Rebuilding Customer Success for the AI Era: Lessons from a VP of Customer Success A conversation with Chad Gorman. Executive Summary This article examines how customer success leaders should rethink AI adoption, using insights from an in-depth conversation with Chad Gorman, VP of Customer Solutions and Success (North America) at LivePerson, on the Revenue Lounge Podcast hosted by Randy Likas. Rather than focusing on automation or AI features, Gorman argues that AI-ready customer success is fundamentally about visibility, data discipline, and relationship intelligence. Readers will learn: Why most AI initiatives in customer success fail before deployment  How unifying fragmented CS data is a prerequisite for AI or automation What an effective early warning system looks like  Why engagement and relationship depth are stronger leading indicators than product usage alone How AI can expose relationship “white space” across complex buying committees Where buy vs build decisions actually differ across enterprise and mid-market segments How to embed AI into CSM workflows over-relying on automation Which metrics matter when measuring AI’s impact on retention, risk, and productivity Why the real promise of AI in customer success is reclaimed time for strategic customer work Facebook Twitter Youtube From Call Centers to Customer Outcomes Gorman’s perspective is shaped by an unusual career arc. He started in contact center operations, moved into IT at DirecTV, and then crossed over to the vendor side after a colleague recruited him to Splunk. “I didn’t even know what a CSM was,” he admits. “But once I saw how customer success could be built as a scalable engine, I was hooked.” — Chad Gorman From Splunk, he went on to lead global cloud customer success at VMware, before joining LivePerson, where he now oversees customer success and professional services across North America. That mix of operator, builder, and enterprise leader shows up in how he thinks about AI. Practical. Outcome-driven. Skeptical of hype. ​​AI Adoption Fails Before Deployment Most AI initiatives stumble long before a model is ever deployed. According to Gorman, the real friction points show up earlier in the buying and approval cycle. The Hidden Gates to AI Adoption Governance reviews and AI councils Legal, compliance, and security documentation Industry-specific scrutiny, especially in financial services Undefined success metrics “You can sell software all day long. But if you are not there to shepherd customers through governance, compliance, and approval gates, adoption will stall.” — Chad Gorman Customer Success Has Become Revenue Insurance In volatile markets, customer success is no longer a post-sale support function. It is a revenue protection layer. That shift forces CS leaders to answer harder questions: Where is risk building right now? Which accounts look healthy but are quietly disengaging? Where is expansion hiding in plain sight? The answer, Gorman says, is an early warning system built on stitched data. https://youtu.be/sDdV747jBJA?si=fVE8O2bqTcf2yTeN The Anatomy of an Early Warning System Gorman is blunt about the prerequisite. “Data is non-negotiable. Full stop.” — Chad Gorman Before AI enters the picture, organizations must understand what their book of business actually looks like. Engagement Is the Most Underrated Risk Signal Product usage is table stakes. Engagement is the differentiator. Gorman emphasizes that many churn events are preceded not by usage decline, but by relationship decay. “If engagement drops and you do not notice, you end up ghosted and surprised later.” — Chad Gorman What Engagement Actually Means Engagement is not email volume or meeting counts alone. It is relationship depth across the buying group. Who shows up to meetings? Who stopped showing up? Which roles are missing entirely? Who influences decisions but never engages directly? This is where Gorman believes AI has its most immediate impact. Relationship Intelligence: Where Art Meets Science Gorman describes relationship intelligence as the intersection of human judgment and system-derived insight. “We think we know our accounts. AI shows us the white space we missed.” — Chad Gorman AI-Assisted Relationship Mapping AI can analyze: Calendar data and meeting attendance Email and collaboration patterns Role changes and stakeholder turnover Sentiment from meeting notes and transcripts At LivePerson, Gorman’s team increasingly relies on workspace-level intelligence using Google Gemini to surface patterns across meetings, documents, and communications. You can literally ask, ‘Who used to attend and no longer does?’ and get an answer.” — Chad Gorman Buy vs Build Is No Longer Binary Enterprise customers increasingly want flexibility. Some bring their own LLMs. Others