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.

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)

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.

• 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

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.

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

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.

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.

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

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

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