 Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count.    In Today's Episode with Matt Rosenberg We Discuss:   1. From Miserable Lawyer to World Beating Sales Leader:    How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence?    2. The Playbook and Hiring The Team:    How does Matt define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire?    3. Discounting, Champions and Urgency:    What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting?    4. Developing Great Sales Talent:    How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally?  

20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt R

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. 

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

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 Nikesh Arora is the CEO @ Palo Alto Networks, the leading cybersecurity company in the world with a market cap of $102BN. Before joining Palo Alto Networks, Nikesh was the President and COO of SoftBank Group. Before that, he spent ten years at Google as a senior exec, and President of Europe, the Middle East and Africa. Before that Nikesh was CMO for the T-Mobile International Division of Deutsche Telekom AG. Nikesh serves on the board of Compagnie Financière Richemont S.A. Previously, he served on the boards of SoftBank, Sprint, Colgate-Palmolive Inc., Yahoo! Japan and Tipping Point.    In Today's Episode with Nikesh Arora We Discuss:   1. From Investing with Masa @ Softbank to CEO of Largest Cyber Company:    What are Nikesh's biggest lessons from working and investing with Masa @ Softbank?  What are Nikesh's biggest takeaways from 10 years at Google and working with Eric Schmidt?  What does Nikesh know now that he wishes he had known when he started his career?    2. What Makes the Most Valuable Businesses in the World:    How does Nikesh think about competition and monopolies?  How does Nikesh assess the idea of defensibility, moats and sustaining competitive advantages?  What are the most common reasons why incumbents are overtaken?  How have Palo Alto Networks been so successful in their M&A; strategy?  What has worked in M&A;? What has not worked? What is their process?    3. What Makes the Best Leaders in the World:    Does Nikesh agree that the best CEOs are the best resource allocators?  How do the best leaders communicate with large teams at scale?  How do the best leaders approach decision-making? What is Nikesh's framework?  How does Nikesh approach the idea of delegation? What does he delegate vs what does he not?    4. Behind the CEO: Nikesh Arora: Husband and Father:    How does Nikesh reflect on his own relationship to money today?  What are Nikesh's biggest lessons in what it takes to bring children up in a world of affluence and ensure they have hunger and ambition?  What are some of Nikesh's biggest lessons on parenting?  How does Nikesh reflect on what it takes to have a great marriage?    

20VC: Palo Alto Networks CEO Nikesh Arora on How to Create and Sustain Competitive Advantage and Defensibility | What Makes Masa Son a Genius Investor of Our Time | How the Best Leaders Communicate an

Jiaona “JZ” Zhang is the Chief Product Officer at Linktree, the world’s leading link-in-bio platform empowering 45M+ creators, brands and SMBs. JZ joined Linktree from Webflow, where she served as SVP of Product. Before that, she spent four years at Airbnb where she built and led numerous teams on the host side. JZ’s also held leadership roles at the likes of Wework, Dropbox and teaches at Stanford University and Reforge. In Today’s Episode with Jiaona Zhang We Discuss:   Entry into the World of Product     How did JZ first fall in love with product?   Why does JZ believe the best PMs have experience in the gaming industry?   Does JZ think Linktree could be a $100BN business? How could Linktree become a $100BN business?     Mastering Product Metrics     Why does JZ think product is the most chameleon role? Where does product start & end?    Why does JZ think every function should have tension with product?   What is a KPI tree? How does JZ branch business & product metrics?   When does JZ think startups should set up a metric infrastructure?   What are the three levers of product? How does JZ determine which ones to trade off?     How to Run Product: Planning, Strategy, & Rituals     Why does JZ think planning should not exist?   What are strategy and rituals? When should founders do either?   What are JZ’s three core rituals?   What is the scorecard method? How do they help team transparency?   What are product jams? When does it work? When does it not work?     Product Career Advice     When does JZ think founders hire a product person?    What are the most common mistakes early stage founders make when hiring for product?   Does JZ think domain expertise is important? What does she look for in product hires?   What is JZ’s advice to PMs who want to get promoted today?    What is JZ’s advice to young people who want to get into product?    

20Product: How Linktree, Webflow and Airbnb Used Rituals and Product Principals to Guide Product Roadmap, Why All Product Teams Should Have a Scorecard and How to Use it & How to Run the Best "Product

