Across the Funnel

Hyperengage & Dextego
  • 5.0 (5)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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

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

    1D AGO

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

    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 resolve issues without escalation. They unpack how this “third superpower” shifts customer service from deflection metrics to an “advocacy index,” why trust and speed are what get pilots into production, and how Riptide onboards in roughly 30 days by wiring into existing tools, building a “digital twin” of the customer, and continuously coaching the system like an employee. The conversation closes on focus as a growth strategy, patterns for expanding across verticals, and how teams should think about using multiple models for low-latency interactions, deeper analysis, and emerging voice workflows.

    1h 3m
  2. Ep # 173: Qualification as Risk Management: The Discipline Behind Predictable Pipeline ft. Colin Wood (VP, US Sales, SG Analytics)

    JAN 30

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

    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 “initiative, champion, economic buyer” check). Colin also breaks down how he onboards reps with business context, real customer stories, and a technical buddy system, why call recording helps coaching without turning into a gotcha, and what he wants next from sales tech: non-distracting, real-time guidance that nudges reps when key questions are missed. The conversation closes with leadership lessons (stop hoarding deals, build a bench), manager cadence, and where GTM is heading in 2026, including smaller entry projects that prove value before expansion, more outcome-based pricing, and a new reality where vendor research is shaped by AI and peer reviews.

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

    JAN 15

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

    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 credible training dataset, and why combining separate models for facial cues and voice tone can create a clearer read than text summaries. The conversation also connects this to practical use cases for SaaS and customer success leaders: coaching sales reps by spotting second-by-second drop-offs during a pitch, improving manager authenticity to reduce talent churn, and strengthening hiring workflows as deepfakes become harder to detect. Adil and Chandra close on what makes adoption work across segments, from self-serve analysis for smaller teams to enterprise deployments where privacy and sensitive video data matter, and how to frame ROI in plain numbers that CROs and CEOs will actually act on.

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

    JAN 13

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

    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 websites, why lazy signal-based outreach is turning into a spam cannon, and what it takes to engage with real context rather than a single click. They also dig into practical GTM choices for chaotic markets, including month-to-month experimentation, freemium and pay-per-use models that reduce commitment risk, and a value-first approach that earns expansion instead of forcing it. The conversation closes with lessons from building lean teams in an AI era, using agents to do more with fewer hires, and advice for first-time founders to win early by delivering clear value and owning a distinct point of view in a crowded category.

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

    JAN 8

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

    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 sales roms. Kyle shares how Proposify navigated SaaS market cycles, moved from early scrappiness to raising capital, then returned to a profitability-first operating style, plus why adding products matters when markets are big but not infinite. He and Adil also pressure-test the AI hype, including the Dunning–Kruger trap where “easy to build” often means “easy to build something fragile,” and they connect that to real-world product work like tech debt, replatforming, and why Proposify 3 existed as a reset for modern shipping speed. On the customer side, Kyle walks through onboarding and time-to-value, including a candid example where an AI template generator hurt conversions because it was slow and produced mediocre outputs, which pushed the team toward simpler AI uses and a more reliable services-led “launch kit” to get customers live faster with the right setup, guidance, and early support.

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

    JAN 6

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

    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 alerts so merchants can refund early and keep dispute rates low; they dig into why matching issuer alerts to processor transaction records is hard across tokenized payment methods, how Chargeblast moved from being Stripe-first to supporting 35+ processors and gateways, what onboarding looks like when setup takes minutes instead of months, the tradeoffs of staying on Stripe versus routing volume across multiple processors to improve acceptance and lower fees, the most common dispute-heavy categories (subscriptions, telehealth, iOS apps moving to Stripe, and other higher-risk verticals), why pre-launch sales often trigger dispute spikes, how Chargeblast grows through a mix of direct sales, partnerships (including with payment platforms), and strong referral loops, plus the operating model behind white-glove support, including a large Philippines-based team, a portfolio-wide chargeback log that flags spikes or bad data, and rapid 24/7 live chat, ending with Patrick’s view on where AI can help most next: assembling clear, structured evidence packs for banks during dispute fights by pulling usage and customer proof from whatever systems a merchant uses.

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

    12/23/2025

    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.

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

    12/18/2025

    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.

    46 min
See All (173)

Ratings & Reviews

5
out of 5
5 Ratings

About

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

Information

  • Creator
    Hyperengage & Dextego
  • Years Active
    2021 - 2026
  • Episodes
    173
  • Rating
    Clean
  • Copyright
    © Hyperengage & Dextego
  • Show Website
    Across the Funnel