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

Shay's Tactic Toolkit: How You Work Questions FOUR ACTIONABLE LEADERSHIP TAKEAWAYS Write down every priority you could work on, then narrow it down to the top 3 and be okay letting things burn. Don’t stop drilling in on those priorities until your team starts to complete your sentences and tattle on themselves. If you wanna get your teams prospecting, set daily expectations, put them in calendar invites in an operating rhythm, then get wildly tactical on how to do it. Use the “How You Work” questions to get to know the human behind the seller and push them to the next level. PATH TO PRESIDENT’S CLUB Senior Director of Commercial Sales @ CaptivateIQ Senior Director of Global Commercial NL Sales @ Outreach Director of Sales, Global New Logo @ Outreach Director of Sales, New Logo @ Outreach RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

21 Des 202332min

ACTIONABLE TAKEAWAYS Hit adversity head-on. If you got hit with the RIF — tell them you probably could have survived, and here’s how. Never be surprised — get the cheat code questions to the interview from your recruiter and interviewer. Be concise. Start with the 4-step process, then ask them how deeply you want them to unpack each. Golden hour follow-ups. Within 60 minutes, hit the recruiter and interviewer — and stand out by sharing what you could’ve done better in the interview or maybe even your favorite cold emails. PATH TO PRESIDENT’S CLUB Manager, Commercial Sales @ Gong Mid-Market Account Executive EMEA @ Gong Senior Commercial Account Executive @ Gong Founder @ TrackmanRentals.com RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

19 Des 202332min

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS Split 1:1s and deal reviews — don’t try to combine a professional development chat with a pipeline review! Before a pipe review, ensure your reps pre-select the deals they want to review and prepare win strategy docs, mapping out all key external stakeholders. Beat up the deals with the so-what train. Keep asking so-what to uncover the implication of the pain — until you don’t have an answer anymore, that’s what you need to find out. Two questions to determine if a rep is ready to be a manager: Can they clearly communicate why they’re winning? And are YOU learning from that rep? PATH TO PRESIDENT’S CLUB Director of Enterprise @ 6Sense Head of Sales, EMEA @ Outreach Director of Strategic Enterprise Sales, EMEA @ Outreach Strategic Sales Director, East & EMEA @ Outreach RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

14 Des 202332min

Every 10th episode, we tear down one topic. This time, we’re talking about landing your forecast in Q4. Bonus: Get the 30MPC Forecasting Guide ACTIONABLE TAKEAWAYS The forecast should never be a surprise to your manager. You should be able to give one-sentence pipeline review updates and get through over 15 deals in a 30-minute pipeline review into your forecast. For your forecast, you're going to call your key deals and your worst case and move to your commit, which is your bet on what will actually happen. Play the spread. If your commit consists of one deal landing, you should probably have two to four in inventory. Throughout the month or the quarter, your forecast will start to taper. Don't be a sandbag - don’t set a goal or forecast that's way too high. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

12 Des 202327min

Kyle’s Competency Framework FOUR ACTIONABLE LEADERSHIP TAKEAWAYS Pick 1-3 competencies to coach a rep on max. Train your team, then establish a coaching rhythm to reinforce the training and a metric to track it. Get your managers bought in otherwise your training will fall flat. Turn your managers into microphones instead of filters. Give your reps multiple ways to get to a “good day” — build a Good Day Framework that assigns points to both inputs and outcomes. If you have a rep who isn’t willing to work hard at the professional development plan that both you AND they agreed to… why would you keep working with that rep? PATH TO PRESIDENT’S CLUB RVP, High Tech Acquisition for North America @ MongoDB RVP, High Tech Acquisition - Midwest, Northeast, and Canada @ MongoDB RVP of Sales, Corporate Midwest @ Qualtrics RVP of Sales, Midwest CX @ Qualtrics RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

7 Des 202332min

But wait! Want more from Grace & Outreach? Check out the 30MPC X Outreach: 1 Sequence to Create and 5 Templates to Close FOUR ACTIONABLE TAKEAWAYS Brainstorm how you're going to advance each of your opportunities before you have your pipeline review with your manager. Don't show up like a deer in headlights. Block time for immediately after your pipeline reviews to take action on the things you agreed to do to drive your deals forward. Structure your forecast calls - cover updates, health scores, next steps, amount, and close dates. Avoid spending the entire time on one deal by scheduling big bets calls for complex deal reviews. Utilize a zero inbox strategy by organizing your inbox into action items, read through later, awaiting a reply. PATH TO PRESIDENT’S CLUB Senior Account Executive @ Outreach Commercial Account Executive @ Outreach Enterprise Account Executive @ Dell EMC Account Executive @ Nasuni RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

5 Des 202329min

Mark Kosglow's Course FOUR ACTIONABLE LEADERSHIP TAKEAWAYS Re-evaluate your Q4 incentives. Lots of sales reps aren’t making money now. Throw in SPIFs and kickers that squeeze the juice out of ICP deals or even a $500 referral SPIF for customers. Build your 2024 model for efficiency instead of growth. Sell your CEO, board, or finance team on healthy attainment to keep your best reps fed. They will carry you through a downturn. Consider running hot. Your top sellers will over-perform and make up for a gap in capacity you might have with a bloated team. Get everyone on the same page on healthy growth. No one wants a horrible CAC payback, a burning sales team, or a team that can’t keep their top reps. PATH TO PRESIDENT’S CLUB Growth Partner @ Emergence Capital Mentor &Advisor @ Sales Assembly Mentor & Advisor @ Forum Ventures Mentor @ GrowthX Academy RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

30 Nov 202329min

FOUR ACTIONABLE TAKEAWAYS Back Pocket Questions - Prepare multiple questions for your sales calls that you can pull out at any time. Use them if you get "stuck" at any point. Strategic Social Proof - instead of simply namedropping customers, use customer story examples that are relevant to how you’d envision your buyer using your service, ex. Having a similar use case. Make Discounting "Weird" - When you get hit with a price objection, your response needs to signal concern/confusion. You want to signal that this request is not biz as usual. Alternative Video Use Cases - Video isn’t just for prospecting. Use video for "pre-call context" + "post-call recaps" + "Exec Summaries" PATH TO PRESIDENT’S CLUB Founder @ 30 Minutes to President’s Club Senior Account Executive @ Time by Ping Enterprise Account Executive @ SurePoint Technologies Account Executive @ Aderant RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

28 Nov 202332min