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/

Our Guest: Scott Leese is a six-time Sales Leader and a two-time best-selling Amazon author in the category of sales. He maintains active communities like GTM United and is also focusing on helping companies build revenue-driving motions across the organization. 

Episode Topics:

• Scott's view on shifting away from traditional VP career paths and expectations.
• What are the qualities to look for in someone who is a first-time VP of Sales?
• Scott’s advice for someone who is considering transitioning into an account executive (AE) role + Director/VP Sales level.
• The type of leaders or CEOs that Scott gets along with.
• Overall framework of the evolution of Sales from Go-To-Market to Go-To-Network.
• What type of seller performs best?
• Scott on the sales productivity of Go-To-Network approach versus cold outbound strategy.
• Scott's take on Sapphire Non-AE GTM Bloat - 90% of GTM spend is non-AE, down from 70% in 2018.
• Strategies or approaches that are currently successful in the broader environment.
• Scott elaborates his Linkedin post on self-inflicted errors: “Most deals die from predictable self-inflicted errors. Avoidable problems turn into cyclical failures caused by a lack of focus on reverse engineering root causes.”

Resources:

https://www.surfandsales.com/ 

https://twitter.com/SaaSletter/status/1700517476017246334?s=20 

https://www.linkedin.com/posts/scottleese_you-dont-get-good-at-anything-by-giving-activity-6990657671431405568-lVpl?utm_source=share&utm_medium=member_desktop

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: Ashley Acosta, Founder and CEO of Maca. Previously, Ashley was the VP of Revenue at Pipe, on the founding team at Brex, and a Mentor at First Round Capital. Now, she's pioneering the first operating system for value-based pricing through Maca, empowering growing companies to achieve greater revenue efficiency through AI-driven data insights.

Episode Topics:

• How much potential revenue are companies losing by not optimizing their pricing strategies?
• Maca’s methods of sourcing data + understanding their insights engine.
• Ashley's insight on the growing complexity of revenue management in growing companies and hidden revenue channels.
• Twitter Question #1: What are the top key results in metrics to determine pricing effectiveness? 
• Twitter Question #2: How do you think about testing pricing and gathering learnings for long sales cycle products?
• Ashley expounds on her Tweet: “Test pricing using your sales levers, not by changing your list price. This will promote learnings about internal levers faster and you'll be less likely to upset your customers by changing pricing on your website, requiring less internal uplift to change pricing.”
• How to determine pricing decisions + levers for software products by understanding overall ROI at the feature level
• Benefits of Maca's data-driven model over the traditional pricing consultant model (i.e. engaging Simon Kucher).
• The scale and type of software companies that Maca works with.

Resources:

https://maca.io/

https://www.linkedin.com/in/ashley-acosta-8aa28132/

https://twitter.com/ashleyacosta75/status/1678455416261419022

https://cloudratings.com/roi-of-it-software/

https://cloudratings.com/software-roi-drivers/

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: Eldar Tuvey, CEO and Founder of Vertice, an automated SaaS purchasing platform that simplifies buying, renewals, and management of software applications, helping businesses streamline their procurement and save on SaaS spend. They recently launched a Cloud Cost Optimization platform, a new product built for finance leaders to optimize their AWS spend.

Episode Topics:

• Eldar’s earlier experiences as an operator buying + renewing software that led to the launch of Vertice.
• Profile of Vertice's ideal customer profile (ICP) in terms of software spend, number of customers, and employees.
• How do software vendors view “working against” SaaS purchasing platforms like Vertice?
• What inning of the cloud cost optimization game are we in?
• The potential impact of Vertice on reducing wasted cloud spend - a recent Vertice report showed organizations "wasting as much as a third (32%) of their cloud budget."
• Understanding how cloud cost optimization is achieved - “50% to 55% of savings come through financial elements (like EDPs and Reserved Instances) and 45 to 50 from engineering, different scaling, processing, etc.”
• The time to value for cloud cost optimization.
• Eldar's insight on Morgan Stanley's survey that cloud optimization efforts could ultimately increase cloud spending.
• Eldar on the 66% of companies exceeding their cloud budgets.
• How are Vertice customers responding to the average 12% price increase software vendors are implementing?
• Vertice’s recommended playbook for customers dealing with significant price hikes from vendors for must-use tools.

Resources:

https://www.vertice.one/inside-saas/cloud-cost-optimization-launch

https://www.vertice.one/inside-saas/reports/cloud-spend-report-2024

https://www.vertice.one/inside-saas/cloud-spend-insights-september-2023

https://www.vertice.one/saas-purchasing-insights

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: Andy Willson, Co-Founder and former CEO of Logikcull, a cloud-based eDiscovery solution trusted by hundreds of legal teams to automate discovery and legal holds for disputes, subpoenas, investigations, record requests, and more. After 19 years of building, Logikcull was acquired by Reveal in late August 2023.

Episode Topics:

• How Andy is feeling post-exit.
• How Logikcull created an inbound GTM motion with product-led growth dynamics.
• Andy's insights into managing customer expectations in the context of artificial intelligence (AI) in legal tech.
• Andy's advice and strategies for people outside legal tech expanding into AI.
• We then dive deep into Andy’s excellent “19 Lessons From 19 Years” 
• “#1.  The team you build is the company you build. Want to build a great company? Find great people and never settle”.
• “#4.  Get written agreements for the work you need done, not assumed expectations. ASSUME = ASS + U + ME.”
• “#5.  Hire leaders that run at high tempos with high energy & high capability. The team will mirror them and the force will multiply.”
• “#8.  Build something people want and value. Price accordingly.”
• “#9. No customers -> No employees -> No revenue -> No business. Focus on customers and have all employees, especially engineers, frequently interact with customers. This will create empathy and empathy drives urgency.”
• “#16.  Small teams with high agency & chips on their shoulders will win. Keep your teams small and give them the direction & freedom to succeed. More customers and more revenue is > more employees. “Chips on shoulders puts chips in pockets.” - Josh Wolfe”
• “#18.  Extinction-level events will happen (we had a few ourselves =). The team you build will define whether your business lives or dies during these times. So, when in doubt, hire for grit. Tough times don’t last. But tough people do.”
• “#19.  Never give up.”
•  A final question: How did Andy maintain a healthy relationship with a co-founder for two decades?

Resources:

“19 Lessons From 19 Years” Twitter Thread: https://twitter.com/iDedupe/status/1678381125042044931

https://www.logikcull.com/

https://resource.revealdata.com/en/press/logikcull-ipro-acquisition

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: Account-Based Marketing Software, Cap Table + Equity Management Software, Lead Routing Software, Sales Training + Onboarding Software, and Sales Conversation Intelligence 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/