Head of Product and Technology

About Tax Guardian

Tax Guardian is building a next‑generation tax‑technology (“TaxTech”) product, focused on regulated tax compliance workflows (including IRS APIs), secure data processing, and scalable cloud‑native services. We’re at the 0→1 stage and looking for a leader who combines hands‑on build experience and strategic leadership to define and deliver our technology platform.

Role Summary:

We are seeking a dynamic, technically deep and business‑savvy leader to serve as our first technology executive. The ideal candidate will define our technology vision and architecture, build and lead the engineering team, collaborate tightly with product and design teams, ensure compliance and security at a high level, and evolve the engineering organization from early execution into a scalable technology organization.

If this sounds like you, please take a few minutes without distractions to complete this work traits survey. Please copy and paste the following link into your browser: https://go.cultureindex.com/p/2HAaEo9ggXXNJuZB.

Key Responsibilities:

• Define and communicate the technology roadmap aligned with product strategy, business goals and regulatory requirements.
• Architect the core platform from 0→1: select tech stack, design system architecture (cloud infrastructure, APIs, data layer, microservices or serverless, caching, etc.).
• Be hands‑on in early phases: writing or reviewing code, making architecture decisions, establishing engineering standards, mentoring engineers.
• Build, hire, and lead the engineering organization: frontend, backend, DevOps, QA, security/compliance. Define team structure, culture, processes (Agile/Scrum/Kanban), key metrics.
• Collaborate closely with product management, UX/UI/design to align technical implementation with product vision, market needs and user experience.
• Establish DevOps/CI‑CD pipelines, infrastructure automation, monitoring, performance tuning, incident response, and manage technical debt.
• Own the compliance and security posture of the product: ensure controls for data privacy, integrity, availability; lead readiness for audits (such as SOC 2) and regulatory interfaces (e.g., IRS data flows, tax‑regulation environment).
• Make build vs buy decisions, manage third‑party/vendor relationships (cloud services, APIs, external contractors).
• Represent technology to stakeholders: investors, board, partners; assist in technical due diligence, scalability planning and risk management.
• As the organization grows, transition into strategic leadership: setting architecture and engineering standards, guiding senior engineers, overseeing scalability, cost‑efficiency, reliability, and performance.

Required Qualifications & Skills:

• 10 years technology/engineering experience; ideally 5 years in a leadership role (e.g., engineering manager, head of engineering) in an early‑stage startup (0→1 or seed stage).
• Proven track record of building a product from scratch (0→1) and architecting or scaling it for growth.
• Deep technical expertise across full stack: frontend technologies, backend services, cloud infrastructure (preferably Azure or similar), microservices/API design, data systems, caching (e.g., Redis).
• Hands‑on coding ability and strong architecture/system design skills: able to define trade‑offs, choose tech stack, ensure scalable, maintainable systems.
• Experience in regulated environments (fintech, tax, compliance, security) strongly preferred.
• Strong leadership and people skills: building and scaling engineering teams, mentoring, establishing culture and operational excellence.
• Excellent communication skills: translating technical concepts for business stakeholders, aligning technology with business strategy.
• Entrepreneurial mindset: comfortable with ambiguity, rapid change, resource constraints, early stage culture.

Preferred Qualifications and Skills:

• Prior experience in TaxTech or working with tax workflows, IRS APIs, tax‑compliance systems or similarly regulated data environments.
• Experience with React (frontend), Azure/.NET stack, Redis or comparable caching technologies.
• Experience managing cloud infrastructure cost, performance tuning, security/compliance certification frameworks (SOC 2, ISO 27001, etc.).
• Experience with vendor management, external contractors or scaling engineering offshore/onshore.

Technology Profile and Environment:

We are developing a TaxTech product built on a cloud‑native stack (Azure preferred) with microservices architecture, caching layer (e.g., Redis), API‑first design, front‑end using React, back‑end services in .NET / C#. You will be responsible for designing and delivering the platform that supports heavy data flows, security and compliance demands, high availability, monitoring, and scalability.

Compliance is a core part of the technology mission: implementing controls to support SOC 2 readiness and ensuring alignment with other regulatory and tax‑industry standards. This includes IRS data handling, privacy, access control, and secure management of personally identifiable information (PII) and tax data.

What You’ll Get:

• A leadership seat in a company at an early stage of building a high‑impact TaxTech product.

• Direct influence over architecture, technology strategy, team building and product roadmap.

• A hybrid role: initially hands‑on execution, evolving into strategic leadership.

• Collaborative environment: you’ll report to the COO and partner closely with Product, UX/UI, Design, and Engineering teams.

How to Apply:

Please submit your resume and a cover letter describing:

• Your 0→1 startup experience (product you built, your role, technology outcomes)

• A major architecture or technical decision you made (why, what trade‑offs, result)

• Your experience or interest in TaxTech, regulated data environments, compliance (SOC 2 and similar)

• Your willingness to relocate (or already based in Dallas/OKC region)

Summary:

This is a unique opportunity for a hybrid technologist‑leader to join a TaxTech startup and shape its foundational architecture, team and technology culture. If you have the blend of hands‑on builder and strategic leader, thrive in early stage startups, and are excited about building a next‑gen regulated tax product, we’d love to hear from you.