Vice President, Creative Director (Chicago)

VP, Creative Director

The VP, Creative Director is a senior creative force at Highwire — a strategic thinker and hands‑on leader who drives creative excellence across multiple client accounts while elevating the work of the teams around them. This role sits at the intersection of creative vision, client partnership, and team development, owning the creative direction for high‑profile campaigns while helping shape how the agency's creative practice evolves.

The VP, Creative Director brings a sophisticated design sensibility and sharp strategic instinct, translating client challenges into compelling, insight‑driven creative solutions. They lead with confidence in client settings, command the trust of their teams, and set a high bar for innovation and quality in everything they touch. They are equally concepting bold ideas in a whiteboard session, presenting to senior client stakeholders, and rolling up their sleeves to ensure flawless delivery. We expect this to be a hands‑on role.

Key Responsibilities

Creative Strategy & Direction

• Define and drive creative strategies that align with client objectives and Highwire's broader agency goals.
• Lead the development of innovative, insight‑led campaigns across multiple accounts simultaneously.
• Partner with Digital Leads, strategy, and communications teams to ensure creative is fully integrated into holistic campaign thinking.
• Set and uphold high creative standards across all client work, championing quality and originality at every stage of the process.
• Stay ahead of emerging creative trends, tools, and platforms, bringing fresh thinking and cultural relevance to every brief.

Campaign Development & Execution

• Oversee concept development and creative execution across integrated campaigns spanning digital, social, paid, earned, and owned channels.
• Ensure all creative outputs — from visual assets to copy — are strategically aligned, on‑brand, and delivered to the highest standard.
• Drive creative workflows and quality assurance processes that allow the team to deliver consistently and efficiently at scale.
• Contribute to the scoping and sequencing of creative projects, providing clear input to project management and operations teams.

Client Engagement

• Act as the primary creative point of contact for key clients, building trusted partnerships and delivering creative counsel that inspires confidence.
• Lead client‑facing presentations with clarity, authority, and a compelling creative narrative.
• Collaborate with account and strategy teams to identify opportunities for creative innovation within existing client relationships, contributing to organic growth.
• Contribute to new business pitches, developing creative concepts and presenting ideas that differentiate Highwire in competitive processes.

Team Leadership & Mentorship

• Mentor and develop Art Directors and Lead Designers, providing ongoing coaching, feedback, and creative direction that supports their growth.
• Foster a collaborative, inclusive team culture where bold ideas are encouraged and creative risk‑taking is celebrated.
• Partner with agency leadership to identify creative talent needs and support hiring efforts that strengthen the team.
• Develop and implement creative frameworks and best practices that can be applied across the agency.

Thought Leadership & Agency Growth

• Represent the agency at industry events, panels, and forums, showcasing Highwire's creative perspective and capabilities.
• Develop frameworks for creative strategy that elevate agency‑wide standards and can be applied across client verticals.
• Partner with senior leaders to identify growth opportunities for Highwire's creative services.

Success Factors

• 10+ years of creative experience, with a proven track record in a creative leadership role within an agency or in‑house environment.
• A compelling portfolio that demonstrates strategic, cross‑channel creative thinking with measurable impact.
• Strong conceptual skills and the ability to develop bold, original ideas rooted in client insight and strategy.
• Proficiency across the Adobe Creative Cloud suite and a strong understanding of design principles across digital, social, and web channels.
• Experience leading and presenting creative concepts to senior client stakeholders.
• Proven ability to mentor and develop creative talent in a fast‑paced, collaborative environment.
• Excellent communication and presentation skills, with the ability to articulate creative vision to both creative and non‑creative audiences.
• Experience contributing to new business pitches, from concept through to presentation.
• Demonstrable commitment to DIBs principles, ensuring creative work is inclusive, representative, and resonant across diverse audiences.
• Impeccable attention to detail, with a zero‑tolerance approach to errors in final deliverables.

Salary Range & Benefits

Salary range: $130,000 to $175,000, with the final offer based on a combination of factors, including education, relevant experience, skills, prior training, internal equity, and local geographic market data.

• Competitive medical, dental, and vision coverage.
• 401(k) matching.
• Generous paid time off.
• Additional perks designed to support overall well‑being and growth.
• Flexibility and a hybrid work model tailored to schedule and lifestyle.
• Generous vacation policy, including extended summer and winter breaks.
• Early log‑off on Fridays through the Empower Hours program.
• Advanced health and wellness programs.
• Paid parental leave benefits.
• Commuter benefits.
• Annual Growth Mindset stipend for books, events, or learning experiences.
• Monthly technology reimbursement.
• Wellness benefit program for mental and physical health.
• 501(c)(3) donation matching program.
• Mentorship and ongoing professional development opportunities.
• Monthly recognition and team celebrations.
• Employee referral and new business referral bonuses.
• Quarterly Highwire events and team gatherings.
• Dog‑friendly office environment.
• Supportive, inclusive, and collaborative workplace where you can grow and do your best work.

Location & Work Environment

Highwire offers both remote and hybrid work options, depending on where you live.

Hybrid: Candidates located within commuting distance of our New York, NY or San Francisco, CA offices follow a hybrid schedule, with three in‑office days per week.

Remote: We hire for fully remote roles in the following states: California, Colorado, Connecticut, Florida, Georgia, Illinois, Iowa, Kansas, Maryland, Massachusetts, Michigan, New Hampshire, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, and Washington, D.C. Candidates must reside in one of the listed locations at the time of hire.