How to Use ChatGPT Plus for Enterprise Sales

How I use ChatGPT as my unfair advantage in sales (and how you can too) Last year, I was stuck. I had too many tasks on my plate: cold outreach, writing follow-up emails, handling objections, prepping for discovery calls. And then it hit me: What if I could make AI my assistant? Not to replace me. But to free up my time, sharpen my game, and help me win more deals. Here’s the framework I’ve built (and it works like magic): 1️⃣ Start with the right question Bad input = bad output. Instead of “write me a cold email,” I ask: 👉 “Write a cold email to the VP of Marketing at a SaaS company, who recently raised Series B funding.” That’s context. And context changes everything. 2️⃣ Detect the intent (what do I actually need?) Am I struggling with: Lead research? Messaging & positioning? Objection handling? Sales strategy? Example: If I keep hearing “We don’t have budget”, I’ll feed that into ChatGPT and ask it to roleplay as a buyer → I practice objection handling before the real call. 3️⃣ System setup = framing the role AI works best when you tell it who it is. I say: 👉 “You are my sales coach.” 👉 “You are a top SDR who crushes cold calls.” Suddenly, the responses are sharper, practical, and usable. 4️⃣ Parsing the query = break it down Every great sales play needs clarity: Who’s the target? What’s the offer? What’s the goal? Example: If I want LinkedIn messaging for a CMO in retail → I ask specifically about pain points in retail marketing. 5️⃣ Retrieval + Reasoning Boost This is where ChatGPT shines. I combine raw data (prospect research, news, press releases) with decision frameworks (SPIN, MEDDIC, Challenger). Example: I found a company blog where a CEO complained about hiring bottlenecks. I asked ChatGPT to draft a 3-line outreach that directly solved that pain point. Got a reply in 24 hours. 6️⃣ Agents at work Agent A: Research Prospects → scrapes company blogs, press releases, LinkedIn posts. Agent B: Market Context → looks at competitor moves, industry trends. Together, it’s like having 2 interns who don’t sleep. 7️⃣ Memory Layer = long-term advantage This is where AI becomes a coach, not just a tool. I keep a log of: What objections I faced. What messaging worked. What deals I lost and why. Over time, ChatGPT “remembers” and gives me better, personalized responses. I have a virtual SDR + Sales Coach + Market Analyst. All in one. It doesn’t do the selling for me. But it makes me 10x sharper in every conversation.

A few weeks ago I told my team that AI needs to do 92% of their work or they'll get left behind. Here’s how we're doing it (and why): Step 1: Get ChatGPT Plus/Pro Step 2: Create your master prompt • Tell AI: "I'm [your role] at [company type]. Create a master prompt for me. Ask me every question you need to give me the most context possible." • Spend 30-45 minutes answering everything it asks • Save the output as a PDF • Upload this to every new chat so AI knows your full context Step 3: Build system prompts Master prompts tell AI who you are. System prompts tell AI HOW to work. Here's the process: • Ask AI to create any output (email, ad, report) • Keep refining until it's perfect (3-6 iterations) • Then ask: "Write the system prompt that would have generated this output" • Save that prompt - it's now your intellectual property Now you have the exact formula to get that quality every time. Step 4: Use project folders  Think of these like rooms in your office with all context on the walls. • Create a project for each major area of your life/business • Upload your master prompt + all relevant documents • Every conversation builds on previous context • Share folders with your team for instant knowledge transfer I use this for investment decisions, business strategy, even family planning. Step 5: Set your custom instructions This makes AI remember how you like outputs formatted. Go to Settings → Personalization → Custom Instructions: • Tell it your communication style (short, bullet points, no fluff) • Remove AI language like "delve" and "moreover"  • Set your default tone and format preferences Never repeat formatting requests again. Step 6: Turn everything into custom GPTs These are your AI employees that do specific tasks consistently. • Take your best system prompts • Create custom GPTs for each repeatable task • Share them with your team • Update once, everyone gets the improvement I have custom GPTs for: emails, content creation, financial analysis, hiring, strategy docs. Step 7: Refine and improve Use AI to teach you AI. • Ask it to create your master prompt • Ask it to write your system prompts  • Ask it to suggest custom instructions • Ask it to help you build better prompts Here's what 92% actually looks like: - Content: AI does research, outlines, first drafts. You edit and add your voice. - Operations: AI creates SOPs, analyzes processes, suggests improvements. You decide. - Finance: AI analyzes reports, creates models, finds insights. You make decisions. - Strategy: AI processes information, suggests options. You choose direction. The 8% that stays human: Vision, taste, final decisions, and emotional intelligence. My team went from thinking AI was "kind of helpful" to saying it's their most valuable employee. It could be yours too. -DM P.S. If you want my complete prompting template and the 7 system prompts that save me 15+ hours per week, MESSAGE ME the word "AI" and I'll send it over. My gift to you 👊

