20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

Dan Fougere is one of the most successful sales leaders of the last decade. Most recently, Dan was Chief Revenue Officer for Datadog, growing revenues from $60 million to $1BN ARR. Before Datadog, Dan was Head of Global Sales at Medallia where he created the Mediallia sales playbook. In addition, Dan is also a minority owner of the New York Yankees.

In Today’s Episode with Dan Fougere:

1. Lessons Scaling Sales to $1BN in ARR at Datadog:

  • What did Datadog not do that Dan wishes they had of done?

  • What did they not do that Dan wishes they had done?

  • What does Dan know about scaling sales to $1BN in ARR that he wishes he had known at the beginning?

  • What stage of the scaling process was hardest? Why?

2. How to Hire the Best Sales Team:

  • What are the top signals of the best sales candidates?

  • How does Dan structure the interview process for new candidates?

  • How does Dan use tasks and take-home assignments to test candidates?

  • What does Dan think of hiring panels?

  • What are the biggest hiring mistakes Dan has made? What did he learn?

3. Discounting, Logos and Deal Reviews:

  • Is discounting always wrong? How should sales leaders use it?

  • How important is the quality of logo in the early days vs revenue in the door?

  • What is the right way to structure deal reviews? What makes good vs great?

  • Is outbound dead in 2024? Advice to founders on outbound?

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James Altucher: Ideas, Investing and Entrepreneurs

James Altucher: Ideas, Investing and Entrepreneurs

James Altucher is a successful entrepreneur, investor, board member, and the writer of 11 books including the recent WSJ Bestseller, "Choose Yourself!" (foreword by Dick Costolo, CEO of Twitter). He has started and sold several companies for eight figure exits. He's on the board of a billion $ revenue company, has written for The Financial Times, The New York Observer, he's run several hedge funds, venture capital funds, and is a successful angel investor, having invested in over 30 startups alongside Silicon Valley's Top VC's. In today's conversation Harry and James discuss how to continuously come up with great ideas, what tasks activate the 'idea muscle', what tactics have produced the greatest investing returns for James, what traits do great founders have, how has James' investing strategy developed, what is the future for Uber, the scam that is University and much more... Items Mentioned in Today's Show: Alternatives to College and Careers: Learn to Become an iOS Developer, Learn to Become a Web Developer James Altucher: Choose Yourself! Tim Ferriss: AngelList Syndicate Shyp: The Easiest Way To Ship Your Stuff

4 Juni 201528min

Jason Calacanis: The World's Greatest Angel Investor

Jason Calacanis: The World's Greatest Angel Investor

Jason Calacanis is arguably the world's greatest angel investor with over 60 investments including the likes of Uber (1st round), ThumbTack and Calm, just to name a few. Jason is also the Host of This Week In Startups, the world's biggest startup podcast and Founder of Launch and Launch Festival, the world's biggest startup festival. In this interview we discuss, how Jason invested in Uber's 1st round, what Jason looks for in startups, how Jason can tell whether a founder has got what it takes, which VC's Jason most likes to work with, which entrepreneurs Jason most likes to invest in, what pisses Jason off more than anything, what inspires him more than anything, what industries will see the most disruption in the coming years, what makes a great entrepreneur and how startups can position themselves best for entering a round of funding. Enjoy! All show notes, links and resources from this episode can be found at http://www.thetwentyminutevc.com and you can follow Harry, Jason and The Twenty Minute VC on Twitter. Mentioned in Today's Show: Bill Gurley, Jonathan Triest, Chamath Palihapitiya Bento: Delicious Asian Food Delivered in Minutes Butterfleye: Google's Nest Meets Dropcam Birdi: Better Than A Smoke Detector

1 Juni 201555min

20 VC 040: The Required Qualities To Be A Great Founder, with Scott Taylor, CEO @ miDrive

20 VC 040: The Required Qualities To Be A Great Founder, with Scott Taylor, CEO @ miDrive

Scott Taylor is the CEO @ miDrive, a startup focussed on reinventing the learner driving experience. Scott is also an advisor to leading London based VC firm EC1 Capital. If that wasn't enough he is a mentor at Richard Branson's Virgin Startup Program and an investor in Coupang and Mavrx. Prior to miDrive, he was Chief Product Officer at Livedrive, one of Europe's leading cloud storage providers, assisting with its sale to j2 Global. Items Mentioned in Today's Show: TreeHouse: Learn Web Design, Web Development  LifeCake Acquisition FestivalFriends App Crowdcube: Online Investing, Equity Crowdfunding The Hard Thing About Hard Things: Ben Horowitz Into The Woods: John Yorke In Today's Episode You Will Learn: 1.) Where it all began for Scott and how he made his move into technology and venture? 2.) Having founded several successful companies, what Scott believes the qualities required to be a good founder are? 3.) The hardest part for Scott in building companies and how he overcome them? 4.) What is Scott's role at EC1, what is he looking for in companies at EC1 and how does that differ from his own angel investments? 5.) At Virgin Start Up, what is the process like to attain funding? 6.) What are Scott's views on early stage funding? Does he agree with the friends and family round? 7.)What would you suggest to entrepreneurs looking to gain external capital? The episode will then finish with a quick fire round. Where we hear Scott's thoughts on: Next 5 years for Scott? Asian tech market? Favourite book and why? Most recent investment and why he said yes? You can follow Harry, Scott and The Twenty Minute VC on Twitter

