Overview
You design and build the core architecture for Taxwire's sales tax automation platform. This means defining how the system handles tax calculations across different jurisdictions, products, and edge cases - creating the foundational abstractions that the rest of the team uses to ship features. You work directly with the CTO and a small engineering team to make architectural decisions that will define how the product scales.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Senior/Staff Engineer - Architecture |
| Team Structure | Small team (~5-10 engineers), direct to CTO |
| Focus | Core platform architecture, not feature delivery |
| Product Stage | Early - defining foundational systems |
| Tech Complexity | High - multi-jurisdiction tax rules, compliance logic |
| Autonomy | Very high - you define how things work |
Company Context
Stage: Early-stage (16 employees total)
Size: 16 employees
Growth: Actively hiring, building out core team
Market Position: Small player in sales tax compliance space (competing with established players like Avalara, TaxJar, Vertex)
What You'll Actually Do
Time Breakdown
Architecture/Design (40%) | Coding (35%) | Collaboration (25%)
Key Activities
- System Design: Define data models for tax rules, jurisdiction hierarchies, product categorization, and filing workflows. This is abstract work - you're creating the "laws of physics" for how tax logic works in the system.
- Core Platform Code: Build the foundational services and APIs that handle tax calculations, compliance checks, and data aggregation. Not building UI features - building what UI features are built on.
- Technical Decision-Making: Choose databases, service boundaries, API contracts, data pipelines. Small team means your choices have outsized impact and are hard to reverse later.
- Context Management: Stay current on sales tax regulations across jurisdictions, understand edge cases customers hit, translate business requirements into technical architecture.
The Honest Reality
What's Hard
- You're designing systems with incomplete information. Sales tax rules vary wildly by jurisdiction and product type - you have to build abstractions flexible enough to handle edge cases you don't know about yet.
- Small team means you wear multiple hats. You might design an architecture in the morning and debug production issues in the afternoon.
- The problem space is complex and boring. Sales tax compliance isn't sexy - it's detailed regulatory logic, exception handling, and data accuracy. You need to care about getting things precisely right.
- Early-stage constraints. You're building for scale before you have scale. Hard to know which architectural decisions will matter and which are premature optimization.
- Limited resources. No dedicated DevOps team, no SRE support. You build the architecture AND figure out how to deploy/monitor it.
What Success Looks Like
- Your abstractions make it easy for other engineers to add support for new jurisdictions or products without touching core systems
- The platform handles edge cases correctly - no major customer-facing tax calculation errors
- New engineers can understand and extend the system without constantly asking you how things work
- The architecture scales to 10x the current customer volume without major rewrites
Who You're Working With
Internal Stakeholders:
- CTO (Steven Schmatz): Your main partner. He cares deeply about architecture vs execution split mentioned in the post. Expect opinionated technical discussions.
- Product/Design: Small team, probably 1-2 people defining what customers need. You translate their requirements into technical building blocks.
- Other Engineers: Mix of people building customer-facing features on top of your foundation. They're your internal customers.
What They Care About:
- CTO cares about: Clean abstractions, modularity, maintainability, avoiding technical debt
- Product cares about: Velocity - can we ship new features without major platform work?
- Other engineers care about: Clear APIs, good documentation, not having to understand all the tax logic details
Requirements
- 5+ years building complex backend systems, ideally at scale
- Strong systems thinking - can design abstractions that handle messy real-world requirements
- Experience with highly regulated or compliance-heavy domains (fintech, healthcare, tax, legal) is valuable
- Comfortable with ambiguity - willing to make architectural decisions without perfect information
- Can write production code, not just design docs - this is a small team where everyone ships
- Opinionated about architecture but pragmatic about execution - know when "good enough" beats "perfect"