E56: Becoming a CFO Whisperer & Revenue Architect (Allison Metcalfe, CRO @ Zenoti)

Jonathan Moss, EVP of Growth and Partnerships at Experity, joins Kyle Norton to lay out the six layers under every agent his team runs: data, the brain, intelligence, orchestration, agents, and the interface. He built them in the wrong order first, starting at the agent and working down to the data. Topics include the GTM Intelligence Center that lets anyone at Experity pull a three-year trend with insights in under 30 minutes without RevOps in the middle, the decision that almost put the company's business logic and IP inside a third-party product, and running all of it in HIPAA-regulated health tech on Snowflake and AWS AgentCore. Plus, why budgeted headcount rather than an ROI pitch got the data team engaged, the shift from functional RevOps silos to acquisition, expansion, retention and value realization pods, and a tour of his personal stack of 121 agents and 57 skill files. Key Takeaways: - Build your system from the data up if you want durable results you can build from. Jonathan's six layers run from data at the bottom to the interface at the top. His framing: "if you're not thinking about the system that you're building, you're not going to be able to scale it." - AI added to an existing process costs an extra step, and rarely revolutionizes anything. As he put it: "AI is not something that you add into an existing process because then all you're typically doing is you're just adding one extra step or one extra layer, but you're not really solving the business outcome or the root problem." - The AI brain is the one layer you do not hand to a vendor. Experity came close to putting its business logic and company context into a third party before Moss pushed back: "one of the decisions that was almost about to be made was we were about to put all of this into a third party. And I was, and I was like, whoa, whoa, whoa, before we do that, how are you going to port it over to something else?" He is not against buying a platform, but he applies one test: "the portability is the most important factor if you're going to do it." Connect with the Hosts & Guests: Host: Kyle Norton, CRO & Advisor - https://www.linkedin.com/in/kylecnorton/ Guest: Jonathan Moss, EVP of Growth and Partnerships at Experity - https://www.linkedin.com/in/mossjonathan/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/

Lauren Hughes, VP of Revenue Effectiveness at Justworks, joins Kyle Norton to walk through cutting new-hire ramp time from 18 months to 8 while AE bookings grew 28% in a year. She took the enablement team from 16 people to 6, and to fill the gaps she rebuilt a Claude skills library her team feeds with ride-along notes and onboarding results. Topics include the signals that tell her in a new hire's first few days whether they will make it, why she inherited a stack of 70 go-to-market tools and started by inspecting it instead of buying more, and how moving sales development under revenue effectiveness doubled pipeline productivity with four fewer people in seat. Plus, build versus buy with a product team, the exception report that replaced a 120-page weekly deck, and why she will not act on a hypothesis until she has checked the data. Key Takeaways: - Ramp time is a balance-sheet number, not an enablement metric. Justworks sells a compliance-heavy PEO product to reps who have never worked in HR or health insurance, and the fix was structure and measurement rather than more training hours. As Lauren Hughes, VP of Revenue Effectiveness at Justworks, put it: "When I first joined Justworks, our average time to ramp for a new sales hire was 18 months… We've gotten it down to 8 months and we have a pretty clear path to get it under 6." That happened across 300 revenue-facing hires in a single year. - The roles worth cutting are the ones that exist to maintain content. Lauren eliminated instructional designer, LMS admin and field enablement, and killed an onboarding coordinator role before it was ever filled, because scheduling, progress measurement and manager alerts now run through Tangelo and AI. On why the old team was sized the way it was, she said: "we needed 32 people to keep Confluence updated." Justworks no longer runs an LMS at all. - Enablement only scales when it is staffed like an operations function. Lauren merged revenue enablement and revenue operations into one team and changed what she hired for, telling the enablement side: "the new hat you need to wear is you need to be a systems thinker. You need to understand technology and understand what's going on in the market and how fast GTM technology is changing." Her diagnosis of the old model was high activity, low results. - Removing friction outperformed adding headcount in sales development. After the SDR team moved under revenue effectiveness, Lauren inspected the existing tech stack first, had a dialer in a POC within four days, migrated the engagement platform, added a pipeline ARR component to comp and built a signal system: "we're running at 2x productivity of pipeline opportunities, logo count, 2x productivity of pipeline ARR… And I'm down 4 in seat just from attrition of people moving to AE roles." She is candid that there was no single lever: "I wish I could say some, like, big aha thing, but it was really just this team needed focus." Connect with the Hosts & Guests: Host: Kyle Norton, CRO & Advisor - https://www.linkedin.com/in/kylecnorton/ Guest: Lauren Hughes, VP Revenue Effectiveness at Justworks - https://www.linkedin.com/in/laurenehughes10023/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Lauren Hughes 02:02 Diagnosing The Org With Data 05:26 Taking Enablement From 16 To 6 07:41 Roles They Stopped Staffing 13:00 Ramp Time From 18 Months To 8 14:09 Measuring Cohort Attainment 17:49 Building The Persona Layer 21:41 A Claude Skills Library For GTM 28:40 Marrying RevOps And Enablement 39:25 What Actually Cut Ramp Time 44:19 Removing Friction From The Day 48:35 Thirty Minutes To Prospect One Lead 52:06 Doubling Pipeline With Fewer Reps

