"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

This week, Sasha Orloff is joined by Andrés Ugarte to explore the rise of Copilot Money after Mint's shutdown announcement, sharing his journey from frustrated user to founder of a privacy-focused personal finance app, and discussing the challenges of building a product-driven company in a shifting financial landscape. For full show notes, visit: https://highlightai.com/share/31895f5b-d783-4eaa-ab11-ac3214b21ddb

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📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess 

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SPONSOR:

🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/product/ai?utm_source=podcasts&utm_medium=upstreampod

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LINKS:

Copilot Money: https://copilot.money/

https://www.linkedin.com/in/andresugarte/

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X/SOCIAL:

@chuga (Andrés)

@sashaorloff (Sasha)

In this episode of Turpentine Finance, host Sasha Orloff sits down with Paul Barnhurst, a passionate FP&A educator and content creator who shares insights on financial planning & analysis, teaching methodologies, and the evolution of financial tools. For full show notes, visit: https://highlightai.com/share/1823b417-abe8-49bb-8f00-d673e24077b1

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📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess 

--

SPONSOR:

🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

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LINKS:

The FP&A Guy: https://www.thefpandaguy.com/

https://www.linkedin.com/in/TheFPandAGuy/

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X/SOCIAL:

@sashaorloff

In this episode, host Sasha Orloff interviews Brad Wiskirchen about his journey with Kount, the AI-driven fraud prevention company he bootstrapped and sold to Equifax for $640 million, while sharing insights from his experience as a founder and now a partner at CVC Capital Partners. For full show notes, visit: https://highlightai.com/share/eec1be56-ae04-4afc-bb24-7ed8523b2176

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📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess 

--

SPONSOR:

🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

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LINKS:

Kount: https://kount.com/

https://www.linkedin.com/in/bradwiskirchen/

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X/SOCIAL:

@sashaorloff

@KountInc

In this episode, Sasha Orloff is joined by Aneal Vallurupalli, CFO at Airbase, who drops insights on modern spend management and his journey from M&A to leading finance at a Paylocity acquisition target. Aneal discusses his career trajectory, the impactful role of a CFO in spend management, and how Airbase revolutionizes non-payroll spends in the AI era. Aneal also offers essential advice to CFOs navigating today’s dynamic financial landscape.

🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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SPONSORS:

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Trusted by Notion, Anthropic, and Vanta. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

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LINKS:

Airbase: https://www.airbase.com/

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X/SOCIAL:

@sashaorloff

@AVallurupalli

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TIMESTAMPS:

(00:00) Preview

(01:16) Intro

(01:43) Meet Aneal Vallurupalli, CFO of Airbase

(02:28) Understanding Airbase's spend management

(04:33) Aneal’s journey to Airbase

(08:08) Evolution and impact of Airbase

(09:43) Role and strategy as CFO

(17:34) Sponsor: Anrok

(18:59) Balancing flexibility and control in spend management

(21:36) Importance of change management

(23:58) Memorable customer success stories

(27:35) Evolution of software in the CFO's office

(31:21) Trends in selling to different industries

(37:08) Future of Airbase and business spend management

(39:36) Insights on M&A and career journey

(43:37) Reflections on buy-side and sell-side experiences

(45:39) Wrap

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, the leading platform for buying and selling online businesses. Blake shares insights from his career (Xero, Lonely Planet, Good44), and explains how Flippa operates as the ‘investment bank for the 99%,’ providing a marketplace for subscale business transactions. The episode dives into the opportunities presented by the marketplace, key deal characteristics, and the different buyer segments. They also discuss the importance of financial literacy for subscale businesses, provide tips for first-time buyers, and offer predictions for the future of flipping businesses.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

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SPONSORS:

RIPPLING

Imagine total control over your company’s spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

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LINKS:

Flippa: https://flippa.com/

https://www.linkedin.com/in/blakehutchison/

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X/SOCIAL:

@sashaorloff

@Flippa

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TIMESTAMPS:

(00:00) Preview

(01:20) Intro

(02:26) Blake's career journey

(03:37) Flippa: The investment bank for the 99%

(05:55) Focus on digital assets

(07:20) Selling and buying on Flippa

(14:20) Buyer types and market dynamics

(18:30) Sponsors: Rippling | Anrok

(21:22) Investing in digital assets

(26:28) Navigating the first-time buyer market

(28:05) Buyer intent and market trends

(33:47) Common deal breakers in business sales

(36:46) Financial literacy and cloud accounting

(44:27) Future trends in online business flipping

(47:47) Getting started with Flippa

(49:02) Wrap

In this episode, Sasha Orloff welcomes Jane Lee and Aditya Reddy of Sapphire Ventures to unpack their paper, “Rise of the Next Gen CFO,” which features a market map of CFO tools and identifies key trends and predictions. Jane and Aditya discuss how finance roles are transforming, the convergence of finance and data science, the influence of AI, and emerging investment strategies in this fast-paced sector.

Nothing presented within this podcast is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures (“Sapphire”). Information provided reflects Sapphires’ views as of a time, whereby such views are subject to change at any point and Sapphire shall not be obligated to provide notice of any change. No assumptions should be made that investments or strategies described were or will be profitable. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. Nothing contained in this podcast may be relied upon as a guarantee or assurance as to the future success of any particular company or strategy. Past performance is not indicative of future results.

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SPONSORS:

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

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LINKS:

Rise of the Next Gen CFO: https://sapphireventures.com/blog/rise-of-the-next-gen-cfo-the-evolution-of-finances-role-and-tech-stack/

Sapphire Ventures: https://sapphireventures.com/

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X/SOCIAL:

@sashaorloff

@leejane09

@adityareddy97

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TIMESTAMPS:

(00:00) Preview

(00:53) Intro

(01:18) Viral market map by Sapphire Ventures

(02:23) Rise of the Next Gen CFO

(06:25) Key findings from the paper

(10:57) Impact of AI on finance

(18:09) Sponsors: Anrok | Netsuite

(20:36) Complexities with crypto assets

(24:22) AI affecting different industries

(28:22) Investment insights from Sapphire Ventures

(34:58) Sponsors: Metaview | Omneky

(36:27) Platform risks

(41:06) Sapphire Ventures' focus

(43:37) Wrap

In this episode, Sasha Orloff is joined by Eugene Spevakov, the Treasurer and Head of Corporate FP&A at 6sense, treasury expert, and veteran CFO. Sasha and Eugene dive deep into the Treasury function: how it differs across industries, how a scaling startup will know when it’s time to hire for the role, how to structure the function, and what separates a great treasurer from merely good. Eugene offers a masterclass on leveraging treasury to drive growth, improve cash flow, and allocate risk strategically in an uncertain world.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

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SPONSORS:

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

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LINKS:

https://www.linkedin.com/in/eugene-spevakov-cfa/

6sense: https://6sense.com/

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X/SOCIAL:

@sashaorloff

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TIMESTAMPS:

(00:00) Preview

(00:49) Intro

(01:14) Understanding treasury

(02:22) Meet Eugene Spevakov: A treasury expert

(03:39) Basics of treasury functions

(05:40) Real-world treasury challenges and risks

(09:12) Industry-specific treasury insights

(14:07) Sponsors: Anrok | Netsuite

(16:30) Treasury in software companies

(22:32) Risk management and allocation

(27:29) Sponsors: Metaview | Omneky

(28:58) When to hire a treasury professional

(30:07) Understanding and managing business risks

(32:40) Challenges and solutions in treasury functions

(37:08) Role and excitement of treasury

(43:12) Tools and resources for treasury management

(47:40) Advice for building a treasury function

(50:32) Wrap

In this episode, Sasha Orloff sits down with Camille Ricketts, former Co-Head of Marketing at Notion, Editor of First Round Review and Elon’s comms manager at Tesla, to talk about the ROI of content as a growth driver. Camille, currently a partner at XYZ Venture Capital, played a key role in persuading Sasha years ago to invest in content as a revenue channel. In this episode she shares her invaluable insights from her roles at Notion, Tesla, and First Round Review. Tune in to hear Camille’s compelling arguments for CEOs and VPs about the strategic value of content marketing. This is a must-listen for founders, finance leaders, and anyone eager to leverage content for growth.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

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SPONSORS:

NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

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LINKS:

https://www.linkedin.com/in/camillericketts/

XYZ: https://www.xyz.vc/

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X/SOCIAL:

@sashaorloff

@camillericketts

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TIMESTAMPS:

