Cloud Radio | A SaaS Operator Podcast

Cloud Ratings
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Operator-level insight into the business of software. Cloud Radio is the operator podcast from Cloud Ratings, the data-driven software research firm. Host Matt Harney, Founder of Cloud Ratings and author of the "SaaSletter" newsletter, sits down with SaaS founders, executives, and researchers to get past the talking points on how software companies actually grow, sell, and spend. Conversations cover: • Go-to-market efficiency and sales performance • How software is bought, and how AI is changing it • SaaS metrics, pricing and finance • Building and leading software teams in the age of AI Guests have included G2 co-founder and CEO Godard Abel, G2 Chief Innovation Officer Tim Sanders, martech authority Scott Brinker, and leaders from Zylo, ChartMogul, Vantage, Vertice, and Logikcull. Made for SaaS operators, and for the investors who want to understand how software companies really run. For investor conversations, listen to our companion show, "Cloud Returns": https://cloudreturns.cloudratings.com/ Newsletter: https://www.saasletter.com Research + Firm: https://cloudratings.com

  1. 2d ago

    Tim Sanders - G2 - Crossing The Agentic AI Chasm

    Our Guest: Tim Sanders is the Chief Innovation Officer at G2 and a fellow at Harvard’s Digital Data Design Institute. Tim leads G2’s research on AI adoption and the market for AI agents. His latest discussion focuses on G2’s 2026 AI Agents Report, “Crossing the Agentic Chasm,” based on a survey of 1,019 B2B decision-makers and 2,500+ AI Agent Builder reviews. Episode Topics: Why 66% of organizations now have agents in limited or scaled productionAgent builder platforms (42%) vs ready-made agents (27%) and what that mix means for traditional SaaS vendorsWhy 56% of buyers expect agents to moderately reduce new SaaS purchases by 2030The “harness”: how SaaS moves from database + business logic to skills, connectors, and context engineeringWhy vibe coding is not the real threat to enterprise softwareThe shift to pay-as-you-go pricing and what it means for gross margins, ARR, and ARPAHow consumption pricing lowers buying friction and weakens vendor loyaltyThe Distrust Tax: why oversight and rework can consume more than a quarter of expected agent gainsWhy the Distrust Tax is recurring, not a one-time implementation costHow human oversight grows with company size, and the mid-market speed advantageAnt Financial’s 3-1-0 loan model and budgeting for acceptable failure ratesHow buyers verify vendor claims, and why evaluation is becoming the longest stage of software buyingWhy “agent evaluator” may be a job with a real futureSelling pragmatic, measurable gains (like an 11% improvement in book-to-cash) instead of 10x promisesResources: https://sell.g2.com/g2-2026-ai-agents-insight-report https://company.g2.com/news/2026-ai-agents-report https://learn.g2.com/g2-2025-ai-agent-insight-report

  2. May 28

    Guy Rubin - 2026 GTM Benchmarks

    Our Guest: Guy Rubin is with Fullcast and was the founder and CEO of Ebsta. Guy is known for his deep work in GTM data, revenue insights, and sales efficiency. His latest discussion focuses on Fullcast’s 2026 State of GTM Benchmarks report, based on data from 316 B2B software and services companies with more than $75 billion in pipeline. Episode Topics: The 2026 GTM benchmark report and what $75B in pipeline reveals about sales efficiency today.Why sales efficiency dropped by 28% and what’s driving the decline.The growing gap between top-performing sellers and the rest of the sales team.Why AI-generated volume does not automatically create better revenue outcomes.How companies using AI for rigor, qualification, and process are increasing revenue per seller.Why territory balance matters and how overloaded sellers lose depth, relationships, and win rates.Moving beyond round-robin lead distribution toward smarter routing based on seller expertise.Why forecasting based only on deal stage is no longer enough.How CRM, email, calendar, call recordings, and relationship data can create a more accurate revenue picture.The role of Revenue Insights as a Service for private equity firms and portfolio companies.Why generic BDR/SDR pipeline often creates noise instead of quality opportunities.How AE-led outbound, partnerships, communities, and customer introductions are becoming more efficient growth channels.Why ICP definition should be dynamic, data-backed, and based on real buying signals.How leadership teams can use simple, visual revenue insights to align around better GTM decisions.Why relationships still drive revenue, even in an AI-enabled sales environment.Resources: https://www.fullcast.com/ebooks/2026-benchmarks-report-the-state-of-gtm-in-2026/ https://www.fullcast.com/content/guy-rubin-inside-the-go-to-market-benchmark-report/ https://www.joinpavilion.com/resource/2025-gtm-benchmarks-ebsta-pavilion  About Cloud Radio by Cloud Ratings: Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software. Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack. https://cloudradio.cloudratings.com/ https://twitter.com/SaaSletter https://www.saasletter.com/ About Cloud Ratings: Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/

