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 a Fortune 50 company isn’t a straight shot—it’s a multi-threaded, high-stakes game where you have to win over three completely different audiences at the same time. 👑 C-Suite (aka "The Big Picture People") – They care about risk, revenue, and competitive advantage. If your pitch doesn’t tie back to a business outcome, it’s dead on arrival. Keep it short, strategic, and dollar-driven—they have about 30 seconds before they mentally check out. 🧠 Technologists & Strategists (aka "The Architects of the Future") – These folks are your deal-makers or deal-breakers. They want to know if your solution fits their long-term IT roadmap, scales, and won’t become next year’s tech debt. If you can’t show how your product integrates seamlessly with what they already have, you’re in for a long road. ⚙️ Practitioners (aka "The Ones Who Actually Use the Thing") – These are the engineers, security teams, and network admins who will either champion your solution internally… or fight it tooth and nail. If your product makes their lives easier (less manual work, better automation, no fire drills at 2 AM), they’ll become your secret weapon in getting the deal done. 🎯 The Trick? Selling to All Three in Parallel. C-suite? Tie it to revenue and risk. Technologists? Prove it’s a strategic fit. Practitioners? Make their job easier. The best enterprise salespeople aren’t just selling—they’re orchestrating. Every great deal is won at multiple levels. How do you navigate selling to different stakeholders? Drop your best tips below! ⬇️ #EnterpriseSales #TechSales #StrategicSelling

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

I asked 100 CEOs: "What's your biggest challenge in sales?" Expected answers: "Not enough leads" "Long sales cycles" "Competition" "Price objections" Actual #1 answer: "My sales team can't tell our story." 97% of salespeople can't explain why their solution matters. They know features. They don't know impact. Feature-focused pitch: "Our platform has advanced analytics, automated workflows, and integrated CRM capabilities." Impact-focused story: "Last month, our client reduced their sales cycle from 6 months to 6 weeks. Their revenue per rep increased by 340%. The CEO told me it was the best investment they've made in 5 years." The difference: → Features describe what you do → Stories describe what happens next Your prospects don't care about your product. They care about their future. Stop selling features. Start selling outcomes. The best salespeople are storytellers. Not feature-tellers. P.S. What story does your solution tell? #sales #revops #gtm

Want to know the secret to selling to C-suite executives? Stop selling. Most reps fail because they pitch products instead of solving Business Priorities. Here's what actually works: 1. Do Your Homework Research their company inside out. Know their market challenges. Understand their goals. Because wasting a CEO's time is career suicide. 2. Improve The Conversation Forget product features. Focus on: Impact. Opportunities. Strategic objectives. Because business leaders care about direction, not details. 3. Master the 60-Second Story Share a relevant case study that: Address similar business goal. Articulate a few challenges Demonstrate quantifiable value. Showcase outcomes. Because stories sell when data doesn't. 4. Connect Through Problems Focus on outcomes, not process. Lead with impact, not implementation. Share how you've solved similar challenges. Because shared problems create connection and build trust. 5. Master the Subtle Transition After sharing your story, say: "I don't know if this matches your situation, but I thought it might be close." It'll open the door without forcing it. 6. Let Them Lead Listen more. Speak less. Don't assume their priorities. Let them guide the conversation. Because the best insights often come from silence. The lesson? Executives don't buy products. They invest in solutions to Business Issues. Questions? DM me.