rely on vendor-provided AI. Most land somewhere in between. Enterprise: Build and bring your own models Upper mid-market: Hybrid Down-market: Out-of-the-box AI The common denominator remains the same: clean, structured, accessible data. Embedding AI Into CSM Workflows Even the best insights fail if CSMs do not trust them. Gorman stresses three adoption levers: Data transparency Always link insights back to source systems. Prescriptive guidance Do not just flag risk. Recommend next steps. Respect experienceAI should augment gut instinct, not override it. Measuring AI Impact in Customer Success AI success is not measured by novelty. It is measured by outcomes. What’s Next: Agentic AI and Time Reclaimed The next wave, according to Gorman, is not better summaries. It is execution. The thing CSMs hate most is admin. AI agents that actually do the work change everything.” — Chad Gorman Examples include: Auto-generated QBRs with live data Scheduled reporting without manual pulls Automated follow-ups and task execution The payoff is not speed. It is reclaimed time for strategic customer work. Leadership Lessons From the Field When asked what advice he would give his younger self, Gorman’s answer is simple. “Know your book. Be curious. Admit what you do not know.”” — Chad Gorman Growth mindset Curiosity within and beyond the “box” Meticulous organization Executive presence Tight partnership with the AE  Want to hear more stories from revenue leaders? Subscribe to The Revenue Lounge podcast to never miss an episode! More Resources

A RevOps Playbook on the GTM Power, Careers and Hiring Strategies A conversation with Andy Mowat Executive Summary Andy Mowat has navigated the go-to-market journey from every angle—entrepreneur, operator at four tech unicorns (Box, Culture Amp, Carta), and now founder of Whispered. In this conversation, Andy shares hard-earned lessons on what separates strategic RevOps leaders from tactical executors, why the GTM tech stack is dying, how to take control of executive interviews, and why most people are dangerously cheap about investing in their careers. This isn’t theory. It’s a playbook built from someone who’s been the “wrong person for the job” four times and figured out how to win anyway. Readers will learn: RevOps is evolving from an execution function into a strategic GTM decision engine. The best RevOps leaders earn trust by forcing trade-offs, not by saying yes to everything. Legacy GTM stacks are breaking. Data fluency and AI-ready systems are becoming mandatory. GTM engineers are emerging under RevOps to automate execution and scale insight. Most executive roles are never posted. Senior hiring happens through networks and backchannels. Hiring favors builders who can get into the weeds, not just managers of managers. Strong candidates take control of interviews and show how they think, not just what they’ve done. Career leverage now comes from networks, reputation, and visible thinking, not applications. Facebook Twitter Youtube From Accidental RevOps to GTM Architect: Andy’s Career Arc Andy did not plan to end up in revenue operations. He stumbled into it the way many of the best RevOps leaders do. Early in his tech career, he joined Upwork. There was no CRM. So he built one. There was no outbound engine. So he figured out how to send a million emails. There was no formal RevOps function. So he became it. This pattern repeated. At Box, post-IPO, he took over post-sales operations, then marketing ops. At Culture Amp, he helped scale revenue from roughly $5M to $150M. At Carta, he entered during another inflection point, surrounded by leaders who understood that GTM decisions compound quickly, for better or worse. Across these roles, Andy learned something that most operators learn too late. RevOps is not a service desk. It is the economic engine room. The Real Difference between Tactical & Strategic RevOps Most RevOps leaders think their job is to execute requests efficiently. Andy believes that is how RevOps loses credibility. The inflection point in his thinking came at Box, when the company’s CCO told him “he’s not getting headcount unless the business gives it to him”. Instead of asking for budget, Andy began forcing trade-offs. He showed Sales, Support, and Customer Success how RevOps leverage could outperform incremental hiring. When leaders realized that one RevOps hire could unlock more growth than two frontline hires, budget appeared quickly. Andy’s rule is simple. If RevOps says yes to everything, it is not strategic.If RevOps forces prioritization conversations with executives, it is. “The wrong answer is ‘We got it.’The right answer is ‘Here’s the priority order I see. If we disagree, let’s take it to the CRO.” — Andy Mowat Where RevOps is Actually Headed Andy does