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Director of Digital Strategy

Director of Digital Strategy

Grand Circle CorporationBoston, MA, United States
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Summary

The Director of Digital Strategy will serve as the strategic lead for all paid media marketing efforts — driving measurable growth through SEM, YouTube, Display, and other digital channels. This leader will own the paid media strategy and test-and-learn agenda, manage execution in partnership with our external media agency, and work cross-functionally with Brand Marketing, Creative, and Finance to ensure digital campaigns deliver against business goals.

This role is central to our digital transformation, ensuring that paid media is not only a growth engine for new customer acquisition, but also a key driver of efficiency, scalability, and innovation.

Key Responsibilities

  • Paid Media Strategy & Campaign Leadership : Own the strategy for paid media channels including SEM, YouTube, Display, and emerging platforms
  • Translate acquisition goals into paid media strategies that deliver measurable passenger and revenue growth
  • Partner with external media agency to ensure flawless campaign execution, optimization, and ROI delivery

Testing & Learning

  • Develop and own the digital test-and-learn agenda across paid channels
  • Drive structured experimentation (creative, targeting, platforms, formats) with the goal of delivering incremental pax and conversion improvements
  • Share learnings broadly with Brand and Creative to inform omni-channel campaigns
  • Performance & Reporting

  • Lead channel-level reporting for SEM, YouTube, and Display, with a focus on CAC, ROI, and passenger delivery
  • Monitor and optimize spend allocation across paid channels to maximize impact
  • Deliver timely insights to inform broader acquisition and renewal strategies
  • Cross-Functional Leadership

  • Collaborate with Brand Marketing, Creative, and Finance to ensure paid media campaigns are aligned to brand narrative, budget pacing, and financial objectives
  • Act as the primary connector between internal teams and external media partners
  • Deputy Leadership

  • Establish frameworks for campaign planning, reporting, and governance
  • Serve as a senior leader within the digital team, providing strategic continuity and cross-functional influence
  • Ideal Candidate Profile

  • 8–10+ years of experience in digital marketing, with a deep focus on paid media strategy
  • Hands-on expertise with Google platforms : SEM, YouTube, and Display
  • Proven success scaling acquisition through paid media while optimizing CAC and ROI
  • Experience managing external agencies and holding partners accountable to performance
  • Strong analytical orientation; comfortable interpreting channel data and funnel metrics
  • Skilled cross-functional communicator and collaborator
  • Grand Circle Corporation is an equal opportunity employer.

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