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Across the Funnel
Hyperengage & Dextego
167 episodes
11 hours ago
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 & Dextego Want to join in as a guest, drop an email at podcast@hyperengage.io
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Entrepreneurship
Business
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All content for Across the Funnel is the property of Hyperengage & Dextego and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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 & Dextego Want to join in as a guest, drop an email at podcast@hyperengage.io
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Entrepreneurship
Business
Episodes (20/167)
Across the Funnel
Ep # 168: Pricing and Packaging for AI Usage Plans: Credits, Metering, and What Actually Works ft. Vova Feldman (Founder, Freemius)

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 monetization has too many moving parts, especially once global tax rules and subscription complexity enter the picture. They break down why “just use Stripe” often hides the full cost of cross-border fees, billing, taxes, and invoicing, and why founders should measure their payment stack like any other growth decision, with real unit economics, not assumptions.

The conversation also gets practical about GTM and retention: Freemius reduces churn by making value visible, shipping features tied to revenue lift and support reduction, and building a tight maker community that drives product ideas and creates buyer and investor connectivity. Looking ahead to 2026, they discuss how AI is pushing more products toward usage-based billing, and why pricing and packaging will become a core operator skill, including Freemius’s plans for pricing recommendation tools and pricing page feedback.

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1 week ago
50 minutes

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

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 territory design for outside sales teams. The conversation then shifts into bootstrapping: why a sellable first version matters, when “investible” is the real question (not preference), and how funding choices change speed, product maturity, and competitive pressure.

On the customer side, they argue that customer success is a direct churn and LTV lever, not a nice-to-have. Steve shares a practical view of how to staff CS early (including renewals ownership), why fast customer support still protects retention, and why usage data plus ecosystem partnerships (like CRM integrators) often decide whether a customer gets real value or quietly drifts.

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1 week ago
46 minutes 2 seconds

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

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, timing, and relevance rather than generic sequences. He argues that automation made it easy to message everyone, but it also raised the bar for what earns a reply: specificity, usefulness, and genuine understanding.

The conversation also covers early-stage growth and customer success realities: why simple products that non-sales roles can use quickly matter, why small accounts can become the doorway to bigger deals through trust and referrals, and why usage (not signups) is the clearest signal for retention and product-market pull.

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2 weeks ago
40 minutes 47 seconds

Across the Funnel
Ep # 165: Bootstrapping A Support Platform In An AI Hype Cycle ft. Vlad Shlosberg (CEO, Foqal)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Vlad Shlosberg, CEO of Foqal, to explore how Slack and Microsoft Teams are reshaping modern support operations, why AI adoption in support is now driven from the top down, and what actually matters in messaging-based support metrics. They unpack the shift from resolution-time obsession to first-response expectations, and how in-channel support changes both customer behavior and SLA design. Vlad breaks down the differences between B2B SaaS and open source communities in Slack, when it makes sense to build your own community versus piggybacking on existing ones, and how community strategy ties back into GTM. The conversation also gets into agentic workflows and why data sources and MCP-style connectors matter more than prompt cleverness when building AI support agents. Finally, Vlad shares how Foqal thinks about expansion: moving from external support to internal IT/HR/RevOps use cases, using Slack virality to land-and-expand across teams, and navigating a crowded market where bootstrapped focus and word-of-mouth often beat high-burn competitors.

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2 weeks ago
45 minutes 5 seconds

Across the Funnel
Ep # 164: Fraud, Signals, And Spend: How Modern Risk Engines Really Work ft. Robert Kraal (CEO & Co-Founder, Silverflow)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Robert Kraal, Co-Founder at Silverflow, to explore how modern card processing infrastructure is reshaping payments for banks, acquirers, and SaaS companies. They unpack why legacy mainframe-era platforms struggle with new card features, regulation, and data needs, and how a data-first approach to recurring payments, tokenization, and authorization can materially change subscription revenue and recovery from declines. Robert walks through the different go-to-market motions in Europe versus the US, the realities of selling core payment rails into banks, and how fraud systems read behavioral signals across devices, IPs, and transaction patterns. The conversation closes on how Silverflow uses AI in operations, why agentic commerce and stablecoins are on their radar, and how Robert thinks about building a knowledge-heavy, founder-producing culture inside a global fintech team.

