Director of Digital Strategy

Reports to: VP, Digital Analytics

Location: Boston, MA - Hybrid

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.