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Welcome to SaaS Expert Voices presented by Maxio with host, Randy Wootton, 3x SaaS CEO (public, private, VC and PE backed), and board member of multiple private companies. On this show, Randy engages in conversations with SaaS and finance experts, delving into the challenges they face, the victories they’ve achieved, the lessons they’ve learned, and what they see on the horizon for the industry. Whether you’re a seasoned leader or just stepping into the world of SaaS, join us as we explore t ...
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Sit Down Startup

Adam O'Donnell

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Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)
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Scale Your SaaS

Matt Wolach

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Each week we talk with those who have succeeded and inspired in the world of software. How they did it, what advice they have, and what's coming in the future with new innovation. All aimed at helping you generate more leads, close more new customers, and Scale Your SaaS.
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Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Mark Doble, Co-Founder of Alexi, to explore his inspiring journey in the legal tech space and the challenges of achieving product-market fit while raising over $10 million in funding. Join us as Mark shares his experiences transitioning from law to en…
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In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Daniel Saks, co-founder and CEO of Landbase, to delve into his entrepreneurial journey, including the successes and challenges he faced while building AppDirect. Daniel shares invaluable insights into the evolution of AppDirect, which has grown into a unicorn valued at over ha…
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Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Randy Wootton, CEO of Maxio, to delve into the intricate dynamics of sustaining product-market fit in the ever-evolving landscape of B2B SaaS. Join us as Randy shares his unique journey from military leadership to the helm of a transformative billing …
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Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Kaustav Das, co-founder of Efficient Capital Labs, a pioneering venture focused on transforming funding for SaaS founders. Join us as Kaustav shares his remarkable journey in navigating the complexities of cross-border financing and the critical importance …
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Welcome back to this Thanksgiving week's episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Angie Westbrock, CEO of Standard AI, to explore her inspiring journey from the manufacturing sector to leading a cutting-edge retail technology company. Discover how Standard AI pivoted from autonomous checkout to leveraging computer visi…
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Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Scott Stevenson, co-founder and CEO of Spellbook, the first generative AI copilot for lawyers, to discuss his remarkable journey in the legal tech space. Uncover the invaluable insights Scott gained about resilience, the struggles of achieving product-marke…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Chris Heaslip, a four-time Founder and Executive Chairman. Randy and Chris talk the importance of unlocking team potential and the critical competencies required for leadership success. Chris shares insights on personal development, emphasizing that taking jobs for lea…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Pete Kazanjy, entrepreneur, author, and early stage GTM expert. Exploring the evolving dynamics of sales in the tech industry, Pete and Randy discuss the current sales landscape and the challenges faced by organizations in adapting to rapid changes. They also discuss t…
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In this episode, Adam O'Donnell sits down with Driss Benamour, co-founder and CEO of Exponential.fi, to explore the journey of building a decentralized finance platform amidst the challenges of the crypto winter. Driss shares his insights on achieving product-market fit by focusing on user needs and simplifying access to DeFi investments. He discus…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Roee Hartuv, Head of Revenue Architect Practice at Winning by Design. Roee sheds a light on the drastic drop in IPOs from 98 in 2021 to just a handful in the subsequent years, underscoring a trend that has left many private companies in a precarious position. This bott…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dave Woolliscroft, Finance Leader and Big 4 Managing Director. Randy and Dave discuss the key differences between venture capital and private equity, particularly focusing on what it means for companies preparing for a sale to a PE firm. The conversation highlights the…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Tami Reiss, Founder and CEO of The Product Leader Coach. Tami shares how understanding customer needs and creating a compelling vision that aligns with the company’s goals, leads to successful product management. Randy and Tami talk about the value of coaching for prod…
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In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Jensen Harris, co-founder and CEO of Textio, to explore his remarkable journey in the world of AI-driven management solutions. Jensen shares how Textio has evolved over the past decade, transforming the way managers deliver feedback and recruit talent in an increasingly compet…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Drew Neisser, Founder and CEO of Renegade Marketing. Drew shares his extensive experience and key insights into the dynamic relationship between CEOs and CMOs, especially for early-stage founders. Randy and Drew explore crucial aspects such as hiring strategies for the…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Matt Tresidder, Co-founder and CEO of Leadr, a software company dedicated to enhancing personal and professional development. He is also the author of the thought-provoking book, "Management is Dead: There's a Better Way." Randy and Matt discuss the evolving landscape …
