Predictable B2B Success

What if you discovered that 79% of your company’s top-line revenue could be slipping away, right under your nose, all because of outdated billing and invoicing processes? In this episode of Predictable B2B Success, host Vinay Koshy sits down with Randy Wootton, CEO of Maxio, to dig into one of the most overlooked deal killers and revenue drains in B2B SaaS: broken financial operations. With over 25 years in tech and a history of scaling and exiting firms, Randy brings deep, candid insights from the frontlines of SaaS operations. Together, they unpack why so many CFOs still cling to spreadsheets, how to create a culture of accountability and data-driven decision-making, and why getting serious about monetization, beyond customer acquisition and retention, can exponentially boost your company’s valuation. You’ll also hear behind-the-scenes stories of SaaS mergers, the battle to win over finance teams, and why nailing your monetization strategy is now a CEO’s must-have skill. Whether running a startup, growing a SaaS company, or steering a PE-backed venture, this episode is packed with real-world lessons and contrarian takes you can’t afford to miss. Ready to get funded—and stay funded? Let’s dive in. Some areas we explore in this episode include: Problems in B2B Billing & Financial Operations: Common issues like revenue leakage, billing errors, and spreadsheet dependence.What Maxio Does: How Maxio connects CRM and general ledger systems to streamline financial processes for B2B SaaS.Randy Wootton’s Leadership Journey: His background in the military and tech and how that shaped his leadership approach.Execution, Metrics & Growth Culture: The importance of accountability, data-driven execution, and fostering an environment of continuous improvement.CFO Mindsets and the Move From Spreadsheets: Why CFOs resist change and how companies can encourage adoption of automated systems.AI and Data Insights in Financial Ops: How Maxio and similar platforms are moving toward more intelligent, AI-driven analytics and business insights.Monetization Strategies for SaaS Companies: Monetization (pricing, packaging, value capture) matters as much as acquisition and retention.Maxio’s Pricing Model: Details on its billing-based pricing and why this approach benefits customers.Brand Strategy After Merger: Lessons from combining SaaSOptics and Chargeify into Maxio, and the challenges of rebranding.Get Funded, Stay Funded: The “dolphin strategy” for SaaS businesses—balancing growth, profitability, and investor expectations.And much, much more...

In this episode of the "Predictable B2B Success" podcast, host Vinay Koshy delves into the dynamic business consulting and growth strategy world with the versatile entrepreneur and finance expert Tim Calise. Tim, renowned for his meteoric achievements, including raising an astounding $325 million for his first hedge fund by age 25, dives deep into his journey and the insightful lessons he learned. Discover Tim's transition from an inquisitive child with a penchant for recreating systems to a strategic business consultant eager to help others navigate the intricate landscape of entrepreneurship. With a focus on aligning product, pricing, and positioning, Tim shares his unique "product to profit" framework—a game-changer for business owners eyeing sustainable success and lucrative exits. But the episode doesn't stop there. Explore how businesses can differentiate themselves amid stiff competition and the hustle of modern market dynamics. Uncover secrets to transforming acquisition costs into profit centers and discover why a market of one might be your business's missing link. Join us for a conversation packed with actionable insights designed to fuel your entrepreneurial spirit and craft a roadmap for success. Whether you're a seasoned founder or an aspiring entrepreneur, Tim's strategies will ignite your business aspirations. Some areas we explore in this episode include: Tim's Entrepreneurial Journey: Tim shares how he knew he wanted to be an entrepreneur from an early age and his experiences growing up.Business Consulting and Co-creating: Tim discusses his transition to business consulting and why he decided to co-create with other founders and business owners.Challenges for B2B Brands: Vinay and Tim discuss the struggles B2B brands face in aligning profit with business exit strategies.Product to Profit Framework: Tim introduces his Product to Profit framework and how it helps businesses succeed.Personal Area of Strength: Tim identifies his personal area of strength as aligning investor mindset with on-the-ground experience.Customer Acquisition and Profitability: Tim explains how building a profitable acquisition system turns acquisition costs into a profit center.Creating a Market of One: The idea of differentiating by niching down to create a unique position in the market.Strategic Pricing and Tiers: The importance of having a three-tier pricing system to cater to different client needs and maximize profit.Overcoming Entrepreneurial Challenges: Discussion on how to counter the loneliness and mental exhaustion that can come with entrepreneurship by having a support system and focusing on core strengths.Future Business Trends: Tim shares insights on the importance of recurring revenue and how live events can differentiate businesses in a competitive market.And much, much more ....

