Tim McSween
Product Lead · Senior Software Engineer · Platform Modernization
📍 Franklin, NC · Remote-first
I build products where high-stakes compliance meets high-scale performance. Nearly three decades shipping software for 85,000+ professional tax preparers — from greenfield architecture to platform-wide modernization at scale.
Measurable Impact
Led the redesign of the core report engine during platform modernization from Drake Tax Desktop to Taxwell — a ground-up architectural overhaul, not an incremental patch.
Directed a full MFA and authentication overhaul across the platform. Scale-hardened identity infrastructure supporting the full professional tax preparer user base.
Refined e-file submission workflows that form the core revenue engine of the business. Every session directly maps to a client filing — zero margin for error.
Pioneered telemetry implementation across the product stack, shifting prioritization from gut feel to data-validated decisions. Built the instrumentation that made evidence-based roadmapping possible.
Experience
Drive product-critical decisions for Drake Tax Desktop's code modernization into the Taxwell platform — a migration supporting 85,000+ professional tax preparers. Sit at the intersection of product vision and technical execution, owning the code-level trade-offs that determine whether a feature succeeds at scale.
Owned the product roadmap for Drake Tax — one of the dominant professional tax software platforms in the US market. Full ownership of prioritization, feature inclusion and exclusion, and release sequencing for a product with zero tolerance for defects during tax season.
Nearly a quarter century building the foundational architecture of Drake Tax — from early desktop builds through the distributed systems era. Led architectural improvements and workflow design across the full product surface, establishing the engineering standards the platform still runs on today.
Selected Work
E-File Transmission Engine
Zero build failures across 28M+ sessions during the most compressed deadline window in tax software.
Authentication & Login Intelligence
Turned dormant telemetry into actionable product decisions — surfacing MFA gaps, recovery drop-off, and filing-season load patterns across 65K+ preparers.
Print & PDF Subsystem
10+ years owning the last mile of every tax return — then making a decade-old black box observable with cloud telemetry.
Customer-Facing Site Modernization
Migrated two high-traffic customer sites off WordPress and a deprecated IE rendering engine — without breaking a decade of existing installations in the field.
Technical Stack
I sit at the intersection of product strategy and engineering execution — comfortable owning a roadmap in the morning and reviewing an architecture decision in the afternoon. Over 30 years I've built platform infrastructure, led modernization of legacy systems at scale, and most recently integrated agentic AI workflows into daily engineering practice — using Cursor for AI-assisted development and Claude for building and automating production workflows. Fluent across the major AI platforms. I bring a compliance-first, data-validated approach to every product decision, forged across a decade of zero-tolerance tax season deadlines.
Independent Consulting
Available for contract engagements where deep technical judgment and product experience both matter. Best fit for teams navigating platform modernization, architecture decisions, or building product strategy on top of complex legacy systems.
- Platform modernization strategy & execution
- Technical product management and roadmap development
- Architecture review and systems design
- Authentication / identity / compliance systems
- AI-assisted workflow design & agentic tooling implementation
- Engineering team process and tooling
- Startup technical co-founder advisory
Contact
Open to senior product engineering roles, technical product management, and select consulting engagements. Based in Franklin, NC — remote-first with occasional travel.
- Product Lead
- Technical Product Management
- Senior Software Engineering
- Contract / Consulting