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Welcome to the latest episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Tigran Sloyan, an MIT alumnus and the co-founder and CEO of CodeSignal, to discuss his remarkable journey to the forefront of innovation. Uncover the invaluable insights Tigran gained about resilience, adaptability, and the necessity of continuous product e…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Sahil Patel, CEO of Spiralyze, a firm specializing in optimizing website conversions through data-driven A/B testing. The conversation kicks off with an exploration of Spiralyze's mission to make websites the most efficient and productive sales tools for B2B SaaS busin…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, welcomes back Michelle Valentine, Co-founder and CEO of Anrok and a prominent figure in the SaaS industry known for her innovative strategies and effective leadership. Randy and Michelle explore the "Seven Secrets of Success," focusing on delivering results, building winning strat…
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In the latest episode of Sit Down Startup, Adam O'Donnell chats with Lauren Salz, co-founder and CEO of Sealed, about her unexpected journey from aspiring musician to leading a revolutionary home energy startup. Discover the invaluable lessons Lauren learned about resilience, adaptability, and the importance of continuous product evolution, and hea…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Ray Rike, CEO of Benchmark IT, a company specializing in providing the SaaS industry with comprehensive and contextualized benchmarking data. Randy and Ray discuss the growth trends seen among private B2B SaaS companies, emphasizing how certain market dynamics are infl…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Paul Barnhurst, an expert in Financial Planning & Analysis (FP&A). Known as the "FP&A Guy," Paul explores the evolution of FP&A over the past two decades, highlighting shifts from back-office reporting functions to becoming strategic partners within organizations. Rand…
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In this latest episode of Sit Down Startup, Adam O'Donnell chats with Noam Solomon, CEO of Immunai, about his incredible journey from academia to building a groundbreaking biotech startup. Hear Noam's fascinating backstory growing up in Israel and his move to the U.S. for a postdoc at MIT and Harvard, and how that paved the way for the creation of …
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Clayton Whitfield, Co-founder of SaaSOptics, a company that revolutionized financial operations for SaaS businesses by addressing critical gaps in their finance and operational systems. Clayton discusses the evolving roles within the office of the CFO, particularly foc…
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EPISODE SUMMARY In the competitive world of B2B SaaS, understanding the nuances of billing, financial operations, and growth metrics is crucial for success. Recently, we had the pleasure of hosting Randy Wootton, CEO of Maxio, on the Scale Your SaaS podcast with host and B2B SaaS Sales Coach Matt Wolach. With over 25 years of leadership experience …
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EPISODE SUMMARY Scaling a SaaS company is no small feat. The journey is filled with challenges, from generating leads to closing deals and building a robust sales team. On a recent episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach sat down with Brian Parks, Co-founder and CEO of Bigfoot Capital, to discuss how SaaS companies can…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Chris Morgan, CEO of LBMC. Randy and Chris highlight the evolving intricacies in financial operations within B2B SaaS companies. They discuss the necessity for moving beyond simple cash accounting to sophisticated systems capable of managing accrual accounting and prov…
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Welcome to the latest episode of Sit Down Startup! This week Adam O'Donnell hosts Inspectify co-founder and CEO Josh Jensen who leverages his diverse background in engineering and real estate to revolutionize property inspections for single-family homes. Josh brings a unique perspective to the tech space, emphasizing the importance of capturing com…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Cory Sanford, Vice President of Culture and Talent at Guidant Financial. Randy and Cory dig into what it takes to be a successful CEO, offering actionable advice for founders, leaders, and aspiring entrepreneurs. Cory's innovative framework for measuring and fostering …
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EPISODE SUMMARY In a recent episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach sits down with Andy Culligan, a seasoned marketer with a rich background in SaaS, who shared his journey from CMO of Leadfeeder to becoming a fractional CMO, a role that has been gaining significant traction in recent years. Andy’s story is not just ab…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Alex Shartsis, a seasoned expert in go-to-market strategy and execution for early-stage companies. Alex shares his extensive experience working with startups, highlighting crucial aspects such as hiring the right talent, setting realistic goals, and managing investor e…
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EPISODE SUMMARY In the most recent episode of Scale Your SaaS, Steven Webster, co-founder of Asensei, shared insights into the journey of building a cutting-edge technology company that’s redefining the fitness industry with host and B2B SaaS Sales Coach Matt Wolach. From launching their SDK to pioneering movement recognition akin to speech recogni…
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Host Adam O'Donnell is back with this week's episode of Sit Down Startup with guest Zuben Mathews, co-founder and CEO of the financial health app Brigit. Mathews draws from his own experiences of financial hardship and his background in economics to address the critical issue of product-market fit in financial technology. He also emphasizes the imp…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Bill Hollowsky, VP of Accounting Services at Kruze Consulting. Bill shares his journey through various organizations like KPMG, Oracle, and SunGard. He offers insights into the changing landscape of accounting in the startup world, and the importance of implementing ef…