Ian Tickle, Chief Revenue Officer at Freshworks, joins Kyle Norton to walk through why he collapsed a split go-to-market org chart into one revenue organization covering global sales, customer success, and customer experience. Ian is a 30-year SaaS operator who took Omniture through the Adobe acquisition and RightNow through the Oracle acquisition, then joined Freshworks in 2024 to run Europe and became CRO of a nearly billion-dollar ARR business 20 months later. Topics include the symptoms that you are shipping the org chart to your customers, the 8 to 12 week design process behind the reorg, whether a revenue leader should carry the net retention number, and the three questions to ask before unifying sales and CS. Plus, why complexity is not maturity, how shadow orgs get built by well-meaning people, the monthly ritual Ian's leadership team uses to delete process, and the point where poorly connected systems turn AI into a liability. Key Takeaways: - Segmentation is an internal convenience, and customers experience it as friction. Freshworks previously ran separate organizations for sub-500-employee and 500-plus accounts, which produced parent-child account fights, duplicated support teams, and a customer success line that reported into neither cleanly. As Ian Tickle, Chief Revenue Officer at Freshworks, put it: "customers don't care about my org structure. They care about dealing with Freshworks and is Freshworks going to look after them?" His test for whether a redesign is needed is whether the customer is waiting on an internal boundary to get resolved. - Complexity arrives as process that was once justified and never got removed. Ian's sharpest example is from an acquisition earlier in his career: "we would get an order, it would go through our systems, and it'd be provisioned within about 7 or 8 minutes of us, you know, checking the order and making sure everything's okay. Got acquired by one of, one of the companies, and that became a 3-week process." Same due diligence, same deal quality, four or five extra layers of approval, and nobody owned taking them back out. - Accountability blurs in the overlap between teams, not inside them. Ian describes org growth as circles that multiply until the shared area dominates: "Then you get the Venn diagram, which is the gray in the middle, which is where you start to lose the accountability…" His counter is naming a single responsible person per task and then clearing their path, which he frames as an open standing question to his org: "tell me what's stopping you from running faster?" - Getting faster is only a win if the reclaimed time gets redeployed. Ian is direct about tooling and AI efficiency that never converts into output: "what are you doing with that efficiency to make value out of it? Otherwise, there's like a net-net, it washes out at the back end. We're just being quicker, but we're not necessarily being more efficient or effective." He pairs that with a warning that AI layered onto disconnected systems creates a governance problem rather than leverage, and with a preference for exception-based reporting over data-state reporting. Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Ian Tickle, CRO at Freshworks - https://www.linkedin.com/in/ian-tickle-5a463a2/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Ian Tickle 05:19 Why Freshworks Collapsed Two Orgs 10:11 Symptoms Of Shipping The Org Chart 14:53 The Org Design Before And After 20:04 How The Redesign Got Decided 27:22 Should Revenue Leaders Own CS 33:16 Three Questions To Ask First 35:29 Making Leaders Own Retention 42:03 Build

Tim Rutten, CMO at Backbase, runs a 35-person marketing team against a book of business north of $350 million in ARR, and joins Kyle Norton to break down the AI-native go-to-market operating model he built from the ground up. Topics include what AI-native actually means as an architecture principle, throwing out the org chart to rebuild around the real work, and building GTMOS, an in-house go-to-market operating system where 100% of the code is agent-generated. Plus, replacing a signal-engine tool like 6sense with a white-box build, scanning 3,000 target banks against a live ICP model for around $500 a week, and the "love letters" tactic that gets 40% of banking executives to respond. In short, a tactical playbook for AI-native revenue leadership. Key Takeaways: - Tim Rutten treats AI-native as an all-or-nothing bet. As the CMO at Backbase put it: "you either go all in or you don't go at all... in the middle, you're not getting the full value." That conviction let him treat the whole revenue org as an engineering problem and rebuild it around one go-to-market OS. - The competitive edge is a harness good enough to turn business leaders into builders. Tim Rutten's guidance is to "make sure you have a landing zone, a good architecture, really understand how to do this so you can make non-engineers dangerous," so the people closest to the customer can ship agents and workflows without waiting in a GTM engineering queue. - Building in-house is already pulling real cost out of the P&L. Backbase replaced 6sense with a bespoke, white-box signal engine, and Tim Rutten says "before the end of the year, we're taking out at least, at least $100K extra" in deprecated tools, calling the build "the best ROI I've seen in this full year." - One of the highest-return plays is also the lowest-tech. Tim's team writes public "love letters" that champion a target bank's executives by name, and he says "let's say 40% of the actual executives respond" because "people feel special. They feel heard. They feel seen." It gets Backbase into C-suite conversations at a fraction of the cost of a classic ABM campaign. Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Tim Rutten, CMO at Backbase - https://www.linkedin.com/in/timrutten/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Tim Rutten 02:57 What AI Native Actually Means 06:24 Throwing Out the Org Chart 09:21 Which GTM Roles Get Hollowed Out 12:12 Getting the Team Into Claude Code 17:45 Building the GTM Operating System 20:40 The Vercel AI-Native Stack 25:15 Cutting Tools and $100K in Costs 29:29 Making Non-Engineers Dangerous 35:00 Centralized vs Distributed AI GTM 43:00 Reorganizing the Marketing Team 46:16 Scanning 3,000 Accounts With AI 55:55 From Weeks to 15-Minute ABM 1:06:43 The Love Letters Tactic 1:13:40 Quickfire CMO Questions

