"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

Puzzle, Turpentine
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Aug 6, 2025 • 38min

E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee

Join Alex Lee, the co-founder and CEO of Truewind, a pioneer in AI-powered accounting. He discusses how Truewind's technology is revolutionizing traditional accounting by cutting data reconciliation time from hours to minutes. Alex shares insights on the adoption of AI in the industry, the challenges of fundraising in a tough climate, and how customer feedback drives innovation. He also highlights the importance of retaining human oversight in finance, emphasizing that AI enhances accountants' roles rather than replacing them.
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4 snips
Jul 30, 2025 • 37min

E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree

Will Hubbard, Founder & COO of Agree, dives into the creation of a game-changing platform that integrates contracting, invoicing, and payments seamlessly. He shares insights on Agree's rapid growth and the impact of their recent $7.2M seed round. The conversation highlights the importance of user-centered design in finance tech and how AI is reshaping the industry. Hubbard also reveals how their platform simplifies the contracting process, turning tedious tasks into delightful user experiences, and discusses the significance of fostering customer empathy in product development.
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Jul 24, 2025 • 43min

E51: Ramp for Revenue: The Tabs Playbook for Faster Cash Flow with CEO Ali Hussain

Ali Hussain, CEO of Tabs and a former PhD student, dives into how AI is transforming revenue and collections management. He shares insights on reducing days sales outstanding (DSO) and boosting efficiency for finance teams. The discussion covers his $25M funding journey and the integration of AI to streamline financial processes. Ali also highlights the challenges faced by traditional finance systems and the potential for automation to drive scalable growth. Ultimately, he envisions a future where finance professionals adapt creatively to these tech advancements.
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Jul 21, 2025 • 38min

E50: Zuora CFO Todd McElhatton on Why 70% of Finance Stacks Hold Back Growth

Todd McElhatton, CFO of Zuora, shares his vast experience from Oracle and VMware, focusing on the evolving role of finance leaders. He discusses the critical challenges posed by outdated systems and the importance of embracing AI in accounting. Insights from the 'Modern Finance Leader' report highlight how technology can streamline operations. McElhatton emphasizes the transformative potential of modern tools for improving efficiency and reducing administrative burdens, positioning CFOs as strategic decision-makers in the face of rapid technological change.
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4 snips
Jul 16, 2025 • 37min

E49: Why Accel Backed Campfire to Build the Modern GL, with John Glasgow, CEO

In this engaging discussion, John Glasgow, CEO and CFO of Campfire, shares his journey of building an AI-native ERP system designed for finance teams. Fresh off a $35 million funding round, he dives into the challenges of modernizing legacy systems and the critical role of automation in finance workflows. Glasgow also emphasizes the urgent need for innovation in accounting tech, highlighting real-world impacts and success stories that showcase the shift toward strategic finance in today's fast-paced business landscape.
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Jul 9, 2025 • 40min

E48: Why Sequoia Invested $25M in Accounting Software with Rillet CEO Nicolas Kopp

Nicolas Kopp, CEO & Founder of Rillet, is on a mission to reshape accounting with AI. They chat about Rillet's impressive $25 million funding from Sequoia and how their innovative software is revolutionizing financial management for mid-market companies. He discusses the necessity of clean data and the role of AI in streamlining processes, enhancing efficiency, and supporting lean finance teams. Real-world success stories illustrate how Rillet empowers businesses to make faster, more accurate financial decisions.
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Jun 12, 2025 • 39min

E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay

Cindy Turner, Chief Product Officer of Worldpay and former payments expert at PayPal and Visa, dives into the evolving payments landscape. She discusses the impact of stablecoins and agentic technology on global transactions. Cindy highlights how user experience affects digital payment adoption in the U.S. and examines trends like buy now, pay later. She also explores cross-border payment behaviors and the unique surcharging practices in Australia, shedding light on the importance of adapting to regional differences in the digital economy.
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May 21, 2025 • 52min

E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze

Jean-Denis Greze, Co-founder and CEO of Town and former CTO of Plaid, dives into the challenges of tax preparation for small businesses. He discusses the innovative use of AI to automate processes while still emphasizing the role of human expertise. The conversation explores the startup's origin, unique opportunities in the small business sector, and the evolving landscape of tax technology. Jean-Denis also shares insights on market dynamics and the transformative potential of AI, revealing why he believes tax is the ultimate AI challenge.
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Apr 30, 2025 • 32min

E45: Artisan: Stop Hiring Humans, with Jaspar Carmichael-Jack

Jaspar Carmichael-Jack, the Founder and CEO of Artisan, discusses the revolutionary role of AI, particularly their creation Ava, in automating sales and workflows. He shares insights on how AI can enhance decision-making and streamline operations across various sectors. The conversation highlights the balance between automation and human intuition, as well as the challenges of creating human-like interactions. Jaspar also reflects on his entrepreneurial journey, the importance of adaptability, and the innovative potential of AI in transforming modern business.
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Apr 23, 2025 • 37min

E44: From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey

Alan Imberman, CFO of Wealthfront, shares insights from his journey growing the company from $2 billion to $80 billion in assets. He emphasizes a client-first philosophy that enhances trust and long-term relationships. The discussion covers innovative financial products like S&P 500 direct indexing that simplify investing and tax-loss harvesting strategies. Imberman also highlights how Wealthfront leverages machine learning to provide lower fees and better rates, empowering millennials to build sustainable wealth.

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