Rethink:Revenue

Arjun Pillai
  • 5.0 (3)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

Hosted by DocketAI CEO Arjun Pillai, Rethink:Revenue is a must-listen podcast for go-to-market teams and ambitious revenue leaders. Arjun dives deep with top guests, breaking down the toughest challenges, winning strategies, and cutting-edge tech—especially AI—that are driving growth. But it's not just about today; this show looks ahead to the future, where AI will redefine what it means to be a GTM leader. Tune in to learn what today's revenue leaders need to succeed in an AI-driven world.

Episodes

  1. MAR 6

    Driving Durable GTM Performance in a Shifting Market

    Arjun Pillai and Stevie Case unpack what's working right now in B2B GTM and what breaks as you scale. Stevie shares how the CRO role evolves over time at Vanta, expanding from sales to owning the full customer journey globally. She gives a grounded definition of product-market fit: it's not an ARR milestone, it's something you can hear in customer conversations, and if you're constantly fighting for dollars, PMF likely isn't there yet. They dig into pipeline evolution, including why inbound is powerful early but has a ceiling, and how Vanta built a true outbound engine by scaling SDR capacity and operationalizing new messaging, methodology, and AE-SDR collaboration. Stevie also makes a clear case for cold calling, especially for early-stage companies with limited awareness, as long as the outreach is thoughtful and informed. Finally, she outlines Vanta's AI approach: use AI to supercharge reps by automating prep, follow-ups, and repeatable workflows, then democratize top-performer plays and enable teams to build their own agents.

    38 min

  2. FEB 10

    The Trust-First Revenue Playbook : Stop selling. Start advocating. Trust as the real KPI in long enterprise sales cycles.

    Enterprise selling in 2026 isn't just harder. It's different. Buyers have more options, more risk, and less patience for vendor-speak. In this episode of Rethink Revenue, Arjun Pillai sits down with Lax Gopisetty (CEO, Infosys Public Services) to break down what's actually changing in B2B buying and how revenue leaders should adapt.  Lax argues the biggest shift is moving from "selling" to customer advocacy. Especially in a subscription world where the real win is ongoing consumption and trust. They also dig into where AI is moving the needle today, why most enterprises struggle to translate pilots into impact, and a simple framework to prioritize AI use cases across market-facing value, internal efficiency, and experimentation. If you sell to mid-market or enterprise, this episode will help you rethink your GTM approach from the buyer's perspective In this episode, we cover: Why buyer behavior should drive GTM strategy Subscriptions, servitization, and the end of SKU-style selling Trust as the real KPI in long enterprise sales cycles Land-and-expand vs whale hunting (and why you should run both)

    34 min

  3. 09/11/2025

    Chris Andrew on the AI-First Buyer Journey and Why Static Websites Are Dying

    In this episode of Rethink:Revenue, Arjun Pillai (CEO of DocketAI) is joined by Chris Andrew (CEO of Scrunch) for a no-fluff, tactical conversation on how the AI-first buyer journey is rewriting the B2B playbook. Together, they unpack how traditional SEO is giving way to answer engine optimization, why static blue links and vanity metrics are becoming obsolete, and how AI agents are quietly reshaping the way buyers research, evaluate, and purchase. From monitoring AI agent behavior on your site to designing web experiences for AI—not humans—this is a must-listen for GTM, RevOps, and marketing leaders ready to embrace the next era of selling.   ⏱️ Chapters: 00:00 – Intro & why this is not a typical webinar 00:28 – What is the AI-first buyer journey? 01:24 – AI replacing human browsing with personal synthesis 02:19 – Google-optimized content vs AI-optimized content 04:15 – How AI agents are scraping your website right now 06:07 – AI traffic converts 3x higher than Google traffic 07:32 – Why marketers must move past site traffic metrics 08:58 – How to monitor AI visits to your website 10:20 – From inbound marketing to community-driven GTM 12:09 – Answer engine optimization (GEO) vs SEO 13:58 – Tips to make your content more AI-readable 15:23 – Why interactive websites fail AI agents 16:44 – Reddit, reviews, and the importance of third-party sources 18:11 – Autonomous selling and AI-powered digital AEs 20:04 – AI handling the entire SMB buying cycle 21:30 – The trust problem: AI vs mediocre human reps 23:52 – AI agents buying from AI agents: a near-future reality 25:39 – What Scrunch does: monitoring & optimizing AI interactions 27:34 – Websites as AI-facing interfaces 29:00 – Final takeaways & the rise of a non-visual internet