Here’s the step-by-step playbook I give SMB & MM AEs to turn AI into their personal sales assistant. BEFORE YOUR CALL (10 minutes): 1. Prospect Research with ChatGPT → Paste their company URL → Ask: “What are the top 3 challenges this company likely faces?” → Get talking points tailored to their industry 2. Discovery Questions with AI → Input: “I’m calling a [role] at a [company size] in [industry]” → Output: 5–7 custom discovery questions → Way better than generic scripts DURING YOUR CALL: 3. Real-Time Note Taking → Use Fathom or Gong to record and transcribe → Focus on active listening, not writing. AFTER YOUR CALL (5 minutes): 4. Instant Follow-Up Generation → Drop transcript into Claude or ChatGPT (or you can use this one I made: https://lnkd.in/eMZNpJXR) → Prompt: “Create a follow-up email summarizing our conversation and next steps” → Edit for tone → send 5. CRM Updates → Use AI to extract: pain, stakeholders, timeline, criteria → Copy/paste into Salesforce → What used to take 20 minutes now takes 2 6. Call Analysis → Ask AI: “What objections were shared that I never addressed?” → Get coaching insights in 5 min or less Real example from last couple of months with AEs I coach: AEs ran this process on 5 calls. → Before AI: 2-3 hours/day on prep, notes, follow-ups → After AI: 45 minutes/day → More time selling = more deals closed

Most AEs can’t get a meeting with a CFO. My clients are getting them with CEOs, COOs, and CFOs—consistently. The secret? Not magic. Not spamming. Hyper-personalized, multi-channel outreach powered by ChatGPT. Here’s the exact framework we use (that gets replies when “short and sweet” emails fail): When I ask sales teams how many times they follow up with an executive before moving on, the most common answer is: “Two emails, maybe a call.” That’s why you’re losing. Executives don’t respond because: Your outreach is generic You stop before you break through the noise You rely on ONE channel (usually email) Here’s how we fix it. 1. Go narrow before you go deep Stop prospecting to everyone in your patch. Pick your A accounts—the top 10-20 that would change your year if you closed them. 2. Use 3-4 channels every time If you send an email and don’t follow it with a call, a video, and a LinkedIn touch, you’re invisible. I’ll use ZoomInfo or Seamless to get the cell number, call right after sending the email, leave a voicemail, then send a voice note or video if no pickup. 3. Reach out 10+ times (not 2) My largest deals took 10-15 touches before the first meeting. If you believe you can help them, they need to know you’re serious. 4. Hyper-personalize using AI Forget “Hope you’re doing well.” Here’s the structure: Line 1: Personal, sincere compliment tied to research Line 2: Observation about their stated goals/priorities Line 3: The gap between where they want to go and where they are today Line 4: How you can close that gap Close: Soft call to action 5. Steal my favorite ChatGPT-4o prompt “I’m a sales rep at [Company] targeting [Name, Title]. Write a personalized, executive-ready email that speaks to their role, their publicly stated goals or quotes, and how we can help them. Be concise, use bullet points, and end with a soft CTA.” (more in the video below) Combine this with deep account research before you ever reach out, and you’ll have emails that sound like you wrote them just for that exec—because you did. I’ve seen this method work when: - You’re selling to an account that already uses your product (reference it in the first line) - You can’t find public info on a prospect—personalize at the account level instead - You need to enable champions to sell internally You don’t get meetings with executives by sending “short and sweet” emails. You get them by showing you’ve done the work— And proving, in detail, that you understand their business better than 99% of reps hitting their inbox. Get my top 4 ChatGPT prompts for tech sellers here: https://lnkd.in/gbznEjgq