About Us
Webstacks is a high performance website operations and growth marketing agency established in 2020. We have quickly grown into a 45-person company because of our innovative website operations methodology , strong partnerships, and high-growth clients. We are constantly setting larger goals and stopping at nothing to achieve them. Our team’s dedication is humbling, and we are looking for another motivated individual to help us reach the next level. Our mission is to transform the way the world’s most influential SaaS, FinTech, and Blockchain companies compete in today's digital landscape.
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…