Municipality of Port Hope

Purpose of the Position:
The Digital Service Squad (DSS) Team Member will work one-on-one with main street
small businesses in the Port Hope Heritage Business Area (HBIA) to complete a digital
assessment of their business, provide assistance in identifying digital tools /
technologies suited to their business and help businesses to implement digital tools /
technologies e.g. basic website, social media.


On-boarding Assistance
1.1 Conduct pre-business visit research to best understand the HBIA /
neighbourhood and businesses.
1.2 Work with the HBIA, if applicable, to setup appointments and/or go doorto-
door to onboard main street small businesses to the Digital Main Street
1.3 Walk-through the on-boarding survey with the business owner and use
appreciative inquiry methods to best understand their business goals and
how digital tools/technology can assist them in meeting their goals.
1.4 Assist the business in staying in touch with Digital Main Street by
subscribing to the e-newsletter and social channels.

Advisory Services
1.5 Once the business has been on-boarded to the Digital Main Street platform, review the Digital Assessment and recommendations with the business owner.
1.6 Assist the business owner in identifying their first priorities and the first digital tools/technology they want to activate.
1.7 Review vendor recommendations made through the platform and lead the business owner to relevant deals/discounts on the platform.

Activation/Implementation Services
1.8 Activate and implement free, easy-to-use digital tools and technologies
that businesses would like to use (i.e., building a basic website, activating
social media accounts, etc.).
1.9 Provide some resources (articles, links, how-to guides, webinars)
available through secondary sources that can help the business owner
learn more about a particular tool that has been activated, or subject
matter of interest.

Reporting and Feedback
1.10 Document field notes and report on a weekly basis to the Digital Service
Squad Administrator.
1.11 Participate in team meetings as set out by the DSS Administrator.
1.12 Ensure ALL DATA is entered on time and accurately within the Digital
Main Street CRM (HubSpot).

Special Projects
1.13 Lead the implementation of special projects and/or community-wide HBIA
initiatives (i.e. Google 360 photography).
1.14 Work with their DSS Administrator to ensure successful activation of
initiatives and increased Digital Main Street engagement.
1.15 Help business owners develop their Digital Transformation Plan needed
to apply for the Digital Transformation Grant, and subsequently help to
implement the plan if approved for the Grant.

Social Media Development
1.16 Work with the DSS Administrator to assist in the growth of all DMS social
media channels, as well as curating content and photos to be used
accordingly. This includes but is not limited to: curating multiple social
media posts every week, coming up with new ways to engage the
audience on social media, and helping with social media development at
DMS events as needed.

1.17 As applicable, attend workshops and events related to Digital Main Street;
communicate the benefits of the program to business owners, and onboard
business owners to the platform.
1.18 Interface directly with the HBIAs and the Digital Main Street corporate
partners; participate in training on the program and if applicable, from the
corporate partners, prior to in-field deployment.
1.19 Other duties, as requested by the DSS Administrator or designate.


2.1. Experience in a sales role and/or marketing environment.
2.2. Previous experience with online and offline marketing is considered a
strong asset.
2.3. Previous experience working with small businesses in BIAs is considered
an asset.
2.4. Intermediate software skills: Microsoft Office Suite (Word, Excel, Outlook,
Power Point) and Slack.
2.5. Knowledge of digital technologies for small business (e.g., web, social
media, e-commerce, etc.). Proficient in ZOOM, Google My Business,
Facebook, Instagram.

Skills and Abilities
2.6. Possess strong communications skills (written and verbal).
2.7. Possess strong interpersonal and relationship building/relationship
management skills.
2.8. Possess excellent organization and time management skills.

3.1 Valid “G” Driver’s License, with access to own vehicle.
3.2 Valid and satisfactory Criminal Record and Judicial Matters Check (Police
Records Check)

4.1 Work independently in an office or from home, in local businesses
establishments and remotely (Local health conditions allowing, the
majority of time spent will be in the field working with businesses).
4.2 Travel in the local area.
4.3 Variety of walking, sitting and standing required.

Reference ID: DSS

Job Types: Part-time, Temporary, Contract

Salary: $19.00 per hour


  • Monday to Friday


  • sales: 1 year (Preferred)
  • customer service: 1 year (Preferred)


  • Secondary School (Preferred)

Work remotely:

  • Yes
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