Stop letting junior SDRs reach out to your C-Suites. Buyers don’t want to talk to salespeople anymore. They want trusted advisors. Domain experts.  Yet, for some reason, 99% of sales teams completely ignore this fact and let their junior SDRs reach out to C-suites — then they sit back and wonder why their outbound doesn’t work. The WHO factor is more important today than ever before. Here’s what it means moving forward: 1. Trusted Advisors vs. SDRs: Would you take medical advice from a first-year med student? Probably not. In the same vein, expecting a junior SDR to convince a C-suite executive is a flawed strategy. Buyers today want insights from those seeped in the industry, not those reading off a script. 2. The New-Age SDR: These SDRs have authority in their field and are the ultimate subject matter experts. They possess a highly relevant audience of ICP and excel in content creation and audience engagement. They understand the nuances and pains of the prospects and create value-driven conversations, not just touchpoints. 3. Team-Selling is a Necessity: If a CFO checked your website, why in the world would you let your SDR reach out? Facilitate outbound requests to your CFO and ask them to personally connect with the prospect from their profile. It’s about leveraging the right person at the right time to build trust and relevance. 4. Signal-Based Selling: Your outreach should be driven by real-time data and intent signals. Spot the triggers: website visits, content downloads, recent funding, etc. Engage with the right person, when the timing is perfect, with the right message from the right person. This isn’t about volume; it’s about precision. TAKEAWAY: In this new era, it's not about how many emails you send, but WHO is sending them and WHY. In 2024, the most successful companies will have GTM teams that look more like consulting firms than old-school sales orgs. The next-gen of successful sales orgs will be the ones that evolve beyond the old playbooks and focus on trust, relevance, and the power of human connection. The future isn’t just lean. It’s personal.

The best advice that I can give anyone who wants to learn how to successfully sell at the C-level, regardless of your role or title, is: ➡️ Be relentless in your pursuit of becoming an expert in the tangible, measurable business value (net cash flows) that 𝙮𝙤𝙪𝙧 𝙘𝙪𝙨𝙩𝙤𝙢𝙚𝙧𝙨  realize with what you sell (product, service , platform, etc.), and where this lands on the P&L, Cash Flow Statement and Balance Sheet. 𝗧𝗵𝗲 𝗖-𝗹𝗲𝘃𝗲𝗹 𝘄𝗮𝗻𝘁𝘀 𝘁𝗼 𝗸𝗻𝗼𝘄 𝘄𝗵𝘆 𝗿𝗲𝗹𝗲𝘃𝗮𝗻𝘁 𝗶𝗻𝗱𝘂𝘀𝘁𝗿𝘆 𝗽𝗲𝗲𝗿𝘀 𝗳𝘂𝗻𝗱 𝗮𝗻𝗱 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝗮𝗹𝗶𝘇𝗲 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂 𝗮𝗿𝗲 𝘀𝗲𝗹𝗹𝗶𝗻𝗴, based on the impact that it has on revenue growth, operating profit, operating/free cash flow and total shareholder return (assuming that they are public). If you understand this, inside out and backwards, and 𝘵𝘳𝘶𝘭𝘺 𝘴𝘺𝘯𝘵𝘩𝘦𝘴𝘪𝘻𝘦 𝘪𝘵, you will demonstrate the expertise and insight that they seek as your selling will shift from that of a curious salesperson 🧐🙄 (𝙫𝙚𝙧𝙮 𝙡𝙤𝙬 𝙫𝙖𝙡𝙪𝙚 𝙩𝙤 𝙩𝙝𝙚𝙢) to that of a consultant providing actionable business guidance. or, more simply put... 𝙈𝙖𝙨𝙩𝙚𝙧 𝙮𝙤𝙪𝙧 𝙠𝙣𝙤𝙬𝙡𝙚𝙙𝙜𝙚 𝙖𝙣𝙙 𝙘𝙤𝙢𝙢𝙪𝙣𝙞𝙘𝙖𝙩𝙞𝙤𝙣 𝙤𝙛 𝙩𝙝𝙚 𝙘𝙖𝙨𝙝 𝙛𝙡𝙤𝙬𝙨 𝙩𝙝𝙖𝙩 𝙩𝙝𝙚𝙮 𝙨𝙚𝙚𝙠 𝙖𝙣𝙙 𝙮𝙤𝙪 𝙬𝙞𝙡𝙡 𝙗𝙚 𝙨𝙪𝙘𝙘𝙚𝙨𝙨𝙛𝙪𝙡 𝙖𝙩 𝙩𝙝𝙞𝙨 𝙡𝙚𝙫𝙚𝙡 𝙤𝙛 𝙩𝙝𝙚 𝙤𝙧𝙜 𝙘𝙝𝙖𝙧𝙩...𝙖𝙣𝙙 𝙮𝙤𝙪 𝙬𝙞𝙡𝙡 𝙣𝙚𝙫𝙚𝙧 𝙝𝙖𝙫𝙚 𝙩𝙤 𝙙𝙚𝙥𝙚𝙣𝙙 𝙤𝙣 𝙗𝙪𝙙𝙜𝙚𝙩𝙨 𝙖𝙜𝙖𝙞𝙣! What I have seen over and over again, regardless of company size or geography, is that most salespeople do not make this a priority, or they delegate it to others on the teams that support them...keeping them in 𝙢𝙞𝙙𝙙𝙡𝙚-𝙤𝙛-𝙩𝙝𝙚-𝙤𝙧𝙜-𝙘𝙝𝙖𝙧𝙩, 𝙗𝙪𝙙𝙜𝙚𝙩-𝙙𝙚𝙥𝙚𝙣𝙙𝙚𝙣𝙩 𝙡𝙞𝙢𝙗𝙤 𝙛𝙤𝙧𝙚𝙫𝙚𝙧. #b2bsales #speakexcel #clevelselling

