Director, Strategic Initiatives

Valet Living•Shaft, MD

12d•$145,000 - $155,000•Remote

About The Position

Build Strategy. Drive Impact. Grow Your Career. Are you a strategic leader who thrives on driving cross-functional initiatives and shaping enterprise priorities? Do you excel at orchestrating complex programs, influencing stakeholders, and delivering measurable results? If so, Valet Living wants you on our high-performance team. Valet Living is hiring a Director of Strategic Initiatives who will report to the VP of Product Management. In this highly visible role, you’ll own and execute the company’s most critical priorities, partnering with leaders across Product, Sales, Operations, Marketing, Finance, HR, IT, Client Experience, and Legal. You’ll lead select initiatives from inception to completion, serve as program manager and strategic advisor, and ensure progress across multiple workstreams. If you’re a strategic thinker with executive presence, comfort with ambiguity, and a passion for driving organizational change, this is your opportunity to shine!

Requirements

Strategic & Analytical Mindset: Demonstrated ability to evaluate opportunities and assess trade-offs.
Cross-Functional Leadership: Proven ability to design, manage, and deliver cross-functional initiatives.
Executive Communication: Exceptional communication and presentation skills, with experience preparing executive- and board-level deliverables.
Financial Acumen: Comfort with modeling business cases and ROI analysis.
Influence & Alignment: Ability to build consensus and alignment across a wide range of stakeholders.
Executive Presence: Confidence and discretion in engaging with senior executives on sensitive or high-stakes topics.
Change Leadership: Demonstrated ability to lead organizational change, drive adoption of new practices, and sustain momentum.

Nice To Haves

Industry Familiarity: Experience with B2B services, logistics, or tech-enabled operations is strongly preferred.

Responsibilities

Lead Strategic Initiatives: Own and execute high-priority projects from concept through successful completion.
Drive Cross-Functional Alignment: Orchestrate collaboration among stakeholders, remove roadblocks, and ensure sustained executive sponsorship.
Design Scalable Processes: Build and maintain processes, tools, and reporting structures to track initiative performance and manage interdependencies.
Develop Business Cases: Lead opportunity assessments and business case development, framing trade-offs and surfacing decision points for senior leaders.
Create Executive-Ready Deliverables: Build dashboards, initiative summaries, and board-ready materials that translate complex initiatives into clear strategic narratives.
Champion Organizational Change: Drive adoption of new processes, behaviors, and practices introduced through strategic initiatives, ensuring lasting impact beyond launch.
Capture Lessons Learned: Document and share insights from initiatives to refine business practices, improve execution discipline, and strengthen organizational alignment.
Coach and Mentor Leaders: Support initiative owners and functional leaders in building business cases, applying program management discipline, and strengthening execution capabilities.

Benefits

Health Benefits: Medical, dental, and vision coverage for you & your family, plus HSA with employer contributions and Flexible Spending Accounts
Flexible Time Off: No preset accruals—manage your time and work-life balance your way, plus 10 company-paid holidays
Financial Security: 401k with company match, life and disability insurance, AD&D, and business travel coverage
Professional Development: Tuition reimbursement up to $5,250 per year and access to our online education center
Additional Perks: Referral bonuses, pet insurance, associate assistance programs, discount programs, rewards, recognition, and free access to Torch Fitness virtual programs

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