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3 weeks ago
50 minutes 53 seconds

Across the Funnel
Ep # 163: The “Appropriate Experience” Test for AI in CS ft. Lincoln Murphy (VP of Customer Experience, ListKit)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Lincoln Murphy, VP of Customer Experience at ListKit, to explore how customer success and post sale GTM are changing in a world of digital engagement and AI tools. Lincoln explains why obsessing over churn keeps teams stuck, and makes the case for focusing on customer outcomes and the overall experience instead. He talks through how COVID era shifts and everyday use of ChatGPT have raised expectations for speed to value, and outlines how ListKit runs a split model with self service GTM customers on one side and high touch done for you cold email programs on the other.

He breaks down his approach to goal discovery, defining goals as an objective, a timeframe and the deeper why, and shows how that drives onboarding, adoption and ongoing performance reviews that often happen asynchronously via Loom instead of long calls. Lincoln shares how ListKit uses AI behind the scenes so teams can handle far more work while still leaving human conversations where customers need to feel seen, heard and validated. Adil and Lincoln close by digging into lifetime value and expansion through a planned Ascension Path, treating churn as a symptom to study rather than the main target, and reflecting on why the customer success software category still struggles to define itself between happy customers and revenue growth.

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3 weeks ago
56 minutes 33 seconds

Across the Funnel
Ep # 162: Turning Personality Insight Into Daily Execution ft. John Betancourt (CEO, Humantelligence)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with John Betancourt, CEO of Humantelligence, to explore how psychometrics and AI coaching are changing the way companies understand people, culture, and leadership at work. John walks through his 25 year journey from Procter & Gamble, Siebel, Reebok, and Puma into building Humantelligence and Ask Aura, a system that turns a 10 minute assessment into live coaching for managers and teams inside tools like email, Zoom, and Microsoft Teams.

They discuss why most recruiting and HR tech fails when it focuses only on skills and experience while ignoring culture fit, values, and work styles, and how that leads to “great” hires who flop when they switch companies or regions. John explains how Humantelligence measures behavior, motivators, and work styles across the organization, then feeds those insights into Ask Aura so leaders can get situation specific guidance on how to communicate, resolve conflict, and manage each person differently instead of relying on one default style. Adil and John dig into adoption and onboarding, the pressure from CFOs to prove ROI, and the reality that many customers mentally quit during onboarding long before renewal because they never see value or understand how to use the product day to day.

From redefining culture fit in hiring and leadership coaching, to tracking usage and success for enterprise rollouts, to the founder grind of ten years of pivots before finding a sticky product, this episode looks at what it really takes to make work more human at scale. John closes with advice for founders on evolving culture at each revenue stage, hiring people who do not always “fit” the original ten person vibe, and accepting that the product that finally works in the market may only faintly resemble the idea you started with.


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1 month ago
54 minutes 34 seconds

Across the Funnel
Ep # 161: How to Build Outbound That Survives Gmail Summaries and AI Filters ft. Vladyslav Podoliako (CEO, Belkins & Founderly)

In this episode of the Hyperengage Podcast, Adil Saleh welcomes Vladyslav, founder of Belkins. The discussion revolves around key challenges in B2B SaaS companies, particularly in customer acquisition and funding. Vladyslav shares insights on the evolution of outbound sales, the impact of AI, and the importance of personalized strategies over sheer volume in email marketing. He highlights Folderly’s innovative approach to email deliverability and warming up emails, differentiating it from other tools by focusing on quality integrations and compliance. They also delve into the significance of content marketing, strategic partnerships, and customer success systems in driving business growth. Additionally, Vladyslav touches upon another of his ventures in Agritech, showcasing his diverse entrepreneurial spirit. The episode concludes with a discussion on future trends and the importance of adaptability in the ever-evolving tech landscape.

