20 Sales: How To Interview Sales People; The Red Flags and What to Look For, How Sales Leaders Should Change Goals and Quotas in Harder Markets and What Reps Can Do To Ensure They Hit Their Numbers in These Markets with Eleanor Dorfman, Sales Leader @ Ret

20 Sales: How To Interview Sales People; The Red Flags and What to Look For, How Sales Leaders Should Change Goals and Quotas in Harder Markets and What Reps Can Do To Ensure They Hit Their Numbers in These Markets with Eleanor Dorfman, Sales Leader @ Ret

Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company's customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering.

In Today's Episode with Eleanor Dorfman We Discuss:

1.) Entry into Sales from Working with the US Education Department:

  • How did Eleanor get her first role as an unpaid intern at Clever?
  • What are 1-2 of her biggest takeaways from her time at Segment?
  • What are the biggest advantages of sales reps having experience in customer success?

2.) The Sales Playbook:

  • How does Eleanor define, "a sales playbook"? When does it need to be created?
  • Does it need to be the founder who creates it or can it be a Head of Sales?
  • Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook?
  • How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion?

3.) Who, What and When: Building the Sales Team

  • Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two's?
  • How does Eleanor structure the hiring process for all new sales team recruits?
  • What are the clearest signals of 10x sales hires? What are red flags in the interview process?
  • How does Eleanor use demo's and case studies to determine technical ability?

4.) The First 30, 60 and 90 Days: The Onboarding:

  • What is the right structure for all new sales hires to be onboarded?
  • Why does Eleanor believe you will always hire your Head of Sales Enablement too late?
  • What are the signs that now is the right time to hire your Head of Sales Enablement?
  • What tools, materials and resources can founders provide to shorten the ramp time for new AEs?
  • What are the single biggest mistakes founders make in the onboarding of new sales reps?

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20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp

Zach Lloyd is the Founder and CEO of Warp, the next-generation developer terminal reinventing how engineers build and collaborate. Warp has raised over $70M from top-tier investors including Sequoia Capital, GV, Dylan Field, and Elad Gil. Before founding Warp, Zach was Principal Engineer at Google, where he led development of Google Docs, and later served as CTO at Time. He's one of the most respected engineering minds redefining the future of developer tools. AGENDA: 04:14 Biggest Product Lessons from Rewriting Google Sheets 07:10 Why I Would Short Google: Leadership and AI Strategy 09:55 Comparing AI Models: GPT, Claude, and Gemini: Who Wins and Loses 17:04 Do Margins Matter in AI? 24:57 Adding $1M in ARR Every Week: Is Triple, Triple, Double, Double Dead? 33:58 How to Build Defensibility in a World of AI? 43:05 OpenAI vs Anthropic: Who Wins and Why? 44:25 Biggest Fundraising Lessons Raising from Sequoia, Elad Gil and GV 50:56 Why Sequoia are the Best VC 53:51 What Every Founder Gets Wrong in Fundraising 01:01:30 Quick Fire Questions and Final Thoughts

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Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams. AGENDA: 00:00 Why Unreasonable Men Win in Startups 07:22 How to Make Co-CEOs Work 13:22 Are We in an AI Bubble? Is Everything Overvalued? 26:46 The Future of Software Development: More or Less Devs 32:53 Do Margins Matter in a World of AI 34:02 The Future of Vibe Coding… 36:35 Does Defensibility Exist in a World of AI 42:09 Is Per Seat Pricing Dead in a World of AI 49:01 The Founder Journey and Leadership 54:28 Quick Fire Round: Parenting Advice, Relationship to Money

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Chris Degnan is the former Chief Revenue Officer at Snowflake, where he was instrumental in scaling the company from less than $1M in ARR to over $3B in annual revenue. He joined as the first sales hires and built Snowflake's go-to-market engine from scratch, growing the team from to more than 6,000 globally. Under his leadership, Snowflake became one of the fastest-growing enterprise software companies in history, achieving a record-breaking IPO in 2020. AGENDA: 04:34 How to Build a Sales Team from Scratch 07:49 How to Hire and Evaluate Sales Leaders 15:23 Four Big Lessons Scaling Snowflake to $3BN ARR 31:30 Comparing Snowflake and Databricks: What Databricks Did Better? 35:26 How to Manage Sales Team Morale in Competitive Markets 43:53 Why Customer Success is BS and What To Do With It 48:31 How Every Sales Leader Needs to Change in An AI World 49:37 Biggest Reflections on Sales Leadership 54:38 Quick Fire Questions and Final Thoughts 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

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Andrew Feldman is Co-Founder & CEO of Cerebras, building the world's fastest AI inference and training. Cerebras recently closed a $1.1BN Series G round at an $8.1 billion valuation, backed by top names including Fidelity, Atreides, Tiger Global, Valor Equity and 1789 Capital. Under his leadership, they've leapfrogged GPU limits in inference, operate at trillions of tokens per month, and are filing to go public soon. AGENDA: 02:43 Why We Did Not IPO and Raised $1BN From Fidelity 05:03 Analysis of Chip and Compute Landscape Today 07:14 NVIDIA Showing Signs They Are Running Out of Ideas 13:57 The Real Questions to Ask on Chip Depreciation 24:54 Energy Requirements for AI: Is it Feasible? 29:25 Mag7 Value Concentration: Feature or a Bug 31:57 Talent is the Bottleneck and Trump Makes it Worse 32:55 The War for Talent: Secrets No One Sees 34:22 Evaluating the Data Centre Economy: Many Will Lose Money 38:01 Three Changes the US Could Make to Beat China in AI 42:30 Why 80% of our Revenues are in the UAE 47:26 Quick Fire Questions 58:59 Why Work Life Balance is Total BS

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20Growth: How to Use Influencers to Scale Growth Insanely Fast | How to Optimise User Onboaring for Growth | How the Best Growth Teams Create Organic Growth and Community | Why LTV/CAC Models are BS with Ketty Slonimsky

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