20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating.

In Today's Episode with Sam Blond We Discuss:

1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR:

  • What are the secrets that very few people know, that led to the success of Brex and Zenefits?
  • What was the single worst sales investment Brex made? What was the best?
  • What are Sam's biggest tips to people picking the rocketship they will join?

2. Who, What and When to Hire:

  • When is the right time to hire your first sales rep?
  • Should the founder be the one to create the sales playbook?
  • What is the right profile for the first sales hire?
  • Does it matter if the new hire has domain experience?
  • Why does Sam always advocate to hire through network and not recruiters?

3. How to Hire the Best Sales Reps:

  • What are the questions Sam always asks in interviews with sales hires?
  • Does Sam do case studies with candidates? What is he looking for?
  • What are the biggest green and red flags a candidate can show in an interview process?
  • What are the biggest mistakes founders make when hiring sales teams?

4. How to Have the Best Performing Sales Team:

  • What are the three ways to measure the success of a rep in the first 30-60 days?
  • Why does Sam believe most startups are doing outbound wrong? What should they change?
  • Why does Sam believe demand gen is the bottleneck for all companies?
  • What can be done to solve the demand gen challenge?
  • How does outbound change in a world of AI?

Jaksot(1410)

20VC: OpenAI and Anthropic Will Build Their Own Chips | NVIDIA Will Be Worth $10TRN | How to Solve the Energy Required for AI... Nuclear | Why China is Behind the US in the Race for AGI with Jonathan Ross, Groq Founder

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Jonathan Ross is the Founder & CEO of Groq, the AI chip company redefining inference at scale. Under his leadership, Groq has raised over $3B from top investors. The company has reached a valuation of...

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20Product: Revolut Business $1BN Revenue: Five of the Biggest Product Lessons | How Revolut Structures Product and Design Teams | How Revolut Experiments and Invests in New Product Bets | How Revolut Ships Product So Fast with James Gibson

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James Gibson is Head of Revolut Business. Under his leadership, Revolut Business now processes over $33 billion in monthly transaction volume and generates more than $1BN in annualised revenue. AGEND...

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20VC: NVIDIA Invests $100BN Into OpenAI | Is Triple, Triple, Double, Double Dead | Navan Files to go Public & Notion Hits $500M ARR | The Impact of H1B Visas on Startups in the US

20VC: NVIDIA Invests $100BN Into OpenAI | Is Triple, Triple, Double, Double Dead | Navan Files to go Public & Notion Hits $500M ARR | The Impact of H1B Visas on Startups in the US

AGENDA: 00:00 Why I am 100% Equities and 0% Cash 04:35 Nvidia's Massive $100BN Investment in OpenAI 08:39 Is Anthropic Negatively Positioned by OpenAI Gaining NVIDIA Investment 27:30 Is Triple, Triple...

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20VC: General Catalyst CEO Hemant Taneja on The Future of Venture Capital: Chanel vs Walmart | Lessons Scaling GC to $40BN in AUM | Investing $5BN+ Into Stripe Over 14 Rounds | Investing Hundreds of Millions into Anthropic at $60BN Valuation

20VC: General Catalyst CEO Hemant Taneja on The Future of Venture Capital: Chanel vs Walmart | Lessons Scaling GC to $40BN in AUM | Investing $5BN+ Into Stripe Over 14 Rounds | Investing Hundreds of Millions into Anthropic at $60BN Valuation

Hemant Taneja is the CEO and leader of General Catalyst, the firm he has scaled over the last decade into one of the largest with over $40BN in AUM. He has been one of the most influential investors o...

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20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

Jesse Zhang is the Co-Founder and CEO @ Decagon, the conversational AI platform for customer experience. As one of the fastest growing companies in the valley, they have raised over $230M at a last ro...

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20VC: Opendoor's CEO on The Greatest Turnaround in Tech | OpenAI and Oracle: How Can Either Afford to Do This | How Anthropic Could Lose 50% of Their Revenue Overnight | Replit Raises at $3BN | Figure, Gemini & VIA IPOs Broken Down

20VC: Opendoor's CEO on The Greatest Turnaround in Tech | OpenAI and Oracle: How Can Either Afford to Do This | How Anthropic Could Lose 50% of Their Revenue Overnight | Replit Raises at $3BN | Figure, Gemini & VIA IPOs Broken Down

AGENDA: 00:00 Opendoor's Potential and Market Valuation 03:32 Why Did Kaz Leave $300M on the Table to Join Opendoor 04:44 Why Does Kaz Believe OPEN Can Be a Good Business When the Market Doesn't 06:34...

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20VC: Mercor: From $1M to $500M in 17 Months: The Fastest Growing Company in the World | How to Think About Margins and Revenue Sustainability in AI | Why Evaluation Benchmarks in AI are BS Today with Brendan Foody

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Brendan Foody is the Co-Founder and CEO @ Mercor, the fastest growing company in history. The company solves talent allocation in the AI economy and they have scaled from $1M to $500M in revenue in ju...

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Amit Bendov is Co-Founder & CEO of Gong, the leading AI-sales platform. The company has raised over $600 million from some of the best in the world including Sequoia, Thrive, Salesforce and more. Gong...

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