SaaS Podcasts

380: Customer Service's AI Shift: Zendesk CTO Adrian McDermott on Deterministic AI and Context Engineering
PodcastMar 16, 202644 min

380: Customer Service's AI Shift: Zendesk CTO Adrian McDermott on Deterministic AI and Context Engineering

In this episode, Zendesk CTO Adrian McDermott discusses the company’s evolution from a product‑led startup to a AI‑driven leader in customer service, emphasizing the shift toward deterministic AI and context engineering. He explains how Zendesk uses generative AI tools to boost...

By AI and the Future of Work
From $7M to $70M Revenue: How RealDefense Scaled Through Acquisitions | Gary Guseinov
PodcastMar 14, 202624 min

From $7M to $70M Revenue: How RealDefense Scaled Through Acquisitions | Gary Guseinov

In this episode, Gary Guseinov, CEO of RealDefense, recounts how he grew the company from a $7M ARR acquisition in 2017 to $70M in revenue and $25M EBITDA today, primarily through a disciplined acquisition strategy that adds synergies, reduces CAC,...

By SaaS Interviews with CEOs
SaaS Distribution Channel: Partner Deals to $100M ARR
PodcastMar 12, 202650 min

SaaS Distribution Channel: Partner Deals to $100M ARR

In this episode, host Omar Khan talks with Zong Xu, co‑founder of Deliverect, about how the company built a centralized platform that connects restaurants to dozens of digital ordering channels and now serves over 80,000 locations, approaching $100 M ARR. Zong...

By The SaaS Podcast (SaaS Club)
Re-Air: Data Tools, Templates, and the Trouble with “Easy” Solutions with the Cynical Data Guy
PodcastMar 11, 202641 min

Re-Air: Data Tools, Templates, and the Trouble with “Easy” Solutions with the Cynical Data Guy

In this re‑aired episode, hosts Eric Dotz and John Wessel chat with regular guest Matt, the Cynical Data Guy, about the rise of low‑code data tools like Clay and the evolving role of the “GT‑M engineer.” They debate whether such...

By The Data Stack Show
Episode 823 | Hot Take Tuesday: Is A.I. Killing B2B SaaS?, ChatGPT Ads, OpenClaw
PodcastMar 10, 202641 min

Episode 823 | Hot Take Tuesday: Is A.I. Killing B2B SaaS?, ChatGPT Ads, OpenClaw

In this Hot Take Tuesday episode, Rob Walling, Tracy Osborne, and Anar Volset discuss whether AI is threatening B2B SaaS, the rise of AI-driven advertising on platforms like ChatGPT, and the rapid growth of the OpenClaw community. They argue that...

By Startups For the Rest of Us
Ep. 190 - The SaaS Founder Bottleneck: Why Founder-Led Sales Stops Scaling
PodcastMar 6, 202633 min

Ep. 190 - The SaaS Founder Bottleneck: Why Founder-Led Sales Stops Scaling

In this episode, fractional CMO Javier Lozano explains why founder‑led sales can’t sustain growth and how to transition to a repeatable, data‑driven go‑to‑market engine. He emphasizes extracting the founder’s successful sales insights, building positioning and a "blue ocean" narrative, and...

By SaaS Backwards
AEC’s Single Source of Truth: Reality or Pipe Dream?
PodcastMar 6, 202642 min

AEC’s Single Source of Truth: Reality or Pipe Dream?

In this episode the hosts explore whether a true single source of truth (SSOT) for construction project data is achievable or merely aspirational. NuFORMA’s Dave Wagner and Carl Beillette argue that a single vendor solution is unrealistic; instead, the goal...

By AEC Business
Special Episode: Rethinking the ERP Upgrade Path
PodcastMar 6, 202621 min

Special Episode: Rethinking the ERP Upgrade Path

In this special episode, Intuit’s Executive Vice President and General Manager of Mid‑Market, Ashley Still, challenges the traditional belief that fast‑growing companies must abandon QuickBooks for a heavyweight ERP. She introduces Intuit Enterprise Suite, an ERP that retains QuickBooks‑like usability...

