Technical Strategist - Websites and Web Applications

Who We Are

Urban Insight is a leading digital agency creating innovative websites and web applications for organizations that make a difference. We specialize in solving complex problems through website and web app strategy, design, and development using open-source content management systems (primarily Drupal and WordPress, and headless or composable architectures). Our clients include some of the most well-known museums, nonprofits, universities, and cultural institutions. Urban Insight has been in business for nearly 25 years and continues to expand each year. We thrive on having a professionally rewarding environment where team members are encouraged to grow, collaborate and focus on meaningful work.

The Opportunity

The Technical Strategist (TS) is a client-facing technical leader who partners closely with Project Managers and Development teams to deliver well-scoped, well-communicated, and successful digital projects. The TS also plays a key role in pre-sales and proposal efforts, helping define technical approaches, shape scope, and ensure estimates are grounded in delivery reality.

This role operates through collaboration and shared ownership. The TS brings clarity to complex problems, aligns technical decisions with project goals and constraints, and ensures that teams have the information they need to execute effectively. The Technical Strategist is also a contributor to Urban Insight’s Innovation Lab, helping explore new technologies, prototype solutions, and shape future service offerings.

Key Responsibilities

Client Strategy & Technical Leadership

• Partner with clients to understand goals, constraints, and opportunities
• Translate client needs into clear, actionable technical approaches
• Align technical solutions with timeline, budget, and delivery realities
• Identify risks early and contribute to mitigation strategies

Collaboration with Project Managers

• Maintain alignment with Project Managers on scope, priorities, and project direction
• Contribute to defining scope, assumptions, and delivery approach
• Participate in project ceremonies including kickoffs, planning, and retrospectives
• Support consistent communication and visibility across the project lifecycle

Technical Planning & Documentation

• Produce clear technical plans, Jira tickets, and specifications
• Ensure plans, decisions, and updates are documented in shared systems (Jira, Notion, etc.)
• Collaborate with Tech Leads and engineers to validate feasibility and refine approaches
• Evolve documentation as projects progress and new information emerges

Engineering Enablement

• Provide developers with clear context, requirements, and direction
• Help remove blockers and reduce ambiguity during implementation
• Align with Tech Leads on technical direction and implementation strategy
• Guide teams toward pragmatic, efficient solutions

Pre-Sales & Proposal Support

• Partner with Sales and the pursuit team to scope projects and define technical approaches
• Develop realistic level-of-effort estimates grounded in delivery experience
• Collaborate with Development and Delivery leadership to ensure proposed solutions are realistic and aligned with team capacity
• Clearly articulate assumptions, risks, and constraints
• Support proposal development and client conversations

Quality & Delivery

• Validate work against acceptance criteria and technical expectations
• Participate in QA and alpha testing as needed
• Support successful, on-time, in-scope project delivery

Innovation Lab

• Contribute to discovery engagements, prototypes, and pilot initiatives
• Explore emerging technologies (AI, APIs, composable architectures)
• Help translate innovation into practical, repeatable solutions
• Share learnings through internal demos, documentation, or working sessions

Process & Continuous Improvement

• Partner with CTO, Dev, PM, QA, and SysAdmin teams to improve workflows and tools
• Contribute to a culture of transparency, collaboration, and continuous improvement

Qualifications

Technical Skills

• 7–8+ years of experience in technical strategy, web development, or technical project leadership, preferably in an agency environment
• Strong understanding of modern web architectures specifically Drupal, WordPress, and headless / composable
• Experience working with agile methodologies such as Scrum or Kanban
• Familiarity with CMS-driven websites, APIs, and system integrations

Collaboration & Communication

• Strong ability to work in close partnership with Project Managers and cross-functional teams
• Excellent written and verbal communication skills
• Ability to translate complex technical concepts into clear, accessible language
• Experience leading discovery, requirements gathering, and technical planning sessions

Organizational & Self-Management

• Ability to break down complex ideas into actionable work
• Strong prioritization and time management skills
• Comfortable managing multiple projects and responsibilities simultaneously
• Proactive, detail-oriented, and accountable

Success Metrics

In the First 90 Days

• Establish strong working relationships with PMs and Development teams
• Contribute to at least one project with clear, actionable technical planning
• Maintain ~70% billable utilization
• Demonstrate clear and consistent documentation practices

In the First Year

• Deliver on quarterly Rocks (≥80%) tied to strategic and technical priorities
• Successfully support multiple projects from planning through delivery
• Improve clarity and alignment across project teams through strong documentation and communication
• Contribute to accurate scoping and reduced rework in pre-sales
• Drive shared clarity across PM, Design, and Development on scope, priorities, and decisions
• Contribute to Innovation Lab efforts through prototypes, pilots, or new approaches
• Support ongoing improvements to process, tools, and team effectiveness

Location & Availability

• Work from any location in the United States, available 9am - 6pm in any U.S. time zone.
• Our office is located in sunny Los Angeles, CA. This position is available for fully remote (U.S. and Canada ONLY), partially remote (a few days in the office), or in-person in our L.A. Office.

About Urban Insight

• Urban Insight is a Los Angeles-based digital agency with over 30 team members. Visit our website.
• We work with some of the best-known museums, nonprofits and other institutions, such as LACMA, The Broad, University of Southern California, City of Los Angeles, and the Japanese American National Museum.
• We’re the top-ranked Web development and Drupal agency in Los Angeles, according to Clutch, an independent analyst. Read what our clients say about us.
• We’ve won numerous design awards including for our work for Stay Housed Los Angeles and the National World War 1 Museum & Memorial.
• We take on cutting edge, challenging projects for appreciative clients, and have a supportive and team-based approach to projects.
• We plan, design, and create innovative websites, and we often use open source web content management systems like Drupal and WordPress.
• We design and develop custom applications using tools like Angular, React, Next.js, node.js, PHP, Javascript, Bootstrap, Tailwind, and MySQL.
• We have a clearly-defined project management methodology and case management system.
• We run on the Entrepreneurial Operating System (EOS).

Why Work at Urban Insight

• We take on interesting, meaningful projects for appreciative clients
• We offer a flexible working environment - work from anywhere in the United States
• We work with you to create a career path that works for you
• The average employee tenure is 6.5 years
• We're stable and growing. We've been in business for ~25 years and continue to grow each year
• We offer a casual and flexible working environment with plenty of opportunities for growth for the right candidate
• We believe in a reasonable life/work balance and enjoy 40-hour work weeks
• We allocate resources and time for training and professional development
• We have weekly events to keep the team connected: Lunch & Learns, Lightning Demos, Game Breaks
• There are many more reasons: Explore careers at Urban Insight

Total Rewards

We offer a competitive salary based on experience.

Total annual compensation range: $130,000 – $147,000

• Medical, Dental and Vision insurance (95% employer-paid)
• Paid time off (15 days, increasing to 20 after four years)
• Holidays (~10 days per year)
• 401(k) with employer match
• Annual training plan and dedicated learning time
• Annual performance and compensation reviews

How to Apply

Please apply through this page. This position is open until filled.