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Added 12 mins ago
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7818 - Assistant Store Manager PT
Lids
Vaughan, ON
- $18.1 USD / hour
- Part-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 12 mins ago
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7734 - 3rd Key(H)
Lids
Lloydminster, AB
- $15.5 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 12 mins ago
AE
Product Guide - Seasonal
Arc'teryx Equipment
Montreal, QC
- Full-time
You are product-obsessed and seek any chance to get outside to experiment and learn firsthand how our product performs. You prioritize your connection with nature and celebrate others doing…
Added 12 mins ago
TH
Assistant Store Manager - Full-Time
Tommy Hilfiger
London, ON
- Full-time
…and inspiring consumers since 1985. Originally established in New York City and infused with the vibrant spirit of Americana, to create the modern uniform of accessible luxury. The TOMMY…
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Personal Banker Trainee - 37.5h
TD
Montreal, QC
- Full-time
…opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices have been…
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T
Personal Banker Trainee
TD
Fort Saskatchewan, AB
- Full-time
…opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices have been…
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AW
Business Analytics Specialist, Temporary
Aviso Wealth
Remote, Canada
- Temporary
- Remote
Commitment to the continuous improvement of our staff through learning & development and an education assistance program
Added 12 mins ago
AW
Business Analytics Specialist, Temporary
Aviso Wealth
Remote, Canada
- Temporary
- Remote
Commitment to the continuous improvement of our staff through learning & development and an education assistance program
Added 27 mins ago
OR
Wireless Sales Associate - 3097 Sudbury North
OSL Retail Services Inc
Sudbury, ON
- Other
…those around us, and we’re always pushing each other to reach new heights. If you're interested in joining an award-winning team, and one of Canada's Top 50 Best Managed Companies, this is…
Added 27 mins ago
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Infirmière Gestionnaire de Cas/Nurse Case Manager - 12 month contract
Cencora
Quebec, QC
- Full-time
Address general inquiries regarding program services, disease states, or product related queries based on provided materials;
Added 42 mins ago
Trainee, Insurance Advisor
Talent Acquisition Team at Westland Insurance. Text reply only.
Lamont, AB
We’re searching for a Trainee, Insurance Advisor. Are you searching for new possibilities?
Added 42 mins ago
Project Manager
ERCO Worldwide
Saskatoon, SK
ERCO Worldwide is looking for a Project Manager to join our Saskatoon team! The Project Manager leads development and execution of projects to improve process safety, operations,…
Added 42 mins ago
PM
Project Manager
POD Marketing
Calgary, AB
- $57,000 to $65,000 CAD / year
- Full-time
Participate in small-scale product development initiatives, contributing ideas and collaborating on implementation.
Added 42 mins ago
T
Account Manager II, Agricultural Services
TD
Mount Forest, ON · Stratford, ON
- Full-time
Solves problems of moderate complexity and recommends new product and service solutions
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5794 - Store Manager
Lids
Timmins, ON
- $20.5 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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5760 - Assistant Store Manager FT
Lids
Medicine Hat, AB
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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5756 - Assistant Store Manager FT
Lids
Saint John, NB
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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7775 - Assistant Store Manager FT
Lids
Kamloops, BC
- $20 to $20.5 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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7732 - Assistant Store Manager FT
Lids
London, ON
- $19 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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5769 - Assistant Store Manager FT
Lids
Sarnia, ON
- $19 to $20 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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7750 - Assistant Store Manager FT
Lids
Rocky View No 44, AB · Rocky View County, AB
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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5798 - Assistant Store Manager FT
Lids
Windsor, ON
- $19 to $20 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
L
7761 - Store Manager (H)
Lids
Rocky View No 44, AB · Rocky View County, AB
- $20 to $21 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
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5709 - Assistant Store Manager FT
Lids
Calgary, AB
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…
Added 42 mins ago
L
7779 - Store Manager
Lids
Kelowna, BC
- $22.5 to $23.5 USD / hour
- Full-time
…professional teams, alongside top brands like Champion, Nike, New Era, Lululemon Athletica, and Mitchell & Ness. We’re also the industry leader in on-demand customization, offering in-store…

SysAid Technologies

Sales Enablement Manager

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Posting language: English
Posted: Oct 26, 2026

Original job description

SysAid is a high-growth SaaS company selling an IT Service Management Platform powered by AI. The ITSM space is experiencing rapid growth as businesses worldwide accelerate their digital transformation and adopt new technologies and workstyles. SysAid has been recognized in the Gartner Magic Quadrant for ITSM and was awarded the AWS Rising ISV Star Award for 2022.

We have over 4,000 customers in 140 countries. We are deployed in 42 languages and used daily by over 100,000 system administrators. Our software impacts the daily working lives of over 9 million end users.

The Role

This is not a traditional Sales Enablement seat. We are building an AI-first enablement engine, and this role is its architect and operator. You will define how a global sales and customer success organization learns, prepares and wins, then use Claude and MCP-connected systems to deliver that enablement at scale, rather than through manual training cycles and static content.

You will be the key driver in turning our go-to-market strategy into seller behavior and results in every region. You will report directly to the revenue leader and partner with Sales, Customer Success, Marketing, Product and Revenue Operations, so your work shapes how every seller prepares, engages and closes.

