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.

Total Rewards
We offer a competitive salary based on experience.

Total annual compensation range: $120,000 – $145,000

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

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