Head of Technology - US

About the Company

We’re CatchCo, makers of Mystery Tackle Box — the original fishing subscription box since 2012. Our mission is to Rescue Humanity From the Indoors. Today, we help millions get outside with products sold at Walmart, Dick’s Sporting Goods, Amazon, and direct-to-consumer. We’ve moved past the venture-backed hype and are now under new ownership, building a lean, profitable, and lasting business. If you believe in getting people outdoors and doing work that matters, you’ll fit right in.

Position Overview

We are seeking an experienced Head of Technology to lead our systems and technology execution for our fully remote organization. This role is ideal for a tech leader who can bridge high-level strategy with hands-on work, driving both day-to-day development and big-picture architecture. We don’t expect anyone to be experienced with all of the systems in our tech stack. Instead, this role is a fit for someone who is never intimidated by new tools or technologies.

Our company’s platform is in the midst of exciting changes – phasing out legacy systems, implementing a new ERP, and leveraging AI (LLMs) as force-multipliers for our team's productivity. If you are passionate about the technology powering commerce, and pushing into the AI era, we'd love to hear from you. 

As the Head of Technology, you will be the technical anchor and strategic driver for the company. This means balancing leadership with hands-on contribution. On any given day you might review pull requests, troubleshoot a critical bug, or write a small feature alongside the team. At the same time, you'll set the architectural vision, plan large-scale system improvements, and make key decisions to align technology with business goals. You will coordinate among colleagues, developers and vendor teams to execute projects, ensuring everyone is working towards cohesive goals. This role involves significant cross-functional collaboration – working with management, marketing, operations, and other departments – to deliver technology initiatives smoothly in a remote environment.

Our Tech Stack & Environment

• Platform: Proprietary Order Management System built on .NET 6 (C#) application using ASP.NET Core, with patterns like MediatR and data access via Entity Framework Core and Dapper.
• Cloud Infrastructure: Microsoft Azure – heavy use of Azure Functions, Azure Service Bus, Blob Storage, and Azure SQL Database for scalable, serverless processing.
• Messaging: RabbitMQ and Azure Service Bus powering our event-driven architecture and inter-service communication.
• Integrations: Shopify (with Recharge for subscriptions), QuickBooks (finance),  Extensiv WMS for warehouse management, and SPS Commerce (EDI) – ensuring smooth data flow across e-commerce, accounting, and fulfillment.
• Data & Analytics: Snowflake as our data warehouse, fed by Fivetran/Stitch pipelines; transformations managed in dbt; reporting and analytics via Looker.
• Marketing Tech: Klaviyo for customer engagement and marketing automation. Google GTM, Elevar, and other tools of consumer web and ad tech.
• AI & Automation: We aggressively embrace AI tools (especially modern large language models) to automate workflows and enhance developer productivity.

Key Initiatives

• Legacy Modernization: Lead the effort to retire or refactor legacy systems and transition to a more streamlined, modern architecture that improves reliability and scalability.
• ERP Implementation: Oversee the successful integration of a new ERP system into our tech ecosystem, aligning it with existing platforms and ensuring minimal disruption to operations.
• AI Integration: Champion the use of AI/LLM-based solutions to improve personal and team productivity, from automating routine tasks to enabling smarter decision-making in our applications and workflows.
• Scalability & Performance: Continuously evaluate and enhance system performance, ensuring our platform and infrastructure can scale with a growing user base and data volume.

Core responsibilities

• Technical Leadership: Own the overall technology strategy and system architecture. Define and enforce best practices in software design, code quality, and DevOps, ensuring our .NET/Azure-based platform remains robust and maintainable.
• Hands-On Development: Contribute to development tasks when needed – from coding and code reviews to debugging and performance tuning. Stay involved in the technical work to lead by example and to support the team on complex issues.
• Project Management: Lead the planning and delivery of major technical projects, such as the ERP implementation and other high-impact initiatives. Break down big projects into achievable milestones and drive them to completion on schedule.
• Team Coordination: Manage and coordinate a distributed team of developers, including external freelancers and vendors. Mentor engineers, remove blockers, and foster a culture of accountability and continuous improvement.
• System Integrations: Oversee the design and maintenance of integrations between our platform and external systems (e.g. Shopify, QuickBooks, WMS), ensuring data flows reliably and securely across all parts of the business.
• Cloud Operations: Ensure our Azure cloud infrastructure is well-architected and cost-efficient. Oversee deployments, monitor system health, and guide the team in leveraging Azure services (Functions, Service Bus, etc.) optimally.
• Innovation & AI Enablement: Stay curious and forward-looking in evaluating new technologies. Experiment with and implement tools (especially AI/LLM-driven solutions) that can improve our workflow or product capabilities. Encourage the team to adopt automation and AI where it can make us faster or more effective.
• Cross-Functional Collaboration: Work closely with other departments (e.g. Product, Finance, Operations, Marketing) to align technology deliverables with business needs. Translate technical plans and progress into clear updates for non-technical stakeholders.

What makes you the right fit

We are not expecting a candidate to know it all. We are looking for the candidate that is excited to come in, make sense of it all, and use all available resources to take our tech stack to the next generation, simplifying wherever possible. Attitude trumps experience with any of these specific technologies.

• AI Enthusiasm: Highly curious and quick to learn new tools. Excited about the potential of AI and LLMs, and fearless in experimenting with them to improve processes and productivity.
• Problem-Solving Mindset: Strong analytical and problem-solving abilities. Capable of diving into the details to debug issues, as well as stepping back to plan strategically.
• .NET Experience: Proven expertise in C# and the .NET ecosystem (we use .NET 6 and ASP.NET Core). You have designed and built complex applications in .NET and stay up-to-date with the latest frameworks and best practices.
• Azure Cloud Mastery: Hands-on experience deploying and running applications on Microsoft Azure. Proficient with serverless components like Azure Functions, event/messaging services like Service Bus, and managing Azure SQL databases and storage.
• Systems Integration Skills: Strong background in integrating systems and designing APIs. Experience connecting cloud services, third-party platforms, and internal applications in a secure, scalable way.
• Architecture & Design: Ability to architect scalable, maintainable software systems. Familiarity with patterns like CQRS/mediator (MediatR) and ORM/SQL tools (Entity Framework Core, Dapper) for efficient data access.
• Data & Analytics Orientation: Understanding of modern data pipelines and analytics platforms. Exposure to tools such as Snowflake, Fivetran/Stitch, dbt, or Looker is a plus.
• Leadership & Execution: Demonstrated success in a technical leadership role (e.g. Tech Lead, Engineering Manager, Head of Technology) managing software teams and delivering complex projects. You are execution-oriented and can drive multiple initiatives to completion.
• Remote Collaboration: Excellent communication and collaboration skills. Comfortable leading and coordinating work across a remote, cross-functional team. Able to keep stakeholders informed and projects on track in a distributed environment.
• Education: Practical experience is most highly valued. BS/MS in Computer Science or a related field is preferred.