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Digital Service Squad – Team Member

The Ontario Digital Main Street Initiative expands the previously existing Digital Main Street program. The Municipality of North Grenville has received funding to hire a Digital Service Squad Team Member.

The four main components of the Ontario Digital Main Street program include:

  1. Digital Transformation Program: Upon completion of their digital assessment and online training, businesses may apply for a grant of up to $2,500 to offset costs as outlined in their Digital Transformation Plan and budget. These funds are available to help businesses strategically adopt technology and meet their digital goals.
  1. Digital Service Squad Program: Digital Service Squads are digital technology specialists in an area or region of Ontario who deliver one-on-one assistance to main street small businesses. These Digital Service Squads can be set up by BIAs, municipalities, Chambers of Commerce or Small Business Enterprise Centres that may apply for funding based on the number of businesses within their designated commercial downtown area.
  1. Access to Support: Ongoing support including access to basic digital services, a list of vendors that can identify technologies and tools businesses need to be digitally ready, and other resources such as assessments, articles, best practices, etc.
  1. Digital Training (online and in-person): Webinars and workshops focusing on specific digital technologies and strategies, including e-commerce, social media, and website development.

Ontario Digital Main Street is currently seeking outgoing, enthusiastic, qualified candidates for the position of Digital Service Squad – Team Member.

As a member of the Digital Service Squad (DSS), you will be a key contributor to the success of the platform and the growth of the program as a whole. Local health conditions allowing, the DSS Member is assigned to specific Business Improvement Areas (BIAs) across Ontario and will be required to independently travel to and visit/service local businesses. Otherwise, particularly under COVID-19 conditions, the DSS Member will be assigned to work remotely with local businesses.

The focus of the role is to work one-on-one with main street small businesses and provide the following services:

Duties / Responsibilities

1. On-boarding Assistance

  • Conduct pre-business visit research to best understand the BIA/neighbourhood and businesses.
  • Working with program coordinator to setup appointments and/or go door-to-door to onboard main street small businesses to the Digital Main Street platform.
  • 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.
  • Assist the business in staying in touch with Digital Main Street by subscribing to the e-newsletter and social channels.

2. Advisory Services

  • Once the business has been on-boarded to the Digital Main Street platform, the DSS Member will walk through the Digital Assessment and recommendations with the business owner.
  • The DSS Member will assist the business owner in identifying their first priorities and the first digital tools/technology they want to activate.
  • The DSS Member will also review vendor recommendations made through the platform and lead the business owner to relevant deals/discounts on the platform.

3. Activation/Implementation Services

  • The DSS Member will 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.).
  • The DSS Member may also 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. 

4. Reporting and Feedback

  • DSS Members must complete their field notes and report on a weekly basis to the Digital Service Squad Administrator
  • DSS Members must attend team meetings as set out by the DSS Administrator.
  • DSS Member must ensure ALL DATA is entered on time and accurately within the Digital Main Street CRM (HubSpot)

5. Special Projects

  • DSS Members will be responsible for leading the implementation of special projects and/or community-wide initiatives (i.e Google 360 photography)
  • DSS Members will work with their DSS Administrator to ensure successful activation of initiatives and increased Digital Main Street engagement
  • DSS Members will be available to help business owners develop their Digital Transformation Plan needed to apply for the Digital Transformation Grant, and can subsequently help to implement the plan if approved for the Grant.

6. Social Media Development

  • Working under the lead of the DSS Program Manager, team members will be responsible for assisting 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 our audience on social, and helping with social media development at DMS events as needed.

The DSS Member may be required to attend workshops and events related to Digital Main Street. There may be other duties, as required, that will be discussed with the DSS Member should they arise.

The DSS Member will have the opportunity to interface directly with the BIAs and the Digital Main Street corporate partners. All successful candidates will receive training on the program and if applicable, from the corporate partners, prior to in-field deployment. Local health conditions allowing, the majority of time spent will be in the field working with businesses.

Qualified applicants will:

  • Possess strong communications skills (written and verbal)
  • Possess strong interpersonal and relationship building/relationship management skills
  • Possess excellent organizational and time management skills
  • Have experience in a sales role and/or marketing environment
  • Be able to travel to and work independently (or remotely) with local businesses
  • Be familiar with digital technologies for small business (e.g., web, social media, e-commerce, etc.)
  • Be able to use basic software and collaboration tools such as Microsoft Office Suite (Word, Excel, Outlook, Power Point) and Slack
  • Previous experience with online and offline marketing is considered a strong asset
  • Previous experience working with small businesses in BIAs is considered an asset
  • Possess a Driver’s License valid in the Province of Ontario

The salary range for the position is $18/hour. The position is for 35 hours a week.  


The Municipality of North Grenville is seeking to fill one temporary position for a Digital Service Squad–Team Member (12 month contract). Interested applicants may submit a cover letter and resume outlining qualification in confidence to Human Resources by 4PM Friday, February 10, 2023.

Please quote “DSS-01”.

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Municipality of North Grenville
285 County Road 44, P.O. Box 130
Kemptville, ON
K0G 1J0

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Municipal Office
285 County Road #44,
PO Box 130
Kemptville, ON K0G 1J0

Monday through Friday
8:30 am - 5:00 pm

General Inquiries

Arena Staff (business hours)
613-258-9569 ext 141 or 175

Arena Staff (evenings/weekends)
613-316-2451 or 613-316-5010

After-hours Emergency Number

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