The AI Playbook for Sales: How to Book More Meetings & Close More Deals With AI | Jake Dunlap | Ep. 286 (Sell)

Mark Kosoglow walks through the key skills, responsibilities, and attributes for a Sales Leader at each phase of company growth Doer Phase (0 to $1M ARR): The initial stage focused on finding product-market fit. The sales leader handles everything, including cold calls, demos, building sales systems, and refining the sales process. They act as an individual contributor, ensuring the company moves forward without distracting other key team members. Key trait: Being a hands-on, self-reliant executor. Builder Phase ($1M to $10M ARR): The leader transitions to hiring and scaling the team, typically starting with individual contributors (AEs and SDRs). Still involved in selling but begins to set foundational systems, processes, and training. They document best practices and create repeatable frameworks while maintaining some "doer" responsibilities. Key trait: Hiring and building effective teams and processes. Doctor Phase ($10M to $25M ARR): The leader becomes more metrics-driven, focusing on diagnosing and optimizing performance based on data. Begins managing managers and spending more time collaborating cross-departmentally (e.g., with RevOps, marketing, and customer success). Key trait: Using data and metrics (L1 and L2) to prevent thrash and fine-tune the organization’s operations. Architect Phase ($25M to $100M ARR): The leader’s role expands to a more executive level, crafting the overall blueprint for the sales organization in alignment with other departments. Focus on segmentation, pricing strategies, and designing compensation plans that drive desired behaviours. They influence larger strategic initiatives and ensure the execution aligns with organizational goals. Key trait: Seeing the big picture and designing a cohesive GTM blueprint. Communicator Phase ($100M+ ARR): The leader’s primary role becomes communication: setting clear expectations, timelines, and evaluating the mental models used by the team to meet goals. The focus shifts outward, ensuring alignment across broader organizational and market dynamics. Key trait: Clear and effective communication to drive alignment and execution at scale. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

21 Nov 202440min

ACTIONABLE TAKEAWAYS: Limit Pricing Options to Three: Offering more than three options overwhelms prospects. Present only the most relevant three to simplify decision-making. Leverage Value-Add Incentives: Highlight low-cost-to-you, high-value items (like waived fees or extra features) to steer prospects toward larger packages. Present Pricing with a Range: Start with a floor price and give a range based on factors, allowing flexibility while avoiding sticker shock. Use Strategic Comparisons: Position your premium option near a slightly lower-tier offer to make it an attractive choice, while avoiding comparisons to much cheaper options. BELAL'S PATH TO PRESIDENT'S CLUB Founder @ LearnToSell.io Head of Sales @ GTM Buddy Enterprise Account Executive @ ClearBit Head of Business Development @ BioIQ RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

19 Nov 202439min

FOUR ACTIONABLE TAKEAWAYS Start by assuming the prospect has researched your solution if they say yes suggest a common objection why they didn't pursue it, if they say no then ask a question to highlight a knowledge gap When explaining your solution, emphasize the before state and the problems associated with it to create contrast with your solution's end-state Ask about specific situations to accurately identify the exact problems the prospect is facing Learn and practice delivering problem stories that are tailored to each potential situation your buyers may be in PATH TO PRESIDENT’S CLUB Founder, Braun Training Former Head of Sales @ Basecamp Former VP of Inside Sales @ Jellyvision RESOURCES DISCUSSED Join our weekly newsletter Josh Braun's Tongue Tied flashcards Things you can steal

18 Nov 202441min

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS Buddy System in Hiring: Involve the new hire’s buddy in the interview process to ensure a strong match. Focused Onboarding Ownership: Assign one person to oversee onboarding, improving retention and team quality. Call Certifications: Require reps to pass intro and demo call certifications to qualify for leads. Hands-On Training: Focus on role plays, shadowing, and practice over slide decks for effective learning. PATH TO PRESIDENT’S CLUB COO @ Growth Assistant VP of Sales @ Lattice Sales Director @ Lattice VP of Sales @ Appcues RESOURCES DISCUSSED Join our weekly newsletter Things you can steal https://www.30mpc.com/newsletter/my-ultimate-4-week-sales-onboarding-program

14 Nov 202441min

ACTIONABLE TAKEAWAYS: Start with “Why Did You Take the Call?”: Kick off by understanding the prospect’s motivation. For inbound leads, ask directly, "What prompted you to reach out?" For outbound, ask, "What made you take this meeting with me?" This reveals their needs and priorities. Reserve Time for Next Steps: Set aside five minutes at the end to confirm logistics or plan a follow-up. If you need more time to dive into key topics, suggest scheduling another call. Demo Based on Pain Points: Order your demo around the most pressing pain points the prospect mentioned. Address their biggest challenges first to maintain their engagement and show value quickly. Recommend, Don’t Upsell: Avoid pushing the premium package. Focus on the solution that best meets their needs to prevent overwhelming them and risking the deal. GARRETT'S PATH TO PRESIDENTS CLUB: Senior Account Executive @ Pipedrive Account Executive @ Pipedrive Junior Account Executive @ Pipedrive Lead Development Rep @ Pipedrive RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

12 Nov 202433min

ACTIONABLE TAKEAWAYS Embrace Silence: Don't fear pauses in conversations. It's natural to take a moment to think about your next question or response during a conversation with a prospect. Setting Conditions for Progress: When faced with a contact unwilling to advance your connection, you have two options: Explicitly ask them what conditions need to be met for them to introduce you to a higher-level contact, like a VP of Marketing. Decide whether to follow their criteria or to prospect directly to reach your goal. Groundswell Motion Strategy: In scenarios where a sales cycle starts with an Account Executive (AE), begin by offering assistance to the AE. This approach often leads to reciprocal help, allowing you to eventually ask for an introduction to your champion. Understanding Motives: It's crucial to discern and address two types of motives, your champion's personal motives and the business or executive motives. Educate your champion on these motives and align them with the broader business objectives to facilitate successful sales efforts. PATH TO PRESIDENTS CLUB Chief Revenue Officer @ Influ2 Vice President of Sales @ Siteimprove Vice President of Sales @ Apruve Vice President of Sales @ Siteimprove Director of Sales @ Siteimprove RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

11 Nov 202437min

ACTIONABLE TAKEAWAYS: Ask About Interview Prep: Ask candidates, “What did you do to prepare?” to gauge their commitment and thoughtfulness. Challenge in Final Interviews: Address yellow flags, past successes, and expected challenges to identify high performers. Empower Experienced Managers in Hiring: Let senior managers make final hiring calls; stay more involved with junior managers to ensure quality. Standardize Key Processes: Create an 80% standardized approach for pipeline reviews, forecast calls, and one-on-ones, with 20% flexibility for personalization. SHANES'S PATH TO PRESIDENTS CLUB: Chief Revenue Officer @ Gong Chief Revenue Officer @ TalkDesk President @ MX EVP of Sales @ Qualtrics RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

7 Nov 202444min

This was a preview from our upcoming course, Cold Calls to President's Club: register for the waitlist here ACTIONABLE TAKEAWAYS: No Value Propositions. Buzzwords make you sound like a telemarketer, and benefits fall flat without the context of a problem. Triggering Problem. Instead, lead with a problem so specific that it triggers your prospect and reminds them of a painful memory. One-Sentence Solution. If you get the problem right, all you need is one sentence to explain your solution (we do X so that the problem goes away). Interest-Based CTA. Validate their interest before you ask for the meeting, using softening language, no-based questions, and mini push-aways. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

5 Nov 202426min