the deal, deliver an amazing POC or demo and then be gone. 3. Discovering more pain. There’s nothing more critical in an enterprise sale than discovery, but unfortunately, most presales teams don’t do it well. Part of that is our fault, but part of it is the system we operate in. For example, I personally came from consulting, and in consulting, they teach you how to take requirements. In sales, if you're taking requirements, you're losing. If you're making requirements, you're winning. The other challenge is that more and more of my clients are struggling because the SC is not being given proper time for discovery. Hence why more and more of our training programs are focused on Discovery-on-the-fly. 4. Selling value. We all like to say that we’re selling value, but are we really? The reality is that value exists in the gap between where your customer is right now and where they would like to be. If they’re happy where they are, then your solution has no value to them. So to be a good “Value Seller,” you have to be good at both discovery to uncover pain, and storytelling to create a vision. If you’re not good at those two things, you’re going to have a hard time selling value. 5. Sales skills. One of the biggest challenges here is that SCs don’t like being seen as “salesy.” But something I learned from my career in sales is that you don’t have to be "salesy" to be good at sales. If we think from our customer's perspective, they have pain. If we have a good solution, and we're confident in the value, then we shouldn't be shy about talking about it. If that's the case, we're not really "selling." We're serving. What’s interesting was what was NOT of interest to the sales team. Only 15% of respondents were interested in their SC becoming more technical. This doesn’t mean we shouldn’t become more technical (I always believe we should), however, there appears to be much less room for improvement when it comes to tech skills in comparison to sales skills. So, what skills do you think are most important for SCs? P.S. Once a month, we provide helpful GTM content to over 250 GTM leaders from Google, Amazon, Atlassian, and others. Get it here: https://lnkd.in/eKaaGeZr

Insights from a CFO: Why Salespeople Win or Lose Deals Selling to the C-suite isn’t for the faint of heart. As a CFO for over 25 years, I’ve seen pitches that were brilliant and others that were, frankly, baffling. This article shares what separates pitches that succeed from those that fall flat. 1. Trust: The Unsexy but Critical Ingredient Trust is the foundation of every deal. C-suite execs can sense insincerity quickly. Be honest about risks as well as rewards and explain how you’ll mitigate them. According to Gartner, 89% of executives say trust is the key factor in deal-making. PRO TIP Address a specific and recognized challenge right away. It shows you've done your homework. EXAMPLE “I noticed you’ve increased spending on supply chain optimization. We’ve helped similar companies reduce such costs by 10-20%.” RED FLAG Dodging requests for references or giving vague replies is a deal-breaker. 2. Speak CFO: Money Talks, Buzzwords Walk CFOs care about financial impact, not buzzwords. Pitches emphasizing ROI have a 32% higher success rate. PRO TIP Lead with numbers—ROI, cost savings, or revenue potential. EXAMPLE “Our solution can cut your cloud storage costs by 30% annually,” is more compelling than vague promises of transformation. RED FLAG Overpromising ROI without solid data raises immediate doubts. 3. Don’t Just Sell—Prescribe The best salespeople diagnose issues and prescribe actionable solutions. PRO TIP Ask questions that reveal underlying problems, then position your solution as the fix. EXAMPLE “Your logistics costs have grown faster than revenue. Here’s how we fixed that for similar firms.” RED FLAG Overemphasis on features instead of solving specific problems is a misstep. 