The Role
CourtAvenue is a company of industry experts accelerating digital transformation for the world’s most ambitious companies.
At CourtAvenue, you will be a part of a culture powered by entrepreneurs, technologists, data scientists and the habitually restless dedicated and energized to design products and services that transform businesses while optimizing them for growth. You will have the opportunity to learn and grow within a culture that values innovation while focusing on redesigning the experience between consumer and service (or product) by leveraging a fluid, seamless, and thoroughly transparent engagement.
At CourtAvenue, a Director of Digital Strategy is a versatile, senior-level strategist who can lead high-impact work across industries and business challenges. This role is ideal for someone who brings a strong strategic foundation but thrives in dynamic environments — seamlessly shifting between digital roadmaps, org design, audits, planning, and new, evolving opportunities.
As the team continues to grow, we are looking for a Director, Digital Strategy who is energized by solving complex problems and thrives in dynamic environments. They bring structure to ambiguity and confidently guide clients through uncharted territory with clarity and insight. This individual is equally comfortable building frameworks and timelines as they are developing strategic narratives and recommendations that resonate with executive stakeholders. They know how to set a strategic vision and are skilled at aligning cross-functional teams to bring it to life.
Responsibilities
- Lead 2–3 client engagements across a variety of industries, acting as the senior strategy owner
- Drive strategic deliverables including digital roadmaps, org design, current-state audits, and long-term planning
- Frame and synthesize insights into clear, actionable recommendations tailored to client needs
- Collaborate closely with creative, data, and experience teams to ensure integrated strategic thinking
- Serve as a trusted advisor to client stakeholders, confidently presenting to senior and executive audiences
- Mentor and support junior team members, offering guidance, feedback, and development opportunities
- Contribute to internal growth by supporting thought leadership, resourcing conversations, and pitch development
- Stay on the pulse of trends, helping clients and internal teams anticipate what’s next
Requirements
- 10+ years of experience in strategy, consulting, or digital transformation
- Experience leading strategic engagements and delivering results across industries
- A strong portfolio showcasing digital roadmaps, strategic frameworks, and executive-level presentations
- Ability to distill complexity into compelling, focused narratives
- Comfort navigating ambiguity — bringing structure and momentum to open-ended challenges
- Excellent storytelling, communication, and client management skills
- Experience mentoring or managing junior strategists
- A curious, collaborative mindset with a passion for learning and adaptability
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The Company
What We Do
CourtAvenue is an Operating Network of digital transformation companies that utilizes data, machine learning and emerging technologies to build powerful relationships between brands and consumers.
