Selling Strategies for CEOs

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 😁

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.

Hey CEOs: Going "upmarket" is not just a sales motion. It’s a company-wide initiative. If you don’t treat it that way? You'll burn time, money, and people. 7-point checklist to go upmarket: 1. Do you have the resources (and stomach)? Most CEOs underestimate how long this takes. It usually takes ~18 months to really get right. • Your cost model will shift. • Your sales cycles will lengthen. • Your risk goes up before it pays off. Can your business withstand that? Can you, personally? 2. Nail your enterprise ICP. This is job #1. Your “upmarket ICP” ≠ your current ICP. • They have different problems. • They require different proof. • They buy differently. Product, marketing, and sales all need to align: Who is our enterprise buyer? How do they buy? 3. Is your product actually enterprise-ready? Be honest here. • Are you missing non-negotiables? • Or can you sell around the gaps? To be clear: You'll always have gaps to sell around: that's ok. But if you're missing any non-negotiables? Don't go upmarket yet. Not seriously. 4. Find the routes to market. Enterprise buyers don’t show up the same way. • Outbound looks different. • Partners matter more. • Credibility matters a lot more. No plan here = expensive Enterprise AEs with no pipeline. 5. Build your operating model. You don’t need perfection—but you need intent. • Where is the “enterprise line”? • How do you cover accounts? • How do quotas and comp change? Figure it out early enough. Or you’ll scale chaos. 6. Design the enterprise sales process. Your SMB process will break here. • Different stakeholders. • Big (risk averse) committees • Long, complex cycles. • More risk to manage. And most importantly: Don’t do this ⬇️ Hire enterprise AEs and expect them to “figure it out.” They won’t. It’s not their job. Strategy is a company responsibility—not an IC one. Yet CEOs make this mistake all the time. 7. Assess talent readiness. Enterprise selling requires a different skill set. • How big is the gap with your current team? • Can it be trained? • Or do you need new talent? Most CEOs think this is just a hiring problem. It’s not. It’s a capability problem. Get this wrong—and you don’t just miss deals… You stall the entire motion. Going upmarket isn’t a sales initiative. It’s a company-wide initiative. Treat it like a hiring exercise? You’ll fail. Treat it like a transformation? You’ve got a shot. What would you add?

A rep on my client's team hit his annual quota in 4 months. $1.5M on a $438K quota. Same market. Same product. Same comp plan as every rep who missed. The difference was 5 strategies the top 1% use and almost no one else does. #1 Stop chasing titles. Chase the “little” Domino. The economic buyer isn't always the highest title in the room. They're the one person who can say yes when everyone else says no, and no when everyone else says yes. Miss them and you lose deals you thought were locked. #2 Run your discovery like a litigator. A lawyer doesn't take every case. They build the case first, then decide if it's worth pursuing. Your first call should do the same. If you can't build a business case, disqualify early and protect your time. #3 Convert latent pain into active pain. Most prospects don't feel urgency because their pain is a scratch, not a wound. Your job is to ask questions that help them realize it's actually gushing. When they feel level 10 pain, they take level 10 action. #4 Coach your champion like they're going into a boardroom. If your champion can't sell internally, you lose. Coach them on every objection their boss will raise. How they explain it to you is exactly how they'll explain it to the decision maker. Fix it before that meeting happens. #5 Audit your deals before they go sideways. Happy ears kill pipelines. Rate every active deal across 8 categories: pain, opportunity cost, desired outcomes, executive influence, resources, fear of failure, trust, and buying criteria. Whatever scores low is your next call. Most reps grind harder when deals stall. The top 1% diagnose faster. P.S. If you're a sales leader reading this thinking "I need to forward this to my reps". Pause for a second. The reason only your top 1-2 reps execute these strategies consistently isn't a talent problem. It's a system problem. The goal isn't to find more reps who naturally do this. The goal is to build a system where every rep on your team does this. If you want to see exactly where that gap lives on your team, grab the free Revenue Leak Diagnostic Playbook: https://lnkd.in/g8DFrh7J

