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

Sid Sijbrandij, Co-founder and CEO of GitLab, shares insights on leading a successful remote-first company. He debunks the notion that everyone will return to the office, emphasizing key strategies for effective remote work. Sid also explores the evolution of his leadership style, the value of CEO coaching, and the importance of written communication in organizations. He discusses GitLab's unique meeting culture and highlights common pitfalls that companies face during the transition to remote work.

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM. In Today’s Episode with Jeanne DeWitt Grosser You Will Learn: 1.) Entry into Sales: How did Jeanne make her way into her first sales job in tech? What did Jeanne learn from her many years at Google about how sales should interact with engineering? In hindsight, what would Jeanne have done differently/improved from her time with Dialpad? How did the role with Stripe come about? 2.) The Playbook: Does the founder need to be the one to create the sales playbook? When is the right time to bring in the first sales hire? Should they be a sales leader or rep? How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion? What are the single biggest mistakes founders make when hiring their first in sales? 3.) The Hiring Process: How should founders structure the hiring process for their first sales hires? What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe? What should be achieved or learned in each consecutive interview? How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product? What are early signs of a 10x sales hire? What are red flags to look out for in the process? 4.) Sales Onboarding: What does the ideal onboarding process look like for new sales hires? What tasks and duties should all sales hires perform in the first 60 days? What are early signs that a new hire is not performing to the right standard? How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company? What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

Harley Finkelstein, President of Shopify and a prominent entrepreneur, shares insights from his journey in building a billion-dollar tech giant. He delves into the importance of vulnerability and authenticity in leadership, revealing personal growth and insecurities. Harley discusses the art of marriage, emphasizing communication and collaboration with his wife. He illustrates how fatherhood reshapes priorities and values, while advocating for balance between work and family life, ultimately inspiring listeners to embrace their own journeys.

Scott Dietzen, Vice Chairman of Pure Storage and a four-time entrepreneur, shares insights from his rich tech journey. He highlights the biggest mistakes founders make when scaling, particularly in hiring top talent. Trust-building in teams is essential; he emphasizes honest communication even about failures. Dietzen connects lessons from startup struggles to parenting, advocating for role modeling as a key to success. His approach fosters transparency, encourages learning from losses, and promotes a supportive company culture.

Sahil Bloom, the Founding Partner at SRB Ventures, previously managed over $3.5 billion at a large investment fund. In this discussion, he reveals how he transitioned from traditional finance to marrying venture capital with media. Sahil shares the secret to building a thriving Twitter audience, emphasizing content consistency and emotional resonance. He argues that traditional venture firms are fading and highlights the newcomers reshaping the landscape. Additionally, he discusses the strategy behind his debut $10 million fund and the evolving nature of VC.

In this insightful discussion, Doug Leone, a partner at Sequoia Capital, explores the rapid ascent of Tiger Global in the venture capital world. He emphasizes the need for a shift in venture terminology, contemplates the enduring craft of venture alongside rising competitors, and analyzes the impact of hedge funds entering the space. Insights from other VC leaders like Bill Gurley and Michael Eisenberg highlight the challenges of increased competition and the strategic advantages of substantial capital in today's evolving market. This conversation unpacks the future landscape of investment.

Max Rhodes, Co-founder and CEO of Faire, shares insights from his journey in the startup world, particularly his impactful tenure at Square. He discusses the essential steps to hire the best candidates, focusing on behavioral interviews and identifying red flags. Max elaborates on the importance of a clear strategy document and how to create it collaboratively. He also highlights the art of referencing, sharing techniques to encourage openness and transparency, ensuring well-informed hiring decisions. Tune in for effective hiring and strategy tips straight from a venture capital success story!

Ed Baker, an angel investor and former VP of Growth at Uber and Facebook, shares his journey from founding a dating site at Harvard to leading monumental growth teams. He discusses the right timing for startups to hire growth leaders and the importance of achieving product-market fit first. Ed outlines his structured interview process, identifying key qualities for exceptional growth hires. He highlights the significance of experimentation in growth strategies, the impact of user experience on conversions, and the collaborative nature of successful growth teams.

Geoff Lewis, Founder and Managing Partner at Bedrock, dives deep into the venture capital world, sharing his investment journey from Founders Fund to launching Bedrock. He challenges the traditional belief that ownership is paramount, emphasizing the importance of principles over rules in firm building. Geoff candidly reflects on his biggest misses and their impact on his investment mindset. He discusses the need for independent thinking, highlights the challenges of narrative violations in investments, and even shares insights on the evolving landscape of cities like Austin and Miami.

Aaron Levie, the Founder and CEO of Box, shares his journey from dorm room to IPO. He discusses the importance of commitment in entrepreneurship and why founders can't hedge their bets. Levie highlights the challenges of over-funding startups and provides insights on effective resource allocation. He reflects on leadership evolution during company growth, encouraging focused decision-making in product strategies. Additionally, Levie offers thoughts on market valuation disparities and the impact of economic pressures on startups. It’s a candid conversation about navigating the complexities of innovation and growth.