HeyDrew! · 1 day ago
Founding Product Manager
United States
Full-time
Remote
Mid, Senior Level
$155K/yr - $180K/yr
4+ years expHeyDrew! is a Series A-funded startup developing an AI tax strategy platform for small and medium-sized businesses. The Founding Product Manager will lead the development of the Dual Brain platform, managing the product roadmap, and ensuring a seamless user experience between complex tax strategies and AI-driven solutions.
Financial Services
Responsibilities
Own the 6-month roadmap to Beta launch, prioritizing what is required for compliance and what meaningfully improves the customer experience
Must have startup experience, preferably seed round
Must 0-1 product experience
You will be an expert in the TaxTech space with a broad understanding and knowledge of all competitor platforms, unique functions and capabilities, benchmarking against them for our product roadmap
Design a concierge product experience where the software does the heavy lifting and the user only engages to connect data, answer key questions, and approve strategies
Define the Dual Brain user experience for two audiences: SMB clients (simple, reassuring) and internal CPA reviewers (fast, data-dense, audit-ready)
Own the “vision layer” requirements so document intake (OCR/vision extraction) maps correctly to the underlying data model used by the AI and tax workflows
Lead integration strategy and requirements for our data “senses,” including financial and filing partners (e.g., Plaid, etc.) and accounting platforms (QBO/Xero)
Productize tax strategies with the Director of Tax Operations by turning complex code into clear, guided workflows (for example, translating a strategy into a straightforward yes/no decision path)
Define success metrics that fit tax (not daily usage), such as time to savings, strategies identified, and review efficiency
Qualification
Required
Must have startup experience, preferably seed round
Must 0-1 product experience
You will be an expert in the TaxTech space with a broad understanding and knowledge of all competitor platforms, unique functions and capabilities, benchmarking against them for our product roadmap
Design a concierge product experience where the software does the heavy lifting and the user only engages to connect data, answer key questions, and approve strategies
Define the Dual Brain user experience for two audiences: SMB clients (simple, reassuring) and internal CPA reviewers (fast, data-dense, audit-ready)
Own the 'vision layer' requirements so document intake (OCR/vision extraction) maps correctly to the underlying data model used by the AI and tax workflows
Lead integration strategy and requirements for our data 'senses,' including financial and filing partners (e.g., Plaid, etc.) and accounting platforms (QBO/Xero)
Productize tax strategies with the Director of Tax Operations by turning complex code into clear, guided workflows (for example, translating a strategy into a straightforward yes/no decision path)
Define success metrics that fit tax (not daily usage), such as time to savings, strategies identified, and review efficiency
Product leadership experience in FinTech, RegTech, LegalTech, InsurTech, or similarly regulated/high-stakes software in a startup environment
4+ years as Product Manager with a successful product launch and post-launch iterations, understanding the whole product life-cycle
0-to-1 product builder who has taken a product from a founder-led vision to launch (startup experience strongly preferred)
Strong systems thinker who can map end-to-end workflows and understand how changes in one step affect the entire experience
Comfort working closely with engineering on APIs, data schemas, and integration requirements
Strong collaboration skills with technical and non-technical teams, including the ability to translate between engineering, tax, and customer language
Strong UX and service-design instincts, especially for low-engagement products where trust and simplicity matter
Managed a team of 2 to 4+ members
Has experience with hiring a team
Preferred
Experience designing concierge-style or workflow-driven products (onboarding, data intake, guided decisions, approvals)
Experience working at a seed-stage startup
Experience with a FinTech, or TaxTech product
Experience working with accounting/tax workflows and documents (K-1s, 1099s, basis, pass-through entities) or adjacent domains
Experience owning integration-heavy roadmaps (data providers, financial APIs, filing partners, QBO/Xero)
Strong analytics and experimentation mindset, with the ability to define meaningful operational and customer outcomes
Benefits
Equity
Company
HeyDrew!
Most small businesses have a CPA who looks backward. At HeyDrew!, we give them an AI strategist that looks forward.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase