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.

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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 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/ali-hussain786

https://tabs.inc/

--

X/SOCIAL:

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:04) Intro

(01:43) Meet Ali Hussain

(03:20) Vision behind Tabs

(07:41) Challenges and opportunities in finance automation

(11:06) Future of finance teams

(15:29) Sponsors: Notion | Puzzle

(16:53) Case study: Success with Statik

(19:09) Example of Tabs in action

(19:49) Future of AI in finance

(21:41) Agentic future and trust

(23:52) Building operational software

(27:32) Favorite features and lessons learned

(30:32) Venture capital and market opportunity

(34:05) Advice for founders

(36:58) Future plans and excitement

(41:41) Wrap

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.

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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 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/todd-mcelhatton-2140761/

https://www.zuora.com/resource/modern-finance-leader-report/_

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X/SOCIAL:

@Zuora (Zuora)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:43) Intro

(01:11) Season 2 focus: Accounting and technology

(01:30) Insights from the Modern Finance Leader Report

(02:13) Interview with Todd McElhatton: Challenges in finance technology

(05:34) The modernization Catch 22

(09:08) AI and the future of finance

(13:46) Sponsors: Notion | Puzzle

(15:26) Practical advice for finance leaders

(16:53) Zuora's impact and client success

(19:20) Role of AI and automation

(21:13) Building a 'Yes' department

(23:27) Advice for new finance leaders

(25:46) Transforming existing finance teams

(30:14) Strategic investment in technology

(32:22) Evolving role of CFOs

(34:21) Joining Zuora and making an impact

(35:29) Client success and product value

(36:39) Wrap

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 thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠

--

RECOMMENDED IN THIS EPISODE:

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

https://campfire.ai/

--

X/SOCIAL:

@john__glasgow (John)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:22) Intro

(01:00) Guest introduction: John Glasgow

(01:51) Journey of Campfire

(05:05) Challenges and innovations in accounting software

(06:47) Shift to modern GL and AI integration

(11:21) Sponsors: Notion | Puzzle

(13:29) Real-world impact and case studies

(19:11) Fundraising and future plans

(20:01) Partnering with John Lockett and Excel

(21:06) AI conference and bigger investments

(21:48) Challenges of a seed-backed business

(22:50) Advice for founders in big industries

(23:36) Product velocity and customer trust

(25:51) Future plans and milestones

(29:24) Origin of Campfire

(30:53) Message to finance leaders and founders

(34:05) Future of finance and AI

(36:13) Wrap

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 and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/nicolas-kopp/

https://www.rillet.com/

--

X/SOCIAL:

@nicckopp (Nicolas)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:00) Intro

(01:28) Meet Nicolas Kopp from Rillet

(02:23) Rillet's mission and market

(03:11) Founding story and challenges

(05:27) Building a modern GL

(11:27) Future of finance teams

(14:56) Real-world examples and success stories

(16:39) Sponsors: Notion | Puzzle

(18:03) AI-powered ERP

(21:28) Building a business with substance

(22:03) Investor perception and challenges

(22:46) Customer obsession and success

(24:31) Advice for founders

(27:49) The Sequoia effect

(30:47) Future milestones and product vision

(32:23) Customer feedback and obsession

(38:47) Wrap

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 efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠https://puzzle.io/⁠⁠⁠

--

RECOMMENDED IN THIS EPISODE:

⁠https://www.linkedin.com/in/lucinda-turner/

⁠http://www.worldpay.com

--

X/SOCIAL:

@Worldpay_Global (Worldpay)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:40) Meet Cindy Turner: Chief Product Officer of Worldpay

(02:08) Cindy Turner's career journey

(06:41) Global payments report

(10:01) Account-to-Account payments: A global perspective

(13:15) Sponsors: Notion | Puzzle

(14:55) Unlocking Open Banking

(17:10) E-commerce and digital payments trends

(20:33) Impact of surcharging in Australia

(21:56) Surcharging trends in the US

(23:23) Cash dominance in certain countries

(26:03) Rise of buy now, pay later

(29:39) Future of payments: Agentic commerce

(33:59) Stablecoins and the future of payments

(37:29) Optimizing payments for businesses

(38:50) Wrap

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 fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠https://notion.com/startups/puzzle⁠⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠https://puzzle.io/⁠⁠