As a CEO, you’ll always have a role in sales, but that role changes as your company matures. Understanding when and how to adjust your involvement is critical to your company’s long-term success. Here’s how to navigate your role at each stage of growth. 1. The Foundation: Founder-Led Sales In the early days, sales is your job. As CEO, you’re the one making connections, closing deals, and setting the tone for how your company approaches sales. This hands-on involvement is crucial for learning what works, understanding your market, and creating a sales strategy that fits. But founder-led sales doesn’t scale. At some point, your business will need you to shift your focus to keep growing. 🎯 Action: Regularly assess whether your direct involvement in sales is helping or holding the company back. If you stay in this role too long, growth stalls. If you step back too soon, the team may lack the foundation needed to succeed. 2. Scaling Up: Handing Over the Reins As your business grows, it’s time to bring in a sales team and eventually a strong sales leader. Your role becomes less about closing deals and more about strategy, mentoring, and ensuring sales aligns with the company’s goals. This stage is about trust. You’ll need to empower your team to take over while staying involved enough to guide the strategy. 🎯 Action: Collaborate with your sales leader to establish clear goals and expectations. Shift your focus to generating high-value leads and supporting your team as a strategic resource. 3. Maturity: Driving Strategy and Building Relationships When a capable sales leader is in place, your role becomes more about big-picture strategy and relationship-building. Now is the time to act as your company’s “chief evangelist.” Represent the brand, build partnerships, and connect with key prospects and clients in ways that only the CEO can. 🎯 Action: Work with your sales leader to identify critical accounts where your involvement will make the biggest impact. Use your platform—whether through speaking engagements, podcasts, or social media—to promote your company’s vision and build credibility. 💡 A guiding question: At every stage, there’s one question you should continually ask: “What are we doing to make it easy to be our customer and harder to be our competition?” Your role in sales is to make sure your entire organization supports the customer journey, creating a seamless and exceptional experience. Your role in sales evolves as your business grows, but it never disappears. Staying tuned into your customers and company’s sales process—whether by leading it, guiding it, or amplifying it—ensures that your team is set up for long-term success. If you’re ready to take a closer look at how your involvement in sales can evolve to meet your company’s needs, I’d love to help. DM me and we'll discuss building the right strategies and tactics to keep your team focused and your pipeline flowing.  

Sales teams are sitting on the most underused follow-up asset: Their CEO's LinkedIn posts. Your CEO posts 3x/week on LinkedIn. Your sales team never references it. That's a missed opportunity. I've been writing LinkedIn content for climate tech CEOs and founders for 2.5+ years. Companies that repurpose founder content for sales enablement shorten their 6-12 month B2B sales cycles. Here's how to write LinkedIn posts your sales team can actually use in follow-ups: Tip 1: Start posts with problems your prospects are facing right now. Open with the exact challenge your ideal customer is dealing with today. Use their language, not yours. For example: "Everyone's talking about scaling from $5M to $20M, but nobody talks about what breaks when you hit $10M." When your sales team follows up, they can say: "Saw our CEO wrote about the challenges at $10M ARR. Curious if you're experiencing any of that?" Instant warm conversation starter. Tip 2: Use the borrowed credibility format to create instant relevance. The format: "I met a [prospect's role] who [achieved impressive result]. Here's what they did differently..." Example: "I met a VP of Operations who cut their energy costs by 40% in 8 months." When your sales team reaches out to similar prospects, they can say, "Our CEO just shared a story about a VP Ops in a similar situation. Thought you'd find it relevant." Tip 3: Reference internal triggers that signal buying readiness. Call out the specific moments when companies realize they need a solution. Things like: "Growing past 5-6 crews," "Drowning in service tickets," "Hitting the limits of spreadsheets." These triggers tell prospects: we know exactly where you are. When sales follows up, they can ask: "Are you hitting any of these inflection points?" It naturally qualifies the prospect. Tip 4: Include real numbers and metrics from your experience. Don't just say "we helped a client save time." Say: "We helped a $25M company reduce their reporting time from 40 hours/month to 4 hours/month." Specific numbers establish credibility and give sales concrete data points to reference. When a prospect asks "can you quantify the impact?", your sales team points to the CEO's post. Tip 5: End with niche-relevant engagement questions that filter for qualified prospects. Don't ask generic questions like "What do you think?" Ask questions that only your ideal customer can meaningfully answer. Examples: • "What's the biggest bottleneck you're hitting between $10M and $20M?" • "CFOs: how are you currently tracking sustainability metrics?" When prospects comment, they're self-identifying as qualified leads. Your sales team can follow up directly with context. — Using CEO content for sales enablement is one of the most underrated tactics in B2B. Your sales team gets warm conversation starters. Your prospects feel understood, not sold to. Your CEO's content drives pipeline. — How often do you repurpose your CEO's LinkedIn content for sales?

Your CEO doesn't hate marketing. They hate uncertainty. I've sat on both sides of this table. 1) As a marketer pitching "brand awareness initiatives" 2) As a CEO watching them get shot down. Here's what I learned: CEOs don't fund activities. They fund outcomes. Instead of: "We need to increase brand awareness." Try: "We need to de-risk our sales process so deals close 30% faster." Instead of: "This content will establish thought leadership." Try: "This content will make prospects come to us already convinced." Instead of: "We should invest in community building." Try: "We should turn our customers into our sales team." Same work. Different frame. Your CEO has seen too many campaigns that looked brilliant in the deck but delivered nothing measurable. They've watched budgets disappear into "brand building" black holes. So they default to what feels safe: more sales people, more ads, more of what they can track. During the pandemic, when we lost $100k in MRR overnight, I didn't ask for budget to "build brand resilience." I said: "Here's how we retain our biggest customers and reduce churn by 40%." Guess which one got approved? Stop selling your strategy. Start selling their success. What business outcome does your CEO lose sleep over? Frame everything around solving that. I've written a book that helps companies stop doing "marketing" and actually grow their business. If you're done chasing tactics and ready to build systems that evolve, follow along.

