Downtown Pittsfield Job Opportunities

Downtown Pittsfield, Inc. (DPI) is currently hiring for the 2021 Downtown Pittsfield Ambassador Program!


Employment type: Part-time, Seasonal, Non-exempt

Compensation: $15.00/hour

Hours: May be full or part-time; up to 30 hours a week.

Number of positions: Subject to available funds.

Estimated start date: Thursday, July 1, 2021

Estimated end date: Monday, September 6, 2021

Location: Throughout Downtown Pittsfield, MA 01201 (the 2-mile Downtown Loop)


TO APPLY: Send resume and cover letter by email to, attention Cheryl Mirer, Executive Director, Downtown Pittsfield, Inc., by May 28. Applications will be reviewed on a rolling basis. Positions open until filled. Program begins July 1.


A great program starts with great people. We are looking for candidates who are willing to learn, can think on their feet, and who can provide a high level of customer service with a smile and a great attitude! If you take pride in your community and want to work to make it better, then this is the job for you. If you are bright, cheerful, friendly, compassionate, and have a desire to make a difference, you may have what it takes to be a part of the Downtown Ambassador team.




The Downtown Pittsfield Ambassador Program is a partnership between Downtown Pittsfield, Inc. (DPI) and the City of Pittsfield Police Department. This year, the program will focus on downtown’s response to COVID-19 by providing masks to people that do not have them and helping guide foot traffic to places to eat and shop.


The job is twofold:

Concierge: The ambassadors are walking concierges; a welcoming, information sharing resource. They help people find parking, offer directions and wayfinding, and provide information on dining, shopping, and cultural activities.

Safety: Ambassadors are trained by the Pittsfield Police Department in CPR, public safety protocol, and are certified in First Aid. Ambassadors observe street activity, and when needed, call for assistance via police radios, which they are equipped with.


Downtown Ambassadors walk in pairs along North and South Streets between West Housatonic Street and Berkshire Medical Center, as well as First and McKay Streets. The Ambassadors wear a distinctive uniform identifying them as official representatives of Pittsfield and greet everyone with a smile. The goal of the program is to create a welcoming downtown environment for everyone downtown by delivering on DPI’s mission to maintain a clean, safe, and friendly district.


Duties and Responsibilities:

  • Always wear a mask and remain at least six feet from others
  • Serve the Downtown Pittsfield community by creating a positive experience for all
  • Actively acknowledge pedestrians with a friendly greeting and identify visitors to provide directions, information, city information, or recommendations
  • Interact effectively, tactfully, and compassionately with the public and use skill to interact with diverse groups of people
  • Answer questions regarding directions, events, building locations, and parking
  • Work effectively with the other Downtown Ambassadors, police department, DPI and members of the public, and respond to inquiries and complaints in a positive and professional manner
  • Cover assigned areas to address quality of life issues, and provide a high level of customer service
  • Keep sidewalks clear of debris
  • Must be punctual and reliable
  • Able to prioritize and respond to situations and emergencies in a positive and professional manner
  • Utilize and refer various Downtown Pittsfield resources
  • Represent Downtown Pittsfield, Inc. at special events
  • Interact with downtown businesses
  • Provide reports of broken infrastructure and graffiti on private property, and provide a log and report of accomplishments and tasks completed
  • Maintain a positive, professional environment in full compliance with applicable laws, regulations, policies, procedures, and overall standards of expected professionalism


Required Qualifications:

  • Positive demeanor and strong communication skills
  • Ability to work and interact with the public in a friendly and professional manner
  • Ability to handle stressful situations, demonstrating diplomacy and tact under pressure
  • Able to stand, walk, or otherwise travel for up to eight hours a shift in various weather conditions
  • Self-motivated, with the ability to work under minimal supervision, as well as work as part of a team
  • Must be able to lift up to 40 pounds on occasion
  • Experience using a smartphone
  • Capability of helping people operate multi-space parking meters
  • Demonstrated customer service or hospitality experience
  • Must be available to work weekends
  • Able to work through September 7, 2021
  • Must be 18 years of age or older


Preferred Qualifications:

  • Knowledge of Downtown Pittsfield and its business and cultural community
  • Knowledge of available social services and other resources available to residents and visitors


*Please note: candidates must pass a background check



Non-benefited position.


TO APPLY: Send resume and cover letter by email to, attention Cheryl Mirer, Executive Director, Downtown Pittsfield, Inc., by May 28.  Applications will be reviewed on a rolling basis. Positions open until filled. Program begins July 1.


The 2021 Downtown Pittsfield Ambassador Program is sponsored by the City of Pittsfield, Guardian Life Insurance Company of America, and Lee Bank.


For more information on the program, visit

About Downtown Pittsfield, Inc.
The mission of Downtown Pittsfield, Inc. (DPI) is to foster the ongoing growth and vitality of downtown Pittsfield, Massachusetts through vision, leadership, and advocacy and to position downtown as the creative and business hub of the Berkshires for the benefit of all.

Since 1983, DPI has been the recognized leader, facilitator, and principal advocate for downtown. DPI has developed strategies and programs, mobilizing resources resulting in a creative, lively, and sustainable environment.

DPI is a nonprofit membership organization consisting of retail businesses, restaurants, cultural and entertainment venues, nonprofit organizations, property owners, and residents joining forces to increase economic activity by promoting downtown as a great place to live, work, and play. DPI works in partnership with various city departments, which has led to major streetscape projects, parking improvements, and marketing initiatives.