4. Speak Our Language If you sound like a techie or scripted, you’ve already lost. Executives are five times more likely to engage when you speak their language. PRO TIP Share relevant stories or lessons from past failures to build credibility. EXAMPLE “You increased R&D spend by 20% last quarter—are you prioritizing innovation or trying to manage to your margin?” RED FLAG Excessive jargon or acronyms is a quick way to lose interest. 5. Follow-Up: The Forgotten Art Deals aren’t closed in meetings—they’re closed in the follow-up. Following up within 24 hours can boost close rates by 60%. PRO TIP Conclude meetings with clear next steps, timelines, and follow-up dates. EXAMPLE A customized ROI analysis sent within 24 hours led us to a signed deal two weeks later. RED FLAG Generic or delayed follow-up suggests a lack of genuine interest. The Bottom Line Selling to the C-suite is about trust, authenticity, and delivering measurable business outcomes. Master these elements, and you’ll build lasting relationships that go beyond a single deal. Anything to add? #SalesLeaders #CSuite #StrategicAccounts #SellingtoExecutives #Executives #CXOs #CEOs #CFOs #ChiefRevenueOfficers #SalesEnablement #LearningandDevelopment #CorporateUniversities

In the last 6 months, we doubled Aligned’s ARR and ACV by moving upmarket. I’ve now led 5 Enterprise Sales orgs through $1M-$100M ARR. And every time - it looked ready but failed before it worked. Here are the 6 warning signs I now look for before committing to Enterprise👇 1. Your team panics without a step-by-step sales process If your AEs need explicit next steps after every call, they’re not ready for enterprise. And you need to find someone who is. Enterprise reps dance. They know every deal is different. Complex. Messy. Their job isn’t to follow steps. It’s to facilitate. To lead. That takes VP-level thinking - planning moves, reading the situation, adapting. If you don’t have that, you’ll be stuck in fake enterprise land. Running big logos through a weak sales motion. That won’t work. 2. You’re cheering for logo meetings, but it’s Wild Wild West after that If your team is celebrating big logo meetings, but when you ask “How’s that IKEA deal going?” your rep mumbles through the problem you’re solving or who the economic buyer is - you’re burning cash (and market). None of these deals will close. Enterprise needs top quality execution, or it becomes the worst investment your company will ever make. This is a red neon warning light that you need to fix execution before landing another meeting. 3. Your leadership team never joins sales calls Enterprise sales teams don’t get far. Only enterprise sales companies do. If your execs can’t or won’t show up to build trust, align vision, or unblock red tape - you’re not ready. One missed VP-VP alignment call can cost you 6 months of climbing to power. And if your competitors are doing it? You’re screwed. 4. Your GTM motion doesn’t attract execs SMB buyers want to try your tool. Enterprise buyers want to trust you. If your pipeline-gen is inbound-heavy, your outbound is mass sequenced, and your brand doesn’t speak to the C-suite - you won’t land with decision-makers. You’ll just fight decision-blockers. Build the motion that gets you to the top, and make them trust you. Early. Referrals, Partners, PLG Sales Assist, ABM, Strategic Outbound. 5. Your product looks great… but sounds small It looks clean. But something’s off. The way it’s pitched on the site, the way reps describe it, the way it communicates with you - it all screams “tool.” A nice one. But small. Enterprise buyers don’t buy tools. They buy transformation. If your story doesn’t speak to a $500K problem - you won’t close a $500K deal. You might land the logo. But not the ACV. And if you’re missing things like infosec, governance, or legal protections - you’re not enterprise-ready. You’re a risk. 6. (Continues in the comments) —— Most teams chase Enterprise too early. The signs are there. You just have to look. Fix the system. Then make the move. P.S. We built Aligned to help manage the deal complexity of Enterprise Sales. 100% FREE Deal Room used by 40,000 sellers. Try it: https://lnkd.in/d_49kHZE