--

RECOMMENDED IN THIS EPISODE:

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

https://town.com/

--

X/SOCIAL:

@jgreze (Jean)

@TownTaxCo (Town)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:20) Jean-Denis Greze: The origin story of Town

(02:10) Challenges and opportunities in business tax prep

(03:41) Role of AI in automating tax preparation

(05:50) Market dynamics and constraints in tax services

(15:49) Sponsors: Notion | Puzzle

(17:14) Unique needs of small businesses

(24:38) Future of AI in tax preparation

(26:12) Segmenting the small business market

(27:15) Building trust and scaling AI

(37:14) Exploring AI agents and their potential

(47:21) Fundraising and future plans

(50:57) Wrap

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 fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠https://notion.com/startups/puzzle⁠

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠https://puzzle.io/⁠

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/jaspar-carmichael-jack/

https://www.artisan.co/

--

X/SOCIAL:

@jasparcjack (Jaspar)

@GetArtisanAI (Artisan)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:38) Intro

(01:08) Jaspar Carmichael-Jack, Founder & CEO of Artisan

(02:53) Concept and evolution of Artisan

(04:09) Challenges and iterations in AI development

(05:09) Expanding Artisan's capabilities

(08:33) Future of AI in the workplace

(10:34) Sponsors: Notion | Puzzle

(11:58) From better data to smarter responses

(13:24) Funding and growth journey

(16:44) Balancing AI and human labor

(27:26) Fun and unusual use cases for AI

(28:45) Final thoughts and lessons learned

(31:09) Wrap

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! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/alan-imberman-cfa-aab2371/

https://www.wealthfront.com/

--

X/SOCIAL:

@Wealthfront (Wealthfront)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:16) Interview with Alan, CFO of Wealthfront

(01:54) Wealthfront's vision and growth

(03:24) Innovative financial products

(04:19) Profitability and business model

(06:03) New product launches and strategies

(15:18) Tax loss harvesting and direct indexing

(17:43) Sponsors: Notion | Puzzle

(19:23) Wealthfront’s tax strategy triumph

(23:13) Bond ladders explained

(28:11) Future of Wealthfront and AI in finance

(33:41) Advice for founders and finance leaders

(36:01) Wrap

This week, Sasha Orloff is joined by Wouter Born, a 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 organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

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

https://cfooffice.io/

--

X/SOCIAL:

@wouter_born (Wouter)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:26) Meet Wouter Born: From founder to AI influencer

(02:39) Wouter entrepreneurial journey

(05:30) Evolution of CFOs in the age of AI

(07:28) Practical AI Tips for CFOs and Founders

(13:01) Future tech stack for CFOs

(17:15) Sponsors: Notion | Puzzle

(18:40) Changing role of CFOs

(21:30) Importance of storytelling in finance

(23:32) Leveraging AI for financial storytelling

(25:54) Building financial tools with AI

(28:51) Future of CFO tech stack

(34:54) Practical advice for AI prompting

(38:39) Connecting with the community

(39:53) Wrap

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 your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

--

RECOMMENDED IN THIS EPISODE:

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

https://www.crunchbase.com/

--

X/SOCIAL:

@crunchbase

@skyspeak (Megh)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:35) Intro

(01:03) Megh Gautam, Crunchbase's Chief Product Officer

(01:48) Megh’s journey to Crunchbase

(04:26) Transitioning Crunchbase to an AI company

(07:06) Crunchbase's AI and data insights

(09:45) User engagement and product development

(14:58) Sponsors: Notion | Puzzle

(16:22) Forbes article on Crunchbase's AI model

(24:58) Pricing strategies and user experience

(29:33) Future of AI in product management

(35:53) Conclusion and future collaboration

(38:27) Wrap