E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee
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.
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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/alexlee611/
https://www.truewind.ai/
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X/SOCIAL:
@AlexLee611 (Alex)
@truewindai (Truewind)
@sashaorloff (Sasha)
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TIMESTAMPS:
(00:00) Preview
(00:28) Intro
(01:07) Guest Introduction: Alex Lee from Truewind
(02:27) Origin of Truewind
(06:18) Impact of AI on accounting
(08:24) Adoption of AI in accounting
(09:59) Future of finance and accounting teams
(12:09) Truewind's approach and strategy
(15:13) Role of automation in accounting
(17:12) Sponsors: Notion | Puzzle
(18:49) Digital staff accountant concept
(19:53) Exploring AI features in finance
(21:07) Government regulations and data sharing
(22:23) Exciting news: Fundraising success
(24:08) Customer-centric approach to product development
(24:57) Advice for founders on fundraising
(27:15) Defining success for Truewind
(35:55) Future of finance and AI integration
(37:08) Wrap
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37:49
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37:49
E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree
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.
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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/wbhub/
https://agree.com/
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X/SOCIAL:
@wbhub (Will)
@AgreeHQ (Agree)
@sashaorloff (Sasha)
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TIMESTAMPS:
(00:00) Preview
(00:41) Intro
(01:23) Meet Will Hubbard: The story behind Agree
(02:19) Agree: All-in-one contracting and invoicing platform
(02:54) Evolution of Agree: From venture fund to B2B payments
(03:54) Delightful user experience of Agree
(06:06) Importance of design in accounting software
(06:57) The Why Now: Bundling contracting and invoicing
(08:51) Innovative features and AI-driven development
(13:38) Sponsors: Notion | Puzzle
(15:03) Favorite features: Tracking and reminders
(17:34) Surprising use cases and rapid development
(20:03) Viral growth of Agree.com
(21:22) Story behind Agree.com
(23:25) Challenges in naming a company
(24:57) Raising the next round of funding
(27:26) Future plans and product development
(29:11) Advice for finance leaders and founders
(34:22) Future of finance: Humans plus software
(35:37) Wrap
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36:30
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36:30
E51: Ramp for Revenue: The Tabs Playbook for Faster Cash Flow with CEO Ali Hussain
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/
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X/SOCIAL:
@sashaorloff (Sasha)
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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
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42:44
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42:44
E50: Zuora CFO Todd McElhatton on Why 70% of Finance Stacks Hold Back Growth
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/
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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)
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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
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37:43
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37:43
E49: Why Accel Backed Campfire to Build the Modern GL, with John Glasgow, CEO
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.
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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/johnglasgow
https://campfire.ai/
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X/SOCIAL:
@john__glasgow (John)
@sashaorloff (Sasha)
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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
Sobre "Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
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. Learn more: puzzle.io
Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co
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