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Accounting Technology Strategist, North America
Dext
Source: Headcount Labs · original listing ↗
Job data: Headcount Labs, ODbL 1.0. Job descriptions belong to their employers.
Source date: 10/30/2026
About this role
Are you an experienced accounting professional looking to use your expertise beyond practice and into the Fintech world? We’re looking for an Accounting Expert, experienced with Accounting domain, market and regulatory expertise to join our team at Dext. This is an opportunity to use your accounting knowledge to help shape and develop software solutions used by accountancy professionals. You’ll work closely with our Product Management and Engineering teams, interpreting legislative and regulatory changes and helping ensure our Bookkeeping, Accounts Production and solutions remain compliant, efficient and market-leading. The role, what you’ll do: We’re looking for an experienced Accountant and Accounting Technology leader to join Dext and shape our position in the North American market. This is a strategic, high-impact role where you will act as the voice of the accounting industry (mostly internally) helping to guide product direction, influence go-to-market strategies, and ensure Dext remains at the forefront of innovation. You will bring deep regional expertise in accounting practices, legislation, and technology trends, and use this to drive alignment across product, sales, and marketing teams. - Strategic Product Guidance: Influence product strategy and positioning by translating North American market trends, customer feedback, and practice workflows into actionable insights and user story acceptance criteria. - Regulatory & Compliance Leadership: Research, analyze, and track upcoming legislative changes across North America to ensure Dext solutions remain compliant and continuously deliver value. - Thought Leadership & External Representation: Act as Dext’s primary industry expert in North America, representing the brand at industry events, advisory boards, and high-impact speaking opportunities. - Cross-Functional & Partner Enablement: Partner with Sales, Marketing, and Product teams on go-to-market initiatives, while building relationships with ecosystem partners to drive integration growth. - Innovation & Efficiency: Leverage the latest AI advancements and industry tools to enhance internal research workflows and product feature capabilities. About You, what we are looking for: - CPA (Chartered Professional Accountant) designation or working toward direct qualification, with experience working in a Canadian accounting practice (essential). - Recognized cloud accounting expert with deep knowledge of leading software ecosystems popular in Canada (e.g., QuickBooks Online, Xero, Dext, Sage). - Proven ability to translate Canadian market insights, practice workflows, and client needs into clear product opportunities. - Confident communicator skilled at delivering demos, presenting externally, and collaborating cross-functionally. - Curious and commercially minded, with a passion for accounting technology and its evolving role in the Canadian accounting profession. It would be great if you also have: - Experience building relationships with tax authorities, regulators, or industry bodies in Canada (e.g., CRA, Revenu Québec, CPA Canada/Provincial CPA bodies). - Exposure to Canadian accounting and tax software packages (e.g., TaxPrep, Cantax, Profile, DT Max, TurboTax or Caseware). - Practical experience applying AI tools or data analytics within practice or product workflows. - Exposure to collaborative research methodologies within a product or design context. What you will be part of: Dext is a highly ambitious, innovative, and market-leading FinTech. We operate at global scale while maintaining the agility, pace, and mindset of a scale-up. We’re driven by a shared ambition to deliver excellence every day and our culture reflects that. Our values guide everything we do: - Be Brave: We speak up, challenge ideas, and push boundaries - Be Exceptional: We set high standards and strive to excel - Be Together: We succeed as one team, not as individuals Our behaviours bring these values to life. They shape how we work, collaborate, and support each other every day: Be Courageous, Considerate, Transparent, Focused, Accountable, Inclusive and above all, Dexterous. 🌟 What we will give you: - Flexible working hours with remote and in-office option in the heart of downtown Toronto - Several Time away from work (TAFW) policies, including but not limited to: - 22 vacation days annually plus Ontario’s statutory holidays - 5 Health leave days annually - Paternity & Maternity Leave Top up programs and - Working abroad days, Volunteering days, summer hours and a day off the week of your birthday! - Up to 5% company pension/RRSP matching - 100% employer-covered benefits through Desjardins(medical, dental, & vision) - available on your first day; and - A Health & Wellness Spending account (myHSA) of $750 annually Ready to take the next step? Click apply now Dext collects and processes personal data in accordance with applicable data protection laws. If you are a European Job Applicant see the privacy notice https://apply.workable.com/dext/gdpr_policy?lng=en for further details. Dext does not discriminate on the basis of race, sex, color, religion, age, national origin, marital status, disability, veteran status, genetic information, sexual orientation, gender identity or any other reason prohibited by law in provision of employment opportunities and benefits.