Work With Us

Join a team that challenges and cheers for one another.

Calypso is made up of writers, communicators, and creatives

who support each other, challenge each other, and make each other laugh.

Our individual creativity grows exponentially when we get together—whether it’s in a formal brainstorming or as we pull up the latest “you gotta see this” YouTube video at the lunch table.

We’re inspired by our work and energized by our clients’ challenges. We offer generous benefits, from group health insurance to a retirement plan with matching company contributions. We respect work/life balance, and our downtown Portsmouth, NH, location offers no shortage of charm—from parks with seasonal outdoor yoga classes, to unique restaurants, to several coffee shops that give us our caffeine kicks.

Yes, there are perks (company Red Sox outings and early-release “summer Fridays” are two of our favorites), but that’s not a reason to work here. Consider whether, as a talented communicator, you want to make a meaningful contribution to your work and your company—not as a cog in a giant corporate machine, but as, well, you. Sound like your cup of tea (or coffee)? We want to hear from you!


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Director of Brand Strategy and Creative Services

Calypso is looking for a director of brand strategy and creative services to join our team. This individual will head up the design team and lead the innovation and optimization of all creative platforms. The right candidate will be an entrepreneur with experience in client services, management, digital strategy, and high growth business leadership.

The ideal candidate will have a strong work ethic and ability to pay close attention to detail. Exceptional writing, communication, and presentation skills are essential. The ability to think strategically, adapt quickly and orchestrate many moving parts is a must.

Job Summary: In addition to meeting annual individual performance objectives, the director of brand strategy and creative services is expected to lead all internal and external visual communications initiatives, demonstrate excellence in graphic design, possess comprehensive knowledge of design principles in a wide variety of media and production methods, have advanced analytic thinking and creative problem-solving skills for visual information design, produce high-quality graphics in a fast-paced work environment, and able to quickly learn and integrate new tools and technologies to meet stated goals.

Essential Functions:

  • Strong writing skills with attention to audience, tone, and nuance
  • Ability to quickly understand complex information
  • Ability to write clear and concise content of varying length and style for a wide variety of audiences (internal, external, stakeholder, consumer) and applications (web, blog, etc)
  • Outstanding project management skills; organized

Responsibilities Include:

  • Serve as creative department lead; assume accountability for all aspects of the design department
  • Recruit and manage creative resources; assume responsibility for and develop effective interpersonal relationships with clients, vendors, and staff
  • Ensure strategic objectives are met; provide counsel to clients on strategic design initiatives
  • Grow and develop existing business, generate new business opportunities, and develop new business proposals
  • Demonstrate in-depth knowledge of practice area with multiple functions
  • Participate in day-to-day contact with senior account service directors

Job Qualifications:

  • College education and 5+ years of related work experience
  • High-level creative, strategic, and global thinking skills; initiate new ideas–offer improvements to processes
  • Advanced prepress skills, and understanding of printing technologies and conventional and digital print processes
  • Strong knowledge of Mac applications of InDesign, Photoshop, Illustrator, Quark XPress, Acrobat, Microsoft Office (Word and PowerPoint)
  • Demonstrate in-depth understanding of small business climate
  • Understand experiences and incorporate them into successful business strategies
  • Knowledge of inbound marketing and experience with the HubSpot COS a plus


Interested? Send us your cover letter, resume, and portfolio.
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Director of Strategic Communications

Calypso is looking for a dynamic communications professional to join our growing team, develop and evaluate top-line strategy, assume a leadership role on assorted accounts, and continually aid in improving the firm’s overall business development.

We’re looking for an experienced professional who can build and manage project teams, knows how to tell a client’s story through a combination of tactics, and is equipped with strong account management skills. Special consideration will be given to applicants with crisis communications or issues management experience.


  • Lead and manage day-to-day client relationships
  • Manage media relationships and conduct media outreach
  • Create and execute strategic communication campaigns, strategies, and tactics
  • Write and edit a variety of content materials (proposals, strategic campaigns, core messaging, press releases, pitches, bylined articles, etc.)
  • Participate in business development initiatives and actively seek new opportunities for Calypso
  • Build and manage project teams


  • 5+ years of public relations experience, preferably on the agency side
  • Strong track record of strategic campaign development, media placement, and community relations
  • Ability to establish, communicate, and meet deadlines and associated budgets
  • Outstanding written and verbal communication skills
  • Ability to work in a fast-moving, dynamic, and team-oriented environment
  • Fast learner with an inquisitive mind and eye for detail
  • Ability to work with multiple clients simultaneously
  • Demonstrate a solid understanding of a small business climate

Interested? Send us your resume and cover letter.

Apply Now

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