Principal Strategist

OVERVIEW

The Principal Strategist owns the work itself: the quality of every strategy we ship, the health of every account's backlog, and the growth of every strategist on the team. Where the Head of Strategy owns the practice, the Principal owns delivery; the standard the work is held to and the people who produce it.

This is a player-coach role. The Principal Strategist carries a deliberate set of our most complex, highest-stakes accounts while managing the strategy team day-to-day.

The Principal Strategist is the reason the Head of Strategy can operate at market altitude. When the work ships client-ready without executive review, when escalations get resolved inside the team, when strategists level up quarter over quarter, that's this role working.

ROLE DETAILS

• Reports to: Head of Strategy
• Manages: Sr. Web Strategists & Web Strategists
• Salary range: $110,000–$130,000
• Work Location: San Diego, CA / Hybrid Remote
• Team: Strategy

RESPONSIBILITIES

• Client Strategy
  • Lead a small set of flagship engagements: the most complex accounts, the highest-stakes relationships, the executive stakeholders who expect our best strategist in the room
  • Model the strategy-to-tactics translation the whole team runs on; every recommendation becomes a roadmap, every roadmap traces to a client business goal
  • Navigate the hard client dynamics: ambiguity, shifting priorities, competing stakeholders and coach the team to do it themselvesKnow your clients' businesses deeply: their model, their market, their internal pressures
• Craft & Quality
• • Own the quality bar for everything the team ships: roadmaps, strategic narratives, and client deliverables
  • Review and pressure-test strategist work before it reaches clients and run those reviews as teaching moments
  • Pilot new frameworks, tools, and strategic models on your own accounts; codify what works into the Webstacks methodology with the Head of Strategy
  • Keep the team's thinking structured and prioritized (i.e., Own how the team thinks by establishing methods of delivery.)

Team Leadership

• Manage the strategy team day-to-day: weekly 1:1s, workload balancing, unblocking, and providing honest feedback that makes people better
• Coach strategists on the craft that can't be documented (client presence, consultative practice to C-suite, strategic storytelling, reading a room, holding ground under pressure)
• Develop Webstacks’ bench of exceptional strategists
• Own performance conversations at the team level; partner with the Head of Strategy on career paths and growth plans

Delivery Operations

• Audit every account's strategic backlog monthly, flag anything stale, or drifting from client goals
• Be the first escalation point for client tension, scope conflicts, and cross-functional misalignment; resolve at the team level what shouldn't reach the executive level
• Keep strategy, PM, design, and dev pulling toward the same outcome on every account
• Read the team's capacity honestly and flag the crunch to the Head of Strategy before it becomes a delivery problem

WHO THRIVES HERE

• 7+ years in digital strategy with agency experience; has led complex web engagements end to end, not just contributed to them
• Trusted by director and VP-level stakeholders 
• A natural coach: gets genuine energy from making other strategists better, not just from their own wins
• Brings structure to ambiguity; the person the room looks at when nobody knows what happens next
• Holds a high bar and delivers the feedback that comes with it; directly, generously, often

WHAT SUCCESS LOOKS LIKE 

• Strategist work ships client-ready, without executive review or rescue.
• No account backlog goes stale for more than 30 days.
• Strategists demonstrably level up — receiving positive client feedback, deliverable quality hit Webstacks’ standards, and show readiness for bigger accounts.
• Flagship accounts renew and expand under the Principal's leadership.
• The Head of Strategy operates at market altitude because delivery doesn't need them.