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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

47:32

E17: Why a16z is All-In on AI for Finance Teams with...

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

2024/08/01

In this episode, Sasha sits down with Seema Amble, Partner at Andreessen Horowitz. Seema shares her research on the transformation of the CFO’s office, and how generative AI is powering financial teams. She discusses how AI can empower CFOs and finance teams to focus on strategic rather manual tasks, increasing client communication through automation, the impact of AI on valuations in service businesses such as law and accounting, and the progression from “service as a software” vs “software as a

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50:01

E16: CFO Dilemmas Decoded: Growth vs. Profit, VC vs....

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

2024/07/25

In this episode of Turpentine Finance, Sasha sits down with Dan Fletcher, CFO of Planful. They discuss how CFOs can build trust with the CEO and the board, balancing growth and profitability across different company stages, the nuances of working with VC versus PE investors, and more. Dan also shares his perspective of working at Planful, building infrastructure for CFOs.-- 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This

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43:40

E15: Building Tax Compliance for Tech Companies with...

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

2024/07/18

In this episode, Sasha sits down with Michelle Valentine, Co-founder and CEO of Anrok, the tax compliance infrastructure for the internet economy. They discuss the complexities of sales tax in the digital age, the historical context, regulatory changes, and challenges faced by startups operating online. Michelle shares her journey from VC at Index Ventures to founding Anorak and provides valuable advice for finance leaders and founders on navigating sales tax issues effectively.-- 🔥 Apply to join

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46:15

E14: Revenue Models 101 & the New Stack with Riya...

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

2024/07/11

In this episode, Sasha sits down with Riya Grover, CEO and Cofounder of Sequence, to discuss the evolving landscape of B2B revenue models and pricing strategies. They dive deep into the challenges modern software companies face in managing complex hybrid pricing models and the increasing adoption of usage and hybrid-based pricing. Riya also shares Sequence's approach to unifying the quote-to-cash process, bridging the gap between sales and finance teams, the limitations of traditional revenue

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79:50

E13: Architecting IPO Readiness from Day One with...

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

2024/06/27

In this episode, Sasha sits down with Nadia Asoyan, former CFO of Strike, Robinhood, and Controller at Square. Nadia shares her journey from EY to Silicon Valley's top fintech rocketships, offering invaluable insights on transitioning from accounting to CFO positions. She discusses the challenges of IPO readiness, the evolution of financial processes in fast-growth startups, and the delicate balance between growth and profitability. Nadia also provides candid advice for aspiring CFOs, emphasizing

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44:25

E12: Customer Obsession Meets Unit Economics:...

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

2024/06/20

In this episode, Tomer London, co-founder and Chief Product Officer at Gusto, shares insights into aligning product and finance teams for responsible growth. He dives deep into the frameworks and practices Gusto employed to make trade-offs between core products, expansion opportunities, and moonshot ideas - all while maintaining a relentless focus on customer needs and healthy unit economics. Tomer discusses Gusto's thoughtful, iterative approach to product development, avoiding the pitfalls of

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59:11

E11: CFO Whisperer Jim Cook of Netflix, Intuit, &...

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

2024/06/13

In this episode, Sasha sits down with Jim Cook, dubbed the CFO Whisperer, after 30 years in Silicon Valley as CFO at Netflix, Intuit, and Mozilla. Jim shares CFO hiring mistakes and the misunderstandings most board members and investors have about the CFO role, why being precise is the finance professional’s Achilles heel, tactical advice for impactful communication in board meetings, and more.This show is a part of the Turpentine podcast network. Learn more:

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49:40

E10: How OpenAI Controller Sowmya Raganathan Uses AI...

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

2024/06/06

OpenAI Controller Sowmya Ranganathan sits with Sasha Orloff to share accounting insights from her experience at Square, Rippling, and OpenAI. She discusses automation and using AI in accounting, how difficult software motivated her to make the move to Controller at Rippling, and how she’s streamlining the accounting workflow at OpenAI, where she is currently Controller. Sowmya also explains how AI is making accounting easier and why future accounting teams may be small and broadly skilled.--- This

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64:31

E9: An Insider's Guide After $2B of M&A with Serial...

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

2024/05/30

In this conversation, Steve Love, a seasoned CFO with over $1 billion raised from VCs and $2 billion in M&A transaction experience, pulls back the curtain on high-stakes M&A. Love shares his insights from overseeing complex acquisitions like Heap's purchase of a complementary "session replay" company and Heap's eventual sale to ContentSquare. He candidly discusses navigating challenges, aligning stakeholders, prepping for diligence, and making strategic M&A decisions as a CFO. Whether you're a CFO,

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47:58

E8: When Your Biggest Competitor Crashes, with...