    Guy Rubin - 2026 GTM Benchmarks

  3. May 6

    Tim Sanders - G2 - The AI Answer

    Our Guest: Tim Sanders is the Chief Innovation Officer at G2 and a fellow at Harvard’s Digital Data Design Institute. A longtime researcher of market trends and business technology, Tim focuses on AI adoption, AI agents, and the rise of answer engines in the software buying journey. Episode Topics: AI’s role in reshaping the B2B software buying journey, from early research to shortlist creation.The rise of “one-shotting” and how buyers now compress days of vendor research into a single AI prompt.How G2 reviews, category rankings, and high-authority third-party sources influence AI recommendations.Why enterprise buyers are moving faster toward AI-assisted buying as teams get leaner and workloads increase.The new importance of “winning the answer” in ChatGPT, Gemini, and deep research tools.Mentions vs. citations vs. recommendations: which ones actually influence software buying decisions?Deep research is the new buying battleground, where the final recommended vendors matter more than general visibility.Why AI-driven traffic may convert better than traditional search traffic.The content shifts from polished corporate messaging to fresh reviews, proof points, Q&A content, and human-answer-shaped thought leadership.YouTube transcripts, podcasts, LinkedIn, reviews, and niche publications are emerging sources of AI visibility.The difference between machine learning, bots, and agents.The executive “30% rule” for AI literacy and why leaders should reframe business problems as prediction problems.Why companies need to close the trust gap between AI reliability and employee adoption.How AI changes hiring and promotion by increasing the value of judgment, curiosity, feedback, and “taste.”Inside G2’s own AI-first experiments, including generative summaries, dynamic FAQs, and learning how to make complex product pages easier for machines to understand. Resources: https://learn.g2.com/g2-2026-ai-search-insight-report  https://learn.g2.com/g2-2025-ai-agent-insight-report  https://www.tryprofound.com/blog/profound-g2-partnership  https://university.tryprofound.com/ https://6sense.com/science-of-b2b/buyer-experience-report-2025/ https://promptwatch.com/  https://spotlightar.com/ https://firstpagesage.com/seo-blog/generative-engine-optimization-geo-explanation/  https://graphite.io/five-percent/ai-is-much-bigger-than-you-think https://www.similarweb.com/blog/marketing/geo/build-prompts-from-keywords/  About Cloud Radio by Cloud Ratings: Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software. Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack. https://cloudradio.cloudratings.com/ https://twitter.com/SaaSletter https://www.saasletter.com/ About Cloud Ratings: Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/

