Head of Creative

Open Position
Richmond, VA | Hybrid 

About Us

Dotted Line is an award-winning, strategically inspired creative agency focused on brand, creative, and content. Our clients are ambitious, and they trust us to help drive growth through clarity, craft, and execution. We are a team that values collaboration, continuous improvement, and pride in the work. From national brands to regional leaders, we build ideas 

that connect, perform, and endure. Learn more at www.dottedline.agency.

About You

  • You are a builder. You’re energized by shaping ideas — not just reviewing them. You are in the work: concepting, writing, refining, and elevating alongside your team.
  • You think in platforms, not just executions. You look beyond the brief to uncover the real business challenge and build ideas that can scale across channels.
  • You understand that creativity is a growth lever. You connect brand thinking to measurable business outcomes.
  • You are both maker and leader — comfortable rolling up your sleeves while also setting vision and direction.
  • You bring clarity, calm, and conviction into the room. You can sell bold ideas with confidence, push back when necessary, and do it without ego.
  • You believe the best work is integrated and collaborative. You respect strategy, media, and data as creative multipliers.
  • You are excited by the opportunity to raise the conceptual bar — not maintain it.

Specifically, you:

  • Have 15+ years of agency or integrated creative leadership experience.
  • Bring a portfolio that demonstrates strong conceptual thinking — not just executional polish.
  • Have built and sold integrated campaigns and brand platforms that drove measurable results.
  • Have a track record of mentoring and developing creative talent.
  • Are comfortable presenting to CEOs, founders, and executive teams.
  • Balance creative ambition with clarity, scope discipline, and execution.
  • Thrive in a fast-moving, growth-oriented environment.

About the Job

As Dotted Line’s Head of Creative, you are responsible for the agency’s creative standard — in the work and in the team. This is a hands-on leadership role. You will actively shape ideas while building the systems, culture, and discipline that allow creative excellence to scale.

You will help us move from strong execution to stronger platforms — building ideas that stretch across brand, content, media, and performance.

What You’ll Do

Elevate the Creative Standard

  • Set and uphold the creative bar across all client and agency work.
  • Strengthen conceptual rigor and platform thinking.
  • Ensure ideas are strategically grounded and built to solve real business problems.
  • Push the work beyond what is expected — and create a culture where strong ideas win.

Be in the Work

  • Concept, write, and refine ideas alongside the team. Model the standard you expect.
  • Lead briefs, brainstorms, and reviews.
  • Provide clear, actionable feedback that improves both the output and the individual.

Build the Team

  • Build a bench that can sustain and scale creative excellence.
  • Mentor and develop creatives at all levels.
  • Identify capability gaps and shape hiring priorities.
  • Create clarity in how we brief, review, and elevate work.

Integrate Across Disciplines

  • Champion integrated thinking as a competitive advantage.
  • Partner closely with Strategy, Media, Account, and Project Management.
  • Integrate media and AI thinking early in the creative process.
  • Ensure creative aligns with performance goals and measurable outcomes.

Drive Agency Growth

  • Help us win more ambitious work because of the strength of your ideas. 
  • Help sell bold ideas with confidence and business clarity.
  • Strengthen DLA’s reputation as a nationally competitive creative agency.

Desired Experience

  • Proven ability to both create and lead high-quality creative work.
  • Strong strategic instinct and ability to connect creative to growth and business outcomes.
  • Demonstrated success mentoring and developing creative teams.
  • Excellent communication, collaboration, and presentation skills.
  • Ability to balance creative excellence with clarity, efficiency, and execution.
  • Bachelor’s degree or equivalent experience.

What Success Looks Like

In 12 months:

  • The conceptual strength of our work is visibly stronger.
  • Creative reviews are sharper and more productive.
  • The team feels challenged, supported, and elevated.
  • We win more ambitious work because of the strength of our ideas.
  • Clients trust creative leadership at the table.
  • Our work fuels agency growth.

Why This Role Matters

This role will:

  • Elevate the quality and distinctiveness of our work.
  • Strengthen and future-proof our creative bench.
  • Enable scalable, repeatable creative excellence.
  • Support our ambition to become a nationally recognized top small agency.
  • Ensure creativity remains a growth driver — not just a deliverable.

Dotted Line Benefits

  • Hybrid work environment
  • Monthly culture-building activities
  • Performance-based, profit-sharing opportunities
  • Health, Dental, and Vision benefits
  • Simple IRA Retirement Plan
  • Unlimited paid time off with 4 weeks minimum
  • 14 paid company holidays including the week between Christmas and New Year’s
  • 2 company-organized paid volunteer days

Company Values We Live Every Day

  • Treat team members, clients, and partners like you want to be treated
  • Always be improving, learning, and growing
  • Collaborate and be a team player
  • Go the extra mile
  • Do work we are proud of
  • Focus on client results

Why Should You Apply?

  • A true opportunity to shape the creative direction of a scaling, ambitious agency.
  • The ability to build platforms — not just campaigns — for growth-minded brands.
  • Direct partnership with agency leadership across strategy, media, and growth.
  • Real influence on team development, hiring, and creative culture.
  • The chance to elevate work at a pivotal moment — and help define what DLA becomes over the next three years.
  • A seat at the table in building a nationally competitive, concept-driven agency.

If interested, please send your resume to lauren@dottedline.agency.