not believe today’s GTM stack survives the next five years. He is tracking more than a dozen “CRM 2.0” challengers. His core criticism of legacy tools is structural, not cosmetic. Current GTM systems have: Clunky user experiences Data models not designed for AI Endless bolt-ons that fragment signal quality The Non-Negotiable Skills a RevOps pro Must Have Data literacy. Know what ETL and DBT actually do. Tight partnership with product and data teams. Embedded analytics and BI inside RevOps. Automation ownership, not tool babysitting. He also pushes back on the myth of the “GTM Engineer” as a shortcut. There is no shortcut. But there is a new function emerging. “GTM Engineers should live under RevOps.Their job is to automate the business and innovate for the reps.” — Andy Mowat https://youtu.be/H3CesaCmKWA What is Whispered? Whispered did not start as a company. It started as a survival mechanism. After a failed startup, Andy found himself asking a question many senior leaders never admit out loud.“Will anyone Hire me again?” At senior levels: Roles are rarely posted. Recruiters control access. Company quality is opaque. Networks go stale quietly. “Your next role won’t be posted. It’ll be whispered.” — Andy Mowat Whispered is designed for VP+ GTM leaders who are curious but cautious. It combines: Career playbooks Company backstory intelligence Unposted role discovery Network swarming across 300,000+ first-degree connections A private community that trades signal, not hype People join for roles. They stay for the network. Strategies for Hiring Senior Executives Through Whispered Hiring, Andy has interviewed dozens of CEOs, CROs, and CMOs about how they evaluate senior talent. Several patterns repeat. 1. Back-Channels Are the Highest Signal Everyone uses them. Everyone admits it. The best advice he heard recently: “Back-channel before you fall in love with a candidate.” 2. Builders Are in Demand Even at senior levels, companies want leaders who can still get into the weeds.AI has increased this expectation, not reduced it. 3. Rigid Thinkers Lose Andy calls it anti-rigidism, not ageism. Leaders who cannot adapt get filtered out quickly. 4. Slope Matters, but Only with Pattern Recognition High-growth companies love people who can outgrow their role. But leadership teams need both: Builders with slope Operators with scars Out perform your next Interview call Andy comments, treat your interview as a Sales call. Andy’s favorite interview opener is disarming. “I’m excited to meet you. What questions do you have?” Then he watches. Great candidates take control. Weak candidates wait to be prompted. Lazy questions kill momentum. Deep questions reveal how someone thinks. Interview Question Upgrade Instead of:“What’s your strategy?” Ask:“Here are three GTM constraints I see. Which one worries you most right now?” The goal is not to impress. It is to create signal. Personal Brand Without Becoming an Influencer Andy draws a line between thought leadership and performance. He writes because he cares and because writing clarifies thinking. It

Building Revenue Engines that Scale: Lessons on Forecasting, Alignment and Multi-Product Complexity A conversation with Jeff Perry Executive Summary This article unpacks the operational blueprint behind scaling a revenue org from $15M to $500M+ ARR, while steering three parallel businesses at once. It’s distilled from an in-depth conversation with Jeff Perry, Chief Revenue Officer at Carta, who brings more than two decades of GTM leadership experience across Oracle, DocuSign, and Carta. Readers will learn: How Jeff’s career evolved through three distinct phases: growth, scale, and building What the “What’s Your Gut?” forecasting method reveals about improving accuracy Why cross-functional alignment is the real competitive advantage in revenue operations How to manage multi-product complexity with different ICPs and buying motions The characteristics that separate great sellers and managers from good ones Where AI fits (and doesn’t fit) in modern revenue operations   Facebook Twitter Youtube The Journey: Three Career Arcs That Shaped a Revenue Leader 1. Oracle: The Growth Phase Jeff started his career at Merrill Lynch depositing physical stock certificates—ironic given he now leads Carta, the company eliminating physical certificates. After a brief stint, he spent many years at Oracle where he learned: Sales fundamentals through structured training programs Leadership principles by observing great (and not-so-great) mentors Scale operations as Oracle grew from 30,000 to 120,000 employees Resources were abundant. Revenue operations, sales strategy, and training programs just happened. You operated inside a well-oiled machine. 