Director of DevOps

About Instead

Instead is a tax platform designed to help taxpayers and tax professionals collaborate to save money on taxes and file tax returns. As the first company in decades to receive IRS approvals to E-file 1040, 1041, 1120, 1120S, and 1065 — we're re-inventing a complex category. Founded in 2023, Instead combines LLMs with tax law to make tax management a continuous, proactive process rather than a dreaded annual deadline.

Instead's investors include Sarah Guo from Conviction (conviction.com) and many of our customers who believe in our mission and vision. The Instead team comprises talented leaders from leading tax, financial services and fintech companies — Gusto, Intuit, Zenefits, Thomson Reuters, Wolters Kluwer, Bloomberg — as well as top tax & accounting firms such as PwC, BDO, RSM, and KPMG.

Instead was a 2024 Innovation Award Finalist in CPA Practice Advisor. Instead's CEO, Andrew Argue, is a CPA and has been named Top 100 Most Influential People in the Accounting Profession twice - Ones To Watch and CPA Practice Advisors 20 under 40.

What You'll Do

• Own and manage our AWS infrastructure across environments (staging, production, internal tools) for a high-availability tax platform
• Design, implement, and maintain secure, scalable cloud architectures aligned with SOC 2 and other compliance requirements
• Build and maintain infrastructure-as-code (primarily Terraform) for repeatable, auditable deployments
• Implement and improve CI/CD pipelines to streamline build, test, and release processes for our engineering teams
• Monitor, troubleshoot, and resolve production issues across our services, networking, and data layers
• Drive observability and reliability through logging, metrics, alerting, and incident response practices
• Collaborate with engineering to design systems that are secure, cost-effective, and easy to operate in production
• Take ownership of core infrastructure components (VPCs, IAM, networking, storage, containers, etc.) and continuously improve them

What You'll Need

• 3+ years of hands-on experience managing production infrastructure in AWS
• Strong experience with Terraform and infrastructure-as-code workflows
• Solid understanding of AWS core services (EC2, RDS, ECS/EKS or similar, S3, IAM, networking, security groups, load balancers)
• Experience operating and hardening Linux-based systems in production
• Familiarity with containerization (Docker) and deploying containerized workloads
• Experience working within security/compliance frameworks (SOC 2, ISO 27001, or similar)
• Proven track record of owning systems end-to-end rather than isolated tasks
• Ability to diagnose and resolve complex infrastructure and performance issues
• Strong communication skills and comfort collaborating closely with engineers and leadership

Nice to Have

• AWS certifications (e.g., Solutions Architect, DevOps Engineer, SysOps Administrator)
• Experience with Kubernetes in production environments
• Experience in at least one programming language (ideally Python) for tooling, automation, and integrations
• Background supporting SaaS or fintech products with high security and uptime requirements
• Experience setting up and tuning observability stacks (e.g., Prometheus, Grafana, Datadog, CloudWatch)
• Experience with secrets management, key management, and identity management at scale

Benefits

• Own core infrastructure at a product-critical layer instead of being a ticket taker on a giant platform team
• Work on a modern stack at the intersection of tax, fintech, and AI, where reliability and security really matter
• Help shape DevOps/Platform practices, tooling, and standards from an early stage, with real influence on architecture decisions
• Partner directly with experienced engineers, tax experts, and leadership
• Join a well-funded company with strong industry investors and partners, building the first new IRS-approved e-file platform for major return types in decades
• Grow your career in a role that blends cloud engineering, security, and reliability while shipping visible, meaningful work

Equal Opportunity Employer - M/F/D/V

We trust our team with sensitive information, so all candidates who receive and accept employment offers must complete a background check before joining us. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.