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20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Release Date: 08/31/2022

20Product: How Canva Builds Products: Lessons Learned, What Works? What Flopped? The Top 5 Product Lessons in Scaling to 185M Monthly Active Users with Canva Co-Founder and Chief Product Officer, Cameron Adams show art 20Product: How Canva Builds Products: Lessons Learned, What Works? What Flopped? The Top 5 Product Lessons in Scaling to 185M Monthly Active Users with Canva Co-Founder and Chief Product Officer, Cameron Adams

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

is Chief Product Officer and co-founder of where he is responsible for heading up the design and product teams. Since launching in 2013, Canva’s global community has grown to over 185 million monthly users in over 190 countries. In 2021, Canva was valued at $40 billion, following a $200m funding round. This saw it become one of the most valuable private software companies in the world. Prior to joining Canva, Cameron found himself working closely with Lars and Jens Rasmussen (co-founders of Google Maps) to realise the design vision for Google Wave. In Today's Episode with Cameron...

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20VC: Brex CEO Pedro Franceschi on What Brex Needs to do to be a Public Company | Brex vs Ramp: Who Wins and How Does it Play Out | Battling Founder Mental Health and The Importance of Secondaries for Founders show art 20VC: Brex CEO Pedro Franceschi on What Brex Needs to do to be a Public Company | Brex vs Ramp: Who Wins and How Does it Play Out | Battling Founder Mental Health and The Importance of Secondaries for Founders

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Pedro Franceschi is the Co-Founder and CEO @ Brex, the AI-powered spend platform with tens of thousands of customers, including DoorDash, Coinbase, Robinhood and Roblox. Pedro has raised over $1.2BN for the company from the likes of Greenoaks, Ribbit, DST, Bond and YC. The latest reported valuation was $12.3BN. Before Brex, Pedro was the first person to “jailbreak” the iPhone 3G in Brazil and co-founded payments company Pagar.me with Dubugras when he was 15. In three years, Pedro scaled it to over 100 people and US$1.5 billion in transactions processed. In Today's Episode with Pedro...

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20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greylock show art 20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greylock

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Saam Motamedi is a General Partner at Greylock, where he has led investments in Abnormal Security (incubated at Greylock), Apiiro Security and Opal Security, as well as AI companies like Adept, Braintrst, Cresta, Predibase, Snorkel, and more. Before Greylock, Saam founded Guru Labs, a machine learning-driven fintech startup, and worked in product management at RelateIQ, one of the first applied AI software companies. In Today's Conversation We Discuss: 1. Seed Today is Frothier than 2021: How does Saam evaluate the seed market today? With seed pricing being so high, how does he...

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20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge show art 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Mark Roberge is a Co-Founder and Managing Director at Stage 2 Capital and a Senior Lecturer at the Harvard Business School. Prior to these roles, Mark was the founding CRO at HubSpot, where he scaled ARR from $0 to $100 million and expanded his team from 1 to 450 employees. Mark was ranked #19 in Forbes' Top 30 Social Sellers in the World. He was also awarded the 2010 Salesperson of the Year at the MIT Sales Conference. In Today's Episode with Mark Roberge We Discuss: 1. Biggest Lessons Scaling Hubspot to $100M in ARR: What are Mark's biggest lessons in what worked in their sales...

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20VC: ServiceTitan Would Not Be the Success if We Raised VC Earlier: How to Build a Dominant Vertical SaaS Business, How to Master Going Into Enterprise, When & How to Launch Second Products with Ara Mahdessian, Co-Founder @ServiceTitan show art 20VC: ServiceTitan Would Not Be the Success if We Raised VC Earlier: How to Build a Dominant Vertical SaaS Business, How to Master Going Into Enterprise, When & How to Launch Second Products with Ara Mahdessian, Co-Founder @ServiceTitan

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Ara Mahdessian is the Co-Founder and CEO @ ServiceTitan, one of the great vertical SaaS business of the last decade. Today the company powers over 11,800 trade customers and has raised over $1.4BN from some of the best including Bessemer, Battery, Index, ICONIQ and more. Their latest valuation pegged the business at a reported $7.3BN. In Today's Episode with Ara Mahdessian We Discuss: 1. We Did Not Want To Raise VC Money: Why did Ara not want to raise VC funding in the early days? What convinced Ara to change his mind? Why did he choose Byron and Bessemer? Does Ara believe that...

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20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady show art 20VC: The Sequoia Investment Process | Investing Lessons from Doug Leone, Roelof Botha & Alfred Lin | Sequoia's Framework for Analysing Founders | The True Benefit of Having Sequoia on a Cap Table & Sequoia's Biggest Threat with Pat Grady

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Pat Grady is one of the most successful growth investors of the last decade. As the Head of Sequoia's growth investing practice, Pat has invested in companies with a combined market cap exceeding $250BN. Among Pat's immense portfolio is Hubspot, Snowflake, ServiceNow, Okta, Amplitude, Zoom and Qualtrics. Pat is also one of the best acquirers of talent in venture hiring Andrew Reed, Matt Huang, Julien Bek. In Today's Episode with Pat Grady We Discuss: 1. The Sequoia Investment Process: What is the Sequoia investment process today? How has it changed over time? What could be improved...