 Dan Siroker is the Co-Founder and CEO @ Limitless, a personalized AI powered by what you’ve seen, said, or heard. For his latest funding round, Dan took an unusual approach resulting in 1,000 preliminary offers with valuations as high as $1BN — and resulted in a $350 million Series A valuation. Prior to founding Limitless, Dan was the Founder of Optimizely, scaling the company to $120M in ARR and raising from some of the best in the business including Peter Fenton @ Benchmark who led the Series A.    In Today's Episode with Dan Siroker We Discuss:   1. Serial Entrepreneurs are More Investable:    Why would Dan always prefer to invest in serial entrepreneurs than first time founders?  How do serial entrepreneurs approach team building and size of team differently?  How do serial entrepreneurs approach focus and prioritisation differently?  How do serial entrepreneurs approach pivoting differently to first time founders?  What is Dan's advice from Elad Gil and YC's Dalton Caldwell on when to pivot?    2. The Secret to Fundraising: How to Speak VC    Should founders always be raising?  What is the right thing to respond to investors when they reach out to you outside of a round?  What question are investors really asking when they ask, how much are you raising?  How should founders approach valuation, what should they say when they are asked for it?  How can founders create urgency in a funding round? What works? What does not?    3. How to Raise the Best Funding Round:    Should founders engage with associates or only worth it with decision-makers?  Why should founders always choose the investor who is on the early arc of their career?  Why was Dan's first meeting with Peter Fenton the best meeting he has ever had with a VC?  Why does Dan believe that taking the highest price is never the right answer?  To what extent does having a true Tier 1 VC lead your round, change the game for your company?    4. Dan Siroker: AMA:    How did becoming a father change the way that Dan operates?  Why is Dan scared we might see technological progress stall for the next 20 years?  Why did Dan not do YC the second time around with Limitless?  What is the story of how Optimizely nearly bought Amplitude?    

20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of Coll

 Tom Blomfield is a Group Partner at YC. Before YC, Tom founded two unicorns in the UK. He was co-founder of Monzo (most recently valued at $5BN), one of the first challenger banks in the UK. Monzo raised more than £1bn and counts 15% of the UK population as customers. Before Monzo, Tom founded GoCardless (YC S11), an online payments processor, most recently valued at $2.1BN.    In Today's Episode with Tom Blomfield We Discuss:   1. From Founding Two Unicorns to YC Partner:    Does Tom believe that all great founders show signs of exceptionalism early?  What does Tom know now that he wishes he had known when he started his first company?  Why did Tom decide now was the right time to switch from founder to investor with YC?    2. The YC Application Process: How it Works:    How do the YC partners select which companies are accepted vs rejected?  What specifically does Tom look for in the problem the company is looking to solve?  In the interview, what are the signals of the highest quality founders?  What questions does Tom always want to ask in YC interviews with founders?    3. The YC Batch: How it Works:    How do the YC partners work with the 25 companies in their batch? What is the interaction?  What are the single biggest mistakes companies make while in YC?  What are the biggest pieces of advice YC gives founders on fundraising approaching demo day?  How do the best YC founders fundraise and use demo day? How do the most nervous fundraise?  How are YC partners measured in terms of their success and effectiveness?    4. AI: Consumer vs Enterprise/ Infrastructure vs Application Layer:    Does Tom believe there is money to be made investing in infrastructure layer models today?  Why is the commoditization of foundation models the best outcome for society?  Why is Tom most excited about the application layer for the next wave of AI?  What are the most exciting opportunities in consumer AI that are wide open today?  20VC: Behind the Scenes at Y Combinator: The Interview Process | What the Best & Worst Do in the Program | Do the Best All Raise Pre-Demo Day & YC's Fundraising Advice to Startups | Why the Value is in Application Layer AI with Tom Blomfield 

20VC: Behind the Scenes at Y Combinator: The Interview Process | What the Best & Worst Do in the Program | Do the Best All Raise Pre-Demo Day & YC's Fundraising Advice to Startups | Why the Value is i

Larry Shurtz is the Chief Sales Officer at Genesys where he oversees the company’s global go-to-market strategies, including commercial activities, field sales and partner ecosystem operations. Larry has nearly three decades of experience in the software industry, from leading Confluent to delivering more than 60% revenue growth and doubling customer count as Chief Revenue Officer, to scaling a 1,300-person team at Salesforce to $2.1 billion in revenue. In Today’s Episode with Larry Shurtz We Discuss:   From Robotics Student to $2.1BN Sales Leader at Salesforce     How did Larry lead 1300 people to $2.1 billion revenue at Salesforce? What were his takeaways?   What did Larry learn about building vertical sales playbooks at Salesforce?   Which framework did Larry learn at Salesforce that he still uses at Genesys?     Mastering Sales Leadership     What are the biggest mistakes sales leaders make on prioritization today?   What are Larry’s “3 Rs” to master prioritization?   What does Larry think are the most common reasons fast-scaling teams break in sales?   Has Larry ever caused bad culture in a sales team? What did he learn from the experience?   Does Larry think sales is more art or science? How does Larry blend the two?     Building the Best Sales Team     How does Larry structure the hiring process for a new sales hire?   How big should your recruitment team be?    What are Larry’s most commonly asked questions when interviewing?   What were Larry’s biggest hiring mistakes? What did he learn from them?   How does Larry structure the comp? How does he get it right? What do most new hires care about today?     The Onboarding: The Dos & Don’ts     How does Larry structure the onboarding process?   Why does Larry onboard new hires with big customers? What is the buddy system?   How does Larry tell if a new hire is bad? What are the biggest red flags to look out for?   What does Larry mean when he says “You can make all the physical errors, you cannot make mental errors?”   Does Larry agree with Max Levchin @ Affirm that “When there’s doubt, there’s no doubt?”  

20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People wit

20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt R

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