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Closing June 26, 2022 - City of Markham - Digital Service Squat (Contract)

20 Jun 2022 8:59 AM | Stephanie Crilly (Administrator)

City of Markham

Digital Service Squad (Contract)

Temporary Full Time

Markham, ON, CA

Requisition ID: 2902

Salary Range: 57,647.00 To 65,507.00 (CAD) Annually

The City of Markhaman award-winning municipality with more than 355,000 residents, is Canada’s high-tech capital and most diverse community, enjoying a rich heritage, outstanding community planning and services, and a vibrant local economy.  Committed to being a model of public service excellence, with a workforce that is representative of the population we serve, we are looking for people who share our values and are champions of innovative practices.  Diversity is one of Markham’s strategic priorities, and we strive to develop and maintain an environment that is inclusive and creates a sense of belonging for all.  

We are pleased to be named one of Canada's Best Employers for 2022 and the best City employer by Forbes for the second consecutive year. The City of Markham is ranked in the top two for Government Services and 15th among the 300 employers on the list, advancing from 18th place in 2021. 

Applications are being accepted for the above Temporary Full time position in the Economic Growth, Culture & Entrepreneurship. To apply, please submit your cover letter and resume on-line by June 26, 2022.

Contract starts from July 15, 2022 to February 28, 2024

Job Description

The Digital Main Street Ontario Grants program expands the previously existing Digital Main Street (DMS) program developed in partnership by the City of Toronto and the Toronto Association of Business Improvement Areas (TABIA). Thanks to a renewed investment in the DMS Ontario Grants Program (OGP) from the provincial government, many more of the province’s small businesses are able to take full advantage of digital technologies and e-commerce platforms to increase their revenues and create jobs.

The four main components of the DMS OGP include:

  1. Digital Transformation Grant Program: Upon completion of their digital assessment, pre-qualification quiz and online training, businesses may apply for a $2,500 grant 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. 
  2.  Digital Service Squad Program: Digital Service Squads (DSS) are digital technology support specialists in an area or region of Ontario who deliver one-on-one assistance to brick-and-mortar small businesses. These DSS can be set up by BIAs, municipalities, Chambers of Commerce, Boards of Trade or Small Business Enterprise Centers and may apply for funding based on the number of brick-and-mortar small businesses in their catchment area that they can reasonably serve. 
  3.  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. 
  4.  Digital Training (online and in-person): Webinars and workshops focusing on specific digital technologies and strategies, including e-commerce, social media, and website development.

The DMS OGP is currently seeking outgoing, enthusiastic, qualified candidates for the position of Digital Service Squad – Team Member. This is a unique opportunity to support the growth of one of the province's most innovative economic development programs. The Digital Main Street program is the first of its kind globally and has experienced excellent traction since its launch in June 2016. 

 As a member of the Digital Service Squad, 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 commercial areas and/or Business Improvement Areas (BIAs) across Ontario and will be required to independently travel to and visit/service local businesses. Otherwise, the DSS Member may be assigned to work remotely with local businesses.

Key Duties and Responsibilities 

1. On-boarding Assistance

  • Conduct pre-business visit research to best understand the community/BIA and businesses. 
  • Work with the municipality/BIA, if applicable, to setup appointments and/or go door-to-door to onboard brick-and-mortar small businesses (i.e., no home-based 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 direct the business owner to resources (articles, links, how-to guides, webinars) that can help him/her learn more about a particular tool that has been activated or is a subject matter of interest. 

4. Reporting and Feedback

  • DSS Members must complete their field notes for each business engagement 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 accurately and completely entered within the Digital Main Street CRM (HubSpot) after each business interaction or on a daily basis. 

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 direction of the DSS Senior Program Manager, team members will be responsible for assisting in the growth of all DMS/OBIAA social media channels.
  • Responsibilities includes, but are not limited to: curating multiple social media posts every week, producing 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. The purpose of such participation is to communicate the benefits of the program to business owners and to on-board them to the platform. 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/municipalities 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. 


  • Possess strong communications skills (written and verbal).
  • Possess strong interpersonal and relationship building/relationship management skills.
  • Possess excellent organizational and time management skills.
  • college diploma in marketing, business administration or data analytics.
  • 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 an asset.
  • Previous experience working with small businesses in BIAs is considered an asset. 

The City of Markham is committed to inclusive, accessible and barrier free employment practices and to creating a workplace that reflects and supports the diversity of the community we serve.  Please let us know if you require an accommodation and we will work with you to ensure a barrier free hiring process.  

The City of Markham has established a mandatory vaccination requirement for staff related to the COVID-19 pandemic.  As a result, should you be a successful candidate for a position with the City of Markham you will be required to provide proof of 2 Health Canada approved vaccination doses upon a conditional offer of employment.  Should you require accommodation in accordance with the Human Rights policy with respect to your vaccine status, you will be required to disclose that at the time of conditional offer so that an accommodation can be developed prior to your start date.

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