TWO OPEN ROLES

TWO OPEN ROLES

TWO OPEN ROLES


Careers at cashtrax
Join us

Careers at cashtrax

Join us

We are seeking two senior leaders for our founding core team. Both will report to the CEO, help shape company strategy, and lead internal and outsourced teams. Montreal-based candidates able to work on a hybrid basis are preferred. Compensation will reflect experience and cashtrax's development stage, with meaningful equity upside.


We are seeking two senior leaders for our founding core team. Both will report to the CEO, help shape company strategy, and lead internal and outsourced teams. Montreal-based candidates able to work on a hybrid basis are preferred. Compensation will reflect experience and cashtrax's stage, with meaningful equity upside.

Contact Illustration

Who you would be building with.

Who you would be building with.

Who you would be building with.

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The fourth venture co-founded by Connor O'Brien and Shark Tank's Kevin O'Leary

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Kevin's brand and media reach give cashtrax a powerful advantage in acquiring customers efficiently and accelerating growth

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Follows three financial-services startups, three exits, over $100 million in strategic value

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cashtrax connects users' accounts and uses AI to track what is coming in and going out. One number shows what they can safely spend today, making cash control push-button simple

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Kevin's brand and media reach give cashtrax a powerful advantage in acquiring customers efficiently and accelerating growth

4

cashtrax connects users' accounts and uses AI to track what is coming in and going out. One number shows what they can safely spend today, making cash control push-button simple

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Montreal, hybrid preferred

Montreal-based candidates able to work on a hybrid basis are preferred.

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Montreal, hybrid preferred

Montreal-based candidates able to work on a hybrid basis are preferred.

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Reports to the CEO

Help shape company strategy, and lead internal and outsourced teams.

Feature Icon
Reports to the CEO

Help shape company strategy, and lead internal and outsourced teams.

Feature Icon
Meaningful equity upside

Compensation will reflect experience and cashtrax's development stage.

Feature Icon
Meaningful equity upside

Compensation will reflect experience and cashtrax's development stage.

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Founding core team

Two senior leaders joining at the start, not after the shape is set.

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Founding core team

Two senior leaders joining at the start, not after the shape is set.

The two seats

Woman writing financial goals in a notebook
01
Head of Product

Own product strategy and the roadmap from beta through scale. Have a passion for simplicity in UI/UX and beyond. Lead customer research, design, analytics, onboarding, activation and retention. Work closely with design and engineering to prioritize, make trade-offs and get new features into users' hands in weeks, not quarters. Experience building AI-enabled consumer products is strongly preferred.

Woman using a phone for automatic investing
02
Head of Growth

Own growth strategy, customer acquisition and revenue. Attracted to leveraging the O'Leary advantage. Lead channel selection, budget allocation, creative testing, activation, lifecycle engagement and retention. Bring strong consumer-marketing instincts, analytical discipline and command of unit economics.

The two seats

Woman writing financial goals in a notebook
01
Head of Product

Own product strategy and the roadmap from beta through scale. Have a passion for simplicity in UI/UX and beyond. Lead customer research, design, analytics, onboarding, activation and retention. Work closely with design and engineering to prioritize, make trade-offs and get new features into users' hands in weeks, not quarters. Experience building AI-enabled consumer products is strongly preferred.

Woman using a phone for automatic investing
02
Head of Growth

Own growth strategy, customer acquisition and revenue. Attracted to leveraging the O'Leary advantage. Lead channel selection, budget allocation, creative testing, activation, lifecycle engagement and retention. Bring strong consumer-marketing instincts, analytical discipline and command of unit economics.

The two seats

Woman writing financial goals in a notebook
01
Head of Product

Own product strategy and the roadmap from beta through scale. Have a passion for simplicity in UI/UX and beyond. Lead customer research, design, analytics, onboarding, activation and retention. Work closely with design and engineering to prioritize, make trade-offs and get new features into users' hands in weeks, not quarters. Experience building AI-enabled consumer products is strongly preferred.

Woman using a phone for automatic investing
02
Head of Growth

Own growth strategy, customer acquisition and revenue. Attracted to leveraging the O'Leary advantage. Lead channel selection, budget allocation, creative testing, activation, lifecycle engagement and retention. Bring strong consumer-marketing instincts, analytical discipline and command of unit economics.