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1 month ago
46 minutes 23 seconds

Across the Funnel
Ep # 160: Rethinking GTM: Aligning Every Team Around the Customer ft. Paul Staelin (ex CCO, Vercel)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Paul Staelin, CCO of Vercel, to explore how customer success can scale in the developer-first era. Paul shares his journey from early startups to leading customer success at a $9B company, where he’s reshaping how enterprises and startups alike achieve outcomes with modern developer tools.

They discuss the evolving role of CSMs as “midfielders” rather than “strikers,” how AI is transforming health scoring, sentiment analysis, and success workflows, and why use case–driven segmentation is key to retention. Paul also dives into building hybrid success organizations, driving up GDR and NDR, and what early-stage founders should prioritize when hiring their first CSM.

From PLG motions and digital CS models to AI-powered playbooks and scaling enterprise relationships, this episode highlights the future of customer success and what it means for SaaS founders, revenue leaders, and GTM teams building for long-term retention and expansion.

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1 month ago
35 minutes 54 seconds

Across the Funnel
Ep #159: The Next UI Revolution: How AI Is Rewriting Human Machine Interaction ft Dennis Mortensen (CEO, LaunchBrightly)

In this episode of the Hyperengage Podcast, host Adil Saleh and guest ****Dennis Mortensen, Founder and CEO of LaunchBrightly, ****to explore how conversational AI and automation are reshaping customer support, product documentation, and startup efficiency.

Dennis shares insights on the evolution of conversational UI, emphasizing that language has now become a “solved science,” unlocking a new era of user interaction and AI-driven experiences. He reflects on how AI democratizes innovation, enabling small teams to build faster and more effectively than ever before, what once required millions now needs just a weekend and a laptop.

The conversation also dives into the impact of AI on jobs, with Dennis arguing that AI eliminates process noise rather than people, creating room for creativity and higher-value work. He discusses the philosophy behind LaunchBrightly, which automates outdated product documentation through smart screenshot generation, keeping help centers current and reducing customer friction.

Dennis also highlights the importance of solving real pain points over chasing new technology, building for long-term customer value rather than trends. They cover how AI-driven agents are transforming customer support, the power of strong workflow integrations and why lean, focused teams often outperform larger, bureaucratic ones. Finally, Dennis reflects on his entrepreneurial mindset focusing on playing the game for the love of it.

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1 month ago
48 minutes 42 seconds

Across the Funnel
Ep # 158: How Postgres Branching Boosts Adoption & Retention ft. Tudor Golubenco (CTO, Xata)

On this Hyperengage episode, host Adil Saleh sits down with Tudor Golubenco, CTO and Co-founder of Xata.io, who explains the shift from an Airtable-style “builder” DB to a Postgres-native platform for real workloads. The new Xata centers on copy-on-write branching (with data), built-in anonymization, and scale-to-zero—ideal for staging/QA without leaking PII. Instead of risky migrations, teams keep production on RDS/Aurora, spin up an anonymized staging replica on Xata, and branch instantly; trust first, production later.

Tudor shares how a ~25-person team and a flatter Postgres-first architecture boosted velocity and reliability, with generic Postgres tools (like blue-green deploys) planned for open source. In private beta, they optimize for revenue and churn while running qualitative loops to learn why accounts expand or leave, using light enrichment and direct founder outreach to spot high-intent users. He also covers investor alignment for patience, what he seeks in A-player engineers (product sense, platform ownership, proactive ops), and why Bay Area customer proximity matters as Europe’s deep-tech scene thrives.

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1 month ago
45 minutes 27 seconds

Across the Funnel
Ep #157: From Spray-and-Pray to Predictive Sales ft. Viktoria Izdebska (Founder, Octrace)

Join Adil Saleh and Viktoria Izdebska, Founder of Octrace, on this episode of the Hyperengage Podcast as they unpack how predictive intelligence is reshaping modern sales. Viktoria shares how Octrace helps companies move beyond “spray and pray” outreach by using data-driven signals to predict when prospects are ready to buy.

