{"id":2368,"date":"2025-07-23T12:00:00","date_gmt":"2025-07-23T12:00:00","guid":{"rendered":"http:\/\/www.blissfulyogaandmassage.com\/?p=2368"},"modified":"2025-07-24T12:55:42","modified_gmt":"2025-07-24T12:55:42","slug":"how-i-meet-with-c-level-and-win-deals-as-a-seasoned-sales-rep","status":"publish","type":"post","link":"http:\/\/www.blissfulyogaandmassage.com\/index.php\/2025\/07\/23\/how-i-meet-with-c-level-and-win-deals-as-a-seasoned-sales-rep\/","title":{"rendered":"How I meet with C-level and win deals as a seasoned sales rep"},"content":{"rendered":"
Most reps aren\u2019t prepared to sell to C-level executives. Here\u2019s my honest take: Most salespeople are overprepared for objections and underprepared for business conversations.<\/strong><\/p>\n They rehearse demos instead of researching pressure points. They come armed with product knowledge, but not enough market insight. And they try to impress<\/em> executives when they should be enabling<\/em> decisions.<\/p>\n In this post, I\u2019ll reveal what it really takes to sell to execs. That includes how to prepare like a strategist, not a seller, and hope to drive action in under 30 minutes. I\u2019ll also share the mistakes I made, the frameworks I use (including multi-stakeholder alignment models), and the exact psychology I apply when stepping into the room with someone who signs the checks.<\/p>\n But first, here\u2019s a little bit about my journey with executive selling.<\/p>\n Table of Contents<\/strong><\/p>\n <\/a> <\/p>\n I\u2019ll never forget the first time I sold to a C-level executive. It wasn\u2019t a Zoom call or a casual check-in. It was a formal boardroom meeting at a multinational company in S\u00e3o Paulo. There were five people in the room \u2014 one CEO, one CFO, two directors, and me.<\/p>\n I had rehearsed my pitch twenty times. I had the deck, the talking points, the case studies, even the objection-handling matrix I\u2019d built the night before. I walked in ready to prove value.<\/p>\n Ten minutes in, I realized I was losing them.<\/p>\n They weren\u2019t asking about product features. They weren\u2019t reacting to benchmarks. They weren\u2019t interested in \u201cwhat our solution does.\u201d They wanted to talk about strategy. Market positioning. Risk mitigation. Internal politics. And when the CFO asked, \u201cWhat are you helping us avoid<\/em> next quarter?\u201d I didn\u2019t have a crisp answer. I froze.<\/p>\n I didn\u2019t lose the deal that day. But I didn\u2019t win their trust either.<\/p>\n And that\u2019s when it hit me: selling to executives isn\u2019t about presenting solutions. It\u2019s about proving strategic relevance.<\/strong><\/p>\n Since then, I\u2019ve sold to hundreds of C-level decision-makers across five continents\u2014from SaaS founders in New York, to CIOs in Dubai, to CFOs in Mexico City, and managing directors in London. I\u2019ve closed over $40 million in enterprise contracts, and I\u2019ve coached SDRs and AEs who struggled to break into the C-suite\u2014until they started shifting from seller to strategic partner<\/em>.<\/p>\n As Brent Adamson (co-author of The Challenger Sale<\/em>) once said, \u201cThe best sellers don\u2019t just deliver insight. They disrupt thinking.\u201d That\u2019s what this guide is about: equipping you with the mindset and tools to stop pitching and start leading executive conversations with clarity, control, and commercial impact.<\/p>\n <\/a> <\/p>\n If you walk into a C-level meeting thinking it\u2019s just a higher-stakes demo, you\u2019ve already lost.<\/p>\n I learned this the hard way.<\/p>\n Years ago, I landed a rare opportunity: a one-on-one with the CEO of a billion-dollar logistics company in LATAM. I\u2019d done the research, practiced my opener, even rehearsed objections. But five minutes in, he leaned back in his chair, raised his eyebrows, and said something that changed my approach forever:<\/p>\n \u201cThat\u2019s all fine \u2014 but, tell me why this matters now<\/em>.\u201d<\/p>\n Not what<\/em> my product did. Not how<\/em> it worked. But why now<\/em>? And more importantly, why him<\/em>?<\/p>\n That moment cracked something open for me. Because selling to C-level executives isn\u2019t about transferring information. It\u2019s about transferring strategic urgency<\/strong>.<\/p>\n Here\u2019s the core shift: Executives don\u2019t care about how your solution works. They care about how it protects or advances their priorities.<\/strong><\/p>\n Over the past 17 years, I\u2019ve sold to CEOs, CFOs, CIOs, CMOs, and Heads of Strategy worldwide. There\u2019s a pattern I see every time.