What You Will Own

1. Enablement Strategy & Sales Readiness

Own the global enablement strategy and roadmap, tied directly to revenue goals, and the readiness plan for every segment, role and region.
Define what great looks like at each stage of the seller journey, from onboarding and ramp through ongoing development and career path, and build the system that gets people there faster.
Lead launch readiness for new products, pricing and positioning, so the field is ready on day one rather than weeks later.
Partner with sales leaders to set the methodology, coaching cadence and standards that run through the organization.

AI-First Enablement Model

Design and own the model for what Claude and connected agents deliver across enablement, such as personalized onboarding, on-demand coaching, call review, deal-specific prep and content generation, and where human-led enablement adds the most value.
Turn Gong call data and Salesforce outcomes into continuous coaching signals, pinpointing the behaviors and messages that win and delivering them to reps at the point of need.
Build and govern AI-powered workflows for messaging, persona and account research, outreach and objection handling, using Clay, ZoomInfo and Lemlist, with consistent quality and brand control.
Set standards for prompts, agents and guardrails so AI output is accurate, on-message and trusted by the field.

Messaging & Content Strategy

Own the sales narrative and messaging architecture across the buyer journey, working with Marketing and Product to align it to customer needs and market position.
Run content as a living, AI-assisted system, with a single source of truth that is kept current, easy to find and measured for usage and impact, instead of a static repository.
Direct the strategy and storyline for major moments such as sales kick-off and quarterly sales meetings.

4. Enablement Performance & Revenue Impact

Define the KPIs for enablement, including ramp time, productivity, win rate, sales cycle, content effectiveness and adoption, and connect each program to revenue outcomes.
Use Snowflake, Salesforce and Gong data, with Revenue Operations, to find where performance gaps are and direct enablement to close them.
Report clearly to executive leadership on what is working, what is not and where to invest next.

5. Enablement Technology & Architecture

Own the enablement technology stack as one connected system (Claude, Salesforce, Gong, Snowflake, Lemlist, Clay, ZoomInfo, Juno and Accord) and the way it supports the seller workflow.
Evaluate and introduce new tools and AI capabilities, retire what no longer earns its place, and ensure sellers are trained and actually using what we invest in.

How You Will Work: AI-First:

Claude, connected through MCP to our core systems, is your primary team. You will be expected to:

Default to AI for content creation, material updates, training design, call analysis, research and reporting, and bring in people where judgment, coaching and relationships make the difference.
Build, test and improve agentic enablement workflows end to end, and measure accuracy, adoption and business results.
Treat every manual, repetitive enablement task as a candidate for automation, and have a clear point of view on what should always stay human.
Teach the global sales organization to work this way, through clear playbooks, live examples and visible wins.

Your Impact:

Be the force multiplier for a global sales organization selling across 140 countries, with enablement that reaches every rep, region and language.
Build SysAid's AI-first enablement program from the ground up, a completely reinvigorated approach with you as its architect.
Convert strategy into measurable results: faster ramp, higher win rates, shorter sales cycles and stronger seller confidence and retention.
Direct visibility and influence with executive leadership, with ownership of a scope that grows as the AI-first model scales.

Requirements

5+ years in a high-performance B2B technology sales organization, in sales, enablement or learning and development, including at least 3 years as a direct-to-market quota-carrying individual contributor. SDR or BDR experience is a plus.
Demonstrated experience using AI and LLM tools such as Claude, agents or MCP-style integrations to build and automate real business workflows; a hands-on builder mentality.
Proven track record of designing, building and iterating a sales enablement program, with measurable results.
Deep understanding of sales processes, methodologies and best practices, and the credibility to coach and influence sellers and sales leaders.
Experience with a modern GTM stack (Salesforce, Gong and similar) and with content and learning management systems; analytical mindset, with comfort using data to drive decisions.
Excellent communication and presentation skills, with the ability to convey complex ideas clearly and concisely.
Based in, or willing to relocate to, Toronto: in office at Liberty Village four days per week.

What We Offer

Competitive compensation package
Medical, Vision, Dental, and RRSP
Life, AD&D, and LTD Insurance
Gender-neutral parental leave
Option plan from Day 1

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More about this job

Responsibilities

You will architect and operate an AI-first enablement engine to drive global sales and customer success performance. This involves defining enablement strategy, designing AI-powered workflows, and aligning sales messaging with revenue goals.

Requirements

Candidates must have 5+ years of experience in B2B technology sales or enablement, including at least 3 years as a quota-carrying individual contributor. You must demonstrate hands-on experience with AI tools and modern GTM technology stacks.

Skills

Sales enablement
AI strategy
Claude
Salesforce
Gong
Revenue operations
Content strategy
Data analysis
B2B sales
Coaching
Workflow automation
Prompt engineering
Go-to-market strategy
Project management
Communication skills

Benefits

Medical insurance
Vision insurance
Dental insurance
RRSP
Life insurance
AD&D insurance
LTD insurance
Gender-neutral parental leave
Option plan

Visa sponsorship

Not detected in the job text

Keywords

Sales Enablement
AI-First
SaaS
ITSM
Claude
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
MCP
Revenue Operations
Go-to-market
B2B
Automation
Prompt Engineering
Sales Readiness
Coaching
KPIs
Workflow Design
Messaging Architecture
Data-driven
Customer Success
Product Launch
Sales Methodology
Toronto
Liberty Village

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