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PODCAST

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

Puzzle, Turpentine

On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week"s biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work. Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making

business management

All Episodes

56:11

E57: Lessons from Brex, SVB, a16z: How Jason Mok...

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

2025/09/25

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 financial infrastructure in place from day one.-- SPONSORS: Notion Boost your startup with Notion—the

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43:03

E56: 5,000 Startups Later: Tax Lessons Every Founder...

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

2025/09/17

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 Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to

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39:55

E55: First Round and YC-Backed Startup 'Eliminating...

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

2025/09/05

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.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by

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38:04

E54: Filling the Gap Between QuickBooks and NetSuite...

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

2025/08/27

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 onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6

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37:49

E53: How AI Agents are Replacing Manual Accounting...

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

2025/08/06

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 customer-centric innovation.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected

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38:30

E52: Building a Viral Contract Platform: Will...

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

2025/07/30

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 trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps

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44:44

E51: Ramp for Revenue: The Tabs Playbook for Faster...

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

2025/07/24

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 ultimate connected workspace trusted by thousands worldwide! From engineering specs to

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39:43

E50: Zuora CFO Todd McElhatton on Why 70% of Finance...

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

2025/07/21

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 ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding

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39:29

E49: Why Accel Backed Campfire to Build the Modern...

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

2025/07/16

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.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by

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42:55

E48: Why Sequoia Invested $25M in Accounting Software...

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

2025/07/09

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 ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding

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42:01

E47: Agentic Commerce, Stablecoins, and Global Trends...

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

2025/06/12

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 worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and

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53:50

E46: Ex-Plaid CTO on Why Tax is the Ultimate AI...

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

2025/05/21

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 connected workspace trusted by thousands worldwide! From engineering specs to onboarding and

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35:07

E45: Artisan: Stop Hiring Humans, with Jaspar...

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

2025/04/30

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 connected workspace trusted by thousands worldwide! From engineering specs to onboarding and

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39:52

E44: From $2B to $80B: Wealthfront CFO Alan...

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

2025/04/23

In this episode, Sasha Orloff is joined Alan Imberman, CFO of Wealthfront, about how a client-first philosophy, transparent access, innovative products like S&P 500 Direct Indexing, and strategic use of machine learning have helped Wealthfront grow to $80 billion in assets and 1 million customers, while delivering lower fees, better rates, and sustainable wealth-building strategies.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide

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44:06

E43: The CFO's Blockbuster vs Netflix Moment: AI...

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

2025/04/16

This week, Sasha Orloff is joined by Wouter Born, finance, AI influencer, and General Partner at Born Capital to discuss how AI is reshaping the CFO role and financial tech stack, drawing lessons from Netflix’s rise over Blockbuster, emphasizing innovation, practical AI adoption, and financial storytelling.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team

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41:27

E42: Can AI predict the next unicorn. Crunchbase says...

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

2025/04/09

This week, Sasha Orloff sits down with Megh Gautam, Chief Product Officer of Crunchbase, to explore the company’s evolution into an AI-driven intelligence platform, discussing its 95% unicorn prediction accuracy, AI-powered user experiences, pricing challenges, and insights for founders, investors, and job seekers.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps

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40:50

E41: Surprising Trends from Deel's Data with Ben Cohen

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

2025/04/02

This week, Sasha Orloff sits down with Ben Cohen, Head of Data from Deel to discuss the company's 2025 Global Hiring Report, covering trends in Gen Z salaries, rising demand for finance roles, global workforce management challenges, domestic hiring shifts, employee termination rates, and the tools Deel provides to support global hires, with an emphasis on trust and asynchronous decision-making for productivity.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace

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45:28

E40: The $500 Domain That Became a Multi-Million...

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

2025/03/27

This week, Sasha Orloff is joined by Kash Ali, Founder and CEO of TaxGPT, who shares how a personal tax issue led to the platform’s creation, its rapid growth after Greg Brockman’s GPT-4 demo, investor interest from Marc Cuban and Jason Calacanis, its shift from a consumer tool to a B2B AI assistant for accountants, its unique advantages over general AI, and his own journey from Pakistan to Silicon Valley, culminating in Y Combinator and a vision for the future of AI-driven tax

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35:23

E39: The AI Economy: How Agents Will Transact Without...

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

2025/03/19

This week, Sasha Orloff sits down with Donald Gossen, CEO of Nevermined, to explore the future of AI-driven payments, highlighting the company's vision for AI agents with independent accounts and transaction protocols, the challenges of dynamic payment systems, the role of blockchain in security, and Nevermined's journey in enabling decentralized AI-to-AI transactions.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From

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36:07

E38: AI-Powered Tax Solutions are Really Here, with...

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

2025/03/12

This week, Sasha Orloff is joined by Ankur Dahiya, CEO and founder of Fifteenth, a B2B fintech startup using AI to modernize the tax industry, as they discuss his journey from navigating complex stock options at Flexport to transforming CPA services, the challenges of scaling a tax-focused business, the role of AI in automating tax processes, and his vision for more efficient, accessible tax advisory following a successful funding round. -- SPONSORS: Notion Boost your startup with Notion—the

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110 results

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