Hyperengage & Dextego

Across the Funnel

Business EN ↓ 189 episodes

Across the Funnel is a weekly, interview-style podcast series uncovering bits of knowledge from some of the greatest minds in tech. We dig into concrete GTM moves across sales, customer success, and account management so you can build revenue that lasts. Powered by hyperengage & DextegoWant to join in as a guest, drop an email at podcast@hyperengage.io

Author

Hyperengage & Dextego

Category

Business

Podcast website

hyperengage.io

Latest episode

Jun 9, 2026

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Episodes

Ep # 190: How to Catch a Bad-Fit Customer Before They Churn ft. Andrew Loomis (VP of Customer Success, Sisense) 09.06.2026

In this episode of Across The Funnel, Adil Saleh sits down with Andrew Loomis , VP of Customer Success at Sisense , to explore how customer success leaders can rethink post-sales execution in an AI-shaped market. Andrew shares why CS teams need to move beyond cadence-based motions and focus more sharply on customer outcomes, predictive health scoring, onboarding risk, and multi-stakeholder alignme...

Ep # 189: Why Post-Sales Messaging Matters More Than Launch Messaging ft. Fahad Aziz (Founder and CEO, PuppyDog) 04.06.2026

In this episode of Across The Funnel, Adil Saleh sits down with Fahad Aziz , Founder & CEO of PuppyDog , to explore why product marketing is becoming one of the most important functions in SaaS growth. Fahad shares lessons from building and exiting Caremerge, explains why customer discovery still matters even in the AI era, and breaks down how faster product releases are forcing teams to rethi...

Ep # 188: The AI Metric Founders Should Stop Bragging About ft. Jeppe Schytte-Hansen (CEO & Co-Founder, Omnidocs) 02.06.2026

In this episode of Across The Funnel, Adil Saleh sits down with Jeppe Schytte-Hansen , CEO and Co-founder of Omnidocs , to explore how enterprise documet automation is changing in the AI era, why complex industries like legal, recruitment, financial services, and public sector need deep workflow context, and how teams should think about AI pricing, customer success, implementation, and adoption wh...

Ep # 187: 97% Trial-to-Paid, 21-Day Sales Cycles, and the New SaaS ROI Bar ft. Sara Wyman (CEO, Stackpack) 07.05.2026

In this episode of Across The Funnel, Adil Saleh sits down with Sara Wyman , Founder & CEO at Stackpack , to explore how vendor management is changing as companies deal with AI spend, tool sprawl, renewal pressure, and the need for clearer ROI. Sara explains why finance teams are often the first wedge into an account, how Stackpack helps customers get fast visibility into contracts and spend,...

Ep # 186: Why Land and Expand Breaks Without Post Sales Discipline ft. Paige Tyrell (Chief Growth Officer & Co-Founder, Prefixbox AI) 08.04.2026

In this episode of Across The Funnel, Adil Saleh sits down with Paige Tyrrell , Chief Growth Officer at Prefixbox , to explore how AI is reshaping e-commerce product discovery, why AI is not a substitute for broken go-to-market fundamentals, and what it really takes to make AI useful in sales and post-sales. They unpack the flood of AI tools hitting the market, the pressure on SaaS teams to drive...

Ep # 185: How Stronger Handoffs Create Better Retention Outcomes ft. Kelly McGuire (VP of Customer Success, Everstage) 25.03.2026

In this episode of Across The Funnel, Adil Saleh sits down with Kelly McGuire , then VP of Customer Success at Everstage , to explore how revenue teams can turn commission management into better seller visibility, tighter operational discipline, and clearer board-level answers on what growth actually costs; Kelly explains why strong customer success starts before the handoff, why post-sales teams...

Ep # 184: How to Use Client Intelligence to Build Trust in Technical Sales ft. Julie Barberio (VP of Client Solutions, Sequence Inc.) 24.03.2026

In this episode of Across The Funnel, Ioanna Onasi sits down with Julie Barberio , VP of Client Solutions at Sequence Inc. , to explore how a 25-year marketing career, spanning McDonald's corporate PR to life sciences consulting, shapes a modern approach to client intelligence, trust-based selling, and brand loyalty. Their conversation covers relationship-driven sales in close-knit industries,...

Ep # 183: The Sales Psychology Behind Better Outreach, Better Coaching, and Better GTM ft. Zac Blakely (CEO & Co-Founder, Foundations) 20.03.2026

In this episode of Across The Funnel, Adil Saleh and Ioanna Mantzouridou Onasi sit down with Zac Blakely , Co-Founder at Foundations , to explore what actually makes modern Go-To-Market teams work: not just better tools, but better judgment, better coaching, and better use of data. Zac shares how his path from door-to-door sales to building sales engines for scaling tech companies shaped his view...

