Predictable B2B Success

Sproutworth
  • 5.0 (22)
  • Entrepreneurship
  • Updated Weekly

If you lead a bootstrapped or funded B2B tech company and need revenue to be predictable, not just possible, this podcast was built for you. Predictable B2B Success is the only show built exclusively for CEOs at seed-to-Series C tech companies who are ready to replace random acts of growth with a scalable, repeatable revenue system from first dollar to $50M+ ARR and beyond. Each week, host Vinay Koshy sits down with elite revenue operators, GTM leaders, and founders who have solved the hardest problem in funded B2B tech: turning chaotic, unpredictable growth into something structural, a system that holds under investor pressure, market shifts, and scale. What you will walk away with every episode: Operating frameworks for building predictable revenue pipelinesReal playbooks from founders who have scaled B2B companies from seed to Series C and beyondGTM, RevOps, demand generation, and category design insights built for C-suite decisions, not marketing teamsStrategies that compound across your organisation, not one-off tactics that fade Why 500+ episodes and a 5.0-star rating? This is not a show about inspiration. It is a show about operating clarity. Every guest is chosen because they have built systems in sales, content, community, product, or customer success that made revenue predictable. After 500+ episodes, the patterns are unmistakable. This archive is your competitive advantage. Trusted by founders and CEOs at bootstrapped and funded B2B tech companies across SaaS, cleantech, AI, and enterprise software. Rated 5.0 stars on Apple Podcasts. Ranked top 5 B2B podcast by Feedspot (2026). 500+ episodes since 2020. Subscribe now and get a new episode every week, turning your revenue from a moving target into a scalable system. Show notes, frameworks, and transcripts: sproutworth.com Subscribe to The Inclined, the weekly newsletter for funded B2B tech CEOs: sproutworth.com/newsletter Connect with Vinay Koshy on LinkedIn: linkedin.com/in/vinaykoshy

  1. 2d ago

    He Tripled His SaaS Prices, and Not One Customer Left

    Introduction When a customer says to you, “You’re cheap, so you can’t be very good”, what occurs? For Vitalii Sydorenko, this remark completely changed all his previous ideas about pricing and product value. This enlightening episode of Predictable B2B Success traces Vitalii's journey from a founder who set his prices far too low to a bold entrepreneur who tripled them and watched in amazement as not a single customer left. That's only the start, though. Vitalii also exposes the experiments and errors that shape a founder's journey, such as launching free trials that failed and letting one major client gradually become the sole source of income until a crisis changed everything overnight. He shares the lessons he learned from building LOOQME, closing his second startup, Jiffsy, even after securing investors and a Google grant, and helping founders validate their ideas before spending a single cent on development. If you've at any time had concerns about pricing fears, have ever wondered whether automation can actually have a negative effect on sales, or have questioned the risks of putting your hopes on a single "dream client", the insights and lessons offered by Vitalii will challenge your current beliefs. By tuning in, you'll learn how reconsidering value, customer education, and your messaging can help save your business from expensive mistakes. Some topics we explore in this episode include: How low pricing can undermine trustWhat happens when you triple prices overnightValue-based pricing in B2B SaaSSmart ways to test price increasesWhat causes sales to be achieved? Free trials versus high-touch onboarding.Turning customer education into higher conversionsReal lessons from a startup failureThe hidden danger of relying on one big clientWhat actually works in B2B lead generation todayProving product demand before you build

  2. Oct 6

    1 in 20 Trust AI With a Deal: How to Close the Trust Gap

    Why do customers who praise your demo end up not buying? In this striking episode of Predictable B2B Success, Vinay Koshy interviews Dan Mosher, CEO and co-founder of DealGround, about the awkward gap between using a state-of-the-art product and trusting it when it really counts. Since Dan Mosher knows the kind of thing it takes to gain a foothold in difficult markets, having been involved in growing companies such as Postmates, Brightroll, and Presto, and usually getting there a bit too early, he is now addressing the trust gap in commercial real estate, a field in which agents enjoy using AI tools but seldom actually use them to close deals. In this episode, you'll learn why many excellent products stall at the "pilot" stage and what shifts a customer's mindset from curiosity to confidence. You'll learn how Dan Mosher turned a deeply skeptical person into a fan in just one demonstration, and why building trust has nothing to do with features and everything to do with reframing expectations, embracing failures, and quickly bringing forward the "aha!" moments. If you're struggling with market timing, finding it hard to turn trials into trust, or considering your own move from a corporate job to startup life, you won't want to miss the practical advice and hard-earned lessons in this discussion. Some topics we explore in this episode include: Why B2B buyers use but rarely trust AI and what flips the switchThe double standard: Human error vs. AI mistakes in business decisionsHow AI hype sabotages adoption and how to set expectations that build trustWhere commercial real estate agents actually waste the most timeTurning product demos into “aha” moments that change hardened mindsWalking the privacy line: When valuable data becomes “too personal”Leveraging strategic partnerships to punch above your startup's weightAccuracy promises: How to win deals without overpromising on AIWhy startups fail when tech builds for industries they don't understandThe first 90 days: How smart leaders validate ideas before leaving their day job