Who this is for.

We seek creative, self-directed leaders who thrive in a lean team, and have built or grown consumer mobile businesses, ideally in fintech or another trust-sensitive category. Candidates should take initiative, collaborate well, move between strategy and execution, manage competing priorities and deliver ambitious, measurable goals.

We seek creative, self-directed leaders who thrive in a lean team, and have built or grown consumer mobile businesses, ideally in fintech or another trust-sensitive category. Candidates should take initiative, collaborate well, move between strategy and execution, manage competing priorities and deliver ambitious, measurable goals.

We seek creative, self-directed leaders who thrive in a lean team, and have built or grown consumer mobile businesses, ideally in fintech or another trust-sensitive category. Candidates should take initiative, collaborate well, move between strategy and execution, manage competing priorities and deliver ambitious, measurable goals.

Interested or know someone exceptional?

Founding clients get early beta access and a say in what gets built next.

Founding clients get early beta access and a say in what gets built next.

Join the waitlist for priority access

Beanstox Investments Inc. dba cashtrax ("cashtrax") does not provide investment, tax, legal, accounting, credit score, or banking advice. The information provided is for informational purposes only and is not intended to constitute such advice. Readers and App users are encouraged to consult with their personal tax, legal, and accounting professionals for specific guidance.

AI: cashtrax uses artificial intelligence ("AI") to generate material information communicated to users of the App and the Website. Because generative AI produces responses based on vast data inputs and lacks critical thinking, cashtrax can't guarantee factual accuracy and may produce content that's incorrect or misleading. You should do your own research to complement, or verify the accuracy of, AI generated information.

* Plaid Technologies, Inc. ("Plaid") collects information (“Account Information”) about you and your accounts from you and from your financial institutions when you connect an account to cashtrax. By connecting your accounts, you let cashtrax and Plaid securely access and transmit your Account Information on your behalf. cashtrax connects to your accounts on a read-only basis to analyze your spending and help you manage your money. The Account Information accessed may include account balances and transactions from those institutions. cashtrax does not move, transfer, hold, or otherwise handle your funds. You acknowledge and agree that the Account Information you provide to Plaid through cashtrax will be treated by Plaid in accordance with Plaid's privacy policy, available at https://plaid.com/legal/. By choosing to link your financial institution account, you expressly authorize and direct cashtrax and Plaid, on your behalf, to electronically retrieve your Account Information.

ⓒ 2026 cashtrax · Privacy-first by design

  • cashtrax

  • —

Beanstox Investments Inc. dba cashtrax ("cashtrax") does not provide investment, tax, legal, accounting, credit score, or banking advice. The information provided is for informational purposes only and is not intended to constitute such advice. Readers and App users are encouraged to consult with their personal tax, legal, and accounting professionals for specific guidance.

AI: cashtrax uses artificial intelligence ("AI") to generate material information communicated to users of the App and the Website. Because generative AI produces responses based on vast data inputs and lacks critical thinking, cashtrax can't guarantee factual accuracy and may produce content that's incorrect or misleading. You should do your own research to complement, or verify the accuracy of, AI generated information.

* Plaid Technologies, Inc. ("Plaid") collects information (“Account Information”) about you and your accounts from you and from your financial institutions when you connect an account to cashtrax. By connecting your accounts, you let cashtrax and Plaid securely access and transmit your Account Information on your behalf. cashtrax connects to your accounts on a read-only basis to analyze your spending and help you manage your money. The Account Information accessed may include account balances and transactions from those institutions. cashtrax does not move, transfer, hold, or otherwise handle your funds. You acknowledge and agree that the Account Information you provide to Plaid through cashtrax will be treated by Plaid in accordance with Plaid's privacy policy, available at https://plaid.com/legal/. By choosing to link your financial institution account, you expressly authorize and direct cashtrax and Plaid, on your behalf, to electronically retrieve your Account Information.

ⓒ 2026 cashtrax · Privacy-first by design

  • cashtrax

  • —

Beanstox Investments Inc. dba cashtrax ("cashtrax") does not provide investment, tax, legal, accounting, credit score, or banking advice. The information provided is for informational purposes only and is not intended to constitute such advice. Readers and App users are encouraged to consult with their personal tax, legal, and accounting professionals for specific guidance.