Ep # 182: How Strategic Qualification Improves Pipeline Quality and Win Rates ft. Boris Cho (VP Growth, ChangeMakers) 19.03.2026

In this episode of Across The Funnel, Ioanna Onasi sits down with Boris Cho , VP, Growth at ChangeMakers , to explore how trust-based growth works in high-stakes consulting, why credibility has to come before pipeline, and how strong discovery shapes better client outcomes. Boris breaks down the difference between transactional selling and consultative growth, explains why referrals, reputation, a...

Ep # 181: What Revenue Leaders See in the Data That Others Miss ft. Sara Archer (CRO, ChartMogul) 18.03.2026

In this episode of Across The Funnel, Adil Saleh sits down with Sara Archer , Chief Revenue Officer at ChartMogul , to explore how AI is changing revenue operations, why fast experimentation is replacing slower traditional GTM playbooks, and what it takes to balance product focus with expansion pressure in SaaS. Their conversation covers hyper-personalization in account management, retention and e...

Ep # 180: The Consensus Architect: What Modern Selling Actually Demands ft. Cristina De La Cruz (CRO, ISG Partners) 05.03.2026

In this episode of Across The Funnel, Ioanna Onasi sits down with Cristina De La Cruz , CRO at ISG Partners , to explore what 20 years in talent and recruiting actually teaches you about people, sales, and leadership. Cristina shares her journey from working a full desk in a San Francisco branch to building the entire go-to-market function at ISG Partners, an embedded recruitment firm that operate...

Ep # 179: The Digital Sales Room Playbook: Running Complex Deals in One Shared Space ft. Carl Carell (Co-Founder, GetAccept) 05.03.2026

In this episode of Across The Funnel, Adil Saleh sits down with Carl Carell , Co-Founder & CRO of GetAccept , to explore the evolution of AI in B2B sales, the rise and fall of AI SDR hype, and what it truly takes to build an AI-native platform after a decade in the market. Carl shares how GetAccept transitioned from a traditional SaaS product to an AI-native digital sales room, a collaborative...

Ep # 178: First Export as the Aha Moment: Onboarding for Creative Software ft. Laura Burkhauser (CEO, Descript) 04.03.2026

In this episode of Across The Funnel, Adil Saleh sits down with Laura Burkhauser , CEO of Descript , to explore her unconventional transition from VP of Product to chief executive at a half-billion-dollar company and what that shift reveals about leadership in the AI era. Laura opens up about the stark difference between the fast feedback loops of product management and the long, ambiguous learnin...

Ep # 177: AI for Post-Sales: The Quiet Effort Behind Data Modeling and Context ft. Jon Finegold (CEO, Precog) 03.03.2026

In this episode of Across The Funnel, Adil Saleh sits down with Jon Finegold , CEO of Precog , to explore why enterprise AI remains bottlenecked by data readiness and what Go-To-Market leaders can do about it. Jon shares his journey from software engineer to MIT Sloan graduate to scaling Signiant from $5M to $50M ARR before stepping in as CEO at Precog, an AI-native ELT platform that connects SaaS...

Ep # 176: Spotting At-Risk Accounts Without a Fancy Health Score ft. Francesca Smedberg (Former VP of Product, Rillion) 26.02.2026

In this episode of Across The Funnel, Adil Saleh sits down with Francesca Smedberg , Former VP of Product at Rillion , to explore why modern product teams have to stay tightly connected to revenue outcomes, not just feature delivery. They unpack what “good onboarding” actually means in complex ERP environments, starting with a shared definition of where onboarding begins, which teams own which mom...

Ep # 175: Turning Sales Content Into a Sales System: The “In-Home” Playbook ft. Dean Curtis (CEO, Ingage) 24.02.2026

In this episode of Across The Funnel, host Adil Saleh sits down with Dean Curtis , CEO of Ingage , to explore how SaaS and GTM teams should think about AI with clear ROI guardrails, why “vibe-coded” prototypes rarely replace core systems without strategy, and how staying ruthlessly specific about your ICP sharpens positioning in noisy categories; Dean breaks down tying every software purchase to a...

