Technical Director

Webstacks•San Diego, CA

2d•Remote

About The Position

Webstacks is seeking a senior technical craft leader to establish and maintain high standards for architecting, building, and shipping enterprise web experiences. As the company's client base has expanded to include upper mid-market and enterprise B2B technology clients, the technical demands have increased, involving modern web architecture, headless CMS platforms, complex migrations, performance, accessibility, integrations, and AI-assisted development. This role will provide strong technical leadership and consistency across these areas. The Technical Director will act as the senior technical advisor within Webstacks’ client delivery organization, collaborating with various departments to translate client goals into executable technical strategies and define clear technical standards, practices, and expectations. The objective is to elevate the technical quality of Webstacks’ client work, enabling the company to undertake more ambitious and complex projects while consistently delivering modern, fast, scalable, maintainable, and well-built web experiences. This is a director-level craft leadership position focused on impact through technical judgment, client credibility, engineering enablement, and establishing scalable standards, rather than direct management of all technical decisions.

Requirements

Deep experience in modern web architecture.
Ability to form a strong technical point of view while remaining pragmatic about client constraints and business realities.
Comfortable discussing architecture with CTOs.
Ability to work through implementation problems with engineers.
Skill in pressure-testing estimates with Program Management.
Ability to collaborate with Strategy and Design on idea realization.
Strong ability to turn ambiguous business, strategic, and creative requirements into executable technical approaches.
Opinionated about engineering craft, including architecture, code structure, maintainability, performance, accessibility, testing, documentation, and developer experience.
Commercial awareness and understanding of how technical decisions affect scope, timeline, staffing, risk, margin, and client expectations.
Ability to identify patterns across engagements and translate repeated problems into standards, reusable architecture, tooling, and improved ways of working.
Excitement about AI-assisted engineering, automation, and emerging technologies, with the judgment to discern meaningful advances.
Effective mentor capable of raising the technical judgment of others.
Comfortable getting close to the code when necessary, understanding that greatest impact comes from creating leverage across teams and engagements.
Collaborative across Engineering, Strategy, Design, Program Management, Operations, Growth, and Account Leadership.
Ability to influence without direct authority.
Proactive and entrepreneurial mindset.
Ability to recognize where Webstacks needs technical improvement and drive that improvement forward.

Nice To Haves

Experience in modern web architecture.
Experience in forming a strong point of view while remaining pragmatic about client constraints and business realities.
Experience discussing architecture with CTOs.
Experience working through implementation problems with engineers.
Experience pressure-testing estimates with Program Management.
Experience collaborating with Strategy and Design on idea realization.
Experience turning ambiguous business, strategic, and creative requirements into executable technical approaches.
Experience with engineering craft, including architecture, code structure, maintainability, performance, accessibility, testing, documentation, and developer experience.
Commercial awareness and understanding of how technical decisions affect scope, timeline, staffing, risk, margin, and client expectations.
Experience identifying patterns across engagements and translating repeated problems into standards, reusable architecture, tooling, and improved ways of working.
Experience with AI-assisted engineering, automation, and emerging technologies, with the judgment to discern meaningful advances.
Experience mentoring to raise the technical judgment of others.
Experience getting close to the code when necessary, understanding that greatest impact comes from creating leverage across teams and engagements.
Experience collaborating across Engineering, Strategy, Design, Program Management, Operations, Growth, and Account Leadership.
Experience influencing without direct authority.
Proactive and entrepreneurial mindset.
Experience recognizing where Webstacks needs technical improvement and driving that improvement forward.