(00:00) Episode Preview

(00:58) Conversation with Camille Ricketts

(02:11) Camille's journey at Notion

(04:34) Content as a measurable growth strategy

(12:00) Effective use of testimonials and case studies

(15:45) Case studies and emotional engagement

(17:54) Sponsors: Netsuite | Metaview

(19:41) Measuring content success

(24:25) Tactical tips for effective call to action

(26:08) Figma and Stripe

(27:37) Founding story of First Round Review

(30:30) Sponsors: Brave | Omneky

(31:52) Iterating content formats and overcoming fear

(37:04) Role of AI in content creation

(42:57) Insights from Tesla and preparing for the unexpected

(47:24) Wrap

When Y Combinator's Paul Graham released his viral essay "Founder Mode," it sparked a firestorm in the tech world. Based on a private talk by Airbnb's Brian Chesky and endorsed by the likes of Elon Musk and Patrick Collison, the piece garnered over 20 million views. Enter Jim Cook, legendary Silicon Valley CFO (Netflix, Intuit, Mozilla) who just wrote a counterargument to set the record straight. Cook challenges the simplistic notion of founder supremacy — where only 10% succeed — and offers a different Leadership Mode framework for building high-performance, generational companies.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

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SPONSORS:

NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

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LINKS:

Cook’s Playbooks https://jcookflix.substack.com/

Founder Mode PG https://paulgraham.com/foundermode.html

Lenny’s Podcast episode with Brian Chesky https://www.youtube.com/watch?v=4ef0juAMqoE

Product-CEO Paradox by Ben Horowitz https://a16z.com/why-founders-fail-the-product-ceo-paradox/

Hard Thing About Hard Things by Ben Horowitz https://a16z.com/books/the-hard-thing-about-hard-things/

Scaling People with Claire Hughes Johnson https://www.goodreads.com/book/show/63063173-scaling-people

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X/SOCIAL:

@sashaorloff

@cookflix

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TIMESTAMPS:

(00:00) Episode preview

(00:26) Intro

(00:51) Founder Mode essay

(04:13) Challenges of polarized arguments

(07:44) Importance of leadership mode

(10:59) Balancing founder and scaling modes

(15:01) Sponsors: Netsuite | Metaview

(16:49) Trust and transparency in leadership

(20:41) Importance of creating a culture

(24:57) Leading with values and behaviors

(29:48) Sponsors: Brave | Omneky

(31:13) Importance of documentation

(36:45) Balancing founder and manager roles

(39:06) Structuring ownership and accountability

(43:06) Founders as Coaches and Captains

(48:12) Specialized operators in finance

(50:41) Scaling company to public

(53:50) Wrap

In this episode, Sasha Orloff is joined by Chris Sands, Head of Jobs at The F Suite, to discuss the landscape of finance leadership and career advancement in 2024. Sands unpacks the changing role of CFOs and how to navigate compensation from the vantage point of CFOs (and the CEOs hiring for the role). This episode offers invaluable insights on how to stay relevant, adaptable, and ahead of the curve in your finance career.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

--

RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

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SPONSORS:

NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

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LINKS:

http://fsuite.co

https://www.fsuite.co/compensation-survey

http://lsuite.co

http://www.thesuite.com

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X/SOCIAL:

@sashaorloff

@chris_sands_

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TIMESTAMPS:

(00:00) Episode preview

(01:16) Intro

(01:40) Meet Chris Sands: Head of Jobs at The F Suite

(03:06) Evolving role of the CFO

(09:11) Strategies for aspiring CFOs

(12:29) Candidate-first approach in recruitment

(13:56) Then vs Now: Hiring CFOs

(19:14) Preparing candidate for interviews

(22:53) Sponsors: Netsuite | Metaview

(24:40) Best practices in recruiting finance teams

(26:19) Role of CFO in the hiring process

(27:28) Advice for recruiting CFOs

(29:28) Sponsors: Brave | Omneky 

(30:56) Key traits of a great CFO

(32:52) Evolution of CFO roles

(34:10) Misconceptions on job search

(37:56) CFO compensation insights

(44:49) Negotiation strategies for CFOs

(48:04) Non-negotiable compensation offers

(48:59) F Suite: Building a community for CFOs

(52:39) Wrap