This (true) story from a seller is something I call “The Hidden Stakeholder Trap” He had a great meeting with a C-suite exec who was a perfect fit: 1- Clear pain points 2- Budget confirmed 3- Verbal yes. Everything pointed towards a strong close. The only red flag was at the end of the call the buyer said, “I just need final approval from our board.” After that communication slowed, meetings got rescheduled, and pretty soon, he lost all contact. ^ That’s the hidden stakeholder trap. He assumed (like many sellers do) that because he was talking to someone with a C in their title, they’re the ultimate decision maker. But access doesn’t guarantee progress. Even the C-suite rarely buys in isolation. They have boards, users, and other departments influencing the decision. So here’s a six-step process to help you avoid falling into the same trap that this seller did: 1. Go for outcome first Start with the outcome and actually try to DISqualify them early. Ask questions like, “Why wouldn’t this work?” or “Who might push back on this internally?” Healthy friction helps reveal who really owns the goal. 2. Map the obvious Don’t assume that a C-title means they sign the checks. Are they the end user? Do they report to a board? Get visibility into the structure before you assume you’ve reached power. 3. Uncover what’s hidden What hasn’t surfaced yet? Are there departments or users who’ll be impacted but haven’t been involved? Loop them in early so there are no surprises later. 4. Read the power Figure out the real path to budget release and approval. If there’s a board or another layer, identify it early. It’s better to discover it in week one than in week twelve when you’re forecasting the deal. 5. Match their message Adapt your language to who you’re speaking with. If it’s a CFO, focus on numbers. If it’s a CEO, focus on overall business impact. If it’s end users, focus on day-to-day value. 6. Keep the mutual in your mutual action plan Don’t force your buyers through your internal process. Work alongside them, step by step, building a shared plan that fits their buying process. That’s how you keep deals aligned and on track. When you do this well you’re not just selling, you’re guiding. And that’s how you stay out of the hidden stakeholder trap.

Selling to the C-Suite in 2025: Hard Truth 90% of sellers fail. Why? Only 1 in 10 C-Suite execs find sales meetings valuable. 4 tips to join the elite 10%: 1. Start lower. Build from the ground up: - Talk to end users - Create champions - Gather intel 2. Lead with research. Show you've done the work: "Based on our analysis..." 3. Ask strategic questions. Demonstrate understanding: "Your VP mentioned X costs $2M annually. How does this align with your strategy?" 4. Let champions handle logistics. Focus C-Suite on big-picture impact. Close with: Asking them to bookmark your digital sales room Aligned makes it easier to multi-thread with mutual action plans. These tips won't transform your career overnight. But they'll help you stop burning bridges and start closing bigger deals. What would you add?