Ep # 174: AI-Native vs. AI-Powered: Why the Distinction Defines the Future of SaaS ft. Doug Marinaro (CEO & Founder, Riptide) 13.02.2026

In this episode of Across The Funnel, Adil Saleh sits down with Doug Marinaro , Co-Founder and CEO of Riptide , to explore why “customer advocacy” is a distinct AI use case that goes beyond chatbots and task automation. Doug breaks down Riptide’s idea of an always-present AI advocate that can pull context from systems, execute actions, and coordinate real humans and partners in real time to resolv...

Ep # 173: Qualification as Risk Management: The Discipline Behind Predictable Pipeline ft. Colin Wood (VP, US Sales, SG Analytics) 30.01.2026

In this episode of Across The Funnel, Ioanna Onasi sits down with Colin Wood , VP, US Sales at SG Analytics , to explore what it takes to win and coach complex enterprise deals: why buyers care most about ROI and measurable outcomes, how great sellers find urgency instead of forcing it, and how to run tighter discovery through call prep, clear agendas, and structured qualification (MEDDIC and the...

Ep # 172: Beyond Conversation Intelligence: Adding the Emotional Layer GTM Teams Need to Win ft. Chandra DeKeyser (Co-Founder, Voicera) 15.01.2026

In this episode of Across The Funnel, Adil Saleh sits down with Chandra DeKeyser , CEO and Co-Founder at Voicera , to explore why transcripts alone can mislead GTM teams by stripping out the emotional signal that often reveals true intent, especially around renewals and deal risk. Chandra breaks down how Voicera approaches “sincerity” as a measurable layer, including the challenge of building a cr...

Ep # 171: Intent Signals Are Broken: What To Do Instead ft. Omer Gotlieb (Founder & CEO, Salespeak) 13.01.2026

In this episode of Across The Funnel, Adil Saleh sits down with Omer Gotlieb , Founder and CEO at Salespeak , to explore why AI in GTM still rises or falls on trust, not features, and why the next wave of winners will design around the buyer’s experience instead of stacking more internal tools. Omer unpacks how “intent” has gotten messier as buyers research in ChatGPT as much as they browse websit...

Ep # 170: Preventative AI: Replacing Approval Bottlenecks with Guardrails ft. Kyle Racki (Co-Founder & CEO, Proposify) 08.01.2026

In this episode of Across The Funnel, Adil Saleh sits down with Kyle Racki , Co-Founder and CEO of Proposify, and Proposify to explore why proposals remain the “digital handshake” in mid-market and enterprise sales, what teams actually buy proposal software for (speed, consistency, fewer errors, better buyer visibility), and how this category is evolving alongside contracts, CPQ, CLM, and digital...

Ep # 169: AI for Dispute Fighting: Turning Usage Data Into Bank-Readable Evidence ft. Patrick Petteruti (Founder, Chargeblast) 06.01.2026

In this episode of Across The Funnel,  Adil Saleh  sits down with  Patrick Petteruti , Co-founder of  Chargeblast , to explore how fast-growing consumer, DTC, and e-commerce businesses can keep chargebacks from becoming a business-ending payments problem, starting with Patrick’s origin story scaling Cramly.ai on Stripe and getting hit by rising disputes, then building Chargeblast’s chargeback aler...

Ep # 168: Pricing and Packaging for AI Usage Plans: Credits, Metering, and What Actually Works ft. Vova Feldman (Founder, Freemius) 23.12.2025

In this episode of Across The Funnel, Adil Saleh sits down with Vova Feldman , Founder at Freemius , to explore what it really takes to sell software globally when payments, subscriptions, invoicing, and tax compliance start competing with product work. Vova shares Freemius’s origin story: building software was fast, but turning it into a business took a year of implementation work because monetiz...

Ep # 167: The Economics Of Freemium Versus Revenue First ft. Steve Benson (CEO, Badger Maps) 18.12.2025

In this episode of Across the Funnel, Adil Saleh sits down with Steve Benson , CEO at Badger Maps , to explore why field sales still matters for high-ACV deals, and what it takes to build software that supports teams who live on the road. Steve breaks down how his background selling at IBM and Google, including work around the Google Maps API, shaped Badger Maps’ focus on mapping, routing, and ter...

Ep # 166: Account-Based Execution Without the Enterprise Budget ft. Aleksa Mitrović (Founder, Dealmayker) 16.12.2025

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Aleksa Mitrović , Founder at Dealmayker , to explore why modern B2B sales is shifting from high-volume outreach to high-context conversations built on semantic signals and human psychology. Aleksa breaks down how “being the most prepared” beats being the most charismatic, and why teams win when they show up with industry context...

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