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EPISODE SUMMARY In the most recent episode of Scale Your SaaS, Founder & CEO at Humantic AI Amarpreet Kalkat shared his journey in the AI industry with host and B2B SaaS Sales Coach Matt Wolach, reflecting on his experiences since actively engaging with AI in 2014. He noted the significant waves of AI popularity, with the current one being the most…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Michelle Valentine, CEO of Anrok. Michelle’s multifaceted career journey—from civil engineering at Stanford to coding at Airtable, and her foray into finance and venture capital—sets the stage for a deep dive into the evolving role of the CFO in today's dynamic market.…
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EPISODE SUMMARY In this episode of Scale Your SaaS, Chris Hicken, Chief Productivity Officer at ClickUp, shares his thoughts on the current state of the IPO market, the crucial metrics investors focus on, and the strategic decisions software founders face with host and B2B SaaS Sales Coach Matt Woalch. As the market gradually recovers, many SaaS co…
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In this insightful episode of Sit Down Startup, Ashok Subramanian, founder of Centivo, shares his incredible journey from immigrant roots to becoming a successful startup entrepreneur. With $150 million raised, Ashok discusses the challenges and triumphs of disrupting the traditional employer health insurance market to make healthcare affordable fo…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dan Balcauski, Founder and Chief Pricing Officer of Product Tranquility. Randy and Dan explore the nuances of pricing from multiple angles and unravel the intricacies of how to structure effective pricing strategies that align with company objectives to drive both reve…
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EPISODE SUMMARY In this episode of Scale Your SaaS, host and B2B SaaS Sales Coach Matt Wolach sits down with Ken Lazar, Chief Career Officer at Ability Professional Network to discuss his approach to recruiting top-tier sales professionals. If you're looking to build a sales team that drives your SaaS business forward, take Ken’s advice to heart. R…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Nicolas Boucher, an AI Applications in Finance expert. Nicolas shares his rich career trajectory from PwC auditor to corporate finance leader and his eventual transition into AI and finance training. He sheds light on the immense potential of AI in streamlining financi…
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EPISODE SUMMARY In this week’s episode of Scale Your SaaS, I sat down with Sam Dunning, who has carved an impressive path in the world of SEO and digital marketing. His story is as inspiring as it is instructive. From his early days in retail to founding his agency, Breaking B2B, Sam’s journey is a testament to the power of perseverance and the imp…
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EPISODE SUMMARY In the recent episode of Scale Your SaaS, host and B2B Matt Wolach had a compelling conversation with Frank Husmann, CEO & Founder of Maxiality, an ex-SaaS founder turned authority marketing expert. Frank shared valuable insights on how B2B SaaS leaders can leverage their expertise to become industry authorities and drive business g…
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Join host Adam O'Donnell on the latest episode of Sit Down Startup. This week, Jason Barsema, a former financial advisor specializing in managing portfolios for ultra-high-net-worth individuals, has emerged as a groundbreaking figure in disrupting the structured notes market. Barsema initially sought to eliminate the counterparty risk of big banks …
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with two SaaS industry veterans, Amber Wendover, Principal at Thinking People Consulting, and Tom Perry, Chief Career Officer and Founder of Engaged Pursuit. Randy, Tom, and Amber discuss the intricacies of employee engagement and the indispensable role that personal growth…
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EPISODE SUMMARY In today’s rapidly evolving software sales environment, mastering the art of sales is more crucial than ever. This week on "Scale Your SaaS," host Matt Wolach and guest Richard Harris, founder of The Harris Consulting Group and a renowned sales influencer, discuss innovative approaches to selling that can significantly enhance your …
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Josh Aharonoff, CEO of Mighty Digits and Your CFO Guy, and the Founder of Modelwiz. With a diverse background that includes a start at the Big Four accounting firm KPMG, experience as a startup founder, and strategic finance roles, Josh has carved out a niche as a frac…
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EPISODE SUMMARY In a recent episode of Scale Your SaaS, Matt Watson, CEO and Founder of Full Scale, shared his journey from being a customer to leading a successful outsourcing company with host and B2B SaaS Sales Coach Matt Wolach. Matt's insights provide valuable lessons for entrepreneurs, especially those in the SaaS industry. PODCAST-AT-A-GLANC…
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This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Jon Cochrane, Director of the Maxio Institute, to discuss the latest insights from their SaaS Growth Trends report. Randy and Jon delve into the significant findings of the Q1 2024 report, discussing the differences in growth patterns between subscription-based and con…
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EPISODE SUMMARY In the fast-paced world of software sales, finding innovative ways to connect and engage with potential clients is paramount. Recently, I had the pleasure of featuring Donald Kelly, Founder and Chief Sales Evangelist at The Sales Evangelist on the show. Donald’s journey, insights, and strategies offer a masterclass in sales evangeli…
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Join us on the newest episode of Sit Down Startup as Jo Riley, founder of Censia, shares her inspiring journey from the FBI to launching a disruptive AI-driven platform. Host Adam O'Donnell and Jo discuss the importance of persistence, the value of customer feedback, and how Censia is transforming the way companies find and manage talent. Whether y…
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