Kevin Bailey, CEO of Dreamfuel, returns to The Revenue Leadership Podcast for part two of his conversation with Kyle Norton on mental performance. This time they dial in on how revenue leaders cascade these practices through their organizations. Topics include the Greenlight Guru breakthrough story (one breathwork session that converted a skeptical co-founder), the pre-call warmup protocol Kevin used during a solo enterprise sales year that doubled his close rate, and why every executive needs a "serotonin day" every two weeks to recover their dopamine system. Plus, how Owner.com keeps award-winning performers on "Get On Track" plans without spiraling identities, Jim Collins's return on luck for sales slumps, and what to track with WHOOP and Oura to make recovery a competitive advantage. Key Takeaways: - Kevin Bailey's single biggest performance unlock during his solo enterprise sales year was the pre-call warmup Hugh Jackman calls "daily design": 30 rapid belly breaths, a breath hold, fire-up music, then journaling as if the meeting is already over. As Kevin put it: "I did this for every single call. My close rate about doubled… it puts elite behaviors on autopilot. Again, why all athletes do it." The mechanism is mental contrasting: the subconscious can't fully distinguish a vividly-imagined outcome from a real one, so the dopamine and serotonin from the visualization juice neuroplasticity that reinforces hard behaviors. - Kevin's prescription for revenue leaders is one "serotonin day" every two weeks: a full day with no goals, no time pressure, and no phone. The kid-kicking-a-ball-for-the-pure-joy-of-it kind of day, rather than the soccer-with-rules kind. In the age of AI, when an executive's edge is the quality of their thinking and not their grind, the nervous-system reset is what unlocks bottom-up creative insight the rest of the week. - Kyle Norton's process-over-outcome culture at Owner.com has produced something counterintuitive: "tons of our best, very best performers at the company… award-winning performers have been on what we call Get On Track plans, which is our version of a PIP." The setup is Jim Collins's return on luck. Sales swings cut both ways, and a culture that anchors identity to inputs and process (not just W's) lets reps work through cold streaks without spiraling. Kevin's neurochemistry framing of the same idea: "If you learn how to control the dopamine of your team using tools like this, then you have control and you can push through the hard parts where your competitors will falter." - Trying to install seven new mental performance habits at once guarantees zero stick. The brain doesn't want to rewire. Kevin's image is that your brain is a giant interstate and it doesn't want you blowing up lanes to move on-ramps. Pick one practice, get serious about it for 30 days minimum, then move to the next. Connect with the Hosts & Guests: Host: Kyle Norton, CRO at Owner.com - https://www.linkedin.com/in/kylecnorton/ Guest: Kevin Bailey, CEO at Dreamfuel - https://www.linkedin.com/in/kevinjamesbailey/ The Revenue Leadership Podcast is more than a YouTube Channel: Subscribe to The Revenue Leadership Podcast Newsletter: https://www.therevenueleadershippodcast.com/ Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into The Revenue Leadership Podcast: https://www.therevenueleadershippodcast.com/ Chapters: 00:00 Introducing Kevin Bailey 05:53 The Leader Must Embody It First 08:36 Greenlight Guru Breakthrough Story 11:30 Engineering Breakthrough Moments 15:45 Biometric Trackers and Challenges 22:29 Pick One Habit at a Time 26:32 The Pre-Call Warmup Protocol 34:14 Visualization Without the Woo 38:09 Dopamine Triggers Leaders Control 44:11 Return on Luck and PIPs 47:07 Why Every Exec Needs a Serotonin Day 53:13 Why Sitting Still Feels Threatening 58:10 Sleep, Drinking, and the HRV Test 01:05:31 Shared Language and Four Zones