Taxwell helps everyday Americans get every tax advantage they deserve by finding credits and deductions they never even knew existed. Our tax preparation software offers easy guidance and ensures your maximum tax refund. We strive to build a team of like-minded experts in both tax and technology who align with our brand purpose, are advocates for our customers and have a fresh, non-traditional approach to the tax industry.

Drake Software is a leading digital tax filing platform which offers customers professional digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. We are a trusted solution for all users including those with complex tax returns. We strive to attract and retain candidates who exemplify our values: performance, perseverance, progress and partnership. Drake Software is a member of the Taxwell family of products. We are an organization of forward thinkers looking to add industry experts to our growing team.

This role will primarily support Drake Software as we provide the tools and support tax professionals need to build their businesses and attract new clients. We are an organization of problem solvers continually looking for solutions to support our customers. Our customers know they can rely on Drake Software for comprehensive product excellence and value.

Senior Product Manager, Drake Desktop Software

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, accounting, and practice management solutions used by thousands of tax and accounting firms.

This role owns the product roadmap, annual tax season delivery, and long-term evolution of the professional tax, accounting, and practice management 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 and accounting 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 Development

• Identify 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 AI, automation, and modern cloud capabilities

What We Are Looking For

• 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.

At Taxwell, we believe our work benefits from the diverse perspectives of our employees. As such, Taxwell welcomes and celebrates diversity and inclusion and is committed to equal opportunity employment. At Taxwell, you can expect a supportive, open, and inclusive atmosphere and a team that values your contributions.

Taxwell is committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants without regard to race, color, religion, sex, national origin, age, disability, marital status, sexual orientation, gender identity, veteran status, and any other status protected under applicable law. Taxwell considers information gathered in the hiring process, including information on this application, confidential, and only shares it on a need-to-know basis or as required by law.

If you need assistance or accommodation due to a disability, you may contact us at HR@Taxwell.com  or by calling 828-349-5887 to speak with a member of the HR Talent Acquisition team.