Arjun Pillai from Docket on Building Startups, Navigating Acquisitions, and the Future of AI in Sales

I am excited to have Arjun Pillai Cofounder & CEO of Docket, an AI Platform that serves as a Virtual Sales Engineer for AEs to close complex B2B deals. He is a serial entrepreneur with two successful exits and is currently on his 3rd venture. Arjun was most recently the Chief Data Officer at ZoomInfo Technologies Inc. In this episode, Arjun Pillai, Docket's co-founder and CEO, shares his journey from Kerala, India, to Silicon Valley, highlighting early startup experiences, failures, and successes with companies like Profoundis and Incent. He discusses the acquisition of his previous ventures, the evolution of Kerala's startup ecosystem, and his passion for AI, which inspired him to build Docket, an AI-powered virtual sales engineer. Arjun offers valuable insights on topics like building resilient teams, fundraising strategies, and the future impact of AI on SaaS, sales roles, and startup playbooks, and much more! Subscribe on Spotify Subscribe on YouTube Subscribe on iTunes Learn * How did Arjun approach fundraising for Docket * How does Arjun see AI transforming the sales and marketing landscape? * What are the single biggest mistakes people make when hiring sales reps and teams? * What is your favourite business book? –Hard things about hard things * What is your favourite online tool? –Zoom, chatgpt, loom, screen studio * If you could go back to when you started working, what is the one thing you would have focused on? – Nothing Timestamps 03:30 - Arjun's first startup experience with Profounders and early challenges. 05:15 - Importance of frugality and team cohesion in Arjun's early days. 07:10 - Building Profoundis, a successful sales intelligence product. 09:20 - Profoundis’s acquisition by Full Contact, marking Kerala’s first significant startup exit. 12:05 - Kerala’s evolving startup ecosystem following Arjun's exit. 13:40 - Arjun's transition from Full Contact to founding Insent 16:10 - Pivoting Insent’s business model to a buyer-centric platform. 18:00 - Acquisition of Insent by Zoom Info and Arjun's new role there. 21:15 - Arjun's experiences and learnings from working with Zoom Info. 23:05 - Inspiration for Docket, his AI platform for sales engineering. 27:40 - Evolution of SDR roles and potential shifts due to AI. 30:20 - Future of SaaS companies in the era of AI. 32:15 - Cost and efficiency changes in software development using AI. 35:30 - Founders' role in creating playbooks for revenue teams. 37:45 - Timing for hiring a VP of Sales in a startup’s growth phase. 40:10 - Sales team ramp-up expectations and performance indicators. 42:30 - Structuring effective sales compensation plans. 45:00 - Fundraising strategies for founders, including the importance of building investor relationships. 47:30 - Key metrics for choosing the right investors for your startup. Arjun’s Links  LDN– https://www.linkedin.com/in/rarjunpillai Website - https://www.docketai.com/ My Links  Podcast: https://lifeselfmastery.com/itunes YouTube:  youtube.com/lifeselfmastery Twitter: https://twitter.com/rohitmal 5-day email course: www.enterprisesalesexpertise.com Newsletter:  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit partnergrow.substack.com