The Secret to Writing Better Cold Emails in Half the Time with AI | Ep. 322 | Sean O’Brien

The Secret to Writing Better Cold Emails in Half the Time with AI | Ep. 322 | Sean O’Brien

Steal Sean’s Secret to Using AI For Your Cold Emails Sean O’Brien breaks down how to leverage AI to rapidly research prospects and write personalized cold emails that cut your outreach time drastically, so you can send smarter, more effective messages that get real replies. 🎙 ACTIONABLE TAKEAWAYS: Use insights from sales calls and transcripts to train AI on key buying triggers and improve your outbound outreach. Focus your outreach within the same department, get explicit opt-in, and use “off the record” questions to uncover sensitive, valuable info about the buying process. Parrot your prospect’s exact words in email subject lines and messaging for higher engagement and authenticity. Don’t hesitate to have different team members send the same message to a prospect—sometimes a new voice gets the response you didn’t. SEAN’S PATH TO PRESIDENT’S CLUB: Enterprise AE @ Harvey Regional Sales Director @ Diligent Enterprise AE @ Mosaic.tech RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides

Episoder(507)

10 (Sell): Managing every part of the deal process from first calendar invite to close (John Barrows, Host of Make it Happen Mondays)

10 (Sell): Managing every part of the deal process from first calendar invite to close (John Barrows, Host of Make it Happen Mondays)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Send a meeting efficiency survey prior to your calls to get qualification out of the way Setup feeds for all of your top target accounts as the backbone for your disco Ask specific impact ?’s like “what happens to rep attainment if you don’t do this?” Use the subject line ‘Did I lose you?’ with a blank reply email for gone-dark opps John Barrow’s Path to President’s Club: CEO of JBarrows Consulting Host of Make it Happen Mondays RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

1 Jul 202025min

9 (Sell): Death to fluff on your cold calls and pricing tactics (Belal Batrawy #DeathtoFluff)

9 (Sell): Death to fluff on your cold calls and pricing tactics (Belal Batrawy #DeathtoFluff)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Decoy Pricing: $6 (undesirable), $7.50 (acceptable), $8 (just what they need) First 15 seconds explain why you called, say it’s a cold call, then ask a peer question In the agenda, tell the customer you’re gonna give price before they get off the call Use what they want as the rows in your pricing instead of what you want (seats) Belal Batrawy’s Path to President’s Club: Community Leader of #Death2Fluff 7x Startup Seller and Sales Advisor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

24 Jun 202023min

8 (Sell): Getting prospects to agree to their problem with killer discovery (Kevin “KD” Dorsey, VP Sales @ PatientPop)

8 (Sell): Getting prospects to agree to their problem with killer discovery (Kevin “KD” Dorsey, VP Sales @ PatientPop)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Kevin “KD” Dorsey teaches us to get prospects to admit to their problems without asking unnatural, off-putting questions. Killer questioning tactics while still sounding human. Four Actionable Takeaways: Use problem ?’s ending in “so that _____ doesn’t happen.” Then give multiple choice. Use a slight downtone when hearing the response to get prospects to lean in Use bucket questions to get your prospect to agree to 1 of 2 problems they’re having Use “I think this might make sense” before coming in hot with your value prop KD’s Path to President’s Club VP of Inside Sales @ PatientPop Head of Sales Development & Enablement @ ServiceTitan InsideSales Top 10 Sales Leader + Sales Development Executive of the Year RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

17 Jun 202025min

7 (Sell): Stop obsessing over technical problems and start gap selling (Keenan, Author of Gap Selling)

7 (Sell): Stop obsessing over technical problems and start gap selling (Keenan, Author of Gap Selling)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Align on the problem and impact first, then start brainstorming root causes and solutions Build a problem identification chart with the problems, impacts, root causes of your ICP Talk to customers, become an expert. Why did they buy? What problems did you have? You need customers to agree to the problem they have and be willing to solve it with you. Keenan’s Path to President’s Club Author of Gap Selling CEO @ A Sales Guy Consulting RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

10 Jun 202025min

6 (Sell): A cold calling clinic from 5000 dials a month (Ryan Reisert, Reisert Consulting)

6 (Sell): A cold calling clinic from 5000 dials a month (Ryan Reisert, Reisert Consulting)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Open every conversation with “Hey it’s Ryan Reisert”, then stop. When they answer, ask if you can get 27 seconds to tell them why you’re calling? Work in buckets for everything - finding accounts, researching contacts, making dials. Document the path. Every time you hit a phone tree, write the dial path down. Ryan Reisert’s Path to President’s Club: Sales Director, ConnectAndSell Author, Outbound Sales, No Fluff Founder, The Sales Developers RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

3 Jun 202025min

5 (Sell): Break up with the prospect before they break up with you (Richard Harris, Harris Consulting)

5 (Sell): Break up with the prospect before they break up with you (Richard Harris, Harris Consulting)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Use the respect contract as your agenda to give the prospect the right to say no throughout the call Set a timer 5 minutes before the end of your call to drive next steps every time Use “commercial terms” instead of “price” when negotiating your deals When you give price, don’t just go silent. Ask “how does that feel?” Richard Harris’ Path to President’s Club: Founder, Harris Consulting Director of Sales Training, Sales Hacker Host, Surf & Sales Podcast RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

27 Mai 202020min

4 (Sell): Everything you need to crush cold emails (Kyle Coleman, VP Revenue @ Clari)

4 (Sell): Everything you need to crush cold emails (Kyle Coleman, VP Revenue @ Clari)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: 5x5x5: 5 minutes of research. Find 5 insights on the person/account. Write your message in 5 minutes. Use whitespace in your emails and have 1 idea per line. Make the structure and the tone conversational Keep your emails short. If you have to scroll more than once or if an email is over 125 words, fix it. Have your voicemails reference your emails and vice-versa. It boosts your reply rates. Kyle Coleman’s Path to President’s Club VP, Revenue Growth & Enablement @ Clari Sr Director, Sales Development & Optimization @ Looker A massive LinkedIn following with killer content RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

20 Mai 202027min

3 (Sell): Ripping apart the phones and video (James Bawden, Host of the Lunch Break Podcast, Director @ OutboundView)

3 (Sell): Ripping apart the phones and video (James Bawden, Host of the Lunch Break Podcast, Director @ OutboundView)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways: Avoid the double intro on the phone if they ask “wait, who’s this?” Just get on with it. Close the cold call with “here’s what happens next” instead of leaving it in their hands Disarm with “I’m not delusional enough to think I’m calling you at the right moment.” Lead your value prop with your customer’s problems instead of the features in your solution James Bawden’s Path to President’s Club: Host, Lunch Break Podcast Director, OutboundView And a damn well-known Linkedin personality RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

12 Mai 202029min

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