Have you ever wondered if your drive for success could be holding your business back? In this episode of Predictable B2B Success, host Vinay Koshy sits down with Scott Anderson, serial entrepreneur, author of You’re Not Toast, and founder of Double Dare, to expose the hidden dangers of burnout for high-achieving professionals and founders. Scott shares his raw journey: from launching 10 companies and selling eight to hitting a wall of exhaustion that sleep, weekends, and vacations couldn’t fix. You’ll discover why the very grit and hustle that fuel growth in the early days can quietly transform into a ceiling on your revenue—and even endanger your health and business. Scott unpacks the subtle signals leaders often miss, explains why hustle culture is not a strategy for scalable success, and reveals actionable techniques, like his 5-second R&R method, to break the burnout cycle quickly. If you’re secretly feeling stuck, tired, or can’t scale past that next revenue milestone, this conversation will challenge everything you think you know about perseverance, leadership, and growth. Tune in to learn how saying no and letting go might be your smartest business move this year. Some areas we explore in this episode include: Scott Anderson’s Personal Burnout Experience: How Scott recognized his own burnout and began seeking solutions.Burnout in High Achievers: Why successful professionals are especially at risk of burnout.The Double-Edged Sword of Perseverance: How traits that drive business success can also lead to burnout.Scaling Challenges and Revenue Plateaus: Mistakes entrepreneurs make when trying to grow their businesses beyond early milestones.Early Warning Signs of Burnout: Key symptoms and overlooked indicators of burnout in leaders.Delegation and Building Systems: The need for founders to delegate and build scalable systems to prevent burnout and enable growth.Shifting Leadership Mindsets: Moving from founder-centric leadership to a more humble, team-oriented approach.Hustle Culture vs. Sustainable Growth: Debunking the myth that nonstop hustling leads to long-term success.Practical Burnout Prevention Techniques: Tools like the R and R Technique for managing stress on the go.Implementing the Burnout Breakthrough Method: How Scott’s approach boosts cognitive capacity and resilience for leaders and their teams.And much, much more...

In this episode of Predictable B2B Success, we dive into the mind of a true growth marketing maestro, Jason Shafton. With over two decades of experience scaling giants like Google, Paramount, and Headspace, Jason reveals the secrets behind crafting killer marketing strategies that defy the status quo. From his journey of personal resilience, including the poignant stories of overcoming profound personal challenges, Jason shares how authenticity and vulnerability can transform business narratives and inspire teams to achieve the impossible. We explore how brutal honesty, balanced with empathy, can foster environments where teams thrive and deliver exceptional results. Jason takes us through the art of understanding your audience profoundly, creating engaging narratives that resonate deeply with customers, and the importance of zigging while everyone else is zagging. He challenges businesses to break free from the mundane B2B marketing mold and embrace unconventional growth channels, even questioning the reliance on tech titans like Google and Meta. Join us as we unravel the layers of Jason Shafton's growth playbook, where insights meet inspiration, creating a roadmap for any B2B leader aiming for unparalleled success. Some areas we explore in this episode include: Growth mindset and personal resilience in business.Jason's experience as a growth marketer at major companies.Founding and the purpose of his consulting firm, Winston Francois.Understanding customers and developing ideal customer profiles.Personal challenges shaping leadership and business philosophies.Crafting narratives through audience understanding.Balancing radical candor and empathy in leadership.What sets great marketers apart in the B2B tech space?Building a successful growth flywheel with channel strategies.Community building and using unique marketing channels.And much, much more...

