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, a…