20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners.

In Today's Episode with Maggie Hott We Discuss:

1. The Cold Email that Led to a World-Class Sales Career:

  • How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales?
  • What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset?
  • What does Maggie know now that she wishes she had known when she entered sales?

2. The Sales Playbook: PLG and Enterprise:

  • How does Maggie define the sales playbook? What is it? What is it not?
  • Is it possible for early-stage companies to do both enterprise and PLG at the same time?
  • When is the right time to add enterprise to a PLG motion?
  • What are the steps to build an outbound sales engine in enterprise? Where do many go wrong?

3. Building the Bench: Hiring Your First Sales Team:

  • Should founders look to hire a Senior Head of Sales first or a more junior sales rep?
  • Should they be hired one at a time? What are the benefits of hiring many at the same time?
  • What is the right process to hire your first sales hire?
  • What are the core traits and habits that make the first 10x sales hire?
  • What are the right questions to ask to unveil those characteristics?

4. Making the Machine Work: The Process:

  • What can sales leaders do to proactively build relationships with other parts of the org?
  • How can more junior sales reps build relationships with other functions?
  • Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound?
  • Why is it dangerous to make your self-serve product too good?

Episoder(1403)

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

Alex Rampell is a General Partner at Andressen Horowitz, where he leads their $1.7BN apps fund. Just last week, a16z announced they had raised $15BN for their latest funds, over 20% of all capital raised by venture firms. At a16z, Alex has led deals into Plaid, Mercury and OpenDoor to name a few.  AGENDA: 04:55 How to Do 5x on a $15BN Fund Pool?  09:21 What Two Groups of Funds Will Win the Next Decade in VC? 14:39 What Three Things Are the Best Founders Able to Do?  19:22 The Best Companies Have Hostages, Not Customers 31:37 The Two Types of Deals You Want To Do In VC 38:52 The Importance of Founder/Capital Fit 40:34 Multiple Successive Rounds Are Dangerous… Here is Why? 42:13 Challenges of High Valuations 45:27 The Importance of Ownership in Deals 52:47 Is Triple, Triple, Double, Double Dead 58:33 Advice on Selling Companies 01:11:55 What is the Future of Venture Capital

12 Jan 1h 17min

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs

Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at a $6.6B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna. AGENDA:  The $6.6B Growth Engine Behind ElevenLabs Why Luke Said "No" to Investing in ElevenLabs (and Why He Was Wrong) How ElevenLabs Makes a Horizontal Product Strategy Work How to Build Sharded Growth Teams That Actually Scale The 7-Part Launch Playbook That Gets 700K+ Views Per Product The Truth About CAC, Payback, and Performance Marketing in AI SEO Isn't Dead: The Mini-Tool Strategy You Should Steal Kill Your Inbound SDRs—The Case for Voice AI in Sales Why You Don't Need PMs and the Rise of Growth-Led Product Teams

11 Jan 1h 13min

20VC: Groq's $20BN NVIDIA Acquisition | Manus Acquired by Meta for $2BN | Why Sam Altman Does Not Care About Dilution | Navan Trading at 4x ARR & Why Going Public Does Not Make Sense Anymore | The Rise of Invisible Unemployment and Labour Markets in 2026

20VC: Groq's $20BN NVIDIA Acquisition | Manus Acquired by Meta for $2BN | Why Sam Altman Does Not Care About Dilution | Navan Trading at 4x ARR & Why Going Public Does Not Make Sense Anymore | The Rise of Invisible Unemployment and Labour Markets in 2026

AGENDA: 04:30 Groq Acquired by NVIDIA for $20BN: The Breakdown 17:13 Meta's $2BN Acquisition of Manus: Did They Sell Too Early 36:04 OpenAI's Stock-Based Compensation Strategy 47:42 Will AI Replace Venture Capitalists 56:13 Navan Trading at 4x ARR: Who is Good Enough to Go Public? 01:09:46 The Rise of Invisible Unemployment 01:14:21 The Future of Work and Education in an AI-Driven World