If your CEO doesn't "get" SEO, read this. Most CEOs don’t care about backlinks, keyword density, or technical audits. They care about outcomes. Will this make us money? Will this give us a long-term advantage? Will this scale sustainably? When I took a client from 0 to 1.5M organic visitors in 18 months, I realized something: SEO isn’t a marketing tactic. It’s a business strategy. And most marketers pitch it wrong. Here’s how to get your CEO to say “yes” to SEO: → Don't sell SEO as "traffic"; sell it as a competitive moat ↳ Every day your competitors rank for high-intent keywords is another day they're stealing your customers. ↳ CEOs understand competitive advantage. They don't understand "domain authority." → Frame SEO as a financial investment, not a marketing expense ↳ Bad pitch: "We need $10K/month for SEO to improve our rankings." ↳ Good pitch: "For every $1 we invest in SEO now, we'll generate $5 in perpetual revenue. Paid ads stop working when you stop paying." → Use real numbers, not vague promises ↳ Instead of: "SEO takes time, but we'll see results eventually" ↳ Say: "With our current conversion rate, ranking for these 5 keywords would generate approximately 32 qualified leads per month, worth $480K in pipeline." → Connect SEO to business goals your CEO already cares about ↳ Want to reduce CAC? SEO delivers customers at 1/3 the cost of paid. ↳ Want predictable growth? SEO compounds month over month. ↳ Want defensibility? Once you rank, competitors have to spend more to catch up. When I explain SEO this way to founders, their entire posture shifts. Because now we’re not talking about H1 tags or crawl budgets. We’re talking about leverage. And ROI. The marketers who win bigger SEO budgets aren’t the ones who know every Google update. They’re the ones who know how to translate rankings into revenue. Is your CEO skeptical about SEO? Maybe you're speaking the wrong language.

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

There’s no such thing as a great Sales Team—only a great Sales Company. If the CEO doesn’t get sales, Product ignores frontline feedback, or the CRO micromanages every deal, your team’s potential is toast. Wanna crush 2025’s targets? Fix these 7 deadly company-sales culture mistakes, starting now: 1) Product Feedback Falls Into a Black Hole AEs send updates, requests, or must-fix issues, but they never see them implemented. No seat at the table = sales' voice doesn’t matter. The Fix: Treat sales like co-builders. Implement a feedback loop that actually changes your roadmap. If reps see zero traction on feedback, your product will never truly serve customers. 2) Marketing and Sales Act Like Rivals Constant blame games, misaligned messaging, and finger-pointing. If you feel like you’re on different teams, that’s a giant red flag. The Fix: Move to joint accountability. Align Marketing and Sales on SHARED revenue goals and dashboards. Celebrate joint wins, not in silos. You’re ONE Go-To-Market team. 3) Execs Watch Deals from the Bench “We’re here if you need us”, but MIA when a critical call comes up, or an internal strategy session is needed. No top-down involvement = NO ENTERPRISE deals. The Fix: Make CXO sponsorship mandatory for strategic deals. Exec sponsor emails, co-selling, or simply showing up changes your buyer’s entire perception. 4) Revenue is on a Tight Leash Every move is micromanaged and rigidly enforced by RevOps and the CRO. The Fix: Standardize the must-haves—Qualification, CRM hygiene—but trust reps to adapt in the real world. A sales process is an anchor, not a cage. Over-enforcement kills morale and top talent. 5) Salespeople Aren’t the Top Earners Capping commissions signals fear of paying out. If leadership won’t invest in reps' success, they won’t scale real growth either. The Fix: Let them earn big. If your unit economics are not a disaster, big commission checks mean your company’s winning, too. Aim for a sales culture that rewards success, not punishes it. 6)  CEO Doesn’t Speak ‘Sales’ “Sales is easy, just talk to more prospects”—ignoring the nuance of building champions, running deep discovery and aligning stakeholders. The Fix: Bring your CEO into complex deals and enablement sessions. A sales-savvy CEO invests time understanding real pipeline challenges—and it shows. 7) ‘Team’ Is a Buzzword, but Internal Competition Is Brutal Reps fight for scraps, territories feel rigged, and there is no synergy or knowledge-sharing. Everyone’s out for themselves. Growth stalls. The Fix: Change your territory and incentive plans to encourage genuine collaboration. When your AEs share insights instead of keeping tricks for themselves, you unlock unstoppable momentum. —— No matter how good your sales team is. For it to be truly great. I mean world-class great. You MUST build a Sales Company first. No other way. P.S. Who are some of the best Sales Companies out there that deserve a shoutout?