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20VC: Turning a $15M Investment in Monday into $1.5BN in Cash | The Strategy Behind a 37x DPI $45M Fund | The Three Step Process to Selling Positions that has Netted Top Percentile Returns with Avi Eyal, Co-Founder @ Entrée Capital show art 20VC: Turning a $15M Investment in Monday into $1.5BN in Cash | The Strategy Behind a 37x DPI $45M Fund | The Three Step Process to Selling Positions that has Netted Top Percentile Returns with Avi Eyal, Co-Founder @ Entrée Capital

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about. In Today's Episode with Avi Eyal We Discuss: 1. The Biggest BS "Rules" in Venture Capital: Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund? Why does Avi believe that...

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20VC: LLMs Are Reaching a Stage of Diminishing Returns: What is the Next S Curve | The Bull & Bear Case for China's Ability to Challenge the US' AI Capabilities | How AI Changes the Future of War & How Agents Will Reshape Society with Matt Clifford @ EF show art 20VC: LLMs Are Reaching a Stage of Diminishing Returns: What is the Next S Curve | The Bull & Bear Case for China's Ability to Challenge the US' AI Capabilities | How AI Changes the Future of War & How Agents Will Reshape Society with Matt Clifford @ EF

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Matt Clifford is the Co-Founder of Entrepreneur First (EF), the leading global talent investor and incubator. EF has incubated startups worth over $10bn, including Cleo, Tractable and Aztec Protocol. Matt is also Chair of ARIA, the UK’s Advanced Research and Invention Agency, and advises the UK government on AI and in 2023 served as the Prime Minister’s Representative for the AI Safety Summit at Bletchley Park. In Today's Episode with Matt Clifford We Discuss: 1. The Most Important Questions in AI: Are we seeing diminishing returns where more compute does not lead to a significant...

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20VC: Raising $126M Across 3 Rounds in Just 6 Months, Being the Youngest Founder of a Unicorn Company | But Everything Was Not as it Seemed: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires with Vise's Samir Vasavada show art 20VC: Raising $126M Across 3 Rounds in Just 6 Months, Being the Youngest Founder of a Unicorn Company | But Everything Was Not as it Seemed: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires with Vise's Samir Vasavada

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Samir Vasavada is the Co-Founder & CEO of Vise, a technology-powered asset manager. Samir and his co-founder, Runik founded Vise from the Midwest at 16 years old. They bootstrapped the company before dropping out of high school and raising $128M in just 6 months from some of the best including Sequoia Capital and Founders Fund. The company achieved unicorn status when the pair turned 20 years old, making them the youngest founders of a $BN company at the time. In Today's Episode with Samir Vasavada We Discuss: 1. The Biggest Hiring Mistakes That Broke Us: Why is hiring...

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20VC: Klaviyo's Andrew Bialecki on Going Public in an IPO Winter, Is Klaviyo Under-Priced in Public Markets and Why, Why Every VC Turned Klaviyo Down in the Early Days & How Shopify's Partnership Changed the Game show art 20VC: Klaviyo's Andrew Bialecki on Going Public in an IPO Winter, Is Klaviyo Under-Priced in Public Markets and Why, Why Every VC Turned Klaviyo Down in the Early Days & How Shopify's Partnership Changed the Game

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Andrew Bialecki is the Co-Founder and CEO of Klaviyo, the platform that powers smarter digital relationships for businesses and their data. To date, Klaviyo has raised over $778M from the likes of Accel, Summit Partners, Sands Capital, and Shopify, and raised an additional $700M after its IPO in September 2023.  In Today’s Episode with Andrew Bialecki We Discuss: Founding a $6.23BN Machine in Klaviyo: The Aha Moment What was the aha moment for Klaviyo? How important does Andrew think it is for founders to stick with their initial vision vs when is the right time to pivot? Does...

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Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.

In Today's Episode with Annie Pearl We Discuss:

1.) Entry into Product From Consulting:

  • How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
  • What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
  • What does Annie know now that she wishes she had known when she started in product?

2.) PLG vs Enterprise: What, When, How:

  • Is it possible to do PLG and top-down enterprise strategy together from Day 1?
  • Why does every PLG company eventually have to adopt an enterprise strategy?
  • What are the single biggest challenges companies face when moving to enterprise?
  • How do founders know when is the right time to make this transition?
  • How do founders need to restructure their org to make the transition to enterprise?

3.) Building the Product Bench: Hiring:

  • When is the right time to hire your first product leader? What are the core signals?
  • What are the core character traits needed for a first product leader?
  • How do we specifically structure the interview to test for them?
  • Who do we bring into the interview process from other parts of the org?
  • Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?

4.) Product Strategy, Reviews and Alignment:

  • How does Annie assess how often product strategy should be reviewed? When should it change?
  • How does Annie approach post-mortems? What is the right way to structure them?
  • How does Annie create alignment between sales and product? Why is this so important?
  • What is the single biggest product mistake Annie has made? What did she learn?