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Assistant Assistant Jobs in Ontario (NOW HIRING)

Wing Assistant

GTM Sales Associate

Toronto, ON · Remote

Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies get high-quality support across roles like executive assistance, admin ...

Wing Assistant

Sales Enablement Trainer

Toronto, ON · On-site

CA$29K - CA$35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day.

Wing Assistant

Website Manager

Toronto, ON · Remote

CA$110K - CA$135K/yr

  • Medical

  • PTO

About Us Wing Assistant is one of the world's largest virtual talent companies. We are a venture-backed scaleup, based in Silicon Valley, but operate fully remote. Wing is scaling rapidly, and ...

Wing Assistant

Web Presence Specialist

Toronto, ON · Remote

CA$110K - CA$135K/yr

  • Medical

  • PTO

About Us Wing Assistant is one of the world's largest virtual talent companies. We are a venture-backed scaleup, based in Silicon Valley, but operate fully remote. Wing is scaling rapidly, and ...

Wing Assistant

Demand Generation Marketer

Toronto, ON · On-site

  • PTO

These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed ...

Wing Assistant

Field & Events Marketer

Toronto, ON · On-site

  • PTO

These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed ...

Wing Assistant

Events Specialist

Toronto, ON · On-site

  • PTO

These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed ...

Cna

Senior Data Analytics Consultant

Toronto, ON · On-site

CA$90K - CA$105K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. As part of the ...

TLC Laser Eye Centres

Clinical Assistant

Kitchener, ON · On-site

CA$19.55 - CA$22.22/hr

CLINICAL ASSISTANT | Kitchener, ON Working in a TLC Laser Eye Centres clinic (an affiliated entity of Vision Group) is to help improve people's eyesight. It is having the feeling of a mission ...

Linds & Associates

Legal Assistant

Toronto, ON · On-site

Legal Assistant Downtown Toronto Our client, a premier business law firm in Canada is in need of a recent graduate of the Legal Assistant or Law Clerk program to join its team working as a Legal ...

Linds & Associates

Legal Assistant

Toronto, ON · On-site

Legal Assistant Downtown Toronto Our client, a premier business law firm in Canada is in need of a recent graduate of the Legal Assistant or Law Clerk program to join its team working as a Legal ...

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All JobsAssistant Assistant JobsAssistant Assistant Jobs in Ontario

Assistant Assistant information

What is an assistant assistant?

Assistant Assistants are professionals who provide support to executive assistants or administrative assistants, helping them manage tasks such as scheduling meetings, organizing documents, handling correspondence, and performing other clerical duties. Their role is to streamline workflows and ensure that more senior assistants can focus on high-priority responsibilities. Assistant Assistants are often employed in larger organizations that require multiple layers of administrative support. They must be detail-oriented, organized, and skilled at multitasking. This entry-level position is an excellent starting point for those interested in advancing to more senior administrative roles.

What are the key skills and qualifications needed to thrive as an assistant assistant?

To thrive as an Assistant Assistant, you need strong organizational abilities, attention to detail, and basic office skills, typically supported by a high school diploma or equivalent. Familiarity with office software such as Microsoft Office Suite, scheduling systems, and basic communication tools is important. Excellent communication, reliability, and a proactive attitude are soft skills that help you stand out in this role. These skills ensure effective support for higher-level staff, smooth day-to-day operations, and efficient workflow in a busy office environment.

What qualifications do you need to be an assistant assistant?

To become an assistant assistant, candidates typically need a high school diploma or equivalent, strong organizational and communication skills, and proficiency with office software. Some roles may require prior experience in administrative support or related fields.

What is the difference between Assistant Assistant vs Administrative Assistant?

AspectAssistant AssistantAdministrative Assistant
Required CredentialsHigh school diploma or equivalent; some roles may require certificationsHigh school diploma; some positions prefer certifications in office administration
Work EnvironmentOffice settings, support roles in various industriesOffice environments, administrative support in organizations
Employer & Industry UsageUsed across multiple industries for support rolesCommon in corporate, healthcare, education sectors
Search & Comparison IntentOften compared for entry-level support rolesMore established role, frequently searched for administrative support

The Assistant Assistant and Administrative Assistant roles both provide essential support in office settings. While they share similar credentials and work environments, the Assistant Assistant often serves as a more specialized or junior support role, whereas the Administrative Assistant is a well-established position focused on managing administrative tasks. Understanding these differences helps job seekers find the right fit for their skills and career goals.

What are some of the common challenges faced by an assistant assistant in supporting multiple team members?

