Webstacks is a high performance website operations and growth marketing agency established in 2020. We have quickly grown into a 45-person company because of our innovative website operations methodology , strong partnerships, and high-growth clients. We are constantly setting larger goals and stopping at nothing to achieve them. Our team’s dedication is humbling, and we are looking for another motivated individual to help us reach the next level. Our mission is to transform the way the world’s most influential SaaS, FinTech, and Blockchain companies compete in today's digital landscape.

Technical Director

Reports to: Head of Engineering

Role type: People and Craft Leader

Function: Engineering

Overview

Webstacks is looking for a senior technical craft leader to set the standard for how we architect, build, and ship enterprise web experiences.

As Webstacks has grown its portfolio of upper mid-market and enterprise B2B technology clients, the technical complexity and ambition of our work has grown with it. We are increasingly solving challenges that span modern web architecture, headless CMS platforms, complex migrations, performance, accessibility, integrations, and emerging AI-assisted development workflows. The opportunity now is to bring stronger technical leadership and consistency to that work across the portfolio.

The Technical Director will serve as the senior technical voice across Webstacks’ client delivery organization. This person will partner with Account Leadership, Strategy, Design, Engineering, Program Management, and Operations to translate ambitious client goals into technical approaches our teams can execute with confidence, while turning Webstacks’ own ambitions into clear technical standards, practices, and expectations for how we work. They will define what great technical delivery looks like at Webstacks and ensure our architecture, engineering practices, tooling, and ways of working continue evolving to meet that standard.

Across the portfolio, the Technical Director will strengthen our architecture, engineering practices, and approach to modern web development while enabling our engineering teams to do their best work. On select flagship engagements, they may serve as the lead technical authority, staying close enough to the work to ensure strategic and creative intent carries through implementation.

This is a director-level craft leadership role. It does not exist to manage every technical decision or become a bottleneck for delivery. Impact comes through technical judgment, client credibility, engineering enablement, and the ability to establish standards and patterns that make the quality of Webstacks’ technical work stronger and more consistent as we scale.

At its core, the role exists to raise the technical ceiling of Webstacks’ client work, ensuring we can take on increasingly ambitious and complex engagements while continuing to ship modern web experiences that are fast, scalable, maintainable, and exceptionally well built.

Technical Direction & Architecture

Establish and continuously evolve Webstacks’ technical point of view for how modern enterprise websites should be architected, built, migrated, and operated.

Guide architecture decisions across CMS, frontend frameworks, integrations, hosting, infrastructure, data, search, analytics, and other components of the modern web stack.

Ensure technical approaches fit both the client’s requirements and Webstacks’ delivery model, balancing scalability, maintainability, performance, flexibility, speed, and long-term ownership.

Pressure-test proposed technical approaches against feasibility, risk, maintainability, delivery timelines, and the commercial commitments made in proposals and SOWs.

Create clear technical narratives that help clients and internal teams understand architectural decisions, tradeoffs, sequencing, risks, and what successful delivery should look like.

Step into complex delivery moments where senior technical judgment, executive communication, or cross-functional alignment is required.

Flagship Client Delivery

Serve as the senior technical authority on a deliberate portfolio of high-value, technically complex, or high-risk client engagements.

Translate business, strategic, and creative intent into technical approaches, implementation plans, and clear expectations engineering teams can execute with confidence.

Partner closely with Strategy and Design so IA, UX, content architecture, design systems, and creative decisions translate effectively into implementation without unnecessary compromise or rework.

Bring structure to ambiguous technical challenges such as complex migrations, integrations, personalization, multi-property ecosystems, internationalization, and evolving platform requirements.

Identify technical risks and dependencies early enough to influence scope, sequencing, staffing, and delivery approach.

Represent Webstacks confidently with technical and non-technical client stakeholders in conversations around architecture, feasibility, risk, performance, and launch readiness.

Stay close enough to implementation to ensure strategic and creative intent carries through the build without becoming the day-to-day engineer on every engagement.

Engineering Craft, Standards & Reuse

Define what great technical delivery looks like at Webstacks and establish the standards required to achieve it consistently across teams and engagements.

Raise the bar on architecture, clean code structure, modularity, maintainability, performance, accessibility, testing, documentation, code review quality, and technical debt management.

Establish reusable architectural patterns, shared packages, starter frameworks, and engineering practices that improve consistency and accelerate delivery without sacrificing quality.

Champion structured, transformation-minded approaches to content inventories, redirects, migrations, integrations, and other data-intensive areas of website delivery.

Identify repeated client problems and turn them into internal tools, starter kits, generators, shared libraries, and reusable approaches that compound across engagements.

Set and evolve standards for AI-assisted engineering, using AI to increase delivery speed and leverage while keeping engineers accountable for architecture, verification, maintainability, and ship quality.

Identify gaps between Webstacks’ current technical practices and where the organization needs to be, then drive the standards, tooling, and initiatives required to close them.

Delivery Partnership & Estimation

Partner with Program Management, Operations, Strategy, Growth, Account Leadership, and Engineering to ensure technical ambition is matched by strong planning and execution.

Shape technical scope, level of effort, architecture, risks, dependencies, and assumptions during discovery, proposals, SOWs, and change orders.

Help ensure Webstacks sells engagements the organization can successfully deliver while identifying where different technical approaches can create better client or commercial outcomes.

