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Added 2 hours ago
Retail Sales Representative - Vaughan
Encore
Vaughan, ON
At Encore, we possess the expertise in field sales to ensure our clients are successful in their most critical market channels. Going deep with few...being nimble and responsive for us is…
Added 2 hours ago
Retail Sales Representative - Toronto
Encore
Toronto, ON
At Encore, we possess the expertise in field sales to ensure our clients are successful in their most critical market channels. Going deep with few...being nimble and responsive for us is…
Added 2 hours ago
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Sales Development Representative
Aerotek
Calgary, AB
- Other
The Sales Development Representative is responsible for learning the fundamentals of recruiting and the fundamentals of sales, including prospecting, client engagement, req qualification…
Added 3 hours ago
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Inside Sales Rep
United Rentals
Oakville, ON
- Full-time
As an Inside Sales Rep, you will serve as a key customer contact and consultant at our Trench Safety branch, with responsibility for recommending solutions to the customer, quoting, selling…
Added 3 hours ago
M
Sales Administrator
Minto
Ottawa, ON · Kanata, ON
- Full-time
Welcome and greet all visitors to the sales centre; quickly acknowledge customers’ presence and hand off to Sales Rep
Added 3 hours ago
Retail Sales Representative - Quebec City
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Quebec, QC
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Added 4 hours ago
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Inside Sales Rep
United Rentals
Kamloops, BC
- Full-time
As an Inside Sales Rep, you will serve as a key customer contact and consultant at our branch, with responsibility for recommending solutions to the customer, quoting, selling and…
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Inside Sales Rep
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Sherwood Park, AB
- Full-time
As an Inside Sales Rep, you will serve as a key customer contact and consultant at our branch, with responsibility for recommending solutions to the customer, quoting, selling and…
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Team Lead Retail Sales Representative - Calgary
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Calgary, AB
…future opportunity involves spearheading our business growth and entails leading and training a team of part-time sales and merchandising representatives within your designated territory.…
Added 5 hours ago
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Inside Sales Rep
United Rentals
Bonnyville, AB
- Full-time
As an Inside Sales Rep, you will serve as a key customer contact and consultant at our branch, with responsibility for recommending solutions to the customer, quoting, selling and…
Added 5 hours ago
AB
A National Service Manager (Retail & Fixtures)
ACI Brands Inc.
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- Full-time
A National Service Manager (Retail & Fixtures) is typically responsible for ensuring retail fixtures, displays, shelving, signage, and store equipment are installed, maintained, repaired,…
Added 6 hours ago
QSR Brand Manager - ONroute Various Locations
Careers at ONroute
Belleville, ON · Kingston, ON · Mallorytown, ON · South Glengarry, ON
…friendly environment at our 23 travel centres along the busy 401 and 400 highways in Ontario. We are open 24/7/365 to proudly serve over 40 million customers each year who stop in to our…
Added 6 hours ago
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Salesperson
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- Full-time
We are hiring a Sales Rep for a client who are a leading provider of custom bath and shower remodeling solutions across Canada. The ideal candidate will be responsible for engaging with…
Added 8 hours ago
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Manager, Sales Enablement
SysAid
Toronto, ON
- Full-time
Be the force multiplier for a global sales organization selling across 140 countries, with enablement that reaches every rep, region and language.
Added 17 hours ago
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Senior Director, GTM AI Product Leader
Thomson Reuters
Toronto, ON · Canada, Toronto, Ontario
- Full-time
Sales: AI for prospecting and account research, lead and opportunity scoring, call and meeting intelligence, deal inspection and forecasting, proposal and RFP generation, pricing and…
Added 1 day ago
ST
Sales Enablement Manager
SysAid Technologies
Toronto, ON
- Full-time
Be the force multiplier for a global sales organization selling across 140 countries, with enablement that reaches every rep, region and language.
Added 1 day ago
S
Sales Enablement Manager
SysAid
Toronto, ON
- Full-time
Be the force multiplier for a global sales organization selling across 140 countries, with enablement that reaches every rep, region and language.
Added 1 day ago
Restaurant Manager - Trenton South Onroute (Tim Hortons) (Contract)
Careers at ONroute
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…friendly environment at our 23 travel centres along the busy 401 and 400 highways in Ontario. We are open 24/7/365 to proudly serve over 40 million customers each year who stop in to our…
Added 1 day ago
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Business Developer
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Identifying and converting new business opportunities, building strong and lasting client relationships, and contributing directly to revenue growth. The role combines proactive outbound…
Added 1 day ago
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Member Services Rep
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- Full-time
Proactively attract new business through member referrals, corporate lead generation, territory outreach, and telephone inquiries, ensuring consistent follow-up on sales leads.
Added 1 day ago
RM
Inside Sales Representative
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- Full-time
Develop sales opportunities and find new leads through methods such as cold calling, and face to face meetings with the Outside Sales Rep and/or Sales Manager.
Added 2 days ago
FF
Senior Customer Engagement Representative (Senior Business Development Representative)
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- Full-time
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Collaborate: Work with internal teams to support timely and accurate funding outcomes, including Sales, Processing, Underwriting, Collections, and Accounting.
Added 3 days ago
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Account Manager
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Richmond, BC · Fresh Start West Richmond-British Columbia-FSW
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The Account Manager works closely with: Purchasing, Transportation, Processing, Quality Assurance, Customer Service, and the Outside Sales Team.
Added 3 days ago
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Senior Customer Success Manager, Enterprise
Klue
Remote, Canada
- $90,000 to $130,000 CAD / year
- Full-time
- Remote
Lead the Account Team. You own the account, which means owning the strategy and everyone working inside it. Win-Loss Researchers, PMAs, Sales, AI Solutions. You set the direction. They…
Added 4 days ago
KD
Représentant, Ventes de territoire | Territory Sales Representative
Keurig Dr Pepper Canada
Laval, QC
- Full-time
Prior sales and merchandising or retail customer service experience;

SysAid Technologies

Sales Enablement Manager

Toronto, ON, Canada

Full-time

Apply About employer

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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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