8 Jan 1h 23min

20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

I have interviewed 1,000 entrepreneurs over 10 years. Nik Storonsky and our guest today are the two best that I have interviewed.  Joining the show today; Alan Chang, Co-Founder and CEO of Fuse Energy. Alan has scaled Fuse Energy from $2M in revenue in the first year, to $20M the second year to now $400M in the third year. Like Netflix beat incumbents to own media, Revolut beat incumbents to own banking, Fuse will beat incumbents to own energy. Prior to founding Fuse, Alan was one of the first three hires at Revolut where he played a crucial role alongside Nik (Founder) in scaling the company to over $75BN valuation.  AGENDA: 00:04:00 — The interview process that led to the $150M pay packet 00:05:05 — The moment I knew Revolut was going to be a $TRN company 00:06:10 — How Revolut drove speed and urgency in their teams 00:07:35 — Biggest lesson from Nik Storonsky @ Revolut 00:09:40 — If you want to build a generational company, you cannot have work-life balance 00:11:40 — What I disagreed with Nik @ Revolut on most 00:13:35 — Is Nik right that Revolut should have got a banking licence earlier? 00:15:05 — The green movement and the idea of "using less" is BS 00:22:55 — Why China is the shining light for regulation to follow 00:33:00 — What Nik at Revolut taught me about ownership and excuses 00:34:50 — The signs of truly top performing people in a team 00:36:55 — We do not have enough ambitious founders — we need to do more, not focus 00:39:55 — You need to work weekends to win 00:43:50 — Every single year we 10x revenue — now at ~$400M 00:44:35 — Why Eastern European engineers are the best Items Mentioned in Today's Show: Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

5 Jan 56min

20VC: Enterprises Will Not Adopt AI without Forward-Deployed Engineers | Who Wins the Data Labelling Race: How Does it Shake Out? | How Synthetic Data Threatens the Future of Human-Generated Data with Matt Fitzpatrick, CEO of Invisible Technologies

20VC: Enterprises Will Not Adopt AI without Forward-Deployed Engineers | Who Wins the Data Labelling Race: How Does it Shake Out? | How Synthetic Data Threatens the Future of Human-Generated Data with Matt Fitzpatrick, CEO of Invisible Technologies

Matt Fitzpatrick is the CEO of Invisible Technologies, leading the company's mission to make AI work. Since joining as CEO in January 2025, he has raised $100M and accelerated AI adoption across industries from sports to consumer and government. Previously, Matt was a Senior Partner at McKinsey, where he led QuantumBlack Labs, the firm's AI R&D and software development arm. AGENDA: 04:40 Interview with Matt Fitzpatrick: Career Journey and Leadership 09:35 The Single Biggest Barriers to Enterprises Adopting AI 15:26 It is BS That Enterprises Can Adopt AI Without Forward-Deployed Engineers 28:05 Are AI Talent Marketplaces Dead? What is the best model? 46:33 How Does the Data Labelling Market Shake Out: Who Wins/ Who Loses 48:27 Are Revenue Numbers for Data Labelling Real Revenue? Or GMV? 51:20 Best Capital Allocation Decision? What did Matt Learn from it? 53:19 How Important is Brand for AI Companies Selling Into Enterprise? 01:05:59 Remote Work vs. In-Person Collaboration 01:17:06 What Does No-One Know About the Future of AI That Everyone Should Know

31 Des 20251h 23min

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions for 2026: Top Performing Tech Stocks of the Year 35:25 B2B Stocks to Watch 38:31 Why Salesforce Could Be the Buy of 2026 47:11 Google, Meta, Apple, NVIDIA, Microsoft: Buy One, Short One 55:38 IPO Speculations: Who Will Go Public in 2026 01:00:57 The Impact of AI on Employment

22 Des 20251h 9min

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a decade building consumer brands with collaborators such as Microsoft and Ferrari. AGENDA: 00:00 – Why Most "Great Products" Fail to Create Emotion 03:00 – How Perfume Taught Me Everything About Desire & Product 06:10 – The Brutal Reality of Building Physical vs Digital Products 16:00 – Why "Simple Design" Is Overrated and Dangerous 23:00 – Why Vuori is the Brand to Short in Consumer  28:30 – The Biggest Product Mistake: Listening to Customers Too Much 32:10 – On Only Do Tennis Because of Roger Federer 38:30 – Were We Too Late to Marathon Running? A Painful Admission 43:40 – The Most Controversial Product On Has Ever Launched 49:00 – Are Counterfeits Good or Bad in Fashion?

19 Des 202556min

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It Means 23:19 Oracle Hit Hard: Is Now the Time to Buy 28:34 Broadcom's Market Cap Drop and Anthropic's AI Chip Orders 35:04 Cursor Competes with Figma: The Convergence of Design and Coding Tools 46:20 The Biggest Danger for Incumbents: Being Maimed by AI 55:28 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:00:24 Will SpaceX IPO at $1.5TRN and The Elon Option Value

18 Des 20251h 22min

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