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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

20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan show art 20VC: Hiring 101; The Biggest Mistakes Founders Make in the Hiring Process | Fundraising; What to Optimize for, How Profitability Changes Leverage When Raising | SMB to Enterprise; When to Move, What Changes and Dangers of Moving Too Early with Daniel Yan

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

is the co-founder and CEO of , a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including , , Coatue, GV, and IVP to name a few. Prior to Checkr, Daniel was a software engineer and helped develop prototypes of the Mars Rover for NASA. Daniel has been recognized in Forbes “30 Under 30” and recently Checkr was recognized by Forbes as one of America’s best start-up employers. In Today’s Episode with Daniel Yanisse You Will Learn: 1.) The Origins of Checkr: The $5BN Company ...

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20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market show art 20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market

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

 is a General Partner @ , Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.  is the Global Managing Partner @ , one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.  is a General Partner @ , one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on.  ...

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20VC: Accel's Sonali De Rycker on Building a Generational Defining Venture Firm; Hiring, Culture, Incentives | Investing; Biggest Mistakes, Biggest Lessons from Prior Crashes, Why Market Size is Dangerous to Focus On | Decision-Making; Type 1 vs Type 2 Ri show art 20VC: Accel's Sonali De Rycker on Building a Generational Defining Venture Firm; Hiring, Culture, Incentives | Investing; Biggest Mistakes, Biggest Lessons from Prior Crashes, Why Market Size is Dangerous to Focus On | Decision-Making; Type 1 vs Type 2 Ri

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

is a Partner @ , one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify, and many more incredible companies. As for Sonali, Sonali led Accel’s investments in Avito (acquired by Naspers), Spotify (NYSE: SPOT), Primer, Monzo, Letgo (acquired by Naspers), Kry/Livi, Soldo, Hopin, and Sennder. Prior to Accel, Sonali was with Atlas Venture (now Accomplice). She also previously served on the board of Match.com (NASDAQ:MTCH). In Today's Episode with Sonali De Rycker You Will Learn: 1.) From Small Town in India To Leading Venture...

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20VC: From Kitchen Table to $134M Fund II; Raising Your First Time Fund: Lessons from 400 LP Meetings, How To Find New LPs, What Materials to Use, How To Get LPs To Commit, The Challenges on Minimum Check Sizes and GP Commits and more with Henri Pierre-Ja show art 20VC: From Kitchen Table to $134M Fund II; Raising Your First Time Fund: Lessons from 400 LP Meetings, How To Find New LPs, What Materials to Use, How To Get LPs To Commit, The Challenges on Minimum Check Sizes and GP Commits and more with Henri Pierre-Ja

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

is Managing Partner of , on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. From a kitchen table with his Co-Founder, Jarrid, Henri has scaled Harlem in just a few years to their latest fund last year of $134M, well over-subscribed from their $100M target. Prior to Harlem, Henri was in Private Equity at ICV Partners, and before PE was an Investment Banker at Bank of America Merrill Lynch. In Today's Episode with Henri Pierre-Jacques 1.) From Kitchen Table to $134M Fund: How did Henri make his way into venture having had...

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20 Sales: Why Founders Should Not Be The One To Create The Sales Playbook, How To Structure Each Interview in the Hiring Process For Sales Reps, How To Use an 20 Sales: Why Founders Should Not Be The One To Create The Sales Playbook, How To Structure Each Interview in the Hiring Process For Sales Reps, How To Use an "Interview Panel" Effectively and more with Zhenya Loginov, CRO @ Miro

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

is the CRO @ , the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas. In Today's Episode with Zhenya...

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20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investments; Twitter, Fa show art 20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investments; Twitter, Fa

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

is a serial entrepreneur and serves as the Chairman of ,  the CEO of  and the Creator & CEO of . Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the...

