Digital Service Squad – Team Member

Digital Service Squad – Team Member

Posted On

Oct 17, 2019

Closing Date

Nov 30, 2019



More Info


Job Description


Digital Service Squad – Team Member


Digital Main Street is a program developed in partnership by the City of Toronto and the Toronto Association of Business Improvement Areas (TABIA). Digital Main Street supports the growth of main street businesses by making the adoption of digital tools and technologies easy. The program has been profiled in the media recently by The Globe and Mail, the Toronto Star, BetaKit, Profit Guide and Notable.


There are four components to the Digital Main Street program which include:


1. Digital Main Street platform ( helps main street businesses by providing them with a free digital assessment that recommends digital tools and technologies that can help them reach their goals, guides them on how to get started, along with connections to trusted vendors, product offerings and deals.


2. The Digital Service Squad (a ‘geek squad’ for Main Street) that helps businesses on-board to the platform and activate easy-to-use free tools to get them started on their digital journey.


3. DMS Academy that supports the learning needs of businesses through workshops that tackle topics relevant to main street businesses.


4. DMS Lab that enables early-stage start-ups to pilot their products/services with main street businesses in a BIA in Toronto.


Digital Main Street 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 Toronto'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. The Digital Service Squad is assigned to specific Business Improvement Areas (BIAs) in Toronto and will be required to travel independently across Toronto.


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


1. On-boarding Assistance

• Conduct pre-business visit research to best understand the BIA/neighbourhood and businesses.

• Working with the BIA Co-ordinator to set-appointments or go door-to-door to onboard main street 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 Team Member will walk through the Digital Assessment and Recommendations with the business owner.

• The Team Member will assist the business owner in identifying their first priorities and the first digital tools/technology they want to activate.

• The Team 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 Team Member will activate and implement free, easy-to-use digital tools and technologies that businesses would like to use (i.e.: Building a Shopify store using the extended 30 day free trial, activating social media accounts, etc.).

• The Team Member may also provide some resources (articles, links, how-to guides) 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

• Team Members must complete their field notes and report on a weekly basis to the Digital Main Street Program Co-ordinator and Program Manager.

• Team Members must attend Team Meetings as set out by the Program Manager.

• Halfway through the employment term, an interim performance evaluation will occur to ensure fit.


The Team Member may be required to attend workshops and events related to Digital Main Street. The purpose of which 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 Team Member should they arise.


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 and work independently in various BIAs in Toronto.

• 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.


This position is a contract with TABIA for 35 hours per week. The Digital Service Squad Team Member will report day-to-day to the Manager Digital Service Squad Program

Please submit your resume to