They discuss the evolution of outbound in the age of AI, why timing now matters more than volume, and how Octrace’s models combine CRM data, macro shifts, and trigger events to deliver 6× stronger performance. Viktoria also explains how her lean team uses AI agents internally to stay fast and efficient, the importance of hiring generalists over pedigrees, and why the real SaaS moat is shifting from technology to data and distribution.

From enterprise sales to predictive GTM motion, this conversation is a masterclass for founders and GTM leaders navigating the new era of AI-powered growth.

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2 months ago
33 minutes 27 seconds

Across the Funnel
Ep #156: The Fast-Fashion Era of SaaS ft. Joseph Lee (CEO, Supademo)

Adil Saleh from Hyperengage Podcast interviews Joseph Lee, the founder of Supademo. They discuss the challenges and strategies of SaaS startups, highlighting the significance of platforms in enhancing onboarding processes and customer value. Joseph Lee shares his journey from working at Fresh Line to founding Supademo, based on the need to effectively demonstrate product value in non-tech-native industries. The conversation covers the role of AI in making onboarding processes interactive and personalized, the importance of building a user-friendly product, and maintaining rapid product development. Joseph Lee emphasizes the significance of being scrappy, moving quickly, and maintaining a lean team. They also touch on the company's growth strategies, including freemium models, product velocity, and SEO, and discuss operational principles and the future of tech evolution with AI. Lastly, Joseph Lee talks about the importance of SOC compliance for startups aiming to work with mid-market and enterprise customers.

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2 months ago
41 minutes 30 seconds

Across the Funnel
Ep # 155: Building a Data-Driven SaaS Estate for CS & GTM ft. Oliver Quittek (CRO, Viio)

This episode of the Hyperengage Podcast features Adil Saleh in conversation with Oliver Quittek, the CRO at Viio, a platform aiding in SaaS spend management for enterprises. They discuss the challenges startups and enterprises face in managing AI and SaaS expenses, emphasizing the need for a 360-degree overview of SaaS applications. Oliver details Viio's approach to discovering and optimizing SaaS tools usage, their integrations with various systems, and the importance of data security. He also highlights the shifts in responsibilities within organizations regarding SaaS spend management and how Viio assists different personas from finance to IT in achieving cost savings and compliance. The conversation concludes with a discussion on company culture, market expansion plans, and an invitation to networking events across the US by Adil Saleh.

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3 months ago
34 minutes 25 seconds

Across the Funnel
Ep #154: The Future of Data Warehousing in the Age of AI ft. Jacqueline Cheong (CEO, Artie)

In this episode of the Hyperengage Podcast hosted by Adil Saleh , Jacqueline Cheong, CEO and co-founder of Artie, shares insights about her company’s unique technology that optimizes time and manages data storage efficiently. Jacqueline explains how her husband, Robin Cheong, who co-founded the company and has extensive experience with databases and distributed systems, was pivotal in addressing data streaming challenges faced at companies like Zendesk and Opendoor. She discusses the evolution of their product from its inception at Y Combinator, the complexities they encountered with enterprise-level data streaming, and the importance of real-time data processing. Jacqueline also touches on AI’s role in enhancing data infrastructure, the challenges of enterprise sales cycles, and their future product roadmap, which includes expanding database support and introducing sophisticated features. Additionally, she highlights the value of her personal coach, Roz, and recommends the book The Score Takes Care of Itself by Bill Walsh for leadership inspiration. The conversation also emphasizes the importance of women in leadership roles and overcoming imposter syndrome.

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3 months ago
28 minutes 30 seconds

Across the Funnel
Ep #153: Scaling SaaS with No-Code Mobile Apps & AI ft. Kaius Meskanen (CEO, Choicely)

In this episode of the Hyperengage Podcast, Adil Saleh sits down with Kaius Meskanen, CEO of Choicely, to explore how no-code and AI are transforming mobile app development. Kaius shares his journey from architecture and military service to building Choicely, a platform that enables anyone to create production-ready mobile apps in just a day, without writing a single line of code.

They discuss how Choicely’s AI-powered builder can turn websites into mobile apps in under 90 seconds, the growing demand for native mobile experiences, and why mobile apps are becoming essential for SaaS businesses of all sizes. Kaius also dives into customer success strategies, scalability challenges, and how Choicely is making enterprise-grade apps accessible to SMBs at a fraction of the cost.

From AI agents and SDK integrations to customer adoption and retention, this episode highlights the future of app development and what it means for entrepreneurs, SaaS founders, and product teams looking to deliver world-class mobile experiences.

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4 months ago
34 minutes 8 seconds

Across the Funnel
Ep # 152: Why AI Could Replace Your Sales Team ft. Dan Thomson (Founder & CEO, Sensay)

On this episode, host Adil Saleh interviews Dan Thomson, CEO and founder of Sensay.io, to explore Sensay's journey in the AI industry. Sensay.io is a hybrid platform focused on building hyper-personalized AI chatbots for various use cases like sales, marketing, and customer support.

Dan discusses how the concept of digital immortality inspired the platform's development and the challenges of maintaining focus in a rapidly evolving AI landscape. The conversation also covers Sensay’s efforts in customer education, the economic aspects of API usage, and the company's principles like using AI to optimize workflows.

This episode goes over the importance of niche targeting for customer acquisition and effective communication in managing remote teams.

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4 months ago
37 minutes 23 seconds

Across the Funnel
Ep # 151: Revealing the Million-User Milestone from Day One ft. Simone Macario (Founder of Sharly.ai)

In this episode of the Hyperengage podcast, we welcome Simone, the founder of Sharly.ai, an AI-first platform focused on improving workflow management and operational excellence. Simone discusses the journey of onboarding a million users in the first year, challenges faced by startups, and the importance of staying grounded and data-driven.

He emphasizes the critical role of AI in enhancing productivity and the evolving landscape of automation for business functions. The conversation dives deep into customer success, retention strategies, and the future of AI in various industries, offering valuable insights for tech enthusiasts and aspiring entrepreneurs.

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4 months ago
46 minutes 56 seconds

Across the Funnel
Ep # 150: AI is Changing Sales – Here's What You Don't Know ft. Ioanna Onasi (CEO & Founder, Dextego)

Join Adil Saleh and Ioanna Onasi, Co-Founder & CEO of Dextego, on the Hyperengage podcast as they explore the transformative impact of AI on sales coaching and talent development. Ioanna shares her journey from an HR and psychology background to leading an AI-powered startup focused on improving sales performance through proactive coaching and human-centered AI models.

The discussion covers Dextego's unique approach to integrating with CRM systems, the importance of specialized AI coaches, and how AI can amplify the influence and coachability of sales teams. Ioanna also highlights the significance of empathy and trust in leadership, and offers a glimpse into Dextego's future plans, including expanding into customer success and other company departments.

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4 months ago
51 minutes 23 seconds

Across the Funnel
Ep #149: Why Accountants are Ditching Spreadsheets ft. Emily Maxie (Interim SVP of Sales & Marketing, Firm360)

Join Adil Saleh and Emily Maxie, Interim SVP of Sales & Marketing at Firm360, on this episode of the Hyperengage podcast as they explore how Firm360’s all-in-one platform is transforming accounting firms with AI-driven sales and customer success strategies. Emily shares her journey from marketing leader to sales leadership, the importance of mastering fundamentals, and how custom GPT tools are boosting sales team efficiency. They discuss Firm360’s unique focus on accounting workflows, robust onboarding and retention processes, and building a lean, motivated team culture. Emily also offers inspiring insights on women in tech leadership and the future of SaaS innovation in niche verticals.

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5 months ago
1 hour 14 minutes 37 seconds

Across the Funnel
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 & Dextego Want to join in as a guest, drop an email at podcast@hyperengage.io