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20VC: The Scaling Story of Soho House: Overcoming Dyslexia, Building a Global Brand, Scaling into The US, Retaining Exclusivity with Scale and The Journey to Going Public with Nick Jones, Founder & CEO @ Soho House show art 20VC: The Scaling Story of Soho House: Overcoming Dyslexia, Building a Global Brand, Scaling into The US, Retaining Exclusivity with Scale and The Journey to Going Public with Nick Jones, Founder & CEO @ Soho House

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

is the Founder & CEO @ , it all started in 1995 when Nick opened the first location above his restaurant, Cafe Boheme, a members’ club for the local artists and actors of London. Today, Soho House is a global brand, a private members club that includes 33 Houses in 14 countries, with more openings in Europe, Asia, and North America on the horizon. In 2021, Nick took Soho House public on the NASDAQ, 25 years since opening the first location. If that was not enough, Nick is also the owner of Babbington House and Cecconi's, one of my favorite restaurants in London. In Today's Episode...

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20 Growth: Viral Loops; How To Create and Sustain Them, Why Interviews for Product and Growth Hires are BS and What To Do Instead, Mastering the Onboarding Process; Structuring the First 90 Days with Adam Fishman, Former Head of Growth @ Lyft show art 20 Growth: Viral Loops; How To Create and Sustain Them, Why Interviews for Product and Growth Hires are BS and What To Do Instead, Mastering the Onboarding Process; Structuring the First 90 Days with Adam Fishman, Former Head of Growth @ Lyft

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

is one of the leading growth practitioners of the last decade. Most recently, Adam was the Chief Product and Growth Offer at Imperfect Foods, where Adam built a 40-person product and growth organization, responsible for 70% of overall company metrics and growing revenue by 400% in one year to $600M annually. Before Imperfect, Adam spent 4 years as VP of Product and Growth @ Patreon, driving the company pivot and rebrand and helping the company scale to $1BN GMV and $100M in revenue. Finally, before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee...

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20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Face, Angel Investing Rules; No Founder Meetings and No Due Diligence, SMB vs Enterprise; Lessons on Pricing, Distribution and Why You Should Resist Going Enterprise show art 20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Face, Angel Investing Rules; No Founder Meetings and No Due Diligence, SMB vs Enterprise; Lessons on Pricing, Distribution and Why You Should Resist Going Enterprise

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

is the Founder and CTO @ , a full CRM platform with marketing, sales, service, and CMS software. Dharmesh started Hubspot in 2006 and today it is a publicly-traded company (NYSE: HUBS) with over 3,500+ people and a market capitalization of $16.9 billion. Prior to founding HubSpot, Dharmesh founded , which he bootstrapped with less than $10,000 and after 11 years of CEOship, Dharmesh helped the company get acquired in 2005 by . In addition to co-authoring “Inbound Marketing" Dharmesh founded and writes for OnStartups.com -- a top-ranking startup blog and community with more than...

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20VC: Why and How Traditional Venture Firms Need to Innovate, Building Spreadsheets To Figure Out Relationships to Money, Ego and Identity Management with Success and The Biggest Lessons from Working with Mark Zuckerberg in the Early FB Days with Ruchi Sa show art 20VC: Why and How Traditional Venture Firms Need to Innovate, Building Spreadsheets To Figure Out Relationships to Money, Ego and Identity Management with Success and The Biggest Lessons from Working with Mark Zuckerberg in the Early FB Days with Ruchi Sa

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

is a Founder and Partner @ South Park Commons Fund, a home for the most talented technologists, builders, and domain experts figuring out what's next. Prior to SPC, Ruchi was the first female executive at Dropbox and served as their Vice President of Operations. Prior to Dropbox, Ruchi was the first female engineer at Facebook, and was instrumental in implementing the first versions of key features like News Feed, Facebook Platform, Facebook Connect and Privacy. Ruchi has also served as a director on the board of Paytm, India’s largest mobile payments platform. Prior to SPC, Ruchi was an...

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More Episodes

Oliver 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?