Principal Strategist

Webstacks•San Diego, CA

1d•Hybrid

About The Position

The Principal Strategist owns the quality of strategy delivery, the health of account backlogs, and the development of the strategy team. This player-coach leads a deliberate set of complex, high-stakes client accounts while managing the strategy team day to day. The role ensures strategy work is client-ready, escalations are resolved within the team, and strategists continue to grow. The Principal Strategist leads flagship engagements, translates strategy into tactics and roadmaps tied to client business goals, and navigates complex client dynamics. They set and maintain quality standards for team deliverables, review work as a coaching opportunity, and pilot and codify effective frameworks and methods in partnership with the Head of Strategy. The role manages team operations and development, including regular one-on-ones, workload balancing, feedback, coaching, performance conversations, and career growth. It also monitors strategic backlogs and team capacity, serves as the first escalation point for client and delivery issues, and coordinates strategy, project management, design, and development toward shared account outcomes. The position is based in San Diego, CA, with a hybrid remote work arrangement, and reports to the Head of Strategy.

Requirements

At least 7 years of experience in digital strategy, including agency experience.
Experience leading complex web engagements end to end.
Trusted by director- and VP-level stakeholders.
Demonstrated ability and genuine interest in coaching other strategists.
Ability to bring structure to ambiguity.
Ability to maintain high standards and deliver direct, generous, and frequent feedback.

Responsibilities

Lead a small set of flagship engagements, including complex accounts and high-stakes client relationships.
Model the translation of strategy into tactics and roadmaps tied to client business goals.
Navigate difficult client dynamics and coach the team to manage them independently.
Develop a deep understanding of clients’ businesses, markets, and internal pressures.
Own the quality bar for team roadmaps, strategic narratives, and client deliverables.
Review and pressure-test strategist work before it reaches clients, using reviews as teaching opportunities.
Pilot new frameworks, tools, and strategic models, and codify successful approaches into Webstacks’ methodology with the Head of Strategy.
Establish methods of delivery that keep the team’s thinking structured and prioritized.
Manage the strategy team day to day through weekly one-on-ones, workload balancing, unblocking, and direct feedback.
Coach strategists in client presence, consultative practice with C-suite stakeholders, strategic storytelling, reading a room, and holding ground under pressure.
Develop Webstacks’ bench of exceptional strategists.
Own team-level performance conversations and partner with the Head of Strategy on career paths and growth plans.
Audit every account’s strategic backlog monthly and flag work that is stale or drifting from client goals.
Serve as the first escalation point for client tension, scope conflicts, and cross-functional misalignment, resolving issues at the team level where possible.
Keep strategy, project management, design, and development aligned on account outcomes.
Assess team capacity and flag potential crunches to the Head of Strategy before they become delivery problems.