    34 min

  4. 07/01/2025

    Hannah Ajikawo on Rethinking the Buyer Journey and the Real Role of AI in GTM

    Listen in as host Arjun Pillai, Cofounder & CEO of Docket, sits down with Hannah Ajikawo, GTM consultant and founder of Revenue Funnel. They unpack how most organizations are still built around sales processes instead of buyer experiences, why AI is creating both urgency and opportunity for CROs, and how leaders should rethink pipeline, conversions, and executing with lean teams. Hannah shares frameworks on optimizing the entire funnel, common mistakes in revenue orgs, and the value of running consistent audits to spot overlooked growth wins. They also explore what AI tools she sees as "non-negotiable" today, from conversation intelligence to content repurposing and agents that draft follow-ups. Chapters 00:00 Introduction & Hannah's background 03:17 What keeps Hannah up at night as a revenue leader 04:20 The role of AI in GTM and where most orgs go wrong 07:19 Buyer alignment vs sales process misalignment 11:00 Why mid-market may close as fast as enterprise 14:13 The cost of unprepared sales teams & buyer trust 16:00 Top 3 problems CROs bring up: pipeline, execution, AI 19:00 The non-negotiable AI tools for GTM teams today 21:40 How Hannah would automate her own sales workflows 23:55 The power of outside audits & overlooked funnel fixes 27:00 Final thoughts and where to find Hannah

    30 min

  5. 06/13/2025

    Deven Budgujar on Scaling Sales Teams Without Burning Them Out

    In this episode of Rethink Revenue, Arjun Pillai (CEO, DocketAI) sits down with Deven Budgujar, Director of Sales at Datarails, to talk about the pressures facing today's sales leaders — and how to scale GTM teams with intention. From enabling reps to focus on what they do best, to the pitfalls of sales training that doesn't stick, Arjun and Deven break down the mindset shifts modern leaders need to navigate the ever-changing B2B landscape. 🎯 You'll hear practical insights on leading through change, unlocking just-in-time enablement, and why sometimes the best thing a leader can do… is get out of the way. Chapters 00:00 – Introduction 01:48 – What Keeps Sales Leaders Up at Night 05:12 – Scaling a Sales Team with Role Clarity 08:45 – Creating Focus: Let Reps Do What They Do Best 12:10 – The Real Problem with Traditional Sales Training 16:33 – Just-in-Time Enablement and AI Support 20:40 – Coaching in a Fast-Changing Environment 25:08 – Final Thoughts and Advice to Sales Leaders 🎧 Tune in to rethink how you build, scale, and empower revenue teams in 2025 and beyond.

    30 min

  6. 03/20/2025

    Peleg Israeli on AI with a Human Connection

    Listen in as host Arjun Pillai, cofounder and CEO of DocketAI,  and Peleg Israeli, the CRO of Voyantis, discuss the role of AI in sales and marketing, and the importance of human connection in a tech-driven world.  Arjun and Peleg examine the shifts in the advertising landscape due to AI, the misconceptions surrounding predictive AI, and the need for continuous learning about AI.  Tune in for more on the potential of AI in enhancing customer onboarding processes. Chapters 00:00 Introduction  02:33 Challenges of Rapid Growth as a CRO 04:20 The Role of AI in Sales and Marketing 07:19 Shifts in the Advertising Landscape 11:22 Human vs. Machine: The Value of Human Connection 15:38 AI's Potential in Customer Onboarding 17:35 Common Misconceptions about Predictive AI 20:18 Continuous Learning and Leadership 23:55 Final Thoughts and Observations on AI in Revenue Strategy

