Technical Sales Strategies

I've done thousands of discovery calls with technical executives: CTOs CIOs VPs of Engineering VPs of Product VPs of Data VPs of Software Selling to them is hard. Here are 5 tips for selling to a technical audience (#5 is pure gold). 1. Be Technical -- most of these folks wrote code. They will respect you more if you know your stuff. Here's how: Write down 20-30 technical terms you hear often Research what they actually mean Write it back in your own words on flash cards Keep doing this with new terms. You don't need to be an engineer. You do need to be fluent. 2. Don't BS -- if you don't know the answer to a question, tell them. They will trust you more when you do know something. 3. Tell great customer stories -- Have 10 stories down pat. Start with one and master it. Stories should cover: Who was the champion? (someone like them) What their situation was (something similar to them) What wasn't working? (not too similar to them) What happened after they moved to your product? Use them only after uncovering pain. There is no hero in a story without pain. If there is one thing I'd want you to takeaway from this post. It would be learning one great customer story. 4. Know your competitors -- Technical execs want to talk about their existing stack. If you don't know those products, you're toast. Try this: Write down your top 5 competitors. Write down 3 weaknesses for each Write "trap-setting" questions to surface those challenges Once the challenges roll in -- tie it back to the business. 5. Have "stop them in their tracks" moment -- Technical execs like to have equals. Someone who can have an honest conversation with them. Here are some great ways to stop them in their tracks: Say something good about a competitor (but not the thing they want) Tell them you are not the cheapest product on the market (and aren't trying to be) Tell them it can take a little while to implement your product (it's more important it's done well, than fast) Tell them something about your product you don't love (but not something they need) These anti-sales statements break the pattern and lower defenses. That's when they start listening. and last but not least... Be grateful you are selling to these folks. They're often the smartest people in the room. Be curious about their world and they will in turn be curious about yours. What's one tip you'd have on selling to technical execs?

Spending 20 minutes crafting ONE impactful email beats blasting out 1,000 automated emails every time. Tech sales isn't about brute force anymore—it's about insight. Here's why buyers have changed and 7 tips to help you thrive: I’ve managed 100s of reps, sales teams and managers. In the early days, success came to those who could out-work the competition. Successful reps didn’t “always” need deep product knowledge or a clear grasp of the competitive landscape. Hard sales skills were enough. But those days are over... What sets today's top performers apart is their ability to research and understand the market. Buyers want insights. The reps who thrive are the ones who bring intense domain knowledge to the table. Here's why: 1. Buyers Are More Educated Today’s buyers know more about your product than the average rep does. They expect tailored answers to specific questions. If they sense a lack of knowledge, they’ll move on. 2. Market Is Flooded with Substitutes With so many similar products, the gap between competitive products has nearly disappeared. Relying on product superiority is outdated — sales reps need an understanding of both their product and competition to offer value. 3. Knowledgeable Sales Reps ARE the True Moat As product differentiation fades, your real edge lies in your GTM strategy and a core team of AEs who can navigate complex buying cycles. Buyers trust and buy from knowledgeable sellers. Here's how sellers must adapt: 1. Stay Updated Insist on regular marketing and competitive updates from your Product and Marketing teams. Knowledge is power, and staying ahead keeps you sharp. 2. Keep it Real Don’t rely on outdated claims about being better than competitors. Your competitors make the same claims. Buyers are smart; honesty about your strengths and weaknesses builds trust and credibility. 3. Deliver Insights Provide value with deal-specific insights at every interaction. Custom content, detailed responses to objections, and actionable advice will make you a trusted advisor. 4. Be a Hub of Knowledge Share anonymized best practices and insights gleaned from your conversations with other clients, you can position yourself as THE go-to expert. 5. Create Aha Moments Your buyer is likely well-informed and eager to move forward. Don't waste their time. Cut to the chase. Spark that "aha" moment and watch the deal accelerate. Make them successful at their jobs. They'll reward you. 6. Don’t Disappear After the Sale Keep sharing best practices and stay engaged after the sale. Building long-term relationships leads to repeat business and referrals. 7. Stay in Your Domain Stick with your niche when switching jobs. Choose to work for multiple companies in the same space. Over time, deep knowledge and connections in your field will provide an unfair advantage. The days of the pushy seller are over. Buyers are more demanding than ever. They want answers, not more meetings. The question is, will you evolve?

