Oliver Jay

Oliver Jay, a highly successful sales leader and former CRO at Asana, shares invaluable insights from his extensive experience in tech sales. He discusses what truly makes a sales playbook effective and why it should evolve with the company. Jay emphasizes the delicate balance between product-led and enterprise sales and highlights the essential qualities to look for in sales rep candidates. He also explores the importance of proper onboarding and the art of tackling complex sales compensation plans to drive team motivation.

Oliver Jay, former CRO at Asana, discusses common mistakes PLG companies make, how to avoid the 'PLG trap', transitioning to enterprise, building an enterprise sales team, and breaking $10 billion market cap. He also explores the challenges of transitioning from individual to enterprise usage in PLG companies and the growth of Atlassian's product ecosystem.

Oliver Jay, former Chief Revenue Officer of Asana, discusses product-led growth (PLG) in B2B sales. He explains PLG's impact, different models, factors to consider, managing trials, and combining PLG with sales-led growth. The importance of measuring metrics and analyzing user behavior is highlighted, as well as challenges and strategies for expanding upmarket in PLG.

Stop looking at playbooks, and start looking at the learnings. Because success is always about context.And with the right planning, PLG startups can set themselves up the PLG trap – where PLG companies with around 5 billion dollar valuation tend to stall, while others break out to 20 billion dollars or more.Host Mark Roberge is joined by Oliver Jay, (Founding CRO, Asana) to discuss the inappropriate cut and paste of PLG practices. In this episode learn more about: The importance of running experiments on the side (to unleash new growth opportunities before they’re needed) The power in a joint mindset with the rest of the leadership team Leverage your influencing skills The difference between an exceptionally run company vs. average run company The Science of Scaling is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network in collaboration with HubSpot For Startups // Produced by Matthew Brown.

Former Product Led Sales leader at Dropbox and CRO at Asana, Oliver Jay, discusses the challenges of scaling PLG models. Topics include PLG dominance dynamics, struggles for non-leading companies, compatibility with enterprise sales, hybrid scalability approaches, and the layered nature of PLG growth.