By CFO THOUGHT LEADER
LawNext on Location: At A Sonoma Winery, A Conversation with Briefpoint CEO Nathan Walter About Discovery, Disruption and, Of Course,...
PodcastMar 5, 202650 min

LawNext on Location: At A Sonoma Winery, A Conversation with Briefpoint CEO Nathan Walter About Discovery, Disruption and, Of Course,...

In this LawNext on Location episode, host Bob Ambrogi chats with Nathan Walter, co‑founder and CEO of BriefPoint, while sipping wine at Paradise Ridge Winery in Sonoma. Walter recounts his unconventional path from philosophy student to public defender, to civil...

By LawNext
Will The Trade Desk Right-Size Its Margins?
PodcastMar 5, 202644 min

Will The Trade Desk Right-Size Its Margins?

The episode dissects the Trade Desk’s ongoing tension over its OpenPath platform, agency relationships, and high margin model, especially in light of recent earnings and competition from Amazon DSP. Guest Sarah Caputo argues that the Trade Desk’s effective take rate...

By The Big Story (AdExchanger)
How Ledge Reached $1M ARR with 24 Customers Paying $3K/Month | Tal Kirschenbaum
PodcastMar 5, 202626 min

How Ledge Reached $1M ARR with 24 Customers Paying $3K/Month | Tal Kirschenbaum

In this episode, Tal Kirschenbaum, co‑founder and CEO of Ledge, explains how his AI‑native financial close platform reached $1M ARR by serving roughly 24 mid‑market enterprise customers at an average of $3,000 per month. He details Ledge’s focus on automating...

By SaaS Interviews with CEOs
207. Adam Dorrell, CEO & Co-Founder of CustomerGaige - Founder-Led Sales vs Scaling: The Hard Transition Nobody Talks About
PodcastMar 5, 202652 min

207. Adam Dorrell, CEO & Co-Founder of CustomerGaige - Founder-Led Sales vs Scaling: The Hard Transition Nobody Talks About

In this episode, Adam Dorrell, CEO and co‑founder of CustomerGauge, discusses the challenges of transitioning from founder‑led sales to a scalable commercial organization. He shares how he and his co‑founder initially handled sales themselves, the pitfalls they faced hiring sales...

By The SaaSiest Podcast
SaaStr 844: The Top 5 Issues Managing Multiple AI Agents in Production with SaaStr's CEO and Chief AI Officer
PodcastMar 4, 202655 min

SaaStr 844: The Top 5 Issues Managing Multiple AI Agents in Production with SaaStr's CEO and Chief AI Officer

In this episode, SaaStr’s CEO and Chief AI Officer discuss the practical challenges of running dozens of AI agents in production, outlining their top five pain points: the cognitive load of context switching across heterogeneous agents, the disruptive "blackout" period...

By The Official SaaStr Podcast
Stories that Sell: The Marketing Strategy Algorithms Can’t Kill
PodcastMar 3, 202645 min

Stories that Sell: The Marketing Strategy Algorithms Can’t Kill

In this episode of SaaS Stories, host interviews Henry DeVries, publisher of Indie Books International, about the power of storytelling in business. DeVries outlines eight core story archetypes—monster, underdog, comic solution, tragic solution, mystery, quest, comeback, and "escape from crazy...

By SaaS Stories
Product Update: AI-Driven Onboarding and Workflow Automation in Semaphore
PodcastMar 2, 20260 min

Product Update: AI-Driven Onboarding and Workflow Automation in Semaphore

In this episode, Pete outlines Semaphore's new AI-driven assistant that streamlines CI/CD onboarding by converting natural language descriptions into fully configured pipelines. The assistant also offers ongoing workflow insights, error explanations, reruns, and configuration suggestions while preserving full developer control...