I know it because I have done it ... both on the sales floor and interviewing for a sales role. Most sellers bomb when pitching to the C-suite. Bad Example: A rep walks in and says: “Our platform has 25 integrations, a modern UI, and real-time analytics.” The CFO’s eyes glaze over. The CEO checks their phone. Good Example: Another rep walks in and says: “Right now, your team is losing $2M a year in inefficiencies. We can cut that in half within 12 months, without adding headcount.” The CFO leans forward. The CEO asks, “How soon can we start?” C-level selling isn’t about features. It’s about outcomes, growth, ROI, risk, and strategy. Same goes for the job search. If you don’t know who you’re talking to, recruiter, hiring manager, or VP, you’ll miss the mark. Speak their language, and doors open. Then close more deals and interviews ... Truth. Picture Credit to Haris Halkic. #Techsales #JobSearch #Executives

"Beware the Lag Between Presales and Reality in SAP Projects" While reviewing some of my past solution designs, I found myself double-checking: Are these still up to date with SAP’s latest offerings? And it hit me. How often do system integrators propose architectural solutions based on what was true two years ago? An SAP client buys BTP licenses in 2025. - The proposal? Based on a 2023 template. - The solution design? Already outdated. - The contract? Signed. Delivery kicks off. Consultants start digging into the architecture. 🔍“Why are we building custom bots? SAP Build Process Automation handles this now.” “Event Mesh takes care of this - why are we bringing in Kafka?” “Do we stick to the outdated scope, or rearchitect mid-flight?” Sound familiar? Too often, proposals are built using yesterday’s understanding of SAP. But the tech moves fast and solution decks don’t always keep up. 🧩 As architects, consultants, and project leads, we must re-validate the assumptions baked into those decks during onboarding. 📌 A proposal is a starting hypothesis, not a final blueprint especially in fast-evolving platforms like BTP. If we don’t challenge yesterday’s design, we risk building a solution that’s already behind the curve. 🎯 Let’s build what’s right - not just what was written. Have you run into this gap before? 🔹 As end users, how do you feel when the solution delivered doesn’t reflect the capabilities you thought you were buying into? 🔹 As consultants, how do you address these mismatches when onboarding onto a project with outdated assumptions? Would love to hear how your teams are navigating this. #SAP #SAPBTP #EnterpriseArchitecture #SAPConsulting #DigitalTransformation #Presales #ArchitectureMatters #BuildSmart

𝐏𝐎𝐕: 𝐘𝐨𝐮'𝐫𝐞 𝐚 𝐂𝐄𝐎 𝐭𝐡𝐚𝐭'𝐬 𝐭𝐢𝐫𝐞𝐝 𝐨𝐟 𝐫𝐞𝐜𝐞𝐢𝐯𝐢𝐧𝐠 𝐚 𝐦𝐚𝐬𝐬 𝐨𝐟 𝐚𝐮𝐭𝐨𝐦𝐚𝐭𝐞𝐝 𝐁𝐃 𝐩𝐢𝐭𝐜𝐡𝐞𝐬. The inbox of a C-suite leader is a fiercely contested space, often filled with a mass of automated messages. Landing a response is a hurdle, but the real win lies in initiating a conversation to explore a potential partnership. How can we be heard amidst the noise of automated business development approaches? 𝑯𝒆𝒓𝒆 𝒂𝒓𝒆 𝒔𝒐𝒎𝒆 𝒕𝒊𝒑𝒔 𝒇𝒓𝒐𝒎 𝒎𝒚 𝒂𝒑𝒑𝒓𝒐𝒂𝒄𝒉: 𝐈𝐧𝐬𝐢𝐠𝐡𝐭-𝐃𝐫𝐢𝐯𝐞𝐧 𝐑𝐞𝐬𝐞𝐚𝐫𝐜𝐡: Go beyond surface-level data. Analyse their company's strategic direction, dissect their challenges, and identify potential opportunities where the right talent could be a catalyst for growth. 𝐕𝐚𝐥𝐮𝐞-𝐂𝐞𝐧𝐭𝐫𝐢𝐜 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐜𝐚𝐭𝐢𝐨𝐧: Your outreach isn't about selling your services; it's about offering relevant insights. Share emerging market shifts, innovative talent acquisition strategies, or potential solutions to their known pain points. 