Ex-Splunk Exec: Fix Your Sales System Before You Hire Reps

What if your most celebrated sales hire turns out to be your company’s biggest mistake? Or your product wins raving fans yet no one pays for it? In this episode, the conversation focused on what happens behind the scenes of fast-growing companies when the numbers don’t add up and how top leaders confront, learn from, and benefit from their biggest losses. One concept discussed was the myth that sales excellence is easily transferable, a lesson shown through stories of teams that soared in one environment but stumbled in another. The discussion explored how to know if you’re hiring the right head of sales, the subtle difference between a product-market fit issue and a sales execution problem, and the art of facing a board when targets are missed. A key theme was the necessity for founders to learn sales firsthand before building a sales team and why AI, despite its promise, can’t replace the vital human element in B2B selling. Several points were raised, including overlooked warning signs in go-to-market strategy, how to build trust with your board, and the surprising type of company that found hidden value in entrepreneurial lessons. Curious if your company’s next big move could be its undoing or its greatest pivot? Listen in and discover the hard-earned wisdom every founder needs before making their next sales decision. Some areas we explore in this episode include: Why top salespeople sometimes fail in new environments and how to spot if yours will.The hidden test for hiring a head of sales that most founders overlook.What every founder should do themselves before hiring a sales leader (almost no one does this).The real reason sales forecasts break down and what you can do about it.How to keep your board’s confidence even when your numbers are tanking.The trait that predicts whether a failed founder will win a second chance.How Wasabi Cloud cracked the code on channel sales with one surprisingly simple metric.What to do when your partner channel goes silent after their first sale.Is your sales problem actually a product problem? Here’s how to tell.Will AI replace your sales team or unlock their hidden superpowers?

The conversation focused on the one question every B2B exec should be asking: Are you leaving revenue on the table by not using your own contact list? It's entirely possible to book 14 sales meetings in 6 minutes without running new ads or cold calling. One concept that came up was database reactivation, a potent, underused technique for re-engaging old leads via SMS to massively increase the number of sales calls you book. The central theme was why so many companies, after spending so much on lead generation, don't use their own list. The discussion is about the origin story of Chatify.app, a platform that takes the onerous work of reactivating old contacts off the sales team so they can focus on meetings and closing. There's a whole lot of discussion around why it's not as simple as just re-engaging your existing list, the various gotchas around compliance, culture, and tech, and what the difference is between a good campaign and a bad one. You'll hear practical insights on how to spot the potential in your existing lists, what reply and meeting conversion rates to expect, and why timing and channel matter. If you're interested in using the leads you already have to feed your pipeline and want practical advice on how to do it properly, this episode is for you. It's full of answers and inspiration. Some areas we explore in this episode include: Unlocking revenue from 'dead' leads: find out how contacts you've previously lost can be the key to a massive new sales pipeline.Why SMS tactics fail in most companies: find out the hidden obstacles that stop database reactivation from working in-house.Compliance minefields: is your outreach illegal? Find out what could be costing your company thousands per text.SMS vs Email vs LinkedIn: who wins? Which one actually gets you meetings?The secret ingredient: automation or the human touch? Why a hybrid approach might be the only way to get replies.Who in your old list will buy and who won't? Find out which of your 'stale' contacts could be your hidden goldmine.Industries where this works (and where it doesn't): is your business missing out on the easy meetings?Why the first minute decides your fate: how response speed makes or breaks your entire campaign.Brand Power: Does Trust beat Copywriting? Is it your message or your reputation that really matters?The future of SMS sales outreach: will AI, the new rules and channel saturation make it all obsolete or indeed make it even more valuable?

The conversation focused on one of the most common and expensive errors CEOs make after raising money: hiring more salespeople before the company is actually ready. The assumption is that more salespeople = predictable growth. The episode makes clear that that's rarely the case, and you often end up in chaos, with high churn and the dreaded "doom loop" of declining revenue. One concept focused on the subtle signs your sales engine isn't working and why operational readiness, not headcount, determines success. It's all based on experience scaling companies like Splunk from $60m to over $1bn. The guest talks through the key metrics and behaviors that make revenue truly repeatable. A major theme was the power of focusing on existing customers before chasing the next big deal. Some companies achieved triple (or even quadruple) growth, and it wasn't by getting new logos at all. It was by learning to serve existing customers better and grow that customer base. What will make your next board meeting less stressful? What hard truths should every founder face before they even start to hire? All of the above, plus counterintuitive strategies and practical advice to keep your revenue engine running no matter how fast your company grows. Some topics we explore in this episode include: Why Hiring More Salespeople Can Hurt Your RevenueThe Hidden Dangers of Skipping Product-Market FitEarly Warning Numbers: The Secret to Predictable GrowthWhat Most Teams Overlook in Their Rush for New CustomersUnlocking Growth with a Repeatable Revenue EngineThe Ramp-Up Myth: Are your sales targets built on sand?Skill vs. Will: The Unexpected Formula for High-Performing TeamsThe Surprising Power of Compensation Plans in Driving the Right BehaviorsCoaching Secrets: What Great Sales Leaders Do Weekly That Others IgnoreAI or Human Touch? Where the Real Competitive Edge Lies in B2B Sales

Almost 8% of sales leaders say their teams could get on just fine without any cold outreach at all (those emails, calls, and LinkedIn messages to people they've never met before). Less than 20% of them, however, have a real way to get introduced to new buyers. That's the paradox. What if you could tap into a powerful network within your team, your investors, and your customers, turning every piece of outreach into a warm handshake rather than a cold call? In this episode of Predictable B2B Success, Vinay speaks with Olivier Roth, co-founder of The Swarm. The Swarm maps the invisible networks of relationships your business may be missing entirely as a secret growth lever. Olivier's tech-enabled approach explains why even well-funded competitors get left behind, why sales teams are so scared to ask for an intro, and how companies from the most ambitious startups to the largest global firms are changing their sales in a very real way. Are warm intros a massive underused superpower or just another sales term? Why do so many founders keep their network all in their head? What does it take for an organization to use its network to drive growth, not just talk about it? Listen in and get ready to completely upend everything you thought you knew about business relationships. Some topics we explore in this episode include: Warm intros vs cold outreach: the surprising truth about why companies still use cold outreach and what's stopping them from making more warm introductions.Startup Wars: The Swarm vs Commsor: How The Swarm outmaneuvered a better-funded competitor in the race to own the introductions market.Integrations that actually get used: why embedding your intro tools into the existing sales workflow is a game changer.The hidden fear in sales teams: why most reps are terrified to ask for an introduction and what can be done about it.Profitability over hyper-growth: how running lean gives founders more control and why that matters in a market full of SaaS startups.Building a network effect: discovering the hidden connections within your company, your partners, and your customers to massively accelerate growth.Culture eats technology. The real barrier to warm intro adoption isn't software; it's change management.Inside Success Stories: Lessons from companies that radically improved their results through the systematic introduction of new things.Getting Connectors to say yes: what makes someone excited or annoyed about making the introduction (and some clever incentive ideas).AI and the future of sales relationships: how AI can uncover the real relationship 'gold mines' without necessarily losing the human element.

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

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

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?

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.

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?

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.