By Semaphore CI/CD Weekly
Perplexity Max Debuts Multi-AI Agent Tool
PodcastMar 1, 202610 min

Perplexity Max Debuts Multi-AI Agent Tool

The episode breaks down Perplexity's new Max plan, a cloud‑based multi‑AI agent that can orchestrate up to 19 different models and even spawn sub‑agents to complete complex, multi‑step tasks like financial analysis or legal research. While the tool is aimed...

By AI Chat
From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
PodcastFeb 26, 202628 min

From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman

In this episode, Jared Gaiman, co‑founder of Boxed and current CEO of Spresso, recounts the rise of Boxed from a $187 M e‑commerce business to its Chapter 11 filing and subsequent pivot to a $5 M ARR SaaS model focused on enterprise software...

By SaaS Interviews with CEOs
What Are True to the Core Deep Dives at TDX?
PodcastFeb 26, 202619 min

What Are True to the Core Deep Dives at TDX?

In this episode of the Salesforce Admins Podcast, host Kate Lessard explains the new "True to the Core" deep‑dive sessions debuting at TDX, which are built from community feedback to explore core platform topics like Flow, Automation, and Lightning Web...

By Salesforce Admins Podcast
The ERP Minute Episode 226 - February 24th, 2026
PodcastFeb 25, 20264 min

The ERP Minute Episode 226 - February 24th, 2026

In this brief episode, host Rebecca McCabe highlights Sage Intacct's new AI-powered features for finance teams, including a finance intelligence agent, close automation, cash intelligence, and a data cloud, aimed at reducing system switching and enhancing decision‑making. She also covers...

By The ERP Advisor
BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee
PodcastFeb 25, 20260 min

BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee

In this episode, Dan Lee, co‑founder and CEO of Nooks, unveils the new Agent Workspace and AI Sequences, explaining how AI‑native tools are reshaping the top‑of‑funnel sales process. He contrasts Nooks with legacy sequencing platforms, highlighting its ability to automate...

By The GTM Newsletter
EP 721: 3 New NotebookLM Updates You Can’t Miss: Editable Slides, Mobile Updates and More
PodcastFeb 25, 202640 min

EP 721: 3 New NotebookLM Updates You Can’t Miss: Editable Slides, Mobile Updates and More

In this episode Jordan dives into three major NotebookLM updates: enhanced mobile capabilities that let users edit infographics, slide decks, and generate full‑screen video overviews on their phones; a new conversational studio generation workflow that lets users iteratively chat with...

By Everyday AI
SaaStr 843: Software Stocks Have Massively Crashed. Here's What Founders Need to Know.
PodcastFeb 25, 202643 min

SaaStr 843: Software Stocks Have Massively Crashed. Here's What Founders Need to Know.

In this episode, SaaStr host Jason Lemkin discusses the recent crash in software stock valuations and what it means for SaaS founders, emphasizing that true AI companies must show accelerating growth. He critiques public SaaS companies for superficial AI hype...

By The Official SaaStr Podcast
Episode 92: Inside the Deal with Robin Fisk
PodcastFeb 20, 202619 min

Episode 92: Inside the Deal with Robin Fisk

In Episode 92 of the Tech M&A Podcast, Robin Fisk, co‑founder and CEO of Donorfy, recounts the decade‑long journey of building a bootstrapped SaaS CRM for nonprofits and its eventual acquisition by The Access Group in November 2024. He explains why they chose to...

By The Tech M&A Podcast
Software Update: AI Saas Scare Haunts Capital Markets
PodcastFeb 20, 20260 min

Software Update: AI Saas Scare Haunts Capital Markets

Recent AI upgrades, notably Anthropic’s Claude Co‑worker agent, are unsettling SaaS valuations and complicating IPO plans for many software firms. The devaluation of SaaS‑related loans is eroding the collateral base of collateralised loan obligations, with similar pressures hitting chemical‑sector loans....