Welcome to another episode of the Predictable B2B Success podcast, where we delve into the often overlooked yet powerful catalysts for sustainable revenue growth in the B2B space: packaging and trust. Host Vinay Koshy is joined by Nathan Yeung, founder of Find Your Audience, to explore these crucial elements that can differentiate your brand while navigating the complexities of the B2B market. Nathan brings over a decade of experience in marketing, finance, and management consulting to provide a fresh perspective on building effective strategies that align with market needs and internal company culture. In this episode, Nathan shares his frustration with the subpar advice given to founders and explains how strategic insights from marketing can play a pivotal role in long-term growth. Discover why first impressions, akin to the packaging in B2C, are just as vital in B2B digital branding. Learn how to measure trust within your customer base truly and why creating customer evangelists could be your most underutilized marketing channel. Plus, Nathan unveils actionable insights on maximizing the potential of your current marketing channels and why embracing bold strategies can set you apart in a crowded market. Tune in for a conversation rich with actionable insights and real-world examples that could transform your approach to B2B success. Some areas we explore in this episode include: Packaging and Trust in B2B: The significance of packaging and trust in driving sustainable revenue growth.Nathan Yeung's Founding Journey: Insights into why Nathan started Find Your Own Audience based on his diverse professional experiences.Role of Marketing Strategy: The importance of marketing strategy in identifying opportunities and positioning through insights.Understanding Marketing Tactics: Realizing that all marketing tactics can work, but priorities should be set based on constraints.Branding as B2B Packaging: How branding acts as packaging and its effect on first impressions and company perception.Assessing Trust with Customers: Potential overconfidence among CEOs regarding customer trust and its implications for customer management.Creating Customer Evangelists: Shifting focus to building customer evangelists and long-term relationship investment.Building Community via Events: Effective community building through thoughtfully programmed events offering personal, social, and commercial benefits.Empathy and Communication Challenges: The critical role of empathy in marketing and the importance of communicating in customer language.Advice for New Marketing Teams: Guidance on assembling marketing teams and standing out in competitive environments.And much, much more...

Welcome to another insightful episode of the Predictable B2B Success podcast! Join us as Vinay Koshy dives into an engaging conversation with Richard "RJ" Kedziora, the co-founder of Estenda and an innovator in the healthcare technology space. With over three decades of experience in software product design and development, RJ shares his journey from leading university associations to revolutionizing healthcare with data-driven solutions. In this episode, we explore the evolution of healthcare technology, from paper-based systems to today's data-rich landscapes, and discuss how the industry is harnessing data to enhance patient care. Discover how empathy is not just a buzzword but a fundamental driver for success in building B2B relationships and driving revenue growth. RJ provides a fascinating look into the unique challenges of healthcare, from balancing regulatory compliance to the complex dynamics of who pays and who benefits. Tune in to learn how his team at Estenda innovates by using a systematic, empathy-driven approach to problem-solving and client engagement, ensuring impactful solutions in a rapidly changing environment. Whether in healthcare or B2B industries, this episode contains insights that can transform your understanding of trust, empathy, and innovation. Some areas we explore in this episode include: Leadership and Early Experiences - RJ's journey and early leadership roles that shaped his career.Estenda's Origin - The motivation behind founding Vistenda and how their focus has shifted over time.Empathy in Business - The critical role of empathy in building trust in B2B relationships and the software development process.Healthcare Data Challenges - Transitioning from data acquisition to using data effectively in healthcare.Problem Solving Skills - RJ's strength in problem-solving and its impact on developing empathetic solutions.Customer Collaboration - Working with clients who have a general idea of their needs to create practical solutions.Regulatory Compliance - Turning compliance requirements into opportunities for revenue growth.Approach to Unknowns - Strategies for handling unknown factors in software development projects.Team Building with Empathy - Engaging team members to empathize with users and teach the patient journey.Building Trust and Partnerships - Methods for maintaining trust and developing long-term client partnerships.And much, much more...