  3. Sep 29

    Selling Prevention: How Blue Goat Cyber Built Demand Bootstrapped

    So why do so many medical device startups fail to account for a danger that could bring their whole business crashing down? In this episode of Predictable B2B Success, Vinay speaks to Christian Espinosa, the founder of Blue Goat Cyber, about the little-known aspects of cybersecurity in the medtech field a risk that is so badly underestimated that even the best industry articles and founder discussion forums fail to touch on it. Nevertheless, Christian Espinosa has built a successful, bootstrapped business by charging as much as $150,000 per engagement to address this oversight, having supported more than 250 FDA submissions in the process. Why is cybersecurity still treated as something added at the end rather than an essential part of device design? What are the consequences when a shortcut costing $5,000 turns out to cost $500,000? How do you achieve steady revenue and provide a written guarantee on your website when prospects only realize they need you after regulators have said "no"? Vinay puts Christian Espinosa on the spot on pricing, positioning, industry reactions, and lessons from a previous exit that went wrong. If you care about security, entrepreneurship, or overcoming market indifference, you won't find this point of view anywhere else. Listen in for valuable insights under pressure, useful takeaways, and a frank look at the challenges facing the overlooked medtech sector behind the scenes. Some topics we explore in this episode include: An invisible threat that few startups discuss: why is cybersecurity omitted from the vast majority of medtech failure post-mortems, and might your industry be ignoring a similar risk?The demand for things that no one is actually buying: how do you promote a solution for CEOs who don't (at this stage) think they need it? Learn about unorthodox methods to build awareness and create urgency.What really occurs when essential compliance work is delayed until the 11th hour? Regulatory surprises that cause product launches to failCan you carry out bold positioning campaigns without losing sight of your company's values?Why will some customers pay 20 times as much in a commodity market, and how can you design your offerings so that competitors can't realistically match them?Security (or indeed any technical service): could the actual value lie in the paperwork that goes uncredited?How failing to address security early can blow up your timeline: a real account of thousands of vulnerabilities discovered right before launch. When is your 'oh no' moment?Should you assess risk based on what matters most to your customers, or are you merely following industry dogma?Can offering your best tools for free generate more leads than lead magnets and email campaigns?What would you do differently if you had trusted the wrong people to be promoted, or if you realized that your highly praised exit had, in fact, not been a success?

  4. Sep 22

    How to Grow Revenue 20% Inside Customers You Already Have

    You've seen the report saying organized retail crime is causing serious damage to stores and behind almost half of all inventory losses. Yet what if that idea is nothing more than a myth? In this episode, Vinay invites Russ Hawkins, president and CEO of Agilence, someone who has, for nearly twenty years, assisted retail, grocery, and restaurant chains in identifying the true causes of loss, which are often overlooked and hidden in plain sight. Russ Hawkins uses concrete figures and industry insights to refute the stories that have long shaped loss prevention priorities. He shows that losses from employee theft and operational mistakes exceed those caused by high-profile professional theft rings, and explains how companies can use their current data to identify leaks they weren't aware of. You'll get honest accounts from the front lines regarding the surprising situations that arise when you ask your competitors for advice, how to redevelop a product around AI without losing the trust (or the contracts) of its 180 enterprise customers, and what actually changes when a company "graduates" from venture capital to private equity. This is an eye-opening masterclass on finding growth and resilience when others aren't even looking, whether you run a multi-location chain or a B2B software business aiming for steady growth. Some topics we explore in this episode include: The facts about retail shrink and why industry myths persist.How Agilence tackles invisible losses like employee theft and errors.Unexpected insights from interviewing competitors.The difficulties involved in moving from hardware to SaaS and in selecting cloud partners.What truly enables a business to be scalable and what prevents growth.How to demonstrate return on investment when industry data is not trustworthy.Rethinking customer success to increase retention and loyalty.The process of turning software into modules: lessons concerning upselling and pricing.Introducing AI to an established product without disrupting what's already working.The actual effect of switching from venture capital to private equity.