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

2024/05/23

How do you navigate the tide turn when your competitor collapses during one of the biggest banking crises in recent history? In this conversation, Sasha Orloff sits down with Immad Akhund, founder and CEO of Mercury*. Immad pulls back the curtain on the chaos and critical decisions made when Silicon Valley Bank fell. From mobilizing an all-hands effort to rapidly onboard new customers to developing new product features virtually overnight to instill confidence, Immad provides an unvarnished look at

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48:05

E7: The Dealmaker’s Secrets: Steve McLaughlin on...

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

2024/05/16

In this conversation, Sasha Orloff sits down with Steve McLaughlin, CEO and Managing Partner of FT Partners. Steve provides an insider’s look into the high-stakes world of capital raising and dealmaking for high-growth private companies. From being Goldman Sachs’ Former Head of Fintech to founding FT Partners, a global fintech investment firm, McLaughlin shares his strategies for crafting compelling narratives that unlock massive fundraising rounds - like the $33 billion valuation for Revolut and a

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44:56

E6: Behind the Scenes of General Catalyst: The VC...

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

2024/05/10

Ever wondered what the financial operations look like when you have billions in AUM at a top-tier VC firm?In this episode, Sasha sits down with Mark Allen, CFO at General Catalyst. Mark discusses the non-obvious complexities of managing billions in assets across hundreds of portfolio companies, from capital reserve strategies, geographical breakdowns, to reporting requirements. He shares candid insights on navigating intense moments like the Silicon Valley Bank collapse, tech innovations being

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49:22

E5: Bringing Fun Back to Finance: Redesigning...

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

2024/05/02

Get an inside look at Runway - the visually stunning finance platform that's breaking conventions and captivating users with its approach to making finance fun again.In this interview, founder and CEO Siqi Chen shares the arduous 3-year journey of iterating on the product from its inception during a meeting with the a16z team, working alongside early design partners, and the key inflection points that transformed Runway into what it is today. He emphasizes the importance of storytelling, having

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46:30

E4: Can Turning Down a Huge Upround Lead to a Greater...

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

2024/04/25

In this episode, Sasha sits down with Razzak Jallow, CFO at FloQast, to discuss the evolving role of the modern CFO as a strategic partner across the organization. They dive into how he builds trust with the CEO, his approach to fostering product innovation responsibly, and why he turned down a financing round that would have doubled FloQast's valuation. Razzak also offers advice for aspiring CFOs on evaluating their first CFO role, skills like "precision Q&A", and hiring great talent This show is

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47:20

E3: Chris Bakke on Negotiating with Elon Musk and...

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

2024/04/18

Ever wonder what it's like to get a call from Elon Musk, wanting to buy your company?In this episode, Sasha sits down with serial entrepreneur Chris Bakke to find out. Chris is the co-founder behind several successful startups, including Laskie, which was acquired by Elon Musk's X, and Interviewed, acquired by Indeed. Chris shares insights on: building a content-driven growth strategy as a founder that's led to his 200k+ follower base, navigating the M&A process and negotiating a deal directly

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50:51

E2: When COVID Hits and You are CFO at Instacart with...

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

2024/04/11

In this episode, Sasha sits down with Sagar Sanghvi, Current Partner at Accel and former CFO at Instacart. They discuss how Sagar drove the change in financial culture at Instacart and adapted rapidly to Whole Food’s acquisition by Amazon, scaling Instacart during the COVID pandemic, the balance between growth at all costs and unit economics, Sagar’s transition from CFO at Instacart to being Partner at the venture firm Accel, and much more. This show is a part of the Turpentine podcast network

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50:36

E1: Making Decisions in Hyper Growth with Former...

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

2024/04/08

In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'. This show is a part of the Turpentine podcast network. Learn more:

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62:43

E52: A CFO & CEO Walk Into a Bar | CJ Gustafson &...

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

2024/04/01

Today is a special episode where CJ Gustafson and Sasha Orloff (3x founder and current CEO of Puzzle) go deep on the CFO-CEO mindsets…and talk podcasting. They cover: highlights and memorable advice from CJ’s 50+ interviews on this feed, how to have impact as a CFO & CEO, the challenges of building finance software, each host’s biggest mistakes, and how to make a successful podcast. Turpentine Finance hosted by Sasha Orloff will debut later this week and this season will feature firsthand stories

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61:50

E51: A Crash-course in Global Payments with Brex COO...

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

2024/03/28

In this episode, CJ discusses the business of global payments and B2B fintech with Camilla Matias Morais, COO of Brex. Camilla came up in the FP&A world and is a stellar guide to Brex’s strategic bets and moats. Also covered is how she balances the COO role of risk management and company strategy while also being in the weeds with customer feedback.— **PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple:

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55:58

E50: What to Know About Layoffs in 2024 with HR...

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

2024/03/25

In this episode, CJ talks with the original duo of the HR Heretics podcast, Kelli Dragovich and Nolan Church about tech layoffs in 2024. Kelli and Nolan hold no punches and give straight answers to tough questions on layoffs, the job market, and employment best practices. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links

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