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

ACTIONABLE TAKEAWAYS:

1. Identify Strategic Initiatives: Focus on big company bets that are close to revenue, such as IPOs, international expansions, or mergers and acquisitions.
2. Double Personalize Outreach: Combine company-specific observations with industry trends to create messaging that feels hyper-relevant.
3. 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.
4. 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

FOUR ACTIONABLE TAKEAWAYS

1. 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.
2. Evidence-Based Questions Only: Avoid hypotheticals. Ask for proof of past performance (P.O.P.) to assess real experience and capabilities.
3. 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.
4. 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

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

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

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

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

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

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

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

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