🤖 AI-powered upgrade

In partnership with

To access all my premium resources, please upgrade to Premium

The Future of Sales: Agents Take Over

Agentic Distribution Summit – Sept 16–18 | Free & Online

3 days. 100+ CXOs. 30+ exec roundtables.

Learn how AI agents are replacing broken GTM channels and running Sales, Marketing, CS, and RevOps end to end.

Speakers from ZoomInfo, Salesloft, Gainsight, Lovable, Meerkat + more.

Register here

If you haven’t attended an HSE event this year, this one is a must - they’re doing amazing work!

Build research engines with ChatGPT folders

Ryan Staley teaches how sales executives use ChatGPT’s agentic features to automate prospect research and routine tracking in minutes. Free up your hours and gain leverage:

1. Create personal workspace

➤ Build a new ChatGPT thread and folder called Automations

➤ Use multiple project subfolders for different categories:

➤ Example: prospect research, competitive intel, deal alerts

➤ Example: In prospect research, store weekly funding rounds

➤ Example: In deal alerts, track quarterly renewal deadlines

➔ Clear organizations minimizes potential scaling clutter.

2. Identify own responsibilities

✔ One-off reminders → “Email CFO slides before meeting on 9/12.”

✔ Personal reminders → “Pipeline cleanup every Friday at 4 pm.”

✔ Scheduled updates → “Send top 10 LinkedIn posts from my ICP.”

✔ Conditional watchdogs → “Alert me if [Company] posts a VP of Sales role.”

✔ Active projects→ “Follow-up on your clients with 90+ days of inactivity.”

3. Schedule timeframes properly

✱ Ask ChatGPT for 5 automation ideas tailored to your pipeline.

✱ Prepare scheduled investigations around department signals:

❖ “Series A cybersecurity funding in the past 30 days”

❖ “Banking CIO position role normally changes in Q3”

❖ “Healthcare SaaS partnerships announced today”

✱ Improve results by layering filters: ARR, region, or headcount

4. Refine workflow automations

📌 Test and validate:

Run experimental outputs for a week to check accuracy.

If everything’s too disorganized, tighten keyword usage.

📌 Add parameters:

Instead of “funding news,”, apply persuasive descriptions.

Look for “US-based SaaS Series A funding >$20M with 50–500 employees.”

📌 Output consistency:

Provide LinkedIn URLs, or ARR estimates for prospect-ready info analysis.

Everything must be repeatable from scratch with disaster-proof outcomes.

📌 Maintain regularly:

Remove your outdated projects before customer engagements.

Workflows should be maintained and checked for more problems.

📌 Evolve with goals:

If your priority changes to renewals, high-level alerts should be reprogrammed to flag potential contract expirations or M&A activity in different customer accounts.

📌 Check your sources:

Utilize ChatGPT to pull from multiple sources (press releases, LinkedIn).

Ensure AI workflows remain verifiable, and precise for your audiences.

Examples of refinements:

→ From “Send me all SaaS funding” into “Send me only SaaS funding in APAC above $50M, with HQ in Singapore or Sydney.”

→ Add columns like “primary executives hired in the last 90 days” for lead generation.

How ChatGPT makes roleplaying unlimited

Sam Urpani breaks down how sellers can use ChatGPT their live roleplay partner and instant coach to practice calls, handle objections, and sharpen tonality for the real-world:

Practice with AI roleplays

1. Open ChatGPT (advanced version) → Works on desktop or phone.

2. Give context in the prompt → Example:

   
   “You’re a homeowner lead who downloaded my seller’s guide. I’m the agent calling to book an appointment. After the roleplay, critique my tonality, objection handling, and rapport building.”

3. Running the prospect calls→ You speak as the rep, ChatGPT answers as the lead.

4. Get customer feedbacks → ChatGPT analyzes performance with own feedback.

Example: In Sam’s roleplay, he booked an appointment with “Jackie” by confirming she downloaded the selling guide, confirming about timing, and offering free valuations.

ChatGPT praised his confidence but suggested building rapport earlier.

Customize your difficulty

You don’t have to roleplay “nice” leads.

You can instruct ChatGPT to:

🔑 Act as a busy executive who keeps cutting you off.

🔑 Raise objections like:

🔑 “We already work with another agent”

🔑 “This isn’t our main priority right now.”

🔑 Remain skeptical, or distracted for adaptability.

Example:

“Act as a CFO who’s annoyed with being cold called. Push back hard on budget concerns.” 