𝐂𝐨𝐧𝐜𝐢𝐬𝐞 𝐚𝐧𝐝 𝐈𝐦𝐩𝐚𝐜𝐭𝐟𝐮𝐥 𝐌𝐞𝐬𝐬𝐚𝐠𝐢𝐧𝐠: Time is precious and in limited supply at the C-suite level. Be direct in your purpose, clearly articulate the value of a brief discussion, and frame your offering in terms of tangible business outcomes that are specific to them. 𝐁𝐮𝐢𝐥𝐝 𝐓𝐫𝐮𝐬𝐭 𝐓𝐡𝐫𝐨𝐮𝐠𝐡 𝐏𝐫𝐨𝐯𝐞𝐧 𝐑𝐞𝐬𝐮𝐥𝐭𝐬: In an industry often plagued by empty promises, tangible evidence speaks volumes. Share case studies or, ideally, leverage client testimonials that directly support your ability to deliver high-calibre talent and contribute to company growth. 𝐓𝐫𝐚𝐧𝐬𝐩𝐚𝐫𝐞𝐧𝐜𝐲 𝐢𝐬 𝐚𝐭 𝐭𝐡𝐞 𝐡𝐞𝐚𝐫𝐭 𝐨𝐟 𝐚 𝐩𝐚𝐫𝐭𝐧𝐞𝐫𝐬𝐡𝐢𝐩: Honesty about your capabilities and limitations fosters trust. Be upfront about what you can and cannot deliver. This builds a foundation of realistic expectations, setting you apart from those who overpromise and underdeliver. 𝐘𝐨𝐮𝐫 𝐍𝐞𝐭𝐰𝐨𝐫𝐤 𝐈𝐒 𝐲𝐨𝐮𝐫 𝐍𝐞𝐭 𝐖𝐨𝐫𝐭𝐡: Your network is a powerful asset. Identify and strategically engage mutual connections who can vouch for your expertise and integrity. 𝐀𝐜𝐭𝐢𝐯𝐞 𝐋𝐢𝐬𝐭𝐞𝐧𝐢𝐧𝐠: This is one area where so many consultants fall short. Stop waiting for your turn to speak and actively listen to what your prospect is saying. Ask yourself, "What value can I add? What solutions can I provide?" 𝐏𝐞𝐫𝐬𝐨𝐧𝐚𝐥𝐢𝐬𝐚𝐭𝐢𝐨𝐧: Generic outreach shows a lack of investment. If you aren't taking the time to tailor your communication, why should they take the time to respond? Personalise your outreach to reflect an understanding of their specific role, the company's unique challenges, and how your expertise can directly contribute to their strategic objectives. The key to engaging C-suite leaders lies in providing genuine value, building trust and standing out amongst a noisy inbox. PS- I'm not a CEO (yet)... 😉 #elite100recruitmentleader #thecaffeinatedrecruiter #businessdevelopment #companyinsights

I had one of those conversations at Nutanix Next that reminds me why I like hallway tracks more than sessions. A sales engineer from a VAR recognized me and pulled me aside. He’s working with a publicly traded company that needs a Business Impact Assessment (BIA) to move forward with its DR strategy. The problem? They can’t afford the six-figure engagement. So he asks me: “How do I package a BIA as a pre-sales activity?” And that’s where I stopped him. You’re solving the wrong problem. This isn’t about figuring out how to give away a BIA for free. It’s about figuring out how to make the BIA inevitable. If you’re dealing with a publicly traded company, there is always a business initiative in flight. Cost optimization. AI rollout. ERP modernization. Regulatory pressure. Something tied to revenue, risk, or the board. And somewhere inside that initiative… is risk. The kind of risk a BIA exposes almost immediately. The shift isn’t tactical. It’s professional. This is the difference between a pre-sales engineer and a pre-sales architect. An engineer asks: “How do I help my customer get this thing done?” An architect asks: “Should they even be doing this without understanding the risk?” The job isn’t to backdoor a free services engagement. The job is to connect the dots: “This initiative you’re betting the business on? Here’s the operational risk you’re carrying. Here’s what happens if it goes sideways. Here’s why you need a BIA before you make another move.” Now the BIA isn’t a cost. It’s a rounding error. This is where a lot of ecosystems get stuck. They’re optimized to sell hardware. So every conversation becomes: “How do I get to the Nutanix deal?” Instead of: “How do I help the customer make a better decision?” Ironically, that second path is how you actually get the deal. If you’re in pre-sales and you’re looking to level up: This is the transition. Not more technical depth. Not more product knowledge. A change in how you frame the problem. That’s how a pre-sales engineer becomes an architect.