In this episode of Predictable B2B Success, host Vinay Koshy welcomes James Brown, the innovative founder of BizTech Guru, to delve into the intricacies of systemization and its pivotal role in transforming businesses. Listen as they unpack the staggering statistics behind businesses with well-documented systems experiencing 280% higher growth and the everyday hurdles companies face when implementing these systems. James shares insights from his rich background in various industries, shedding light on Systemology's transformative power and his collaboration with David Jenens, which unearthed a game-changing approach to systemizing businesses. Discover the critical client flow concept—a vital component for revenue generation—and explore when a startup should begin to focus on creating systems. This episode doesn't just stop at providing a roadmap for achieving operational efficiency but goes further to explore the potential of leveraging AI in systemization. Whether you're a business owner overwhelmed by daily operations or in the early stages of a startup journey, James Brown provides valuable perspectives on harnessing systems for substantial time freedom, allowing for innovation and explosive growth. Tune in for a riveting discussion that redefines how you think about your business processes. Some areas we explore in this episode include: Systemizing Business Operations: How systemization can drive business growth.Common Barriers: Challenges like documentation issues and resistance to change.James Brown's Background: His journey and why he founded BizTech Guru.Importance of Systems: Key elements in freeing up time and unlocking growth.Timing for Systemization: When startups should start implementing processes.Critical Client Flow: Understanding the revenue-generating core of a business.Change Resistance: Handling resistance from crucial team members.Systemology Overview: The essentials of systemology in business.Innovation Balance: Maintaining innovation while systemizing.Systems Champion Role: The importance and identification of a systems champion.And much, much more...

In this episode of the Predictable B2B Success podcast, we're joined by AJ Rounds, a seasoned entrepreneur and co-founder of RevRoad, a unique venture services firm. With a rich background as a two-time CMO and four-time founder and having experienced three successful exits, AJ brings a wealth of knowledge to the conversation. With host Vinay Koshy, AJ delves into the motivating factors behind starting RevRoad and offers insights into the venture's distinctive approach of combining human capital with financial investments to help startups scale up successfully. Discover how RevRoad aims to flip the traditional narrative by reducing startups' 90% failure rate to a promising 67% success rate through a focus on expertise, collaboration, and strategic growth. AJ shares strategic insights into identifying ideal customer profiles, the importance of culture in scaling businesses, and the critical elements that make startups investable. Whether you're grappling with building company culture or just curious about how capital can be infused effectively for business growth, this episode offers valuable lessons from AJ's entrepreneurial journey and RevRoad's innovative model. Tune in for an inspiring conversation filled with practical advice and real-world experiences. Some areas we explore in this episode include: AJ Rounds' Background and Experience - This includes his journey as a cofounder and his previous startup experiences.The Concept and Origin of RevRoad - How and why RevRoad was started, and its mission to solve the high failure rate of startups.RevRoad's Business Model - Infusion of human capital and services before raising financial capital for startups.Scaling Startups - Strategies and processes for taking startups from initial stages to being investable by RevRoad Capital.Ideal Customer Profiles (ICP) - The importance and process of defining and focusing on target customer profiles.The Importance of Customer Feedback - Encouraging startups to engage with customers early to validate and refine products/services.Culture and Recruitment - The significance of company culture in startups and AJ's insights on recruitment strategies.Evaluating Startups at RevRoad - The use of the "Five H's" (Head, Hands, Heart, Humor, Humility) in assessing potential RevRoad companies.Global Impact and Social Responsibility - Examples of how entrepreneurship is used to solve global problems, including RevRoad's involvement in the virtuous cycle.Challenges and Myths in Scaling - Common misconceptions about growing a business and the reality of venture success.And much, much more...

