Cloud Radio | A SaaS Operator Podcast

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/

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/

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/

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 lie
• Incumbents vs. startups: Why the next decade will reward incumbents with data and trust, and AI-first challengers with 10x user experiences
• G2’s AI strategy: From generative engine optimization (GEO) to G2 AI as a buying assistant
• Future of software buying: Will AI shorten shortlists? How buying cycles, transparency, and seller roles are evolving
• Marketing in the AI era: Risks of losing optimized website conversion funnels and how vendors must retool
• Endurance in entrepreneurship: Lessons from the Leadville 100 on perseverance and keeping vision through valleys

Resources:

G2 2025 Buyer Behavior Report

Godard Abel LinkedIn

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

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 spend
• The 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/

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/

Our Guest: Guy Rubin is the Founder and CEO of Ebsta, a Revenue Intelligence Platform that provides insights into what drives over 500 B2B companies' success. 

Episode Topics:

• What is Ebsta’s 2024 B2B Sales Benchmark report?
• Reliance on top sales representatives - 17% of reps generate 81% of revenue.
• Difference in deal progression between average and top performers - average performers tend to lose deals during negotiation, whereas top performers experience more losses during the qualification and discovery stages.
• Guy’s insights on increasing pipelines and adopting best sales methodologies.
• How does AI fit within Ebsta’s product suite?
• How does discussing ROI accelerate the sales cycle?
• Based on poor quota attainment and certain layoffs, has sales forecasting gotten harder?
• Guy's insight on improving forecasting accuracy.

Resources:

https://www.ebsta.com/2024-b2b-sales-benchmarks/

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/

Our Guest: Matt Slotnick is the Co-Founder and CEO of Poggio Labs, an AI Sales Workspace purpose-built for Account Executives. Poggio is backed by Accel and Spark Capital.

Episode Topics:

• Understanding end-user workflows in GenAI applications.
• How understanding customer workflows influences team construction?
• How Poggio Labs handles the new challenge of managing user expectations for AI.
• Insights and lessons from early adopters of Poggio Labs software.
• Potential competitive tensions arising from intersecting workflows.
• Matt’s take on incumbent’s ability to innovate and why the “data is the new oil” narrative might not be true
• How does an iterative approach drive real product innovation?
• Implications for building AI versus established playbooks in SaaS.
• What aspects of Poggio are generating raving enthusiasm among users?
• Matt’s lessons learned from his cycling passion applied to entrepreneurship and company building.

Resources:

https://poggio.io/ 

Thread on building AI products + emerging moats: https://twitter.com/matt_slotnick/status/1747686262914568444

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/

Our Guest: Scott Brinker, VP of Platform Ecosystem at HubSpot, shapes Hubspot's platform strategy and leads business programs for its global technology partner ecosystem. He is also an editor at chiefmartec.com, with over 50,000 readers, analyzing topics at the intersection of marketing, technology, and management. 

Episode Topics:

• How much does Scott Brinker see AI impacting marketing headcount?
• Scott on the need to adapt and rethink categorizations in light of the evolving MarTech landscape.
• What are some concerns about the sustainability of the current level of saturation in the martech industry? 
• How should companies in the torso (top 100 companies) and head (top 10 companies)  navigate the presence of a large number of competitors in the long tail (12,000 companies)?
• What does composability truly mean for MarTech? 
• The business and technical risk of composability.
• Scott's recommendations and principles to CMOs and marketing leaders for implementing composability. 
• How does competition among major platforms provide opportunities and leverage for smaller, long-tail partners in ecosystems?

Sources:
https://chiefmartec.com/2023/12/major-trends-in-martech-for-2024-the-real-changes-underway-in-a-99-platitude-free-report/

https://chiefmartec.com/2023/10/products-in-the-long-tail-of-martech-have-a-wide-range-of-different-strategies-and-aspirations/

https://www.saasletter.com/p/mckinsey-cloud-roi-ai-roi

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/