2. DocuSign: The Scale Phase Jeff made what many considered a lateral or downward move: from leading 250+ AEs at Oracle to managing a 20-person SMB team at DocuSign. Why he did it: He needed to prove he could operate in a smaller, scrappier environment where: You’re hands-on with planning and execution Resources aren’t automatic You build the machine, not just run it Over four years, Jeff doubled his team size and took on additional verticals. This experience opened the door to Carta. 3. Carta: The Building Phase Jeff joined Carta in late 2018 when the company was at ~$15M ARR with 275 employees. Today: $500M+ ARR 1,800 employees Three distinct businesses operating under one roof “Sometimes you have to get one door opened up to lead to the next door. Oracle opened the DocuSign door. DocuSign opened the Carta door.” — Jeff Perry The Multi-Product Challenge: Managing Three Companies Inside One When Jeff joined Carta, it was a single-product cap table business. Today, it’s three distinct revenue engines. Venture-backed companies Venture Capital firms Private Equity The Growth Strategy: Classic Spreadsheet-to-Software Carta’s playbook: Identify a spreadsheet problem (cap tables, back office GL, ownership tracking) Build software to solve it Add adjacent products that create cross-sell and upsell opportunities “I can’t have one AE that sells cap tables to venture-backed C-Corps and fund administration to private equity firms. We’ve built teams within that align to the ICPs” — Jeff Perry Building Multi-Segment GTM Systems Without Chaos Each market Carta serves has its own logic: Startups care about cap tables, compensation benchmarks Venture firms care about GL automation, fund admin Private equity teams want scenario modeling and ownership accuracy The Challenge Different products have different: ICPs (leading to data segmentation issues) Sales cycles (transactional vs. enterprise) Buyer journeys Conversion benchmarks Example issue:A prospect reaches out to Jeff about their product. Jeff searches the CRM. The company isn’t there. Why? They were doing business under a different name. The data doesn’t connect. The RevOps Implication: As you add products with different ICPs, you can’t force unified systems. You need: Separate sales teams aligned to buyer personas Different quota structures Distinct sales motions (transactional vs. enterprise) The “Don’t Lose Alone” Philosophy: Why Lone Rangers Fail Jeff flips the classic advice: people say “Don’t try to be the hero.” He says don’t lose alone. Early-career reps want to be the savior who lands the big deal at the end of the quarter, makes a bunch of money, and gets recognized as the hero. Why this backfires: You limit your access to support and expertise Leadership lacks visibility to help you close You give yourself a lower probability of winning You don’t build career capital beyond the one deal The better approach: Involve your leadership team, product experts, and delivery teams early. “It does no good to be at the end of a quarter and say, I delivered this X hundred K deal and be the hero. You give yourself a better chance to win by involving the right people along the way.” — Jeff Perry Your future relationship builders are the SDRs learning your business today. If you automate away those roles, you lose the talent pipeline that becomes your future AEs and managers. Cross-Functional Alignment: The Secret Competitive Advantage Carta’s gone from 275 employees in 2018 to ~1800 today. Alignment usually decays with scale. But Jeff argues the opposite is possible, if leaders treat every metric like a shared asset. Marketing isn’t feeding leads to sales.Marketing and sales are feeding the same revenue engine. “Nicole, Carta’s CMO, doesn’t look at it as Jeff’s revenue number. She sees it as our revenue number.” — Jeff Perry Sales + Marketing: One Team, One Number The old model: Marketing owns lead generation Sales owns revenue Finger-pointing when numbers miss New model: Shared pipeline ownership Joint accountability for closed revenue Integrated planning across demand gen and sales capacity No classic sales-marketing friction Product isn’t building in a vacuum.Product is reacting to customers at lightning speed. He describes a moment at a Napa event: Prospects gave feedback at 11am.By evening the CPO confirmed engineers were already building on it. That’s alignment at operational speed. RevOps as the Connective Tissue Jeff’s perspective on where RevOps fits: It depends on company culture and structure, but: RevOps often has the clearest view of: The buyer journey Data flow across systems Change management needs Narrative resonance through metrics Many CEOs include RevOps in the small leadership group for exactly these reasons. The “What’s Your Gut?” Forecasting Method The problem with traditional forecasting is that most forecast calls