28 Maj 201517min

How to Pitch a Top VC with Simon Menashy @ MMC Ventures

How to Pitch a Top VC with Simon Menashy @ MMC Ventures

Simon Menashy is Investment Director at MMC Ventures where he is responsible for leading new and follow on investments as well as supporting existing MMC portfolio companies. He also sits on the board for WeDo, Boticca and Sky Futures and works closely with a number of other B2B and B2C businesses including Growth Intelligence, Mubi, Small World, Somo.  Prior to MMC Simon worked in European tech and media consulting, working with clients including the BBC, Virgin Media, BT, Thompson Reuters and Ofcom as part of the Deloitte Strategy team in London   Items Mentioned in Today's Show: Base79 Growth Intelligence In Today's Episode You Will Learn: 1.) How Simon made his move from consulting into the world of VCs? 2.)Simon recently tweeted how not to pitch to VCs, so what should founders be doing when pitching? What are the fundamentals in terms of required documentation?  3.) Does Simon agree with Peter Thiel’s opinion that disruption is fundamentally bad for society? What industries does Simon feel will be next disrupted? 4.) With the increasing length of time it takes for venture backed companies to IPO, how does Simon feel the funding path is changing? 5.) How does Simon believe the tech eco system is going in London and what can be done to increase VC funding and engender a silicon valley esque feel to London? Today's episode finishes with a quick fire round where we hear Simon's thoughts on the apple watch, what the biggest red flags are when viewing a pitch and his most recent investment and why he said yes? You can follow Harry, Simon and The Twenty Minute VC on Twitter.

25 Maj 201521min

20 VC 038: How Make Connections with VCs and Maximise Employability with Angela Tran Kingyens @ Version One Ventures

20 VC 038: How Make Connections with VCs and Maximise Employability with Angela Tran Kingyens @ Version One Ventures

Angela Tran Kingyens is an associate at Version One Ventures, where Angela manages the day to day activities of the fund from identifying new startups to advising portfolio companies on product. Prior to Version One, Angela Co-Launched Insight Data Science, a Y Combinator backed startup, helping academics transition into a career in industry. In today's episode, Angela describes the best ways to network with VCs, how you can increase employability instantly and the most effective ways to conduct market research! Items Mentioned in Today's Show: mattermark Daily Newsletter Dan Primack: TermSheet Fred Wilson: AVC Good To Great by Jim Collins Headout: Your Best Local Friend in a New City In Today's Episode you will Learn: 1.) How Angela made the transition from a career in academia to a YC backed startup to a Palo Alto Venture Fund? 2.) What can individuals do to network effectively with VCs, even if they have no existing VC contacts? 3.) What advice Angela would give to someone looking to leave the academic path for a career in tech? How can they maximise employability? 4.) What should individuals look for when considering incubators? Do they increase the validity of a startup, from the Version One perspective? 5.) Version One specialise in Marketplaces. Why is that? Is it normal for VC funds to specialise? What Angela thinks the future of marketplaces will look like? 6.) How to identify where there are up and coming areas for disruption? What resources are most effective for this market research? We then finish today's episode with a lightning round where we hear Angela's thoughts on what industry she would never invest in, whether Uber will be a $trillion company, how VCs measure their own success, Angela's favourite business book and her most recent investment and why she said yes? You can follow Harry, Angela and The Twenty Minute VC on Twitter here.

21 Maj 201523min

20 VC 037: How To Get a Job at a Startup, Startup Lessons and Brad Feld's 'Open Office Hours' with Tak Lo, Director @ Techstars

20 VC 037: How To Get a Job at a Startup, Startup Lessons and Brad Feld's 'Open Office Hours' with Tak Lo, Director @ Techstars

