Hall of Fame: Maddy Jackson

FOUR ACTIONABLE TAKEAWAYS Multi Single-Threading: After a big team meeting, send individual follow-up messages to key stakeholders. This helps build relationships without asking for anything, creating future points of contact. Daily Pipeline Review: Every day, look at your deals and think of specific actions to increase your chances of winning, maintaining daily momentum across opportunities. Win One Stakeholder at a Time: Focus on winning over stakeholders one by one at different stages—manager during discovery, director during the demo, and VP at the big team meeting. Structured Sales Cycle: Brian’s sales process follows a clear path: discovery, demo, big team demo, pilot, and finally commercial negotiation. PATH TO PRESIDENT’S CLUB Senior Mid-Market Account Executive @ Gong Mid-Market Account Executive @ Gong Commercial Account Executive @ Gong Senior Commercial Account Executive @ Gong Enterprise Account Executive @ BrightEdge RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS If you feel like you have leverage in a deal, but haven't gotten in front of the right stakeholders to progress the deal, use that as a non-negotiable to begin negotiations Sit down and write down your own "Gives" and "Gets" that you can trade with your buyer during a sales cycle Someone liking your offering does not make them an effective champion, ask questions like "Is {title} aware of these conversations?" to test them When trying to get access to power use labelling statements like "I often hear {title} likes to weigh in, is that the same for you?" PATH TO PRESIDENT’S CLUB Account Executive @ Webflow Account Executive @ SafeGraph Account Executive @ Procore Technologies RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

This is an except from the Tenbound podcast with David Dulany Check out the GTM podcast here: https://tenbound.com/podcasts/ Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS Empower your reps with a clear discount menu, outlining what’s approved for negotiations. Include things like signing during the trial, committing to case studies, or G2 reviews to speed up late-stage deals. Before taking over a team or segment, review call recordings and data like sales cycle length and ACV to identify where you can have the biggest impact. Assess the spacing between sales calls and find opportunities to consolidate steps or reduce gaps to shorten the sales cycle. Introduce a structured proof of concept (POC) with three defined calls over 14 days, dictating trial activities and clear exit criteria for smoother decision-making. CHRIS' PATH TO PRESIDENTS CLUB Head of Commercial @ Common Room Vice President of Sales @ Metadata Head of Sales @ Metadata Sr. Account Executive @ Metadata RESOURCES DISCUSSED Things you can steal Join our weekly newsletter

ACTIONABLE TAKEAWAYS Instead of focusing on quantifying pain, ask deeper questions about the problem’s origins and previous solutions, this will naturally reveal the impact Find out if the problem is known and cared about across the company or just by one person Ask easy, non-pushy questions like “Why is that a problem?” to get the prospect to share the impact without feeling pressured Position involving decision-makers as beneficial for them, making it easier to get in front of power PATH TO PRESIDENT’S CLUB Founder @ DiscoveryCoach.io Sales Enablement Manager @ AlphaSense Lead Revenue Enablement Manager @ CB Insights Senior Sales Training Manager @ CB Insights RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS When you are trying to clone that first rep, make sure that you don’t confuse personality with skill set. Your customers have the answers. Talk to your customers. Do not do the things that you're horrible at. Hire for the things that are not your strengths. Invest your time in enablement. You and your reps should track how you win each deal for ongoing development. PATH TO PRESIDENT’S CLUB VP, Sales @ Tenderly Founding Member, First Hires Program @ First Round Capital Director, Enterprise Sales @ Drift VP, Sales @ AltoCloud RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

This is an except from the Topline podcast with Sam, AJ, and Asad Check out their GTM podcast here: https://www.joinpavilion.com/blog/tag/topline-podcast Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Instead of lecturing a rep who hasn't followed expectations, ask what's preventing them from doing the task. This helps identify roadblocks or allows the rep to own up to the issue. When discussing reasons for making a change, focus on three questions: Why do anything? Why with us? Why now? The "why now" should have a specific date tied to an event. Link the urgency of change to concrete events, such as a software switch, new hire, market trends, or growth initiatives like entering a new market. Ask your reps key questions like when the economic buyer last bought something similar and who typically pays for software in their industry to ensure they understand the buyer’s decision-making process. PATH TO PRESIDENT’S CLUB Head of Sales, Retail @ Ascend Strategic Account Manager @ Ascend Strategic Accounts @ Sourcegraph Head of Enterprise Sales @ Segment Enterprise Sales Executive @ Braintree (a PayPal company) RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS In rip-and-replace deals, start by asking why the existing solution was chosen to understand the problems and motivations behind it. Late in the deal, confirm with your champion if you’re their top choice. Use their guidance to strengthen your position against competitors. When prospects compare you to competitors, suggest specific aspects to evaluate that highlight your strengths and expose competitors' weaknesses. In rip-and-replace deals, emphasize key product gaps that significantly impact the business, and ensure decision-makers are committed to addressing them. PATH TO PRESIDENT’S CLUB Founder & CEO @ Outbound Squad Owner @ Jason Bay Consulting Director of Marketing @ Chamber DS, Inc. Marketing Director & Corporate Sales Trainer @ National Services Group, Inc. RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Do not neglect internal research when you're preparing for a sales call. Find out if your company has spoken to them before and dig internally. Prep for your sales calls by understanding lookalike conversations your team has had in the past. Use the lighthouse email to engage someone at the top, mid-deal cycle. Don’t just pull them into the boat. Let them know that the boat is there and you have an awesome champion so they can affirm you’re in the right place. Don’t say “AI” in your sales call. Instead, focus on the problem they want to solve and what they want to do. PATH TO PRESIDENT’S CLUB Co-Founder @ Handoffs Director, Sales @ Sendoso Manager, MM & ENT Sales @ Sendoso Founding Account Executive @ Sendoso RESOURCES DISCUSSED Join our weekly newsletter Things you can steal