Welcome to another episode of Predictable B2B Success, where we explore the evolving world of loyalty programs with Len Covello, Chief Technology Officer at EngagePeople. As a pioneer in reshaping how loyalty programs operate, Len shares fascinating insights into EngagePeople's innovative approach, which allows program members to pay with points at checkout. With over 51 million active members and an annual processing of $400 million, EngagePeople is not just changing the game—it's revolutionizing it. Dive into Len's entrepreneurial journey, starting his first tech company at just 18, and discover how his relentless quest for innovation continues to drive EngagePeople's success. Len opens up about the complexities and challenges of integrating loyalty programs in the B2B space, emphasizing the importance of data-driven decisions, understanding customer aspirations, and the critical role of having a program champion within organizations. This episode unveils the future of loyalty programs, where personalization, integration, and partnerships are key to creating a sustainable competitive edge. Whether part of a B2B or B2C company, Len's insights will inspire you to rethink how loyalty programs can align with your business objectives to drive unprecedented customer engagement and revenue growth. Some areas we explore in this episode include: Introduction to Len Covello: Len's role as CTO at EngagePeople and an outline of the company's mission.B2B Loyalty Market: Opportunities and challenges in the projected growth of B2B loyalty programs.Len's Journey into Loyalty: His interest in the space is driven by a passion for innovation and customer experience.EngagePeople's Goals: The company's focus on technology to enhance loyalty programs and the challenges faced.Personal Strengths and Insights: Len's cerebral approach to decision-making and insights on planning and execution.Implementing Effective Loyalty Programs: Aligning loyalty initiatives with business goals and customer aspirations.Successful Case Studies: Airline programs are examples of well-integrated loyalty and business strategies.Utilizing Customer Data: The importance of data in understanding customer needs for effective loyalty solutions.Tech-Innovation in Loyalty: How partnerships and innovation are key to loyalty program success, alongside addressing tech challenges.Competitive Loyalty Programs: Strategies for innovation, including personalization and cross-industry inspiration.And much, much more...

In this episode of the Predictable B2B Success podcast, host Vinay Koshy sits down with seasoned marketer Martin Pietrzak of Pinch Marketing to unravel the intricacies of business growth in the complex B2B landscape. Imagine a business world where the power doesn't lie merely in expansive reach but in pinpointing precision—where scaling isn't about casting the widest net but understanding and empathizing with the customer's journey. Martin shares his unique journey from a budding artist to a decisive leader in tech and SaaS, revealing how a pinch led to the birth of his marketing firm. Dive into challenges most companies face today: the illusion of universal appeal, the dangers of optimism bias, and organizational silos that stifle true customer-centric growth. Martin highlights how focusing on truly understanding the market and challenging orthodox perceptions can uncover hidden high-value client profiles. With real-world success stories, he illustrates the strategies businesses can implement to evolve their messaging, storytelling, and customer engagement tactics. Join us to explore how businesses can differentiate themselves in saturated markets, become truly empathetic, and harness the evolving landscape of communication for sustainable growth. This engaging conversation promises to leave you thinking differently about marketing and growth strategies. Some areas we explore in this episode include: The importance of narrowing market focus and adopting a customer centric approach for scalable revenue growth.The complexity of B2B customer journeys and the need to maintain a narrow focus.Organizational silos and their impact on data sharing and customer-centricity.Challenges faced by organizations due to outdated technology and processes.Martin Pietrzak's journey into marketing and the creation of Pinch Marketing.The common perception among C-suite executives that their product is for everyone and the implications on marketing and revenue.The role of proxies within organizations to better understand customer experiences.Strategies for identifying ideal customer profiles and differentiating messaging for various stakeholders.The introduction of empathy and customer-centricity in the discovery process and its impact on strategy.The significance of storytelling in overcoming market inertia and engaging potential customers.And much, much more...