<\/p>\n Executives think in frameworks. They make decisions based on tradeoffs. They are not interested in features. They\u2019re interested in outcomes. They don\u2019t want to know what\u2019s possible. They want to know what\u2019s probable<\/em>.<\/p>\n That means when you walk into a C-level sales conversation, your job is not to educate them on your solution. It\u2019s to connect the dots between their strategic priorities<\/em> and your business impact<\/em>.<\/p>\n According to a Forrester report, 62% of executive buyers<\/a> say sellers lack insight into their business. That\u2019s the gap. And that\u2019s the opportunity.<\/p>\n Most sales conversations operate at the tactical level. Executive sales conversations live at the intersection of risk, revenue, cost, and timing<\/strong>.<\/p>\n When I sell to operational leaders, I talk in terms of efficiency gains, time-to-value<\/strong>, and change management<\/strong>. When I meet with a CFO, I anchor around the cost of delay, margin protection<\/strong>, and budget prioritization<\/strong>. When it\u2019s the CEO, I zoom out even more: market timing, competitive threat, and category differentiation<\/strong>.<\/p>\n You\u2019re not just selling a product. You\u2019re helping them place a bet. And, the clearer you are about the upside and<\/em> the downside, the more trust you earn.<\/p>\n I know that goes against a lot of sales training. But, I stand by it.<\/p>\n Scripts are great for new reps. They help with structure. However, when I\u2019m walking into a room with a C-level decision-maker, I toss the script. That\u2019s because executives can smell rehearsed from a mile away.<\/p>\n Instead, I prep using mental models<\/strong> and deal-specific scenarios<\/strong>. I ask myself:<\/p>\n That\u2019s what real preparation looks like at this level. As Anthony Iannarino puts it: \u201cYou\u2019re not there to sell a product. You\u2019re there to sell a better future.\u201d<\/p>\n If you can\u2019t define what that future looks like in terms they care about, you\u2019re not ready for the meeting.<\/p>\n This is a nuance most reps miss: C-levels move fast, but they don\u2019t make rushed decisions.<\/p>\n That means you need to lead the meeting with clarity, not clutter<\/strong>. Open with the insight. Lead with the risk. Map the path forward early.<\/p>\n In my highest-converting executive meetings, I always do three things in the first 90 seconds:<\/p>\n When I follow that rhythm, I move from vendor to thought partner \u2014 fast. Once you\u2019ve earned that position, the entire conversation changes.<\/p>\n <\/a> <\/p>\n You don\u2019t get a second shot with a C-level executive. That\u2019s why I treat every executive meeting like a campaign \u2014 high stakes, no fluff, and zero guesswork.<\/p>\n Over the years, I\u2019ve built a prep process that\u2019s helped me close $40M+ in enterprise deals across LATAM, the Middle East, and the U.S., and more than $406K in early-stage revenue for startups that had no brand equity to lean on. I\u2019ve used this same framework whether I was walking into the CEO\u2019s office at a Fortune 500 company or jumping on a VC-funded founder\u2019s calendar for a 15-minute call.<\/p>\n Below is my playbook for preparing. It\u2019s not about Googling their name five minutes before the meeting. It\u2019s about showing up as someone who belongs in the room.<\/p>\n This isn\u2019t surface-level LinkedIn scanning. I go deep.<\/p>\n I start by answering three core questions:<\/p>\n I review the company\u2019s most recent press releases, investor updates, and leadership transitions. I read the executive\u2019s interviews or authored content (LinkedIn posts, podcast appearances, earnings calls). If they\u2019ve said, \u201cWe\u2019re focused on expanding in LATAM,\u201d<\/em> then you can bet my opener references go-to-market localization \u2014 because I\u2019ve done that in four languages.<\/p>\n When I walk in, already showing that understanding, the dynamic shifts. I\u2019m no longer an interruption. I\u2019m a strategic input.<\/p>\n Remember: Context is the new closing technique. I know most sales teams skip this step and wonder why they get ghosted.<\/p>\n C-suite leaders don\u2019t buy tools. They buy outcomes. And, those outcomes are personal. A CFO might care about cost avoidance this quarter. A CRO might be under pressure to fix a pipeline hygiene issue. A COO might be tied to operational KPIs like time-to-resolution or onboarding cost.<\/p>\n I tailor my messaging around what they<\/em> care about, not what I want to sell.<\/p>\n Here\u2019s what I ask myself:<\/p>\n I even built a cheat sheet with:<\/p>\n Bonus:<\/strong> I write my first-line cold opener using this prep. That means even if I never land the meeting, my outreach still positions me as thoughtful, not transactional.