As an Assistant Assistant, one of the main challenges is effectively managing competing priorities and requests from various team members. Juggling multiple tasks such as scheduling, document preparation, and communication support requires strong organizational skills and flexibility. It is important to establish clear communication channels and regularly check in with supervisors to ensure expectations are met. Proactively anticipating needs and staying adaptable can help navigate a fast-paced environment and maintain efficient workflow.

What are the most commonly searched types of Assistant jobs in Ontario?

The most popular types of Assistant jobs in Ontario are:

What are popular job titles related to Assistant Assistant jobs in Ontario?

For Assistant Assistant jobs in Ontario, the most frequently searched job titles are:

What job categories do people searching Assistant Assistant jobs in Ontario look for?

The top searched job categories for Assistant Assistant jobs in Ontario are:

What cities in Ontario are hiring for Assistant Assistant jobs?

Cities in Ontario with the most Assistant Assistant job openings:

Assistant Assistant jobs near you
Infographic showing various Assistant Assistant job openings in Ontario as of August 2026, with employment types broken down into 1% As Needed, 69% Full Time, 27% Part Time, 1% Temporary, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution.

GTM Sales Associate

Wing Assistant

Toronto, ON • Remote

Full-time

Re-posted 10 days ago

Job description

Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies get high-quality support across roles like executive assistance, admin support, customer support, sales support, recruiting support, operations support, and other business functions.

Our growth depends on a steady flow of qualified opportunities, and we are hiring a Go-to-Market Associate to help create them. This person will sit at the front line of our revenue motion: identifying companies with active hiring needs, reaching out with a compelling alternative to traditional hiring, and booking qualified meetings for our sales team.

This is a high-energy, high-ownership role for someone early in their career who wants to learn fast, build real outbound skills, and grow into bigger roles across sales, growth, revenue, or go-to-market strategy over time.

It is a great fit for someone who is competitive, well-organized, motivated by clear targets, and genuinely curious about how AI, remote talent, and global workforce solutions are changing the way companies build teams.

What You'll Do

Generate Qualified Opportunities

  • Identify companies actively hiring for roles Wing can support, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support roles.
  • Use job postings, hiring signals, company growth signals, and account research to find strong-fit prospects.
  • Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.
  • Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.
  • Run focused outbound campaigns around active hiring needs, operational pain points, and alternative workforce solutions.
  • Hold early discovery conversations to understand a prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.
  • Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.
  • Book qualified appointments with companies that have a clear hiring need, relevant business use case, or strong fit for Wing.

Turn Hiring Intent Into Conversations

  • Monitor companies that are posting roles Wing can service.
  • Understand what the company is likely trying to solve by hiring that role.
  • Position Wing as a faster, more flexible, and more scalable alternative to traditional hiring.
  • Educate prospects who may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support before.
  • Create curiosity with founders, executives, operators, HR leaders, recruiting teams, and department heads.

Support the Revenue Team

  • Work closely with the sales team to build and protect a healthy, well-qualified pipeline.
  • Hand off opportunities cleanly, with the context needed to move conversations forward.
  • Share key details from discovery calls, including the role the company is hiring for, their current hiring process, pain points, timing, budget signals, and decision-makers involved.
  • Keep activity, notes, and pipeline data accurate and current in our CRM.

Bring the Market Back In

  • Feed what you are hearing from prospects back to the Sales, Marketing, and Product teams.
  • Help refine messaging and outreach based on what is actually landing with companies.
  • Identify patterns in hiring demand, objections, industries, and roles where Wing is resonating.
  • Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.
What We're Looking For

Core Requirements

  • 1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
  • A real interest in go-to-market strategy, pipeline generation, and B2B growth.
  • Proven background in prospecting, cold calling, appointment setting, or high-volume outbound outreach.
  • Strong written and verbal communication; you can get to the point and make it compelling.
  • Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce solutions before.
  • Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
  • Strong organization and the resilience to keep going when a day does not go your way.
  • The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
  • The ability to run your own desk while still collaborating well across teams.
  • A genuine eagerness to learn the product, the market, and the craft of go-to-market execution quickly.
 

Nice to Have

  • Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.
  • Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.
  • Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.
  • Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, sales leaders, or department heads.
  • Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations.
$1,200 - $2,500 a month

In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.

Appointment and Deal Bonuses

  • Earn a bonus for every qualified meeting that shows up.
  • Earn an additional bonus when a qualified meeting turns into a closed customer.

This means you are rewarded not just for booking activity, but for creating real opportunities that move through the revenue process.

Weekly Competitions

We also run weekly competitions to keep the team competitive, motivated, and focused on the right activity metrics.

  • Weekly bonus opportunity for top dial activity.
  • Weekly bonus opportunity for top meeting production.

These incentives are designed for people who are driven by targets, enjoy competition, and want direct upside from their effort.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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