By The GlobalCapital Podcast
Beyond Gantt: The Rise of Flow-Based Production
PodcastFeb 19, 202625 min

Beyond Gantt: The Rise of Flow-Based Production

In this episode, Antti Pukema of Sitedrive discusses moving beyond traditional Gantt chart scheduling to a flow‑based production approach that integrates CPM, Takt, and Last Planner systems into a single "one schedule". He explains how this methodology eliminates idle "white...

By AEC Business
Product-Market Fit: From Edtech Vitamin to $100M Painkiller
PodcastFeb 19, 20261h 1m

Product-Market Fit: From Edtech Vitamin to $100M Painkiller

In this episode, Adam Markowitz recounts his transition from a decade‑long edtech venture to building Drata, a compliance automation platform that quickly proved its product‑market fit as a painkiller rather than a vitamin. He explains how rigorous validation—dog‑fooding the product...

By The SaaS Podcast (SaaS Club)
Can an AI PMS Run Your Short-Term Rental Portfolio?, With Boom Co-Founder & CEO Shahar Goldboim
PodcastFeb 19, 202634 min

Can an AI PMS Run Your Short-Term Rental Portfolio?, With Boom Co-Founder & CEO Shahar Goldboim

In this episode, Shahar Goldboim, co‑founder and CEO of Boom, explains why short‑term rentals (STRs) are the most complex asset class and how fragmented software tools trap hosts in a review‑driven revenue loop. He describes the genesis of Boom—a Business‑as‑Software...

By Tangent – Proptech
What Retailers Actually Think About Agentic Commerce With Stripe's Maia Josebachvili | 5IM
PodcastFeb 19, 20265 min

What Retailers Actually Think About Agentic Commerce With Stripe's Maia Josebachvili | 5IM

In this five‑minute interview, Maya Jose Bakvili, Stripe’s CRO of AI, explains "agentic commerce"—AI‑assisted chat purchases and AI‑delegated buying—and how Stripe’s infrastructure supports retailers in this emerging space. She highlights four persistent retailer concerns: maintaining control as merchant of record,...

By Omni Talk
Why Stack Overflow and Cloudflare Launched a Pay-per-Crawl Model
PodcastFeb 19, 202619 min

Why Stack Overflow and Cloudflare Launched a Pay-per-Crawl Model

In this episode, Stack Overflow’s Janice Manningham and Josh Zhang chat with Cloudflare VP Will Allen about the newly launched pay‑per‑crawl model that lets publishers charge crawlers for access. They explain how AI‑driven content scraping has upended the traditional open‑versus‑block...

By Stack Overflow Podcast
Stop Layering AI on Your GTM Stack
PodcastFeb 19, 20260 min

Stop Layering AI on Your GTM Stack

In this episode, Emir Atli, co‑founder and CRO of HockeyStack, explains why the traditional, tool‑heavy GTM stack can’t simply have AI bolted on—it must be rebuilt around a unified, AI‑native platform with a single data foundation. He outlines HockeyStack’s evolution...

By The GTM Newsletter
The ERP Minute Episode 225 - February 17th, 2026
PodcastFeb 18, 20264 min

The ERP Minute Episode 225 - February 17th, 2026

In this brief episode, the hosts recap Procore's Q4 and full‑year 2025 financial results, highlighting its strong performance in the construction software market. They then discuss NetSuite's new suite of innovations aimed at boosting operational efficiency and supporting rapid growth...

By The ERP Advisor
The Conundrum
PodcastFeb 18, 202619 min

The Conundrum

In this episode of Bootstrapping SaaS, the host reflects on his journey toward achieving $10K in monthly recurring revenue as a solo founder, covering recent product updates, the challenges of juggling design, development, and marketing, and the lessons learned from...

