How to write a cold email to an enterprise account

Had a great July, was able to land the #1 spot across the entire sales org after just 3 full months on the job. I came into this role with zero experience in the medical industry and had never sold software-supported SEO, web design, or proprietary platforms before. In a full-cycle, end-to-end sales role, most hiring managers would probably look at my resume and see uncertainty and risk. In many cases, this alone would be an automatic disqualification from the hiring process. But here’s what I’ve learned: You can learn a product quickly. What you can’t learn quickly are the fundamentals: -Prospecting -Running tailored demos -Negotiating -Creating urgency -Managing pipeline -Following up with consistency I’m constantly seeing high-performing salespeople, and good friends of mine, being passed over just because they don’t check the “X years of experience selling Y to Z” box. In other words, companies prioritize familiarity instead of skill, and they end up hiring reps who are great on paper but only know how to sell one product, one way and end up lacking the adaptability or grit to win elsewhere. Sales is ultimately an exercise of communication skills. Business isn't won because you've memorized single detail, of every single feature of your previous companies software. It's only won through consistent activity, understanding the person you're sitting across from, and knowing enough about your product to convey how it will be used solve their problems. Let this serve as proof: you don't need to study a product for 5 years in order to do that effectively.

Starting your sales team off on the right foot as a start-up can be the difference between making it or breaking it in this economy.

Sales yield at 0.5x rep cost. And you’re hiring closers. That’s why your runway’s disappearing. The Head of Sales at a $20B co showed me this framework: They suggested I read a 20 year old article by Mark Leslie from the Harvard Business Review. Here’s the big idea: Sales follows a learning curve, just like manufacturing. In manufacturing, you track cost per unit. As you learn, costs drop. In sales, you track "sales yield." Revenue per fully trained sales rep. Mark Leslie identified three distinct phases: >Step 1 Initiation Phase: Few customers willing to buy. Those who do need heavy incentives. Your job: Learn how customers actually use the product. "Renaissance reps" who can: - Communicate across the organization - Tolerate ambiguity - Connect customers with product teams Don't set quotas, focus on learning. >Step 2 Transition Phase: Sales accelerate. Critical mass of customers achieved. Sales yield equals fully loaded rep cost. Add "Enlightened reps" who can: - Contribute to evolving sales models - Execute without hand-holding Develop repeatable processes. >Step 3 Execution Phase: Traction achieved. Sales yield hits 2x rep cost. Formula for success established. Now hire "Coin-operated reps." Give them territory, price book, materials. Watch them produce. According to Leslie: Your sales "failure" might be hiring execution reps during the learning phase. Or hiring renaissance reps when you need coin-operated closers. The cure is the right reps for your phase. Know where you are on the curve. Hire accordingly.

State of cold calling 📞 I was chatting with the VP Sales of a industrial tech company that's expanding their operations across both US and Canada now Their # 1 challenge atm? Getting manufacturing prospects on the phone The VP Sales walked me through their current process: "I'll look up Procter & Gamble on LinkedIn, find a few contacts, make phone calls to the appropriate parties. If I can get somebody, they'll usually accept a virtual meeting. Once I get on site, I'm almost guaranteed a sale" But... Getting people to pick up is nearly impossible rn His exact words: "People don't pick up the phone like they used to. If they don't know the number, they leave it. Nobody wants to return a sales guy's message" So they wanted to outsource the calling to AI. ✋🛑 Here's what I told him Honestly? You do NOT want an agency making calls for you. Think about it. Would you trust a BDR who's never worked at your company to call your prospects about specialized industrial cameras that prevent unplanned downtime? Your brand matters too much for that risk Instead, I showed them a different approach We built them an AI agent that does ALL the research their reps normally do: 1) Researches company locations and current technology stack   2) Identifies plant managers, maintenance engineers, and line leaders 3) Finds direct phone numbers and email addresses 4) Writes personalized outreach and prep call script based on their specific pain points 📌 Their new workflow with Redcar AI sales agents: Their reps still make the calls But now they wake up to a list of fully researched, qualified prospects with all the intel they need to have informed conversations No more spending hours researching Procter & Gamble locations No more calling switchboards asking for extensions No more crafting emails from scratch The AI does the $10/hour research work The reps focus on the $500/hour selling work Your reps should be closing deals Not playing detective on LinkedIn This is the way ✌️ -- P.S. Curious how this could work for your reps? Shoot me a DM

