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.
Taxwell is a leading digital tax filing platform formed in 2022 from the combination of Drake Software® and TaxAct®. These two longstanding organizations offer customers professional and do-it-yourself digital and downloadable products that are easy-to-use, best-in-class technology, and provide unparalleled customer support. Taxwell brands 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. Taxwell is an organization of forward thinkers looking to add industry experts to our growing team.
Position Summary
TaxWell is hiring a Software Engineering Manager for the Data Import team. This team builds the systems that help TaxAct, Drake Software, and Taxwell users import tax documents and related financial data into the tax-preparation experience — document upload, OCR and extraction workflows, document classification, import state tracking, partner and financial-institution integrations, and the operational diagnostics that keep production import pipelines healthy.
This is a player-coach leadership role on a cloud-backed, event-driven platform. You will lead and develop a team of software engineers (employees and contractors) building business-critical services in modern C#/.NET on AWS, own the team's delivery outcomes, and be technical enough to earn credibility in architecture, code review, and production debugging.
What You'll Do
- Lead, coach, and grow a team of software engineers: hiring, onboarding, performance, professional development, and career growth.
- Own the team's delivery: planning, prioritization, work assignments, resource planning, commitments to Product, and follow-through to production.
- Own onboarding speed and engineer productivity as explicit outcomes. You build the scaffolding that makes fast ramp normal — not the exception: scoped first tasks sized for early merges, review and pairing support, progressive exposure to production debugging, and the judgment to notice and act when a new engineer isn't ramping.
- Provide technical direction across services and systems: guide design and architecture for document-processing pipelines (ingestion, OCR, classification, extraction, state, delivery), balancing product velocity against security, compliance, and reliability requirements.
- Run and continuously improve the team's engineering practices: CI/CD and release management on a frequent release cadence, automated testing (unit, integration, end-to-end), observability, production incident response, and blameless post-incident learning.
- Support adoption of AI-assisted and agentic engineering tools across the team, with clear standards for reviewing AI-generated output for correctness, security, and maintainability. The engineer remains accountable for all output.
- Coordinate with platform and security teams when centrally-driven infrastructure, hardening, or compliance work lands on the team's services, so it strengthens the product rather than crowding it out.
- Troubleshoot complex, cross-service production issues alongside your engineers: application code, queues, object storage, state records, configuration, logs, and external dependencies.
- Communicate clearly and honestly with Product and business stakeholders: tradeoffs, risks, estimates, delivery status, and operational health.
What You'll Need
- Bachelor's degree in Computer Science, Software Engineering, Information Technology, or a related field — or equivalent practical experience.
- Approximately 8+ years of professional software development experience, with a minimum of 2 years leading or managing software engineers who shipped production software.
- Strong hands-on background in C#/.NET and backend product engineering: APIs, event-driven and asynchronous processing, and cloud-service integration.
- Working knowledge of cloud-native architectures, preferably AWS serverless (Lambda, SQS, S3, DynamoDB or close equivalents); Azure experience is a reasonable substitute if fundamentals are strong.
- Experience owning or jointly owning production support for business-critical services: triage, impact assessment, rollback thinking, and escalation judgment.
- Demonstrated ability to hire, onboard, and ramp engineers quickly, with concrete examples of engineers who became productive under your leadership.
- Strong leadership, communication, coaching, and problem-solving skills, with the judgment to know when to fix, escalate, delegate, or hold the line.
Preferred Qualifications
- Experience managing teams that built document processing, OCR, classification, extraction, data-ingestion, or other event-driven data pipeline systems.
- Experience in tax, financial services, accounting, payments, or other regulated domains handling sensitive customer data.
- Experience managing mixed employee/contractor and distributed or nearshore teams, with clear productivity accountability for each.
- Experience with Kubernetes-based deployment, observability tooling (Splunk, Datadog, or CloudWatch), and structured logging/metrics practices.
- Hands-on experience governing AI-assisted engineering tools (e.g., Claude Code, Copilot, Cursor) on an engineering team — raising the bar, not just permitting the tools.
About the Team's Culture This team values pragmatic product engineering: production safety, careful discovery before changing unfamiliar flows, clear diagnostics and documentation, blameless production learning, useful collaboration with support/product/QA/platform partners, and thoughtful use of AI and automation
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.