By Bootstrapping SaaS
The Signal: The Real "Payment Meets Fraud" Journey with Brian Rust at Worldpay | Episode 467
PodcastFeb 17, 202625 min

The Signal: The Real "Payment Meets Fraud" Journey with Brian Rust at Worldpay | Episode 467

In this episode, Brian Rust, SVP and Deputy CISO at Worldpay, explains how fraudsters now target SaaS platforms and ISVs by exploiting weak onboarding, transaction logic, and refund processes. He outlines the fraud kill‑chain—from synthetic business creation and card‑testing spikes...

By Leaders in Payments
37 | Why Retention Is Now Driving Software Company Valuations
PodcastFeb 17, 202617 min

37 | Why Retention Is Now Driving Software Company Valuations

In this episode, managing director Mike Lyon and senior associate Sarabeth Sandweiss discuss how retention metrics have become a pivotal factor in software company valuations, detailing the heightened scrutiny buyers now apply. They explain the investor framework for assessing retention,...

By The Path to Exit
Google Alerts for Insurance?  Visualping Brings New Technology for Risk Assessment
PodcastFeb 17, 202653 min

Google Alerts for Insurance? Visualping Brings New Technology for Risk Assessment

In this episode, Visualping co‑founder and CEO Serge Salager explains how his company is turning real‑time web monitoring into a "Google Alerts for insurance," delivering instant risk insights to underwriters. He outlines emerging data sources—such as property changes, environmental alerts, and...

By The Insurance Podcast
Talking Drupal #540 – Acquia Source
PodcastFeb 16, 20260 min

Talking Drupal #540 – Acquia Source

In this episode the hosts dive into Acquia Source, the fully managed Drupal SaaS platform, exploring its evolution, pricing, and how it enables organizations to scale and customize Drupal experiences. Guest Matthew Grasmick explains the technical challenges of building a...

By rimzy.net (Yzmir/Sergey)
91: Using AI in Sales to Automate Go-to-Market Execution with Jason Eubanks
PodcastFeb 16, 202644 min

91: Using AI in Sales to Automate Go-to-Market Execution with Jason Eubanks

In this episode, Chris Daigle interviews Jason Eubanks, CEO of Aurasell AI, about the need for an AI‑native go‑to‑market operating model rather than piecemeal AI experiments. Jason explains that simply adding AI to legacy CRM systems won’t shift productivity; a...

By AI at Work
The Most Underrated Signal Brands Should Optimize For
PodcastFeb 13, 20263 min

The Most Underrated Signal Brands Should Optimize For

In this 3‑minute episode, Jordan Cooney talks with Tim Sanders, Chief Innovation Officer at G2, about a surprisingly overlooked SEO signal for AI‑driven search: using concise markdown files that highlight the top four takeaways of a page. Sanders explains that...

By Voices of Search
Bootstrapping to $50M ARR in Vertical SaaS | Vantaca's HOA Software Playbook
PodcastFeb 12, 202622 min

Bootstrapping to $50M ARR in Vertical SaaS | Vantaca's HOA Software Playbook

In this episode, Ben Currin, CEO of Vantaca, explains how the company bootstrapped a vertical SaaS platform for HOA management from under $1M ARR to $50M ARR, first reaching $5–10M without external funding and then scaling tenfold after a minority...

By SaaS Interviews with CEOs
Maor Greenberg - AI-Powered Plans for Residential Homes
PodcastFeb 12, 202631 min

Maor Greenberg - AI-Powered Plans for Residential Homes

In this episode, Maor Greenberg, CEO and co‑founder of Spacial, explains how AI is reshaping SaaS tools for residential construction, recounting his journey from early proptech ventures in Israel to multiple U.S. building businesses. He highlights the challenges of conflicting...

By Proptech Espresso
Beyond Chatbots: How Cara Becomes Your Best CSR
PodcastFeb 11, 202628 min

Beyond Chatbots: How Cara Becomes Your Best CSR

In this episode, Nikhil Kansal, Co‑Founder & CTO of Cara, explains how AI can move beyond chatbots to act as a reliable Customer Service Representative (CSR) that completes end‑to‑end insurance service tasks. He highlights Cara’s role as a coordinating layer...