<\/p>\n Executives hate two things: wasted time and vague meetings. So, I set a clear, tight agenda before the call, then frame it in a way that serves them<\/em>, not me.<\/p>\n Here\u2019s my structure:<\/p>\n I send this agenda ahead of time in my calendar invite and email follow-up. Why? Because it primes the call, lowers resistance, and increases show rates (mine are consistently under 18%).<\/p>\n Controversial take: I don\u2019t walk into exec meetings with a discovery sheet. I walk in with a narrative. And, that narrative starts with the exec, not with me.<\/p>\n This is one most sellers skip, and it costs them the deal.<\/p>\n Before any C-level meeting, I challenge my own pitch:<\/p>\n If I can\u2019t answer those questions clearly, I go back and tighten the value proposition.<\/p>\n Example: Instead of saying, \u201cWe help teams streamline collaboration.\u201d I say, \u201cWe helped a distributed ops team reduce project delays by 22% in Q1\u2014without adding headcount or changing their workflow.\u201d<\/p>\n As the Challenger model teaches, insight wins over information. And executives? They pay attention when the insight costs them something if ignored.<\/p>\n I don\u2019t memorize a script. I rehearse my flow.<\/p>\n I mentally walk through the meeting like an athlete visualizing a race. I prep for likely objections (\u201cWe already have a solution,\u201d \u201cWe\u2019re in budget review\u201d) and match them with business-first counters.<\/p>\n I review the agenda and the call plan out loud. I say my opener to a peer, or record myself and play it back. If I weren\u2019t impressed hearing it from someone else, I would rewrite it.<\/p>\n I\u2019ve coached dozens of reps who stumbled through their first exec meeting because they thought \u201cwinging it\u201d was confident. It\u2019s not. It\u2019s reckless.<\/p>\n Executives respect prep. And they can tell who\u2019s done it by the second sentence out of your mouth.<\/p>\n <\/a> <\/p>\n Let\u2019s be real: C-level conversations aren\u2019t like your average sales call. I\u2019ve had to learn that the hard way. They don\u2019t care about your product. They care about how it protects or advances the business. Period.<\/p>\n And over the last 17 years, I\u2019ve refined a few critical strategies that have helped me stay in the room, win their trust, and drive real executive conversations that convert<\/em>. Let me break it down for you step by step.<\/p>\n When I first started selling to executives, I used to think I had to prove myself in the first 60 seconds. I\u2019d rattle off my experience, my company\u2019s logos, and my metrics. Guess what? They didn\u2019t care.<\/p>\n What shifted everything for me was realizing that executives value relevance<\/em> over resumes<\/em>.<\/p>\n So now, I open with this: \u201cHere\u2019s what I\u2019m seeing in your space right now \u2014 and here\u2019s why I reached out.\u201d<\/p>\n<\/a><\/p>\n
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My First C-Level Sales Meeting<\/h2>\n
Understanding the Executive Mindset: What I’ve Learned From Hundreds of C-Suite Meetings<\/strong><\/h2>\n
C-Level Thinking Is Rooted in Tradeoffs and Timing<\/strong><\/h3>\n
You Need to Speak the Language of Risk and Return<\/strong><\/h3>\n
Here\u2019s the Controversial Take: Scripts Don\u2019t Work in the C-Suite<\/strong><\/h3>\n
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\u201cHow can I help them look smart in front of their board?\u201d<\/li>\n<\/ul>\nThe Executive Mindset Is Fast \u2014 But Not Rushed<\/strong><\/h3>\n
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Before the Meeting: My Proven Preparation Process<\/strong><\/h2>\n
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Step 1: Research the Executive\u2019s Current Context<\/strong><\/h3>\n
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Step 2: Identify the Executive\u2019s Personal Success Metrics<\/strong><\/h3>\n
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Step 3: Build a Strategic Agenda, But Keep It Buyer-Led<\/strong><\/h3>\n
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Step 4: Pressure-Test the Value Prop Before the Call<\/strong><\/h3>\n
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\u201cIs there a quantifiable risk of not<\/em> acting?\u201d<\/li>\n<\/ul>\nStep 5: Rehearse Like an Operator, Not a Performer<\/strong><\/h3>\n
During the Meeting: Executive Conversation Strategies I’ve Refined Over Time<\/strong><\/h2>\n
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Open with context, not credentials<\/strong><\/h3>\n