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

Sasha Orloff sits down with Solon Angel, CEO of Remitian, to explore why tax payments remain one of fintech's most overlooked infrastructure problems. They discuss the outdated systems still powering tax compliance, how AI agents are enabling a new payments layer for accountants and taxpayers, and why the convergence of regulatory change, fraud prevention, and agentic AI could transform the $7 tri...

Sasha Orloff and Jeff Grimes, Perplexity’s Product Lead for Finance, explore the evolution of search from a simple "answer engine" to a high-stakes "action engine." They discuss the disruption of legacy platforms like the Bloomberg Terminal and how Perplexity is building an AI-native operating system designed specifically for the rigors of financial analysis. The conversation tackles the industry'...

In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to "architecting" financial systems and human-centric advisory. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trus...

In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time data-driven decision making" over traditional month-end closes. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace tr...

In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collections to cash application and disputes—delivering a 40% reduction in DSO in the first six months compared to the 3% improvement from legacy software, wh...

In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and internati...

In this episode, Sasha Orloff speaks with Usman Gul, founder and CEO of Metal, about building an AI-driven operating system for fundraising backed by Y Combinator and Andreessen Horowitz that helps founders avoid wasting 80% of their investor meetings by using data-driven insights to identify the most likely investors based on historical funding patterns, industry benchmarks, and relationship inte...

In this episode, Sasha Orloff speaks with Renato Villanueva, Founder and CEO of Parallel, about his journey from finance professional at Divvy to raising $2.4 million from Bain Capital and K5 Tokyo Black for an AI-powered FP&A platform that helps founders model financial scenarios and make confident growth decisions. Renato shares lessons on building products founders are passionate about rather t...

In this episode, Sasha Orloff talks with Yogi Goel, Co-founder and CEO of Maxima, about raising $41 million from Kleiner Perkins and RedPoint Ventures to build an agentic AI platform for enterprise accounting that automates journal entries, reconciliations, and variance analysis for complex companies, helping them close their books 2-3 days faster with 98% automation while strengthening SOX contro...

In this episode, Sasha Orloff sits down with Dan Westgarth, COO of Deel, to explore how the company scaled to 37,000 customers, processes $22B in payroll, and recently raised a $300M Series E to power global hiring in 150 countries. They dive into the future of back-office automation, including real-time payroll, AI-driven operations, and the push toward a unified, seamless global HR and accountin...

In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the tra...

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, to discuss the launch of Lauren AI—Flippa’s new AI tool transforming how online businesses are bought and sold. They explore how Lauren AI uses proprietary data and machine learning to enhance deal sourcing, automate buyer outreach, and streamline deal structuring. The conversation also dives into how AI is reshaping smal...

In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financi...

In this episode, Sasha Orloff talks with Joe Faris, founder of Accountalent, about his four decades of helping over 5,000 startups navigate tax and accounting challenges, covering critical founder lessons from 83B elections and R&D tax credits to payroll compliance and bookkeeping best practices that can save startups from costly mistakes and penalties. -- SPONSORS: Notion Boost your startup with...

In this episode, Sasha Orloff talks with Josh Wymer, Co-founder and CEO of Central HQ, about raising $8.6 million from First Round Capital and Y Combinator to build an AI-first back office solution that eliminates business compliance tasks through Slack-based automation, helping startups handle payroll, taxes, and HR without the administrative burden that typically comes with traditional software....

In this episode, Sasha Orloff talks with Ben Taylor, CEO & Co-founder of SoftLedger, about bootstrapping a modern, API-first general ledger that helps finance teams manage multi-entity businesses beyond QuickBooks without the complexity of Netsuite. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboardi...

In this episode, Sasha Orloff and Alex Lee, Co-founder & CEO of Truewind, to discuss how his company is transforming accounting with AI-powered automation—streamlining tasks like data reconciliation and deposit matching from hours to minutes. They explore Truewind’s journey, recent funding led by Thomson Reuters and Row Capital, and the future of accounting through AI, autonomous agents, and custo...

This week, Sasha Orloff sits down with Will Hubbard, Founder & COO of Agree, about building an all-in-one platform that streamlines contracting, invoicing, billing, and payments. They explore Agree’s rapid growth, recent $7.2M seed round, and how AI and user-centered design are shaping the future of finance tech. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace t...

In this episode, Sasha Orloff talks with Ali Hussain, CEO of Tabs, discuss how the company is using AI to modernize revenue and collections management, reduce DSO, and boost efficiency for finance teams. They discuss Ali’s journey from PhD dropout to fintech founder, Tabs’ $25M raise, and how the platform is reshaping B2B finance operations. -- SPONSORS: Notion Boost your startup with Notion—the u...

This week, Sasha Orloff and Zuora CFO Todd McElhatton discuss the growing complexity of finance operations and the critical role of AI in modern accounting. They talk about the insights from the 'Modern Finance Leader' report, strategies for overcoming legacy systems, and practical advice for finance leaders navigating technological change. -- SPONSORS: Notion Boost your startup with Notion—the ul...

In this episode, Sasha Orloff talks with John Glasgow, CEO & CFO of Campfire, about building an AI-native ERP system that streamlines finance workflows through automation and faster month-end close. Fresh from raising $35 million, John shares insights on modernizing legacy systems, the challenges of building complex financial software, and why now is the right time to innovate in accounting tech....

This week, Sasha Orloff and Nicolas Kopp, CEO & Founder at Rillet, discuss how Rillet is transforming accounting by leveraging AI to streamline processes, improve efficiency, and build lean finance teams. They also talk about the company’s $25 million funding from Sequoia, the importance of clean data, and Rillet’s customer-focused approach. -- SPONSORS: Notion Boost your startup with Notion—the u...

This week, Sasha Orloff and Worldpay Chief Product Officer Cindy Turner explore the shifting digital payments landscape—from stablecoins and agentic tech to global trends in account-to-account payments, regional behaviors, regulatory influences, and innovations like buy now, pay later. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwid...

In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automation and human expertise, strategic market targeting, funding insights, and the transformative potential of AI in tax preparation. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connecte...

This week, Sasha Orloff sits down with Jaspar Carmichael-Jack, Founder & CEO of Artisan, about how their AI employees like Ava are transforming sales and workflows by integrating software into cohesive ecosystems, highlighting breakthroughs in AI capabilities, the balance between automation and human input, and the future of work. -- SPONSORS: Notion Boost your startup with Notion—the ultimate con...