By Insurtech Leadership Podcast
From 1 AI Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM
PodcastFeb 10, 20260 min

From 1 AI Agent to 20+: The Reality of Managing Multiple AI Agents Across Your GTM

In this episode the host shares eight months of experience running 20+ AI agents across SaaStr's go‑to‑market function, generating $4.8 M in additional pipeline and $2.4 M in closed‑won revenue. He explains that the results are additive but require daily hands‑on management,...

By Jason Lemkin
Building AI Product Sense, Part 2
PodcastFeb 10, 20260 min

Building AI Product Sense, Part 2

In part two of "Building AI Product Sense," Dr. Marily Nika, an experienced AI product manager from Google and Meta, outlines a weekly ritual for developing AI product sense—translating model behavior into trustworthy products. She explains why Meta now includes...

By Lenny Rachitsky
B2B Community Growth with Kris Rudeegraap, Co-Founder & Co-CEO at Sendoso
PodcastFeb 9, 202621 min

B2B Community Growth with Kris Rudeegraap, Co-Founder & Co-CEO at Sendoso

In this episode, Jodi interviews Kris Rudeegraap, Co‑Founder & Co‑CEO of Sendoso, about how the company built a multi‑tiered B2B community that fuels a $7 million pipeline and boosts account spend by 71%. Kris explains the ROI of personal advisory groups,...

By FINITE: B2B Marketing Podcast
20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company...
PodcastFeb 7, 202653 min

20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company...

In this episode, Ariel Cohen, co‑founder and CEO of Navan (formerly TripActions), discusses the company’s recent IPO, the sharp drop in market cap, and the strategic decisions driving its next phase. He explains why Navan rushed to go public, how...

By The Twenty Minute VC (20VC)
How Zoom Grew 30x Almost Overnight
PodcastFeb 5, 202627 min

How Zoom Grew 30x Almost Overnight

In this episode, Eric Yuan recounts his journey from a frustrated employee at a video‑conferencing startup to founding Zoom, detailing the company’s rapid 30‑fold expansion during the COVID‑19 pandemic. He explains how Zoom scaled its technology, culture, and operations to...

By Masters of Scale
How to Scale to $12M ARR: The Serial Founder Playbook for Vertical SaaS and Agentic AI
PodcastFeb 4, 202629 min

How to Scale to $12M ARR: The Serial Founder Playbook for Vertical SaaS and Agentic AI

In this episode, Matt Spiegel, founder and CEO of Lawmatics, walks through how his vertical SaaS company scaled to $12M ARR by focusing on high ARPU, agentic AI, and disciplined capital strategies. He shares tactics for acquiring the first 100...

By The Top Entrepreneurs Podcast
Product Walkthroughs, the Next Open Source Product & Other Listener Questions
PodcastFeb 4, 202626 min

Product Walkthroughs, the Next Open Source Product & Other Listener Questions

In this episode, Jason Fried and David Heinemeier Hansson answer listener questions, covering how they record unscripted product walkthrough videos, the upcoming open‑source product Writebook, and the way the 37signals team combines Basecamp with their new kanban tool Fizzy. They...

By REWORK (37signals)
How Dresma Hit $2M ARR With Usage-Based Pricing & AI-Powered E-Commerce Imagery
PodcastJan 29, 202623 min

How Dresma Hit $2M ARR With Usage-Based Pricing & AI-Powered E-Commerce Imagery

In this episode, Siddharth Sinha, co‑founder and CEO of Dresma, walks through how his AI‑powered platform scales studio‑quality e‑commerce imagery and video for global brands using usage‑based pricing and automated workflows. He explains why the usage model outperformed seat‑based pricing,...

By The Top Entrepreneurs Podcast