  5. Sep 15

    How ComplyJet Hit 50% Win Rates by Saying No to Everything

    Imagine establishing a successful and profitable B2B software business serving hundreds of customers in more than 25 countries without using paid advertisements, making sales calls, running referral programs, or securing venture capital. That is what Varun Jain, co-founder and CEO of ComplyJet, aims to demonstrate. In this episode of Predictable B2B Success, Vinay Koshy examines a bold "subtraction" approach: eliminating certain channels, turning down large enterprise deals, stopping discounts, and focusing entirely on content-driven growth. As Varun Jain makes clear, their path has been neither traditional nor straightforward. To maintain velocity, they declined deals worth more than $50,000, chose transparency over sales tactics, and built customer trust in an environment where no one publishes retention figures. We will examine the cost of serving each customer, reveal how they cut the sales cycle in half while increasing deal size, and explain how the founders spend up to 30% of their time providing direct customer support. Could this bold, focused strategy achieve the hard-to-reach goal of 1,000 customers without sacrificing margins or service? Listen as we examine ComplyJet’s revenue engine and discover what can be accomplished by choosing what you won't do to attain 1,000 SaaS customers by means of content alone, without using any advertisements, partners, or referral programs. Some topics we explore in this episode include: What was the reason why Varun Jain risked everything by subtracting products, channels, and segments rather than adding more?What does a marketing channel need to prove to ComplyJet before it is scaled? Do experiments and data suffice?What is the result when you choose to reject large enterprise contracts in order to concentrate on speed and efficiency?How will ComplyJet cope with sudden spikes in support demand, and can its well-known quick responses to customers be maintained at scale?How can transparent pricing and careful use of AI maintain strong gross margins even if there is no funding?What is it about ComplyJet's sales cycle that is making it shorter when those in the industry are seeing theirs lengthen—and how are they managing to maintain high deal conversion rates?What is the real cause of customer churn in the SaaS sector when it comes to early-stage customers, and why doesn't Varun Jain pursue every dollar?How can a nine-person software company win the trust of large enterprises in a sector built on credibility?Isn't the future of B2B security buying already upon us, with AI handling trust and compliance negotiations rather than people?

  6. Sep 8

    Per-Seat Pricing Is Dead: Kevin Surace on What Replaces It

    Is everything you know about software pricing about to change? In this episode of Predictable B2B Success, Vinay Koshy interviews Kevin Surace, tech innovator, CEO of Appvance, and inventor with patents licensed by Apple and Amazon. They discuss why the per-seat SaaS model is becoming obsolete and what is replacing it. Find out how Kevin Surace navigated the transition from seat-based pricing to results-based models, tackling the psychological and organizational challenges businesses face. By citing examples from billion-dollar companies, AI-native platforms, and his own investments, Surace shows that selling 'outcomes' has become an essential ability for B2B software companies. Why do the majority of companies weaken their own AI launches? What questions should you put to a company that describes itself as "AI native"? If the future of software is going to be a simple text box, what becomes of the current complex interfaces and the jobs associated with them? If you are a founder who is having problems with pricing or who would like to know how AI is changing business, then you should join us to find out why an outdated business model might be the greatest risk in the SaaS industry today. Some topics we explore in this episode include: Why moving away from per-seat pricing is essential to future-proof your business.How to implement outcome or usage-based models: Pricing based on measurable business value or actual use can better align your offerings with customer needs.How AI can automate QA: Leveraging AI reduces manual work and costs in software testing while increasing efficiency.How to deal with resistance from an organization: Study the methods for managing and overcoming fear-driven opposition from those teams affected by automation.To win the support of executives: Focus on executive leaders to accelerate acceptance of transformative AI solutions.How to distinguish true AI from "AI washing": Use practical questions to identify genuine AI products versus imitators.Set a benchmark for productivity equal to ten times the current level: make sure that investments in AI result in significant and measurable improvements by setting a goal of achieving a tenfold increase.Leveraging the Right Market Timing: Know when the market is ready for your innovation so you don't launch it too early or too late.Embracing Next-Generation Interfaces: Plan for future product positioning by considering AI-powered, natural-language, or on-demand interfaces.Practical steps for SaaS founders to develop and implement new pricing strategies that capture customer value and protect revenue by incorporating customer feedback.

  7. Sep 1

    Every Software Is an LLM Wrapper, And It Doesnt Matter

    This episode focuses on the seismic changes AI has brought to business, and what happens when the very foundation a company builds is suddenly available to everyone almost for free. Three years ago, Sembly AI’s Artem Koren predicted that artificial intelligence would become the new “building material” for the enterprise, like carbon fiber for modern aviation. What he didn’t foresee: within 18 months, that material would be commoditized, and everything his team had engineered over four painstaking years transcription engines, smart meeting bots would be accessible out of the box. A key theme that emerged was what truly makes a product defensible and valuable in a landscape where the raw tech is no longer enough. The discussion explored the nitty-gritty difference between a “good enough” AI-generated deliverable and one that can genuinely bear your company’s name. Several points were raised, including the pitfalls of generic outputs, where consistency comes from, and why context and brand are the new moats. Expect insights about the future of work, what AI should (and shouldn’t) be trusted with, and lessons learned from missteps in both pricing and product design. If you’ve ever wondered what you can really put your name on in the age of AI, this episode is for you. Some topics we explore in this episode include: AI’s shift from premium technology to a commodity is reshaping business value.How Sembly AI’s pivot from transcription to client-ready documents brought operational challenges and new lessons.The impact of widespread access to core AI on competition and innovation.What happens when cheap, universally available AI services like transcription disrupt business strategies.Why true product value now depends on branding, context, and completeness, not just the underlying AI.The challenge of building high-quality client deliverables with AI and overcoming platform shortcomings.How smaller players are carving out a niche against AI giants like Microsoft and OpenAI.Why consistency, repeatability, and data traceability are critical for professional AI use.The debate between usage-based versus subscription pricing models for AI products.The importance of ethical boundaries, privacy, and consent when deploying AI in sensitive business decisions.

