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

FOUR ACTIONABLE TAKEAWAYS Focus on High-Impact Problems: Prioritize fixing widespread issues over the loudest complaints. High-volume problems drive more meaningful change than squeaky-wheel issues. Leverage 2x Multipliers: Target improvements that can double key metrics rather than marginal gains. Align leadership early so they understand why other issues aren’t top priority. Weekly Wiggle Wednesdays: Hold a one-hour leadership meeting to refine sales tactics. Use the four D’s: define, document, demonstrate, and deliberately practice new strategies. Transparent 1:1 Tracking: Link manager-rep 1:1 docs to the director’s 1:1 doc. Track each rep’s key metric, issue diagnosis, and growth plan for better coaching visibility. 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

6 Feb 37min

ACTIONABLE TAKEAWAYS: Permission-Based Introduction: Identify an executive, then request an intro to their top lieutenant by tying outreach to an executive-level metric they care about. Funding Intent Matters: Don’t just track funding announcements—dig into how the company plans to use the money and align outreach to support that goal. AE & SDR Account Strategy: AEs select accounts, build a POV, and own outreach to execs, while SDRs focus on below-the-line contacts with AE guidance. Account Tiering System: Rank accounts as green (30-50), yellow (130), or red (30-50) based on deal size and buying likelihood to prioritize outreach effectively. MADDY'S PATH TO PRESIDENTS CLUB: Account Executive @ Webflow Account Executive @ SafeGraph Account Executive @ Procore Technologies Account Executive @ Procore Technologies Senior Business Development Rep @ Procore RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

4 Feb 37min

ACTIONABLE TAKEAWAYS Know Competitors' Fiscal Periods: Be aware of when your competitors’ fiscal periods end to anticipate price drops and position yourself better. Phased Approach: When price matters, propose only the essentials for day one to make your quote smaller and easier to accept. Timeline Stack: Identify key timeline drivers, like contract end dates or business seasonality, to create urgency. Turn Want into Why: During discovery, dig deeper to find the real business problem behind a customer’s desire for change. JOHNNY'S PATH TO PRESIDENTS CLUB Commercial Account Executive @ Talkdesk Enterprise Sales Development Manager @Talkdesk Team Lead, Enterprise Sales Development @ Mimeo Enterprise SDR @ Mimeo RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

3 Feb 37min

Nick, Armand, and Mark Kosoglow talk through how and when you should make different sales hires as your sales team grows. ACTIONABLE TAKEAWAYS: Hire Builders First: Early sales hires should create processes, while later hires follow them. CEO Sales Involvement: Founders should sell until they define the product and process, then transition to AEs. Scaling Key Roles: Maintain a 1:1 AE to SDR ratio early, shifting to 2:1 later. Hire RevOps early; SE and enablement depend on need. Manager & Director Timing: Keep managers at 8 reps max, stretching to 10-12 if needed. Delay director hires until managing at least three managers. RESOURCES DISCUSSED: Stages of Sales Leader Episode Join our weekly newsletter Things you can steal

30 Jan 51min

ACTIONABLE TAKEAWAYS: Align Messaging to Roles: End users want simplicity, managers focus on team metrics, and execs care about goals and risk. Match your message accordingly. Use Credible Content: Share third-party sources like Gartner or HBR instead of only company case studies to build trust. Amplify the Problem Early: Send data or insights highlighting the problem’s urgency in the early stages of the sales cycle. Simplify Implementation Late: Provide resources like change management guides to ease rollout and reduce risk. KRYSTEN'S PATH TO PRESIDENTS CLUB: Founder @ KrystenConner.com Enterprise Account Executive @ UserGems Enterprise+ Account Executive @ Outreach Enterprise Accounts, Financial Services @ Tableau Software Strategic Accounts @ PowerSchool RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

28 Jan 36min

ACTIONABLE TAKEAWAYS: Facial Expressions Control Tone: Your facial expressions influence your tone. For example, leaning in creates a concerned tone, while tilting your chin up can convey curiosity. Slow Down Your Questions: Asking questions too quickly leads to poor answers. Slow down the second half of your question to give prospects time to think and respond meaningfully. Master the Five Types of Tone: Use different tones—curious, confused, concerned, challenging, and playful—to guide conversations and elicit the right responses. Challenge Prospects with a Direct Tone: A challenging tone helps push prospects to take action, especially when addressing tough issues like low-quality leads. JEREMY'S PATH TO PRESIDENT'S CLUB: Founder @ 7th Level VP of Sales @ Pinnacle Security RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

27 Jan 36min

ACTIONABLE TAKEAWAYS: Ban Product-Specific Language: Prohibit product-focused terms like "roles-based access" in deal reviews. Instead, prompt reps to explore the customer’s "why" behind their needs, driving better customer questioning and understanding. Tie Incentives to Certifications: Require reps to complete critical certifications (e.g., discovery certification) to access desirable benefits, such as inbound leads, ensuring alignment between AE and leadership goals. Consistency in Value Framework: Maintain your value selling framework across every sales stage—from discovery to demo to proposal—ensuring consistent messaging and alignment throughout the cycle. Embed Framework into Processes: Update all sales processes, stages, and deal reviews to reflect new frameworks. Regularly reinforce these changes in weekly reviews to ensure training sticks and drives lasting behavior changes. 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

23 Jan 35min

Nick and Armand break down the perfect 5 stage sales process to get your deals closed fast.  Stage 1 Problem Agreement: Ensure both parties align on the problem being solved before moving forward. Stage 2 Solution Agreement: Confirm the solution addresses the agreed problem effectively. Stage 3 Power Agreement: Secure buy-in from decision-makers and key stakeholders. Stage 4 Commercial Agreement: Reach consensus on pricing, terms, and conditions. Stage 5 Vendor Approval: Navigate internal processes to finalize and approve the deal. Map these stages to your sales cycle, define clear exit criteria for each, and identify opportunities to combine calls or stages to accelerate deal velocity. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

21 Jan 50min