#526 - The Ultimate Cold Calling Q&A: 16 Questions to Book Your Next Meeting

FOUR ACTIONABLE TAKEAWAYS Create a Not-To-Do List: Identify low-value tasks to eliminate instead of just adding more effort. Free up time for strategic activities like prospecting and closing. Prioritize RGAs: Focus only on activities that create new pipeline or advance existing deals. Everything else is a distraction. Enterprise Deal Timeline: Q1 is for building a POV and landing initial meetings. Q2 is for discovery and securing an executive sponsor. Q3 is for proposal, negotiation, and procurement. Q4 is for closing. Rule of 100 for Enterprise Outreach: Target the top 20% of accounts with high potential. Reach out to 10 executives with at least 10 touches each—totaling 100 strategic touchpoints per account. PATH TO PRESIDENT’S CLUB Founder of Ian Koniak sales training/consulting Strategic Account Director @ Salesforce.com Director of Sales @ Ricoh RESOURCES DISCUSSED Join our weekly newsletter Things you can steal Ian’s free training

25 Feb 37min

ACTIONABLE TAKEAWAYS: Segmented Team Structure: Down-market teams focus on landing new logos, passing them to expand teams, while up-market AEs handle both acquisition and expansion with retention-based comp. Enterprise Sales Strategies: Use top-down (sell wall-to-wall) or land-and-expand approaches, with the latter yielding higher LTV by scaling through business units first. Deal Inspection Triggers: Monitor $50K deals at stage 3 for POCs and access to power, and stage 5 for mutual action plans and the paper process. Consistent Review Rhythm: Reps update pipelines Monday, managers review Tuesday, deal reviews happen Wednesday, and Eleanor finalizes calls Thursday. ELEANOR'S PATH TO PRESIDENTS CLUB: Head of Sales @ Retool Global Head of Commercial Retention & Regional Director of Commercial Sales @ Segment Global Head of Commercial Renewals and Retention @ Segment Head of Customer Success and Solutions engineering @ Clever Inc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal 

24 Feb 35min

ACTIONABLE TAKEAWAYS: Understand Rep Motivation: Identify what drives each rep—money, career growth, or exploration—then get their permission to push them toward that goal, laying the foundation for future coaching. Call Out the Situation First: Before changing a rep’s behavior, acknowledge the dynamic at play so both parties are aligned. This prevents resistance and confusion. Leverage Top Performers: Coach high performers by challenging them to reach the next level and putting them in the spotlight to lead trainings, reinforcing best practices for the team. Coach in Buckets: Break down calls into sections and ensure reps get the fundamentals right before refining their style, making feedback more structured and actionable. ALEX'S PATH TO PRESIDENT'S CLUB: Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

20 Feb 37min

FOUR ACTIONABLE TAKEAWAYS Understand the VEX Scale: Classify prospects as Vetted (using a competitor), Educated (familiar but undecided), Cold (new to the space), or Self-Service. Tailor your approach accordingly. Ask About Their Journey: Send an email upfront asking where they are in their learning process. This helps you position the conversation at the right level. Skip Basic Discovery for Vetted Prospects: If they already use a competitor, focus on their current solution’s gaps and ideal outcomes instead of re-explaining the category. Avoid Restarting Discovery: When new stakeholders join later calls, recap prior findings first, then ask how those problems impact their specific role. JAKE'S PATH TO PRESIDENT’S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

18 Feb 35min

ACTIONABLE TAKEAWAYS: Identify Strategic Initiatives: Focus on big company bets that are close to revenue, such as IPOs, international expansions, or mergers and acquisitions. Double Personalize Outreach: Combine company-specific observations with industry trends to create messaging that feels hyper-relevant. Build a Strategic Research Framework: Create a table to map key initiatives (e.g., IPO readiness) on one side and sources of information (e.g., 10-K reports, CEO interviews, press releases) on the other. Leverage AI for Efficiency: Use tools like ChatGPT or Copy AI to analyze information from sources like job postings, financial documents, or industry trends. KYLE'S PATH TO PRESIDENT'S CLUB: CMO @ Copy.ai CMO @ Clari VP, Revenue Growth & Enablement @ Clari Director Sales Development & Enablement @ Clari Sr. Director Sales Development & Optimization @ Looker RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

17 Feb 36min

FOUR ACTIONABLE TAKEAWAYS Interview Kits for Prep: Send candidates an interview kit outlining expectations, key questions, and details on interviewers. Poor answers indicate lack of prep or poor fit. Evidence-Based Questions Only: Avoid hypotheticals. Ask for proof of past performance (P.O.P.) to assess real experience and capabilities. Screening Videos Save Time: Require a three-minute video on a key trait (e.g., perseverance). Evaluate clarity, instructions-following, and presentation skills before a live interview. Live Deal Review Test: Have candidates walk through a real deal they closed. Assess how they sourced, ran discovery, demoed, and closed, treating it like an actual deal review. KD'S PATH TO PRESIDENT’S CLUB CRO @ Finally SVP of Sales and Partnerships @ Bench Accounting Practice Lead, Revenue Leadership @ Winning by Design VP of Inside Sales @ PatientPop Inc. Head of Sales Enablement & Development @ ServiceTitan VP of Sales @ SnackNation RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

13 Feb 36min

FOUR ACTIONABLE TAKEAWAYS ChatGPT Research Triangle: Before outreach, prompt ChatGPT with the industry (including sub-industry), job title, and your product’s value. This ensures messaging aligns with trends relevant to the prospect. Use Industry Jargon: Ask ChatGPT for insider terminology that VPs in specific industries use. This makes your messaging sound more credible and tailored to their world. Refine Email Sequences: Provide ChatGPT with your email templates and ask it to integrate industry-specific revenue drivers. This keeps messaging structured while adding personalization. Smarter Discovery Questions: Use ChatGPT insights to refine questions that demonstrate expertise. Instead of generic asks, tailor them to industry trends and job-specific challenges. PATH TO PRESIDENT’S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

11 Feb 38min

ACTIONABLE TAKEAWAYS: Signal Prioritization: Categorize signals (e.g., high-intent, time-based) with different response SLAs to ensure timely outreach. Call Blitz Culture: Multiple weekly call blitzes with a virtual sales floor create a high-energy, team-building cold calling environment. Effective Personalization: Don’t rely on signals alone; combine them with company insights to craft personalized, compelling outreach. 80/20 Email Framework: Provide reps with an 80% completed template (signal, company insight, ideal state, light CTA), letting them personalize the final 20%. FLORIN'S PATH TO PRESIDENTS CLUB: Head of Sales Development @ Common Room Director of Sales @ Barley Senior Manager, Sales Development @ Loopio Manager, Sales Development @ Loopio RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

10 Feb 31min