Your new sales hire has a great résumé… but $0 in sales. What gives?! It’s a frustratingly common story... ✓ You’ve dialed in your ICP. ✓ Your pitch deck is tight. ✓ Your onboarding is solid. You've done all the "right" things, yet where's the WON deals? The truth is, the answer lies just beneath the surface. It’s not the script. It’s the casting. One of the most overlooked factors in a great sales function is matching the Salesperson to the Sales Model. Before you hire, you need to be brutally clear on the DNA of your process: → Is it B2B or B2C? → $500 or $500K? → One call close or 9-month sales cycle? → Are you creating a category or competing in one? These answers determine who wins in that seat. A few mismatches I’ve seen (and made): 🚫 B2C closers thrown into consultative B2B. 🚫 Channel reps asked to do outbound hunting. 🚫 Transactional pros expected to evangelize innovation. The skill sets don’t transfer. And hope is not a strategy. → Transactional = speed, volume, closing. → Enterprise = patience, education, multi-threaded trust. The “best” rep on paper means nothing if they’re not built for the game you're playing. Before your next hire: 1️⃣ Get clear on your model & GTM strategy 2️⃣ Define your Ideal Candidate Profile 3️⃣ Then hire for that. It’s the difference between scaling and stalling. 👇 What’s one trait you must have in a salesperson for your model?

WARNING FLAG - B2B SALES LEADERS! I challenge you… I see this overlooked gap on every sales team I coach. There’s always a focus on prospecting and lead generation (which is key) BUT… What are your reps doing on that initial discovery call? MY CHALLENGE Try this at your next sales meeting…. Step 1: Create a common Discovery Call scenario everyone can relate to. Step 2: Ask 2-3 of your salespeople to demonstrate exactly what they do when meeting with a new prospect/contact. Look for the following: - How do they PREPARE? (Using AI?) - What is their call OBJECTIVE? (specifically) - How do they OPEN the business dialogue? (after rapport) - What are their standard 2-3 opening QUESTIONS? (Open ended?) - What VISUALS do they use? (Any good?) - How do they show “SOCIAL PROOF”? (That you’re good!) Each role play can be less than 5 minutes…trust me, you’ll see the wheels come off pretty fast…LOL! In the role plays, focus only on the beginning of the call…because as you know, the way a call begins often determines how it’s going to end up. Here’s why I am challenging you to try this… EVERY SALES TEAM I work with needs their Discovery Call Structure to be GREAT - not just OK. You work too hard to book an "appointment". You need consistency and a strategy all reps can execute. I wave the warning flag because it’s a glaring gap we continue to fix in our B2B sales training programs. YES, it is 100% fixable. And if you accept my challenge, you’ll see why I'm waving the warning flag at YOU. 4 SURE.

𝗣𝗿𝗼𝘀𝗽𝗲𝗰𝘁𝗶𝗻𝗴 𝟭𝟬𝟭 - 𝗦𝘁𝗮𝗿𝘁𝘂𝗽 𝗘𝗱𝗶𝘁𝗶𝗼𝗻 📓 When I started my sales career, I had it "easy." Inbound leads all day: free trials, content downloads, conference attendees. All warm, and (mostly) all ready to talk. And as someone who already liked to yap on the phone, I was thriving. Then came the hard part: figuring out how to find people to call when no one was raising their hand. That transition rocked me. Here are 3 things I wish I knew back then that I utilize now: 1. 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝗮 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝗴𝗿𝗼𝘂𝗽, 𝗻𝗼𝘁 𝗮 𝘃𝗮𝗴𝘂𝗲 𝗰𝗮𝘁𝗲𝗴𝗼𝗿𝘆 👥 Instead of “TA leaders across healthcare,” I go after “Directors of TA at mental health facilities.” The more specific the group, the tighter the message - and the faster I pick up on patterns in objections and pain points. No more starting from scratch every call.  2. 𝗕𝘂𝗶𝗹𝗱 𝗮 𝗿𝗲𝗮𝗹 𝗹𝗶𝘀𝘁 𝗳𝗶𝗿𝘀𝘁. 𝗧𝗵𝗲𝗻 𝗰𝗮𝗹𝗹. 𝗡𝗼𝘁 𝘁𝗵𝗲 𝗼𝘁𝗵𝗲𝗿 𝘄𝗮𝘆 𝗮𝗿𝗼𝘂𝗻𝗱 📋 Yes, there was a time I’d find one prospect, call them, hit voicemail, then go find the next one. This was a 𝘏𝘜𝘎𝘌 waste of time. Now I carve out blocks of time to build full lists and then hit the phones. Way more efficient, way easier to stay in the zone, and helps me understand what strategies make good/bad lists for the future. 3. 𝗟𝗲𝗮𝗿𝗻 𝗵𝗼𝘄 𝘁𝗼 𝗺𝗼𝘃𝗲 𝘂𝗽 𝗮𝗻𝗱 𝗱𝗼𝘄𝗻 𝘁𝗵𝗲 𝗼𝗿𝗴 𝗰𝗵𝗮𝗿𝘁 🔃 Not every prospect is the buyer, but that doesn’t mean they aren’t valuable. If I’m talking to a mid-level manager, I focus on the pain they feel directly, and once I can convince them I have them be a champion to move our conversation internally. If I’m with a VP or C-level exec, I lean on what I’ve seen across similar orgs and talk about 𝘪𝘮𝘱𝘢𝘤𝘵, using their lead to convince their subordinates in future conversations. Different conversations, same goal: 𝘨𝘦𝘵 𝘵𝘰 𝘵𝘩𝘦 𝘳𝘪𝘨𝘩𝘵 𝘱𝘦𝘳𝘴𝘰𝘯 𝘸𝘪𝘵𝘩 𝘢 𝘸𝘢𝘳𝘮 𝘱𝘢𝘵𝘩 🔥    Early-stage sales is different. You wear every hat. You build every list. And most of the time, you’re the one giving yourself advice. Hope this helps someone earlier in the journey than I am. What else would you add? Curious what prospecting lessons others learned the hard way 👇✍️

