Senior Product Manager – Document Intelligence Platform

Note Please submit candidates who are based in the Central or Eastern Time Zones only.

Taxwell is hiring a Senior Product Manager to lead product strategy, 0?1 innovation, and execution for Drake, our professional desktop and emerging cloud-based tax, solutions used by thousands of tax firms.

This role owns the product roadmap, annual tax season delivery, and long-term evolution of the professional tax portals and document import platform. You will focus on improving preparer productivity, ensuring compliance with federal and state tax law changes, and maintaining a high performance, reliable experience during peak season.

We are looking for a strong product leader who understands complex software, values operational excellence, and can balance innovation with stability in a mission critical environment. In addition, this role will identify and build new product capabilities from ideation through launch, helping shape the future of our cloud-based tax ecosystem.

What you will do Product Strategy and Roadmap- Define and own the product vision and roadmap, including both platform evolution and new product innovation

• Balance innovation with platform stability and reliability, in a mission critical environment
• Identify opportunities to improve core workflows, customer value, and new product offerings
• Evaluate opportunities using customer insights, data, and market analysis Annual Tax Season Delivery- Lead planning and execution of annual tax law updates
• Partner with compliance and tax content teams to implement federal and state changes accurately and on time
• Prioritize features and enhancements within fixed regulatory deadlines
• Ensure product readiness and performance during peak tax season Customer Experience and Execution- Improve preparer workflows including return preparation, review, and electronic filing
• Use customer insights and data to drive measurable improvements
• Partner with engineering on performance, architecture, and technical priorities
• Collaborate with support, sales, and go to market teams
• Communicate priorities and trade offs clearly to stakeholders and leadership Innovation & New Product DevelopmentIdentify and validate new product opportunities through customer discovery, data, and market trends

Lead initiatives from

ideation ? validation ? MVP ? launch ? early scale Rapidly test and iterate using

experiments and customer feedback Explore opportunities to apply

The duration for this role is 4 to 6 months, with the possibility of converting to a full-time position.

Direct customer-facing product ownership Owned a commercial B2B SaaS product area—not just projects, internal tools, platforms, or technical infrastructure.

Ideally client portals, document workflows, collaboration, secure sharing, document collection/management, or workflow automation.

Document ingestion / extraction depth Personally led an initiative involving OCR, classification, extraction, AI/ML, or LLM-based document processing.

Can explain document types, technology/model choices, confidence thresholds, human-in-the-loop review, exceptions, validation, accuracy, and measurable outcomes.

Understands security, sensitive data, auditability, and compliance.

End-to-end product ownership Personally owned problem definition ? discovery ? vision ? roadmap ? prioritization ? requirements ? launch ? measurement ? iteration.

Distinguishes their own contribution from what the broader team did.

Fast execution and judgment Has concrete examples of shipping with constrained engineering capacity, competing priorities, or deadlines.

Makes explicit tradeoffs rather than waiting for consensus or extensive direction.

Strong customer/problem orientation Starts with the customer problem and evidence.

Uses interviews, behavioral data, support/sales feedback, experimentation, and other discovery methods to validate opportunities.

0-to-1 / MVP experience Has actually taken products or significant capabilities from concept to MVP/launch.

Can explain what they deliberately didn't build and why.

Provides measurable post-launch results.

Practical AI fluency Uses AI throughout the product lifecycle rather than simply listing AI exposure.

Strong candidates can explain specific workflows for research synthesis, requirements, prototyping, analysis, testing, launch communications, and monitoring.

Cross-functional leadership Comfortable leading through engineering, design, data, AI/ML, security, operations, sales, support, and executives.

Communicates clearly and concisely.

Metrics Can quantify impact: adoption, processing time, revenue, retention, conversion, efficiency, support volume, accuracy, error rates, etc.

Be cautious with candidates who rely on phrases like “improved the experience” without evidence.

Strong hire vs. caution

Strong hire Customer-facing B2B SaaS PM + genuine ownership + document/workflow experience + AI/document-processing fluency + fast shipping + quantified outcomes.

Potential hire Excellent commercial SaaS PM with strong workflow/document experience but limited direct tax experience or limited AI/ML depth. Tax experience should be treated as a bonus, not a prerequisite.

Caution Primarily technical/platform PM, data-platform PM, internal-tools PM, researcher, or project manager who cannot demonstrate ownership of customer problems, product decisions, launches, and measurable commercial/customer outcomes.

Major red flag Answers consistently use “we” without establishing what the candidate personally decided or delivered, focus heavily on ceremonies/backlogs/stakeholder coordination, or cannot provide concrete metrics and tradeoffs.

Requirements

• 6 or more years of product management experience in software
• Experience building or scaling cloud-based / SaaS products
• Experience in tax, accounting, fintech, or compliance driven products is a plus
• Proven ability to manage complex release cycles under tight deadlines
• Strong analytical and problem solving skills
• Strong ability to balance innovation with operational excellence
• Excellent communication and cross functional leadership skills
• High attention to detail and execution
• Demonstrated ability to prioritize effectively using structured frameworks, balancing customer value, business impact, effort, and regulatory constraints If you are passionate about building innovative, high impact software for professional users and want to shape the future of Drake Software, we would love to hear from you.