20 Sales: How To Create and Execute a World-Class Sales Playbook, Why You Should Do Both PLG and Enterprise Sales at the Same Time, Three Non-Obvious Qualities the Best Sales Reps Have & The Four Steps To Sales Team Onboarding with Oliver Jay, Former CRO
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Release Date: 05/25/2022
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Philipp Freise is Co-Head of European Private Equity at KKR, where he manages the largest private fund in Europe with $8BN in the latest fund. Philip has led KKR's investments in FGS Global, Superstruct, Axel Springer SE, BMG Rights Management, Fotolia, GetYourGuide, GfK SE, Leonine, Mediawan SAS, Scout24 Switzerland and Trainline. Previously, Philip worked at McKinsey & Company in and co-founded Berlin-based VC firm Venturepark, Europe's first pan-European incubator. Agenda: 00:00 – "We Lost $500M in Turkey. Here’s Why We’ll Never Do It Again." 01:40 – Inside Europe’s Biggest PE...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Kim Graves is GM, Americas at Notion, where she oversees all Sales and Customer Success efforts across the region. She brings extensive experience in building and scaling high-performing sales organizations, most notably at Slack where she helped grow revenue from $6M to over $1.5B. In addition to her operational role, Kim serves as a founding partner at 20SALES, a GTM-focused VC firm, where she advises early-stage companies on scaling revenue and optimizing sales processes. Agenda: 07:00 – The Secret to Winning a Discount Conversation 09:30 – Notion’s Wild New Sales Method: Mindsets...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: 04:21 - The Meta Acquisition Bombshell: Nat Friedman & Daniel Gross Join Facebook?! 06:00 - Facebook’s $100 Billion Gamble: Can Zuck Buy the Future? 09:27 - The “Magic Room” Theory: Why Only Insiders Get Billion-Dollar Paydays 11:27 - Is Loyalty Dead in Silicon Valley? The Great Talent Exodus 16:00 - Harvey’s $5 Billion Valuation: Genius or Bubble? 19:00 - The AI Gold Rush: Can Software Really Eat Human Labor? 22:00 - The B2B Unicorn Dilemma: Are There Enough $100B Companies? 25:00 - IPO Mania: Why Navan, Canva, and Circle Are Shaking Up the Markets 29:00 - Meme Stocks...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Johannes Reck is the Founder and CEO of GetYourGuide, the $2BN company that started with a holiday to China and nothing to do. For the first two years, GetYourGuide received only 5 bookings. Today the platform is worth $2BN. They have raised from some of the best, including an amazing story with Masa Son and Softbank. In Today’s Episode We Discuss: 01:45 – “I Regret Our Series A — Too Much Dilution” 03:50 – US vs Europe: Why European Founders Are Tougher 06:10 – “Germany Spends €100B on Pensions, €7B on VC – It’s Insane” 08:40 – Why Europe Fails to Build $10B...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Cem Kansu is the Chief Product Officer at Duolingo, where he leads product strategy for over 90 million monthly active learners. Since joining Duolingo, Cem has played a pivotal role in driving record user engagement, revenue growth, and product innovation, including the launch of Duolingo Math and the wildly successful Duolingo Music. Under his leadership, the company has consistently ranked as the #1 education app globally. In Today’s Episode We Discuss: 04:12 – Cem’s Origin Story: From Google Ads to Saving Duolingo’s Business 06:45 – “Mini CEO” Myth: Why PMs Need to...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: 00:00 – Meta’s $14.8B Deal for Scale: The Analysis 05:40 – Will Scale Lose Their $800M ARR? Will All Customers Leave? 13:00 – Who is the Winner from All Scale Customers Leaving? 21:30 – Who Made the Most Money From Scale? 24:00 – LPs Just Got $14B Back. Are They Reinvesting? 26:45 – Chime IPO: The Breakdown 29:20 – Ramp Hits $16B Valuation: Are We Back in 2021? 31:10 – Ramp vs Brex vs Mercury: Who’s the Real Winner? 34:00 – Gusto Going Public with $900M in ARR??? 36:40 – Dropbox vs Glean: Can the Old Guard Survive the AI Wave? 38:50 – Is Slack Dead as a...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses along the way (discussed in the show) in Getir, 23andme and more. Today, Larry manages over $5BN and has invested in all the best from Wiz to Spotify to Revolut and Anthropic. Agenda: 00:00 – From Broke to Billion-Dollar Bets 03:40 – The...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Agenda: 00:03 – Circle’s IPO: Investors Just Left $BNs on the Table 00:06 – CoreWeave & Circle: Are We Back to Meme Stock Madness? 00:11 – Should Stripe and Databricks Finally Go Public? 00:17 – US Stock Markets: How They DOMINATE the Global Game 00:21 – 50% of Unicorns Are DOOMED. What Happens Now? 00:25 – Founders Fund Just Dropped $1B on Anduril. Why?! 00:29 – What Would You Do If LPs Let You Go Wild? 00:36 – What Missing Out on Millions for Docusign Taught Rory 00:44 – Cursor is 20% of SaaS Spend: The Shocking Data Behind the SaaS Slowdown 00:47 – AI vs. SaaS: The...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Micha Kaufman is the Founder and CEO of Fiverr, the leading online marketplace for freelance services. Fiverr has had an insane ride in the public markets, in 2019 the company went public with a $650M market cap, at their peak that hit over $8BN. Today, facing a wave of AI, the company has a market cap of $1.121BN on an estimated $430M EOY revenues. Prior to co-founding Fiverr, Micha successfully founded and led several startups over the last 30 years. In Today’s Episode We Discuss: 00:00 – “Fuck you. It’s not my job to make you better.” Micha’s viral internal email...
info_outlineThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Matt Pohlson is the co-founder and Chairman of Omaze, the most insane story in startups that you have never heard. From near death experience to working with Arnold Schwarzenegger, George Clooney and The Pope. Omaze has raised over $200 million for charity by offering once-in-a-lifetime celebrity experiences and luxury house draws. He's a master storyteller, a purpose-driven builder, and one of the most creative entrepreneurs in modern philanthropy. In Today’s Episode We Discuss: 00:00 — He Died for 4 Minutes… Then Built a $400M Startup 04:00 — The Magic Johnson Moment That Sparked...
info_outlineOliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company's first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, OJ spent 4 years at Dropbox in a period of hyper-scaling for the business where OJ was Head of APAC and LATAM. At Dropbox, OJ scaled the sales team from 0 to 50 while tripling ARR. If that was not enough, OJ is also an independent board member at Grab, the leading Super app in Southeast Asia.
In Today’s Episode with Oliver Jay You Will Learn:
1.) Entry into Sales:
- How did OJ make his way into sales with Dropbox?
- If OJ were to choose 1-2 lessons from his time at Dropbox and Asana that have stayed with him, what would they be? How did they impact his mindset?
- What were some of the non-obvious but crucial things Asana and Dropbox did in sales that led to success?
2.) The Playbook:
- Why does OG disagree with so many definitions of "the sales playbook"? What is the sales playbook to OJ? What are the different chapters?
- Should the founder be the one to create the sales playbook?
- What are the signs that the founder has a repeatable and scalable playbook?
- When is the right time to hire the first sales rep? Should it be a Head of Sales or Sales Rep?
- How does the first hire depend on whether you are PLG or enterprise sales led?
3.) The Hiring Process:
- How does OJ structure the hiring process?
- How does OJ know the qualities that he wants to uncover in each candidate?
- What questions does OJ ask to unpack whether the candidate has those qualities?
- How does this differ when hiring sales reps vs sales leaders?
- How does OJ use the sales demo to test the quality of a candidate? What does he want to see?
- Who does OJ bring into the interview process? When do they get involved?
- What are two questions that will immediately tell whether someone is a good manager?
4.) Sales Onboarding:
- How does OJ segment sales onboarding into 3 crucial steps?
- Chapter 1: Support: Why does OJ believe it is so important for reps to spend their first week with support? What should they look to learn? What questions should they be asking?
- Chapter 2: Market Knowledge: How can sales leaders teach and educate new reps on market landscape, dynamics and competition? Why does this have to come before sales training?
- Chapter 3: Sales Training: In the final step, what does the sales training process? What does OJ look for in the final sales demo? When does OJ let reps speak to customers? How does this differ when comparing enterprise to PLG?