Technical Strategist - Websites and Web Applications

Urban Insight•Los Angeles, CA

13d•$130,000 - $147,000•Remote

About The Position

Urban Insight is seeking a Technical Strategist (TS) to join their team. The TS is a client-facing technical leader who collaborates with Project Managers and Development teams to deliver successful digital projects. This role also involves pre-sales efforts, defining technical approaches, shaping scope, and ensuring accurate estimates. The TS brings clarity to complex problems, aligns technical decisions with project goals, and ensures teams have the necessary information for execution. Additionally, the TS contributes to Urban Insight’s Innovation Lab, exploring new technologies and prototyping solutions.

Requirements

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
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
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

Nice To Haves

Work from any location in the United States, available 9am - 6pm in any U.S. time zone.

Responsibilities

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.
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.
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.
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.
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.
Validate work against acceptance criteria and technical expectations.
Participate in QA and alpha testing as needed.
Support successful, on-time, in-scope project delivery.
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.
Partner with CTO, Dev, PM, QA, and SysAdmin teams to improve workflows and tools.
Contribute to a culture of transparency, collaboration, and continuous improvement.