Support clean handoffs from sales into delivery so technical context, assumptions, constraints, and decisions established early carry through the engagement.

Equip engagement leads with the technical narrative and context needed to manage scope, risk, sequencing, and client expectations effectively.

Help teams make informed tradeoffs when technical quality, timeline, scope, staffing, and client priorities come into tension.

Identify recurring sources of technical friction, rework, or delivery inefficiency and partner with Operations and Program Management to improve the systems and practices behind them.

Team Enablement & Technical Leadership

Increase the technical capability of Webstacks’ engineering organization by making strong technical judgment, patterns, and practices more accessible and repeatable.

Mentor senior and mid-level engineers through technical guidance, pairing, architecture reviews, code reviews, and clear standards without becoming a bottleneck for routine engineering decisions.

Develop technical leaders who can independently carry Webstacks’ standards and architectural thinking into their own engagements.

Create and contribute playbooks, architecture decision records, workshop formats, reference implementations, and other reusable artifacts for the Engineering discipline.

Create mechanisms for sharing technical lessons, emerging practices, architectural patterns, and successful approaches across teams.

Partner with Engineering leadership on hiring bars, interview design, leveling expectations, and the technical capabilities Webstacks needs as the organization evolves.

Evaluate emerging frameworks, platforms, developer tooling, and AI capabilities and establish a clear point of view on where Webstacks should adopt, experiment, or standardize.

Surface patterns and lessons from client work back into Webstacks’ methodology, tooling, service development, and broader technical strategy.

Raise the Technical Bar

The role should establish a clear standard for what great technical delivery looks like at Webstacks and continuously raise that standard as our clients, capabilities, and ambitions evolve.

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, internal tooling, and other technical foundations that make those standards easier for teams to consistently achieve.

Create clear technical practices and checkpoints across the engagement lifecycle, from discovery and estimation through architecture, implementation, QA, and launch.

Identify recurring architectural risks, technical debt, engineering challenges, and opportunities for reuse across the portfolio.

Create mechanisms for sharing technical decisions, lessons, emerging practices, and improvements across engineering teams.

Continuously evaluate where AI, automation, tooling, and new development practices can increase engineering leverage and improve the quality and speed of delivery.

Partner with Engineering, Program Management, Operations, Strategy, Design, Growth, and Account Leadership to ensure Webstacks’ technical standards are reflected in how we scope, plan, build, and deliver our work.

Success Looks Like

Within the first year, Webstacks has a stronger and more consistent technical standard across the organization. Teams have clearer patterns for how we architect and build, technical risks are identified earlier, complex engagements have stronger senior technical leadership, and improvements made on one project increasingly create leverage across the rest of the portfolio.

Technical Quality

Establish clear, adopted standards for architecture, code quality, performance, accessibility, testing, documentation, and maintainability that raise the consistency of what Webstacks ships.

Architecture & Risk

Improve the quality of technical decisions made early in engagements, with major risks, dependencies, constraints, and tradeoffs identified before they create avoidable rework or delivery challenges.

Engineering Leverage

Increase reuse across engagements through shared architecture, packages, tooling, automation, AI-assisted workflows, starter frameworks, and proven implementation patterns.

Delivery Confidence

Strengthen Webstacks’ ability to scope, estimate, plan, and deliver technically complex work by bringing the right technical judgment into the right moments.

Engineering Capability

Develop stronger technical judgment across the Engineering organization so more engineers can independently make high-quality architecture and implementation decisions.

Technical Evolution

Continuously advance how Webstacks builds by identifying, validating, and operationalizing new technologies, tooling, AI capabilities, and engineering practices that meaningfully improve our work.

Who Thrives Here

This role is a strong fit for someone who combines deep technical expertise with strong judgment, client credibility, systems thinking, and a genuine desire to make the entire engineering organization better.

Deeply experienced in modern web architecture and capable of forming a strong point of view while remaining pragmatic about client constraints and business realities.

Equally comfortable discussing architecture with a CTO, working through an implementation problem with an engineer, pressure-testing an estimate with Program Management, or collaborating with Strategy and Design on how an idea should come to life.

Strong at turning ambiguous business, strategic, and creative requirements into technical approaches teams can confidently execute.

Opinionated about engineering craft, including architecture, code structure, maintainability, performance, accessibility, testing, documentation, and developer experience.

Commercially aware and able to understand how technical decisions affect scope, timeline, staffing, risk, margin, and client expectations.

Able to see patterns across engagements and turn repeated problems into standards, reusable architecture, tooling, and better ways of working.

Excited about AI-assisted engineering, automation, and emerging technologies, with the judgment to separate meaningful advances from noise.

An effective mentor who raises the technical judgment of others rather than becoming the person every important decision depends on.

Comfortable getting close to the code when necessary, but understands that their greatest impact comes from creating leverage across teams and engagements.

Collaborative across Engineering, Strategy, Design, Program Management, Operations, Growth, and Account Leadership, with the ability to influence without needing direct authority.

Proactive and entrepreneurial, with the ability to recognize where Webstacks needs to improve technically and drive that improvement forward.

The goal of this role is simple: set the technical bar for Webstacks and continuously raise our ability to meet it as our clients, our work, and our ambitions become more sophisticated.

SD Pay Range

$120,000 — $140,000 USD

All this sound good? Sweet, we can't wait to chat!