I'll never close deals in the same way I used to. After spending these past few weeks reflecting on selling cybersecurity, that's what I told myself. 2024 taught me some hard lessons, and combined with insights from industry veterans, here's what changed my perspective forever: 👉 Buyers Close Deals, Not You: The real magic happens in meetings you're not invited to. I used to obsess over my pitch, but now I focus on enabling my champions to drive internal consensus. The best move? Equipping them with tools they can use 24/7, not just during our calls. 👉 Technical Knowledge Isn't Everything - Yes, I'm an engineer turned sales leader. But I learned that while technical depth matters, what's more crucial is understanding how security fits into business strategy. The best technical pitch won't save a deal if you can't connect it to business outcomes. 👉 Stop Asking About Budget because "No budget" usually means "no justification." This hit home when a CISO told me: "Everyone wants cybersecurity, but nobody wants to pay for it until after the breach." Focus on conveying value, not finding pre-allocated money. 👉 Perfect Discovery is a Fantasy and real conversations don't follow your perfect framework. The best discussions I've had last year focused on three simple things: why do anything, why now, and why us. Everything else can come later. 👉 Trust Beats Transactions My proudest moment? Telling a potential partner our product wasn't the best fit and recommending competitors instead. Six months later, they reached out to help connect me with other vendors. Sometimes walking away from a deal is the best way to win long-term. For 2025, I'm committing to selling differently: 🤜 Less focus on perfect processes, more on enabling buyers 🙌 Building trust through honest conversations 🤙 Helping others achieve their goals What's the biggest lesson from 2024 that changed how you are going to sell this year?

For my first 16 years in tech sales, I averaged 240K/year. In my last 4 years, I averaged 720K/year. I did this by using an approach I call Yo-yo selling: 🪀 It’s how you win large, complex enterprise deals by building credibility with senior executives at the beginning of a sales cycle. This will save you months of spending time with mid or lower level Directors on a deal cycle, only to have your deal stall because it's not a priority for Executives. Here’s the concept: You start at the top, get senior level sponsorship for a deep discovery, drop down into the business, then bounce back up with a report of findings. This is the process I've used for nearly every 7-figure deal I've ever closed. Step 0: Research before outreach Before asking for time, I do deep strategic research. Earnings calls. Investor decks. Press releases. Executive interviews. I also spend time talking to their team to see if the problem that I solve exists in their company. Using that research, I build a Point of View that connects their top business goals to real execution gaps. This earns executive time. Today, AI tools like ChatGPT make this easier than ever. What used to take hours now takes minutes. If you skip this step, you lose your edge. Step 1: Prospect to the top and gain their sponsorship to engage Lead with your POV. The key is to teach them something new about their business which they aren't already aware of, and show them how it's putting their highest level goals at risk. If they lean in, offer up a deep discovery with your team and their team. Lock in a date to come back for a readout. Have them assign a project manager to help you coordinate Step 2: Drop down Once you have executive sponsorship, meet with their team. The key is to have the Exec sponsor send out a note to their team explaining what it's for. This will keep the assessment moving forward. Study workflows. Capture friction. Collect quotes. Do not pitch. Just listen. Step 3: Bounce back up Bring it all together in an executive summary. Show how their vision connects directly to what’s broken below. Present a focused business case. Build a custom demo. Create a roadmap and implementation plan. That’s where deals close. Real example from my career At Berkshire Hathaway HomeServices, we were told “no” on a point solution. Instead of walking away, I stepped back and asked what the company really needed. After deep research, I re-engaged the COO with a transformation POV centered on the experience of 50,000+ agents. The result was one of the largest new logo deals in Salesforce history. But Yo-yo selling alone isn’t enough. Because it's hard to execute and takes patience. Top performers also master their mindset, habits, and discipline. That’s why I put together a free masterclass for sellers who want to break into the top 1 percent. 👉 Watch the free training here: https://lnkd.in/eWD8mTqH If you’re serious about enterprise sales, this will change how you sell.

