Best Maxio CEO Podcasts (2025)

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[$10M+ Raised] Mark Doble, Co-Founder of Alexi, on Overcoming Adversity and Achieving Product-Market Fit in Legal Tech 18:47

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7M ago18:47

18:47

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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[Harnessing AI Technology for Business Growth] Founder Daniel Saks Discusses Persistence, Overcoming Rejection, and the Evolution of AppDirect and Landbase 22:23

8M ago22:23

22:23

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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[Sustaining Competitive Edge] CEO Randy Wootton of Maxio on the Dynamics of Product-Market Fit in a Changing Landscape 22:51

8M ago22:51

22:51

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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[$121.5M in Funding] Efficient Capital Labs' Kaustav Das on Bridging the Funding Gap and Achieving Product-Market Fit 24:31

10M ago24:31

24:31

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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[Pioneering Retail Innovation] CEO Angie Westbrock on Standard AI's Journey from Autonomous Checkout to Computer Vision Insights 27:35

10M ago27:35

27:35

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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[$30M Raised] Transforming Legal Tech: Spellbook Co-Founder & CEO Scott Stevenson on Achieving Product-Market Fit 24:18

10M ago24:18

24:18

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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Navigating Uncertainty: Lessons in Leadership with Chris Heaslip 44:44

10M ago44:44

44:44

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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From Growth at All Costs to Efficient Growth: Adapting Your Sales Strategy with Pete Kazanjy 46:25

11M ago46:25

46:25

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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[Transforming Crypto Access] Co-Founder/CEO Driss Benamour on Building Exponential.fi and Overcoming Crypto Winter 25:20

11M ago25:20

25:20

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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Lessons from the SaaS Trenches: Adapting to a Changing Market with Roee Hartuv 43:20

11M ago43:20

43:20

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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From VC to PE: What Founders Need to Know for a Successful Transition with Dave Woolliscroft 45:17

11M ago45:17

45:17

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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Building Trust in Product Leadership with The Product Coach Tami Reiss 42:56

11M ago42:56

42:56

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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[Navigating the AI Landscape] Co-Founder and CEO Jensen Harris on Textio's Journey and the Future of AI in Management 25:37

12M ago25:37

25:37

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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Creating Customer Champions: How to Cultivate Loyalty and Advocacy with Drew Neisser 47:09

12M ago47:09

47:09

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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From Autocratic to Empowered: Leading the Gen Z Workforce with Matt Tresidder 45:44

12M ago45:44

45:44

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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[~$100M Raised] Transforming Talent Assessment: Co-founder and CEO Tigran Sloyan on Building CodeSignal 26:24

12M ago26:24

26:24

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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Optimizing High-Intent Pages: Secrets to Streamlining Conversion Forms with Sahil Patel 42:13

12M ago42:13

42:13

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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Diagnose Before You Deploy: Smarter Strategies for CEOs with Michelle Valentine 39:40

1y ago39:40

39:40

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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[Revolutionizing Climate Tech] Sealed’s co-founder and CEO Lauren Salz on Raising ~$100 Million and Finding Product-Market Fit 21:50

1y ago21:50

21:50

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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Small Companies, Big Growth: Why SaaS Companies Under $1M are Booming 47:54

1y ago47:54

47:54

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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The Evolution of FP&A: Building Financial Models for Success with Paul Barnhurst 40:36

1y ago40:36

40:36

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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[$300M Raised] Mapping the Human Immune System for Drug Discovery: Noam Solomon on Building Immunai 23:45

1y ago23:45

23:45

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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From Startup to Success: The Journey of SaaSOptics with Clayton Whitfield 41:33

1y ago41:33

41:33

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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From Cash Basis to Accrual: Transforming Financial Reports for SaaS with Chris Morgan 42:12

1y ago42:12

42:12

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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[90% of Co-Founder's Time Spent Speaking to Customers] How Inspectify has Navigated Startup Success 20:27

1y ago20:27

20:27

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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Culture is Connection: How to Empower Your Team with Purpose with Cory Sanford 46:59

1y ago46:59

46:59

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 …

1
Avoiding Early Stage Mistakes: SaaS Growth Strategies Unleashed with Alex Shartsis 49:59

1y ago49:59

49:59

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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Scaling: How to Build a Strong Back Office Early with Bill Hollowsky 48:16

1y ago48:16

48:16

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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[$0 to $20M ARR in 1 year] Creating a Path to Financial Empowerment with Brigit's co-founder and CEO Zuben Mathews 25:21

1y ago25:21

25:21

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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Evolving Skillsets: The Modern and Future CFO's Playbook with Michelle Valentine 32:26

1y ago32:26

32:26

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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[$150M Raised] Navigating Product-Market Fit in Healthcare: Ashok Subramanian on Building Centivo 23:54

1y ago23:54

23:54

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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How to Transform Your Pricing Strategy with the Power of Value Conversations with Dan Balcauski 46:38

1y ago46:38

46:38

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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Revolutionizing FP&A: How AI is Shaping Financial Analysis with Nicolas Boucher 46:38

1y ago46:38

46:38

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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[$3 Trillion Market Revolution] Democratizing Structured Notes with Halo Investing 23:54

1y ago23:54

23:54

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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The Power of Intent: How Clear Communication Drives Success with Amber Wendover and Tom Perry 47:20