  8. Aug 25

    AI Adoption: 54% of Workers Bypass the Tools You Bought

    While it may seem your team is not using your new AI tools, they may be leveraging AI in ways you have not anticipated, often outside the systems you have implemented. In this episode of Predictable B2B Success, host Vinay Koshy interviews Tom Gersic, whose experience includes SaaS adoption at Salesforce, large-scale AI deployments in global banks, and, as founder of ux.ai, developing advanced sales tools. Tom Gersic discusses his experience with “Lightning Adoption,” a major initiative that reported directly to Marc Benioff. He examines the shortcomings of traditional adoption strategies, the limitations of customer logo-based targets, and misconceptions about executive sponsorship. Drawing on extensive experience, he provides a candid perspective on why superior products do not always gain traction and why initial enthusiasm for new technology often fades before its value is realized. This episode offers valuable insights for founders preparing for board meetings and revenue leaders seeking to measure the true value of AI. Listen to learn what truly drives and hinders adoption in the current AI landscape. Some topics we explore in this episode include: Product Adoption Strategies: Focus on user workflows, not just product features, to drive real adoption.Monthly Active Users (MAU) as Key Metric: Moving from vanity metrics to MAU for measuring true engagement.User Experience and Performance Issues: How usability and perceived speed barriers affect adoption.Executive Sponsorship: The critical impact of hands-on leadership on rollout success.Hype Cycle and Disillusionment: Persevering through the “trough of disillusionment” when initial excitement fades.Enthusiasm vs. Sustained Adoption: Why excitement isn’t enough for long-term, meaningful use.Shadow AI Use and Governance: Risks of unapproved AI tool use and the enabling role of strong governance.Embedding AI in Workflows: The imperative to deeply integrate AI into daily business processes.Measuring Productivity and Value: Aligning metrics to true business outcomes instead of surface-level activity.AI in Regulated Industries: Unique challenges and lessons from deploying AI in sectors like finance and insurance.

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About

If you lead a bootstrapped or funded B2B tech company and need revenue to be predictable, not just possible, this podcast was built for you. Predictable B2B Success is the only show built exclusively for CEOs at seed-to-Series C tech companies who are ready to replace random acts of growth with a scalable, repeatable revenue system from first dollar to $50M+ ARR and beyond. Each week, host Vinay Koshy sits down with elite revenue operators, GTM leaders, and founders who have solved the hardest problem in funded B2B tech: turning chaotic, unpredictable growth into something structural, a system that holds under investor pressure, market shifts, and scale. What you will walk away with every episode: Operating frameworks for building predictable revenue pipelinesReal playbooks from founders who have scaled B2B companies from seed to Series C and beyondGTM, RevOps, demand generation, and category design insights built for C-suite decisions, not marketing teamsStrategies that compound across your organisation, not one-off tactics that fade Why 500+ episodes and a 5.0-star rating? This is not a show about inspiration. It is a show about operating clarity. Every guest is chosen because they have built systems in sales, content, community, product, or customer success that made revenue predictable. After 500+ episodes, the patterns are unmistakable. This archive is your competitive advantage. Trusted by founders and CEOs at bootstrapped and funded B2B tech companies across SaaS, cleantech, AI, and enterprise software. Rated 5.0 stars on Apple Podcasts. Ranked top 5 B2B podcast by Feedspot (2026). 500+ episodes since 2020. Subscribe now and get a new episode every week, turning your revenue from a moving target into a scalable system. Show notes, frameworks, and transcripts: sproutworth.com Subscribe to The Inclined, the weekly newsletter for funded B2B tech CEOs: sproutworth.com/newsletter Connect with Vinay Koshy on LinkedIn: linkedin.com/in/vinaykoshy

Information

  • Creator
    Sproutworth
  • Years Active
    2019 - 2026
  • Episodes
    559
  • Rating
    Explicit
  • Copyright
    © Predictable B2B Success
  • Show Website
    Predictable B2B Success