Your sales team isn’t losing deals. They’re losing trust. Not because they lack effort. But because they lack the right approach. Tech founders know this struggle. Your engineers build cutting-edge products. Your sales team delivers polished pitches. Yet somehow — Deals stall. Leads ghost. Sales cycles stretch. The real problem? Your team is selling what your product does. ↳ Your buyers care about what it changes for them. And that disconnect? It’s dragging revenue down. The Fix? ↳ Consultative Selling. Instead of pushing features, Your team needs to start solving real problems. Here’s how we transformed a tech sales team in 30 days: ↳ Week 1: Understand your customer. - Stop guessing. Start diagnosing. - Dig into real pain points, not surface-level. Map your solution to their broader business goals. ↳ Week 2: Speak their language. - Cut the tech-speak. - Reframe features into outcomes. If your buyer can’t explain it in 30 seconds, it’s too complex. ↳ Week 3: Show real value. - Prove ROI before they ask. - Address objections before they arise. Make your solution the obvious next step. ↳ Week 4: Close and grow. - Guide the deal, don’t push it. - Set the foundation for long-term partnerships. Turn new clients into repeat customers. The result for my client? → 30% more qualified leads → 25% shorter sales cycles → Sales team closes without Founder If your team is still selling features, it’s time to shift the approach. Because the best sales teams don’t pitch. They advise. Need help? Book a 1:1 Power Hour with me from the Featured section. Found this valuable? ♻️ Repost to your network 🔔 Follow Surabhi Shenoy for more CEO insights -- Want to level up your CEO game? 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗖𝗘𝗢 𝗠𝗮𝘀𝘁𝗲𝗿𝘆 — my Free Weekly Newsletter trusted by 1700+ Founders. Every Thursday, I share 1 actionable system to grow your business, increase its valuation, and have fun doing it. 🎁 BONUS: Get Rapid Growth Playbook (27 cheatsheets) Click "𝗩𝗶𝗲𝘄 𝗺𝘆 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿" above this post or scan the QR code in the image.

Most tech sales reps make the same mistake. The Secret to Selling Technology? Stop Selling. They jump into a demo, list every feature, and hope the buyer is impressed. But high performers know: Trust > Outcomes > Tech A CIO doesn’t care about your software’s new AI model. They care about reducing security risks and saving time. So before you pitch, ask yourself: Am I leading with problems or products? Am I selling the roadmap or the destination? Am I a vendor or a trusted advisor? Big difference. The best salespeople don’t sell tech—they sell transformation. If you want to level up, start by shifting your mindset. 👉 Are you a seller or an advisor?

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

(So apparently I'm hopeless at posting videos - second attempt! It's a precious 81 seconds that could make a major difference.) Most deals don’t get blocked by a hard “no.” They quietly stall out, and no one knows what happened. That’s why at Mastering Technical Sales , we coach teams to recognize and plan for two silent killers: DNI (Do Nothing Incorporated) and AUC (Alternate Use of Capital). They’re not just outcomes. They’re powerful forces you need to manage from the very beginning. When I was a CIO, I had a list of projects and a limited budget. Sometimes the problem wasn’t urgent enough. Other times, something higher up the list took priority. And here’s the secret: It didn’t matter how good the vendor’s pitch was. If they couldn’t help me make the internal case, the deal went nowhere. That’s why we advise teams to: Get clarity on where the problem sits among the buyer’s priorities. Tie your solution to specific business impacts (not just pain, look for gain) Equip your champion to make the case when you're not in the room. Use a follow-up space (like Aligned) so they always have what they need when it’s time to re-engage Deals don’t just close: They compete. Treat DNI and AUC as real competitors and craft a strategy to defeat them. If you’re not building a case that survives budget reshuffles, you’re not really in the running. What’s one thing you do early to protect your deal from going dark? #salesengineer Up 2 Speed

Most loan officers follow up twice on a $4,000 commission. Tech sales reps touch prospects 12+ times on a $500 deal. I watched a SaaS rep last week hit his prospect eight times across email, text, LinkedIn, and phone to close a $299/month software deal. His commission was maybe $360. Same day, a loan officer tells me he gave up on a qualified buyer after two phone calls. That's a $4,000 commission. Gone. Not to mention the potential lifetime value of that client relationship. Because two attempts felt like enough. Here's what tech sales knows that mortgage still struggles with: Multi-channel sequences work. Not just calls. Not just emails. Everything. Touch 1-2: Call/text within 60 seconds Touch 3-4: Call + follow-up text (day 2) Touch 5-6: Value email + text check-in Touch 7-8: Call attempt + educational content Touch 9-10: Social touchpoint + targeted text Touch 11: Final push - call, text, email Touch 12: Breakthrough or move to nurture Most of this can run on autopilot. Automated emails nurture while you work. Scheduled texts deploy while you sleep. The automation isn't replacing you. It's warming them up for when you actually connect. But mortgage still treats follow-up like it's 1995. Two calls, maybe a voicemail, mark it dead. Then drop 'em in that slick monthly email newsletter system. Meanwhile, that "dead" lead is closing with the loan officer who didn't give up after two tries. Their system kept nurturing - email, text, calls - until the prospect was finally ready to engage. Maybe that was touch #7, maybe touch #12. Doesn't matter. What matters is they were still there when the lead was ready. At $4,000 per loan, every non-responsive lead is a missed opportunity to print money. But you're treating follow-up like you're selling magazine subscriptions. Tech figured this out. Steal their playbook. #mortgage #sales #rebeliQ