1y ago47:20

47:20

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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From Numbers to Narrative: Crafting a Compelling Financial Forecast with Josh Aharonoff 47:08

1+ y ago47:08

47:08

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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SaaS Growth Trends Report 2024 with Jon Cochrane 30:03

1+ y ago30:03

30:03

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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[4x Founder] From FBI to Founder: Jo Riley’s Journey to Product-Market Fit with Censia 41:30

1+ y ago41:30

41:30

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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Winning Long-Term: Creating Media-Led Growth and Driving Revenue with Nathan Latka 44:48

1+ y ago44:48

44:48

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Nathan Latka, CEO of Founderpath. Known for his entrepreneurial spirit, data-driven approach, and thought-provoking insights, Nathan shares his three-phase entrepreneurial journey, starting with his initial foray into the booming social media world and progressing into…

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The Five Components of a Successful CEO: Focus, Communication, People, Values, and Results with Joelle Kaufman 46:58

1+ y ago46:58

46:58

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Joelle Kaufman, a seasoned B2B SaaS expert. Together, they delve into the intricacies of what makes CEOs successful, the importance of executive team dynamics, and strategies for driving company growth in challenging markets. Joelle Kaufman shares her five foundational…

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Efficiency in Finance: Navigating the Essentials of Early-Stage Startups with Alex Diaz-Asper 44:36

1+ y ago44:36

44:36

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Alex Diaz-Asper, Principal & Founder of Tarsus, and an experienced figure in the financial dimension of SaaS businesses. With an extensive background in private equity and M&A, Alex shares key financial concepts and strategies within the SaaS landscape. Randy and Alex …

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Influence vs. Impact: Redefining Success in the Accounting Profession with Rob Brown 53:37

1+ y ago53:37

53:37

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Rob Brown, Co-Founder of Accounting Influencers Roundtable (AIR), and author of the book “Build Your Reputation.” Rob and Randy delves explore the evolving responsibilities of accountants and accounting firms as they navigate an industry that demands a shift from tradi…

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[$30B Market Reimagined] Unlocking Home Care's Potential with Honor 32:16

1+ y ago32:16

32:16

Welcome back to Sit Down Startup! Seth Sternberg, co-founder of Honor ($625M raised), a company dedicated to addressing the challenges faced by senior citizens during the COVID-19 pandemic, was heavily influenced by his upbringing in Connecticut and his entrepreneurial spirit. Sternberg's experiences during the pandemic greatly shaped his perspecti…

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Building Revenue Architecture for Startup Success with Jim Delaney and Kristian Marquez 55:11

1+ y ago55:11

55:11

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Jim Delaney, CEO of Traction AI, and Kristian Marquez, President, CEO, and CFO of FinStrat Management. Randy, Jim, and Kristian discuss the significance of pairing robust revenue operations with meticulous financial strategies to foster startup growth. Jim shares his e…

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The Tech Stack and The Tech Pile: Creating Seamless Data Flow with Anthony Nitsos 48:39

1+ y ago48:39

48:39

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Anthony Nitsos, Founder and CEO of SaaS Gurus. With a background that intriguingly intertwines medical school education and extensive expertise in finance, Anthony has over 25 years of experience building SaaS financial models. Randy and Anthony discuss principles for …

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The Rule of X: The Art of Setting Ambitious and Attainable Targets with Jeff Epstein 43:00

1+ y ago43:00

43:00

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Jeff Epstein, Operating Partner at Bessemer Venture Partners and a distinguished figure in the business and finance sectors. Randy and Jeff discuss the rationale behind budgeting, emphasizing its role in predicting financial futures, resource allocation, motivation, an…

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Leveraging Technology to Drive Better Decision Making with Dawoud Nasraty 25:32

1+ y ago25:32

25:32

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dawoud Nasraty, Director of Consulting at Armanino. After serving as an accountant at a Big Six firm, Dawood's career trajectory includes roles for a European telecommunications company in Afghanistan and as a CFO. Dawoud and Randy talk about the intricate world of dat…

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Impact and Income: Investing in Your Tribe and Borderless Talent with CEO David Nilssen 44:31

1+ y ago44:31

44:31

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with David Nilssen, CEO of DOXA Talent, and a forerunner of revolutionizing how businesses think about and engage with borderless talent. Randy and David take a look at the intricacies of borderless talent acquisition and the attributes that contribute to the success of a C…

1
The Power of Product-Led Growth: Unlocking Innovation with Dave Boyce 48:03

1+ y ago48:03

48:03

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with Dave Boyce, a GTM-focused SaaS Advisor, board member for Winning by Design and Forrester, and professor at BYU. Dave shares his unique approach to career decisions, focusing on his need for challenging work that ensures personal growth and impact. This approach has sha…

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What Makes a Great CFO?: The Journey of Transformation with CFO CJ Gustafson 45:26

1+ y ago45:26

45:26

This week on the Expert Voices podcast, Randy Wootton, CEO of Maxio, speaks with CJ Gustafson, CFO, and writer behind Mostly Metrics, to discuss the CFO's transformation from a back-office statistician to a front-office strategist, the evolving landscape of SaaS, and the future of finance leadership. Randy and CJ discuss the qualities that distingu…