    Tim Sanders - G2 - The AI Answer

  4. Feb 18

    Karim Fanous - Engineering Management in the Age of AI

    Our Guest: Karim Fanous is the Senior Vice President of Engineering at StrongDM, a cybersecurity company, and the writer behind Cumulative, a Substack focused on engineering management, building startups, and how AI is reshaping the craft of software. Episode Topics: Why VPE is “people + product + processes”  and how breakdowns show up as business problems (growth, quality, churn, GTM).How “buggy processes” reveal themselves at the exec level through growth stalls, quality pain, churn, and GTM friction?Executive interview questions that reveal whether an engineering leader can connect engineering to business reality.The common scaling fallacy: doubling engineers does not double output.“AI made us faster… not necessarily better”: how AI boosts strong engineers, but used carelessly amplifies technical debt.Why human review won’t scale in an agent-driven world and why software will need machine verification to move at “GPU speed.”?Engineering shifts toward architecture, integration, trade-offs, experiments, and validation.The “10x engineer” debate in the AI era.AI security risks: non-deterministic systems + autonomous actions require controls beyond RBAC.Inside StrongDM’s approach on agents treated like coworkers with identities, visibility, and feedback that improves behavior. Resources:https://www.cummulative.io/  https://www.linkedin.com/in/karimfan https://www.strongdm.com/https://www.cummulative.io/p/ai-agents-are-here-security-isnt  https://www.cummulative.io/p/preparing-for-a-world-where-humans  https://www.cummulative.io/p/how-do-you-interview-a-vp-of-engineering  About Cloud Radio by Cloud Ratings: Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software. Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack. https://cloudradio.cloudratings.com/ https://twitter.com/SaaSletter https://www.saasletter.com/ About Cloud Ratings: Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/

    Karim Fanous - Engineering Management in the Age of AI

  5. 09/03/2025

    Godard Abel - G2 - Software Buying In The Age of AI

    Our Guest: Godard Abel, Co-Founder and CEO of G2, the world's largest and most trusted software marketplace. He previously built cloud CPQ pioneers BigMachines (acquired by Oracle) and SteelBrick (acquired by Salesforce). Episode Topics: AI across the stack: Infrastructure, data, models, and applications—where the most significant opportunities and risks lieIncumbents vs. startups: Why the next decade will reward incumbents with data and trust, and AI-first challengers with 10x user experiencesG2’s AI strategy: From generative engine optimization (GEO) to G2 AI as a buying assistantFuture of software buying: Will AI shorten shortlists? How buying cycles, transparency, and seller roles are evolvingMarketing in the AI era: Risks of losing optimized website conversion funnels and how vendors must retoolEndurance in entrepreneurship: Lessons from the Leadville 100 on perseverance and keeping vision through valleys Resources: G2 2025 Buyer Behavior Report Godard Abel LinkedIn

  6. 04/01/2025

    Guy Rubin - Ebsta - 2025 GTM Benchmarks

    Guy Rubin is the Founder + CEO of Ebsta, a revenue intelligence platform that guides sales teams to more effective sales processes, pipeline reviews and forecast calls with Revenue Insights.  Episode Topics: Overview of Ebsta’s 2025 GTM Benchmarks Report. Produced in partnership with Pavilion, the report covers $48 billion of pipeline across 655,000 opportunities, analysis of 240,000 minutes of seller discovery calls, and a survey of 2,000+ CROs + Sales Leaders.Guy’s perspective on the 11x velocity gap between top and bottom sales performers – up from 4x in 2022.Why top performers are 455% better at discovery – and what B & C players lack.The importance of engaging 6+ stakeholders early in the sales cycle to boost win rates from 12% to 40%+.The power of visual playbooks, AI-driven nudges, and qualification signals to drive consistency.Ebsta’s approach to forecast accuracy.The return of 360 sellers – handling full-cycle sales for stronger buyer relationships.High-performing sales channels: Partner/Referral (1.3x velocity), Organic (1.2x), Outbound (1.05x), Events (0.78x), Paid (0.68x).Investing in partner programs, communities, and warm referrals to raise win rates.Why disqualifying non-ICP deals early boosts productivity – 24% more likely among top reps.The human factor in sales management – helping the sales team through structure, not micromanagement.Ebsta Client Example: the role of data-driven RevOps in aligning leadership and driving 29% revenue growth.Why relationships still matter – even in an AI-powered B2B sales world.Resources:https://benchmarks.ebsta.com/2025-gtm-benchmarks https://www.saasletter.com/p/value-selling https://www.saasletter.com/p/sales-check-engine-light

