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.
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.
10 Feb 2026
The Trust-First Revenue Playbook : Stop selling. Start advocating. Trust as the real KPI in long enterprise sales cycles.
Infosys Public Services CEO Lax Gopisetty and Arjun Pillai discuss how enterprise selling is evolving, emphasizing customer advocacy and trust as key performance indicators in subscription-based models; this is an interview.
11 Sept 2025
Chris Andrew on the AI-First Buyer Journey and Why Static Websites Are Dying
Arjun Pillai (CEO of DocketAI) interviews Chris Andrew (CEO of Scrunch) about how the AI-first buyer journey transforms B2B selling, making static websites obsolete.
1 Jul 2025
Hannah Ajikawo on Rethinking the Buyer Journey and the Real Role of AI in GTM
GTM consultant Hannah Ajikawo discusses with Arjun Pillai how companies should focus on buyer experience rather than sales processes, and how AI offers opportunities for revenue growth, in this interview.
13 Jun 2025
Deven Budgujar on Scaling Sales Teams Without Burning Them Out
Deven Budgujar discusses scaling sales teams effectively without causing burnout, emphasizing role clarity and just-in-time enablement in an interview with Arjun Pillai.
20 Mar 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
20 Mar 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
20 Mar 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
20 Mar 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
19 Mar 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
Who has been a guest on Rethink:Revenue
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Lax Gopisetty
Chris Andrew
Hannah Ajikawo
Deven Budgujar
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Podcast Authority Score: 29 / 100
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