Responsibilities

Establish and continuously evolve Webstacks’ technical point of view for modern enterprise website architecture, development, migration, and operation.
Guide architecture decisions across CMS, frontend frameworks, integrations, hosting, infrastructure, data, search, analytics, and other modern web stack components.
Ensure technical approaches align with client requirements and Webstacks’ delivery model, balancing scalability, maintainability, performance, flexibility, speed, and long-term ownership.
Evaluate proposed technical approaches for feasibility, risk, maintainability, delivery timelines, and commercial commitments.
Create clear technical narratives to communicate architectural decisions, tradeoffs, risks, and success criteria to clients and internal teams.
Provide senior technical judgment, executive communication, and cross-functional alignment for complex delivery challenges.
Serve as the senior technical authority on select high-value, technically complex, or high-risk client engagements.
Translate business, strategic, and creative intent into technical approaches, implementation plans, and clear expectations for engineering teams.
Partner with Strategy and Design to ensure IA, UX, content architecture, design systems, and creative decisions translate effectively into implementation.
Structure technical solutions for ambiguous challenges like complex migrations, integrations, personalization, multi-property ecosystems, and internationalization.
Identify technical risks and dependencies early to influence scope, sequencing, staffing, and delivery approach.
Represent Webstacks confidently with client stakeholders on architecture, feasibility, risk, performance, and launch readiness.
Ensure strategic and creative intent is maintained through implementation without becoming the day-to-day engineer.
Define and establish standards for great technical delivery at Webstacks, covering architecture, code quality, modularity, maintainability, performance, accessibility, testing, documentation, code review, and technical debt management.
Establish reusable architectural patterns, shared packages, starter frameworks, and engineering practices to improve consistency and accelerate delivery.
Champion structured approaches for content inventories, redirects, migrations, integrations, and other data-intensive areas.
Identify recurring client problems and develop internal tools, starter kits, generators, shared libraries, and reusable approaches.
Set and evolve standards for AI-assisted engineering, ensuring accountability for architecture, verification, maintainability, and quality.
Identify and drive initiatives to close gaps between current technical practices and future needs.
Partner with Program Management, Operations, Strategy, Growth, Account Leadership, and Engineering to align technical ambition with planning and execution.
Shape technical scope, level of effort, architecture, risks, dependencies, and assumptions during discovery, proposals, SOWs, and change orders.
Ensure Webstacks sells engagements that can be successfully delivered and identify opportunities for better client or commercial outcomes through technical approaches.
Support clean handoffs from sales to delivery, ensuring technical context carries through engagements.
Equip engagement leads with technical narrative and context for managing scope, risk, sequencing, and client expectations.
Facilitate informed tradeoffs when technical quality, timeline, scope, staffing, and client priorities are in tension.
Identify and address recurring sources of technical friction, rework, or delivery inefficiency.
Increase the technical capability of Webstacks’ engineering organization through accessible and repeatable technical judgment, patterns, and practices.
Mentor senior and mid-level engineers through technical guidance, pairing, architecture reviews, code reviews, and clear standards.
Develop technical leaders capable of independently carrying Webstacks’ standards and architectural thinking.
Create and contribute playbooks, architecture decision records, workshop formats, and reference implementations.
Establish mechanisms for sharing technical lessons, emerging practices, architectural patterns, and successful approaches.
Partner with Engineering leadership on hiring, interview design, leveling expectations, and required technical capabilities.
Evaluate emerging frameworks, platforms, developer tooling, and AI capabilities, establishing a point of view on adoption and standardization.
Surface patterns and lessons from client work back into Webstacks’ methodology, tooling, service development, and technical strategy.
Establish and evolve technical standards across architecture, code quality, performance, accessibility, testing, documentation, security, and maintainability.
Build reference architectures, starter frameworks, shared packages, reusable patterns, and internal tooling.
Create clear technical practices and checkpoints across the engagement lifecycle.
Identify recurring architectural risks, technical debt, engineering challenges, and opportunities for reuse.
Create mechanisms for sharing technical decisions, lessons, emerging practices, and improvements.
Continuously evaluate AI, automation, tooling, and new development practices for increased engineering leverage and improved quality/speed.
Partner with relevant departments to ensure technical standards are reflected in scoping, planning, building, and delivery.