Tak Lo is Director at Techstars, helping entrepreneurs do more faster - on both sides of the Atlantic through Techstars London and Techstars NYC. Tak is also Founder at Travelst and Frontlyst. Prior to his road into entrepreneurship, Tak was a Consultant at Deloitte, Booz Allen Hamilton and was a specialist in the US ARMY. In today's incredible episode Tak shares his lessons from his own startup experience, the required reading for all entrepreneurs and of course when thinking TechStars, how can we not discuss the man himself, Brad Feld, and how Tak has adopted Brad's use of open office hours. Items Mentioned in Today's Show: Must Read Tech Blogs: Fred Wilson, Brad Feld Thoughts, Tomas Tunguz: Redpoint Capital, Christopher Janz: Point Nine Capital   Must Read Books: Team of Rivals: The Political Genius of Abraham Lincoln, Adam Grant: Give and Take, Peter Thiel: Zero to One, Ben Horowitz: The Hard Thing About Hard Things Must Have Apps: Buffer: Save Time On Your Social Media, Feedly: The Stories You Need To Keep Ahead Networking Tools: Silicon Drinkabout, Meetup  Team of Rivals Adam Grant: Give and Take Peter Thiel: Zero to One Ben Horowitz: The Hard Thing About Hard Things In Today's Episode You Will Learn: How and why Tak made the transition first from the army to a career in consulting and then what made Tak take the entrepreneurial route and start his own company? Tak is renknowned for the amazing service and contribution he brings to every startup. What services does Tak bring and what does Tak feel all entrepreneurs and advisors must add? Does Tak back singular founders, or does he prefer a founding team? Tak is a Specialist on Leadership, for founders wanting to gain or develop their leadership skills, what can founders do, read or learn to further their leadership skills? For individuals contemplating moving into the tech world, how do they know which is the right job? Are there any immediate aspects they must look for or be wary of? What are the biggest misconceptions of the tech industry? How can people find out about networking events  What sector Tak believes is the next to be disrupted and why? What is the premise behind Brad Feld's 'Open Office Hours'? Why has Tak decided to adopt this tactic? What does Tak hope to gain from it? How is it going so far? We then finish today's episode with a lightning round, hearing Tak's thoughts on the greatest leader and why, the future of the asian tech market, his favourite book and why and his most recent investment and why he said yes? Follow Harry, Tak, The Twenty Minute VC

18 Maj 201519min

20 VC 036: The Pitching Process: From Email to Term Sheet with Stephan von Perger @ Wellington Partners

20 VC 036: The Pitching Process: From Email to Term Sheet with Stephan von Perger @ Wellington Partners

Stephan von Perger is an Early Stage VC at Wellington Partners where his primary role is identifying investment opportunities and building lasting relationships with the entrepreneurs behind these companies. Stephan started his career at McKinsey before moving to Stylistpick.com as Head of Operations, he then progressed to setup and run the business operations at CityMapper.com. In today's interview Stephan walks us through the pitching process from the first email to signing the term sheet! In Today's Episode You Will Learn: How and why Stephan made his move from the world of startups to the venture industry? What are the right reasons for a founder to enter a round of venture funding? How should founders go about meeting and connecting with VCs? What can founders actively do to position themselves well and how should founders phrase their emails and communication? Are there any aspects or buzzwords in emails which instantly make VCs interested? What documentation is required for the initial meeting? Is there anything founders must bring? How can founders make the most out of their meeting with VCs? Are there any questions founders should ask? How should founders respond to a question they do not know the answer to? What happens if a VC says they will contact you but a week later the founder has heard nothing? What should the founder do? We then finish todays episode with a quick fire round where we hear Stephan's thoughts on which pitch or communication has impressed him the most, what single thing Stephan most looks for in founders and his most recent investment and why he said yes?

14 Maj 201520min

20 VC 035: The Ultimate Marketing Guide for Startups with Jay Acunzo, VP of Platform @ NextView Ventures

20 VC 035: The Ultimate Marketing Guide for Startups with Jay Acunzo, VP of Platform @ NextView Ventures

Jay Acunzo is NextView Ventures VP of Platform and runs the View from Seed blog. At NextView, he leads the creation of business development and educational resources for startups, from board deck templates to mobile workshops to the popular Hitchhiker's Guide to Boston Tech (bostontechguide.com). Prior to NextView, Jay led content marketing and production teams at HubSpot (IPO) and Dailybreak Media (acquired). A former sports journalist, he began his career in tech at Google. As a result of Jay's tremendous success Jay has been named Top 10 B2B Marketer in Boston, 70 Rising Social Media Stars and 100 Most Influential Content Marketers. Items Mentioned in Today's Show: Kitchen Confidential by Anthony Bourdain  Jay's Article in TechCrunch a16z GoDaddy Wordpress The Weird Things Business People Do On Twitter The Content Marketing Institute   In Today's Episode you will Learn: How Jay made his move into the world of tech with Google and how he then transitioned into the world of venture with NextView? What does VP of Platform really entail? Why has it become an emerging trend in the venture industry? How is the structure of VCs firms changing, with the likes of a16z moving to a much more service orientated venture fund. Are there any individuals or sections of society that should or should not be blogging? How can individuals drive traffic to their blog and what tactics Jay uses to get visitors to his blog? What Jay would suggest to business and startup founders thinking about whether to start blogging? What is the best platform to market your content or startup? Is Twitter really an effective marketing tool? How can individuals and businesses increase engagement on Twitter? What not to do on Twitter? We then finish today's episode with a lightning round where we hear Jay's thoughts on the best and worst aspects as VP of Platform, his best resource for content marketing, his favourite book and why.

11 Maj 201522min

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