AI: cashtrax uses artificial intelligence ("AI") to generate material information communicated to users of the App and the Website. Because generative AI produces responses based on vast data inputs and lacks critical thinking, cashtrax can't guarantee factual accuracy and may produce content that's incorrect or misleading. You should do your own research to complement, or verify the accuracy of, AI generated information.

* Plaid Technologies, Inc. ("Plaid") collects information (“Account Information”) about you and your accounts from you and from your financial institutions when you connect an account to cashtrax. By connecting your accounts, you let cashtrax and Plaid securely access and transmit your Account Information on your behalf. cashtrax connects to your accounts on a read-only basis to analyze your spending and help you manage your money. The Account Information accessed may include account balances and transactions from those institutions. cashtrax does not move, transfer, hold, or otherwise handle your funds. You acknowledge and agree that the Account Information you provide to Plaid through cashtrax will be treated by Plaid in accordance with Plaid's privacy policy, available at https://plaid.com/legal/. By choosing to link your financial institution account, you expressly authorize and direct cashtrax and Plaid, on your behalf, to electronically retrieve your Account Information.

ⓒ 2026 cashtrax · Privacy-first by design

  • cashtrax

  • —

Beanstox Investments Inc. dba cashtrax ("cashtrax") does not provide investment, tax, legal, accounting, credit score, or banking advice. The information provided is for informational purposes only and is not intended to constitute such advice. Readers and App users are encouraged to consult with their personal tax, legal, and accounting professionals for specific guidance.

AI: cashtrax uses artificial intelligence ("AI") to generate material information communicated to users of the App and the Website. Because generative AI produces responses based on vast data inputs and lacks critical thinking, cashtrax can't guarantee factual accuracy and may produce content that's incorrect or misleading. You should do your own research to complement, or verify the accuracy of, AI generated information.

* Plaid Technologies, Inc. ("Plaid") collects information (“Account Information”) about you and your accounts from you and from your financial institutions when you connect an account to cashtrax. By connecting your accounts, you let cashtrax and Plaid securely access and transmit your Account Information on your behalf. cashtrax connects to your accounts on a read-only basis to analyze your spending and help you manage your money. The Account Information accessed may include account balances and transactions from those institutions. cashtrax does not move, transfer, hold, or otherwise handle your funds. You acknowledge and agree that the Account Information you provide to Plaid through cashtrax will be treated by Plaid in accordance with Plaid's privacy policy, available at https://plaid.com/legal/. By choosing to link your financial institution account, you expressly authorize and direct cashtrax and Plaid, on your behalf, to electronically retrieve your Account Information.

ⓒ 2026 cashtrax · Privacy-first by design

  • cashtrax

  • —

Beanstox Investments Inc. dba cashtrax ("cashtrax") does not provide investment, tax, legal, accounting, credit score, or banking advice. The information provided is for informational purposes only and is not intended to constitute such advice. Readers and App users are encouraged to consult with their personal tax, legal, and accounting professionals for specific guidance.

AI: cashtrax uses artificial intelligence ("AI") to generate material information communicated to users of the App and the Website. Because generative AI produces responses based on vast data inputs and lacks critical thinking, cashtrax can't guarantee factual accuracy and may produce content that's incorrect or misleading. You should do your own research to complement, or verify the accuracy of, AI generated information.

* Plaid Technologies, Inc. ("Plaid") collects information (“Account Information”) about you and your accounts from you and from your financial institutions when you connect an account to cashtrax. By connecting your accounts, you let cashtrax and Plaid securely access and transmit your Account Information on your behalf. cashtrax connects to your accounts on a read-only basis to analyze your spending and help you manage your money. The Account Information accessed may include account balances and transactions from those institutions. cashtrax does not move, transfer, hold, or otherwise handle your funds. You acknowledge and agree that the Account Information you provide to Plaid through cashtrax will be treated by Plaid in accordance with Plaid's privacy policy, available at https://plaid.com/legal/. By choosing to link your financial institution account, you expressly authorize and direct cashtrax and Plaid, on your behalf, to electronically retrieve your Account Information.

ⓒ 2026 cashtrax · Privacy-first by design

  • cashtrax

  • —