    27 min

  7. 03/20/2025

    James Buckley on Bridging Generational Gaps in Sales

    Tune in for a conversation between host Arjun Pillai, cofounder and CEO of DocketAI, and James Buckley, host of the Sell Better Daily Sales Show.  Their conversation explores the evolving nature of sales, dissecting the challenges posed by generational shifts in the profession. Listen in as James reflects on his own trajectory in sales, offering insights into the growing influence of personal branding and influencer marketing and shares the importance of prioritizing quality over quantity in sales strategies. Together Arjun and James make the case for closer collaboration between sales and marketing teams as a cornerstone of sustained success. Chapters 00:00 Introduction to the Podcast and Guest 02:30 Challenges in Modern Sales and Influencer Marketing 06:03 James Buckley's Journey in Sales 10:08 Bridging the Generational Gap in Sales 12:04 The Role of AI in Sales 16:18 Challenges Faced by CROs Today 22:16 AI's Impact on Sales Processes 25:33 Personal Automation Preferences 26:32 Recommended Resources for Sales Professionals 28:13 Advice for New Sales Leaders 30:34 Closing Remarks and Contact Information

    32 min

  8. 03/20/2025

    Steve Armenti on The Role of AI in Sales & GTM

    Join host Arjun Pillai, cofounder and CEO of DocketAI, for a conversation with Steve Armenti on his transition from sales to marketing and his tenure at Google and DigitalOcean. In this conversation, they examine the evolving nature of marketing in the age of AI and the shift away from conventional lead-generation models toward a more sophisticated, account-based approach.  In an era of increasing complexity, Steve makes the case for cross-functional collaboration as a necessity for driving operational efficiency and sustainable growth. Chapters 00:00 Journey into Marketing and Sales 10:18 Navigating Uncertainty in Marketing 12:22 Shifts in Go-to-Market Leadership 14:09 Inefficiencies in the Revenue Funnel 19:30 The Role of AI in Sales Development 24:27 The Importance of Data Infrastructure

    29 min

  9. 03/20/2025

    Robert Clarkson on Navigating the CRO Role in Fintech and the Impact of AI on Decision Making

    In this episode, Arjun Pillai, cofounder and CEO of DocketAI, is joined by Robert Clarkson, CRO of the Americas at Stripe. Together they share insights into the challenges and strategies of revenue leadership in the fintech space.  You won't want to miss this discussion on the importance of hiring the right talent, the impact of AI on decision-making, and the dynamics of sales execution in a changing market. Tune in for valuable advice for aspiring revenue leaders. Chapters 00:00 Introduction  03:30 Understanding the Role of a CRO 05:06 Challenges Faced by Revenue Leaders 14:15 Sales Execution and Market Dynamics 22:15 The Impact of AI on Revenue Strategies 30:20 Key Insights for Aspiring Revenue Leaders

    29 min

  10. 03/19/2025

    Jessica Gilmartin on Mastering GTM Growth in an Era of Change and The Transformative Role of AI in Revenue Operations

    In this inaugural episode of the rethink:Revenue podcast, host Arjun Pillai, cofounder and CEO of DocketAI, welcomes Jessica Gilmartin, former CMO and CRO at Calendly. This conversation on mastering growth in an era of change dives into the evolving expectations of CROs, dissecting the complexities of pipeline generation, customer acquisition, and the shifting dynamics between sales and marketing. Together, they examine the transition from marketing leadership to sales, as well as the transformative role of AI in revenue operations. Chapters 00:00 Introduction to Jessica Gilmartin 00:58 The Evolving Role of the CRO 05:46 Transitioning from Marketing to Sales 10:12 Customer Acquisition Costs and Retention 12:00 Navigating PLG and SLG Strategies 19:59 The Impact of AI on Sales 24:08 Continuous Learning and Networking for Leaders

    30 min
  • 10 Episodes

5
out of 5
3 Ratings

About

Hosted by DocketAI CEO Arjun Pillai, Rethink:Revenue is a must-listen podcast for go-to-market teams and ambitious revenue leaders. Arjun dives deep with top guests, breaking down the toughest challenges, winning strategies, and cutting-edge tech—especially AI—that are driving growth. But it's not just about today; this show looks ahead to the future, where AI will redefine what it means to be a GTM leader. Tune in to learn what today's revenue leaders need to succeed in an AI-driven world.

Information

  • Creator
    Arjun Pillai
  • Years Active
    2025 - 2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    Rethink:Revenue