The future belongs to companies who train scientists to sell, not salespeople to fake science Your VP of Sales just doesn't know it yet. Here's a playbook everyone thinks is smart: - Hire generalists to "own the relationship" - Bolt on a team of app specialists to talk tech - Cover more product lines with less sellers What happens in practice: Customer hops on a 1st call with an "account manager" They explain their aggregation problem while the rep googles "protein" Rep schedules a "technical deep dive" for next week. (their app specialist is travelling to a trade show) Specialist re-asks every... single... question. Customer realizes they've been talking to someone who didn't understand their work at all. Trust in your company: Gone. The deeper costs of this model: - Reps can't find the real pain points, so deals die in discovery - Sales cycles drag on with endless "let me check..." emails - Deal sizes end up smaller because reps can't articulate value they don't understand themselves (and run for the discounts). Don't get me wrong, app specialists are essential team members. They give sellers time to prospect by delivering demos and training. The problem is pretending your sales reps don't need to be technical, too. Your customers deserve to speak with someone who deeply understands their workflow, research and business outcomes. If you want to dominate your technical market, stop splitting science and sales. Train your experts to sell. Don't ask your sales people to fake science. Ever been on the other side of this? What's your most memorable example of talking to a rep who clearly didn't understand your work? Drop it below!

Sales is the engine. If sales stall, nothing else moves. Lately, I’m seeing more businesses (even great products) struggle to find good salespeople. Not order takers, real operators who can open doors, run complex cycles, and close. Why is this happening? We’ve over-indexed on “playbooks” and underinvested in the craft. Prospecting, discovery, and multi-threading are skills, not templates. “The product sells itself” became a comfort blanket. It doesn’t, especially in enterprise. Enablement training, Reps need reps. Call blocks, live coaching, feedback loops. Comp plans and territories are misaligned. If you don’t reward pipeline creation and multi-quarter deals, you won’t get them. AI made bad outreach faster. Personalisation and business acumen still win. Buyers want trusted advisors, not feature tours. That’s a different profile entirely. What does this mean for the future? Hybrid sellers who blend commercial skill with product & data literacy will dominate. Founder-led + fractional pods will fill gaps while teams upskill. True sales ops & enablement become non-negotiable. Outcome-based compensation will separate performers from seat-fillers. AI becomes a force multiplier, never a substitute for judgment and grit. Curious to hear from leaders and sellers: Why is it getting harder to find great sales talent, and what’s actually working for you right now?

Early B2B SaaS founders have to be their own first salesperson. Here's why: Your early customers aren't just buying your product. They're betting on you as the founder to solve their problems. I learned this firsthand while building AppArmor, my campus safety software company. As a self-funded founder targeting the public safety sector, I had no choice but to handle all the sales conversations myself. And honestly, that turned out to be my biggest advantage. When I was sitting across from a CTO at a major university, discussing how our emergency notification system would integrate with their existing infrastructure, no junior sales rep could have had that same conversation. I knew every feature, every limitation, every workaround. More importantly, I could make decisions on the spot and commit to building exactly what they needed. These weren't just product demos, they were consultative conversations where I was solving real problems in real time. If you can't sell your own product, training someone else to sell it won't fix the underlying problem. You need to understand your market, your customers' pain points, and your product's value proposition at a deep level first. Only then can you build repeatable sales processes and eventually hire others to execute them. Your early sales conversations aren't just about closing deals, they're about understanding what you're actually building and who you're building it for. That understanding becomes the foundation for everything else.