AI technology roleplays accordingly, forcing to practice your reframing.

Training with actual calls

Beyond fresh roleplays, ChatGPT helps improve on mistakes:

• Upload a transcript from a discovery call:

  What did I do wrong here? How could I have handled this objection better?”

• Examine ChatGPT prompt:

  “Let’s replay this moment where the lead pushed back on pricing. Act as the lead again so I can try a stronger response.”

Upgrade past calls into training loops for better definition.

Real-world applications

💬 B2B SaaS SDRs → Roleplay cold calls where the prospect pushes back with:

“We already use [competitor].” Practice reframing into a meeting.

💬 Account Executives → Simulate late-stage objections “I need CFO approval” and roleplay multi-threading perspectives.

💬 Real Estate Agents → Run seller lead calls everyday with different hooks for booking appointments.

💬 Recruiters worldwide→ Roleplay candidates hesitant to switching job and practice overcoming doubts.

Any industry with live calls benefit from turning AI into roleplay coaches.

FREE ChatGPT Resources

Your competitors are sending generic messages while you're targeting outreach. These ChatGPT prompts eliminate guessworks from cold outreach, upgrading your email responses anf first-touch bases into your effective conversation starter with prospects.

Your competition's hoping for your downfall, while you’re strategically moving. Master AI-powered emailing techniques now and start booking meetings like a precision marksman: because with prompts, you’re reducing competitor noises every single time.

Join thousands of sales reps worldwide to consistently secure more deals.

Download the FREE ChatGPT sales resource now!

AI workflows helping sellers close more deals

Haris Halkic discusses picking the right AI workflows for different scenarios because having the wrong choice means wasting resources fixing outputs instead of closing deals:

ChatGPT → quick, versatile, best for outreach

🎤 Use for: cold emails, LinkedIn outreach, proposal drafts, follow-up sequences

🎤 What it does best: Generates personalized drafts quickly, adapts messages to different buyer personas, integrates with plugins and third-party sales tools

🎤 Where it struggles: Handling large, complex documents in one prompt, vague prompts that create inaccuracies, AI outputs that still need human intervention

• Examples:

  ➔ Draft cold email sequences for healthcare CFOs based on their LinkedIn

  
  ➔ Rewrite complex business studies into persuasive content for executives

  ➔ Generate variations of stalled deal follow-ups for different conversations

  Power move: Feed ChatGPT your ICP + previous client studies → auto-generates various outbound templates organized by industry segment, ready for testing

Claude → depth and clarity for long analysis

✅ Use for: summarizing RFPs, analyzing CRM notes, product documentation

✅ What it does best: Handles long documents, produce compliance outputs, maintain contracts or transcripts, excellent for long-term account handling tasks

✅ Where it struggles: Slower, has problems occuring with creative messaging than ChatGPT, no image generation features, less operational workflow integrations

• Examples:

  
  👉 Condense this 50-page RFP into 10 main buyer priorities

  
  👉 Extract competitor mentioned from call transcript records

  
  👉 Turn your product sheets into buyer language superiority

  
  👉 Analyze transcript objections, grouping them into points

• Power move: Upload your entire sales call library → Claude surfaces patterns in objections, pricing pushbacks, and deal triggers you can use in future pitches

Gemini → lead research and collaboration

• Use for: research proposals, visual chart building, Gmail context preparations

• What it does best: Integration with Google systems, great for mixing text + data + visuals, perfect for collaboration between sales, marketing, finance departments

• Where it struggles: Best when your organization’s fully integrated with Google ecosystem; weaker for deep contract or transcript analysis compared to Claude

• Examples:

  
  📌 Pull recent funding news by auto-populating Google Sheet dashboards

  
  📌 Draft business proposals including live market trend charts from Sheets

  
  📌 Turn scattered Gmail threads with clients into prepared recap documents

  
  📌 Build tracker sheet updating you on job postings, and product launches

• Power move: Have Gemini merge prospect research, Gmail interactions, and proposal drafts into one briefing document → ready for executive-level send outs

AI workflows amplify everything by removing grunt work from selling.

Partnering with these newsletters:

• The Follow Up: We talk about Sales like your friend, not your manager

• Big Desk Energy: Startup stories and lessons

• B2B Whales: Proven B2B sales strategies

• Creator Spotlight: Grow with social media and newsletters

Check them out!

P.S. Get access to all my premium resources and infographics - subscribe to Premium