  7. 02/04/2025

    Ben Pippenger - Zylo - 2025 Zylo SaaS Management Index

    Our Guest: Ben Pippenger is the Co-Founder and Chief Strategy Officer of Zylo, a SaaS management platform that helps businesses gain full visibility into their software usage, optimize licensing, and streamline renewals.  Episode Topics: Overview of Zylo’s SaaS Management Index annual report, which covers $40 billion of SaaS spendThe AI adoption surge in software spend  - 75 percent increase in spending.The Rising of SaaS Costs - increased by 9.3 percent year over year.The shift from traditional seat-based pricing to usage and value-based models.Ben’s takes on the decline of multi-year SaaS contracts in recent data.Ben’s insight to IT’s shrinking influence over SaaS.Increasing SaaS waste - $21 million annually on unused software licenses.Strategies to manage and reduce rising SaaS costs effectively.What are some hidden costs of long-tail SaaS purchases?Ben shares vendor negotiation tactics and cost-saving strategies to optimize software investments. Resources:https://zylo.com/reports/2025-saas-management-index/ https://zylo.com/ https://www.saasletter.com/p/zylo-saas-management-index-2025 About Cloud Radio by Cloud Ratings: Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software. Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack. https://cloudradio.cloudratings.com/ https://twitter.com/SaaSletter https://www.saasletter.com/ About Cloud Ratings: Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/

    Ben Pippenger - Zylo - 2025 Zylo SaaS Management Index

  8. 04/30/2024

    Sally Duby - Sales in 2024: SaaS AE Metrics Report

    Our Guest: Sally Duby is the Chief Sales Officer at The Bridge Group Inc., a sales strategy consulting firm for B2B companies looking for more from sales development, sales, and customer success.  Episode Topics: Marketing contribution to the pipeline rose from 33% in 2022 to 40% in 2024.Characterization of the account manager and customer success manager.Who is responsible for renewal, upsell, and cross-sell?Average years of experience required at hire by Annual Contract Value (ACV).The increasing Account Executive (AE)’s average ramp time.How tenure and ramp time affect productivity time - Median time at productivity sits at 24 months.Increasing trend of quotas across all bands from $5k to $250k+ by ACV.Win rates declining from 23% in 2022 to 19% in 2024.Decreasing trend of quota attainment among AEs from 2012 to 2024.Common problems of clients The Bridge Group works with.The Bridge Group playbook for improving sales.Sally’s viewpoints on outbound sales and SDR functions.Effective strategies for outbound sales efforts. AI’s role in improving SDRs and AEs productivity. Resources: https://blog.bridgegroupinc.com/2024-ae-metrics-compensation-benchmark About Cloud Radio by Cloud Ratings: Made for "full stack" cloud + SaaS operators, Cloud Radio is a SaaS podcast covers all aspects of the business of software. Our host - Matt Harney - is active on Twitter @saasletter and writes "SaaSletter", an investing-oriented SaaS newsletter on Substack. https://cloudradio.cloudratings.com/ https://twitter.com/SaaSletter https://www.saasletter.com/ About Cloud Ratings: Cloud Ratings is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software, Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, and Sales Training + Onboarding Software. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/

    Sally Duby - Sales in 2024: SaaS AE Metrics Report
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About

Operator-level insight into the business of software. Cloud Radio is the operator podcast from Cloud Ratings, the data-driven software research firm. Host Matt Harney, Founder of Cloud Ratings and author of the "SaaSletter" newsletter, sits down with SaaS founders, executives, and researchers to get past the talking points on how software companies actually grow, sell, and spend. Conversations cover: • Go-to-market efficiency and sales performance • How software is bought, and how AI is changing it • SaaS metrics, pricing and finance • Building and leading software teams in the age of AI Guests have included G2 co-founder and CEO Godard Abel, G2 Chief Innovation Officer Tim Sanders, martech authority Scott Brinker, and leaders from Zylo, ChartMogul, Vantage, Vertice, and Logikcull. Made for SaaS operators, and for the investors who want to understand how software companies really run. For investor conversations, listen to our companion show, "Cloud Returns": https://cloudreturns.cloudratings.com/ Newsletter: https://www.saasletter.com Research + Firm: https://cloudratings.com

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