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Added 1 min ago
HM
Account Manager
Highlight Motor Group
Toronto, ON · Greater Toronto Area, Canada
- Full-time
We are seeking a results-driven Account Manager responsible for developing new business opportunities while expanding and maintaining strong relationships with existing clients. This role…
Added 1 min ago
TC
Salesforce Project Manager
Tata Consultancy Services
Waterloo, ON
- $90,000 to $100,000 CAD / year
- Full-time
…highest standards of innovation, engineering excellence and customer…
Added 2 mins ago
T
personal banker
TD
Kingston, ON
- Full-time
…relationships with our customers by performing a broad range of customer service transactions and providing information and advice on services, products, and solutions to existing or…
Added 2 mins ago
T
Financial Planner - Westmount
TD
Montreal, QC
- Full-time
…career, development, and performance conversations with your manager, as well as access to an online learning platform and a variety of mentoring programs to help you unlock future…
Added 2 mins ago
T
Financial Planner - Town of Mount Royal
TD
Montreal, QC
- Full-time
…career, development, and performance conversations with your manager, as well as access to an online learning platform and a variety of mentoring programs to help you unlock future…
Added 2 mins ago
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Personal Banking Associate Trainee
TD
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- Full-time
…relationships with our customers by performing a broad range of customer service transactions and providing information and advice on services, products, and solutions to existing or…
Added 16 mins ago
TS
Christmas Kettle Campaign Assistant Coordinator
The Salvation Army Canada and Bermuda Territory
London, ON
- Full-time
…provide support to the Kettle Coordinator, Community Engagement Manager, and other members of the London Community Services management team on a temporary basis during the Christmas…
Added 16 mins ago
B
Manager business enablement
BMO
Montreal, QC
- Full-time
Develops and delivers sales programs and initiatives to achieve sales results targeted to customer needs.
Added 30 mins ago
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Business Development Manager/Field Sales - (Parcel Lockers) - Vancouver, BC, Canada
Quadient
Vancouver, BC
- $80,000 to $108,196 CAD / year
- Full-time
Quadient is a global leader in business communications, customer experience, and parcel locker solutions, helping organizations simplify the delivery of physical and digital communications.…
Added 1 hour ago
S
Manager, Sales Enablement
SysAid
Toronto, ON
- Full-time
…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…
Added 1 hour ago
Senior Engineering Manager - Analytics Platform
Faire
Kitchener, ON · Toronto, ON
We’re hiring a Senior Engineering Manager to lead Faire’s Analytics Platform team. You will manage data warehousing, ETL pipelines, medallion data sets, BI tooling, and agentic analytics…
Added 1 hour ago
Retail Experience Lead
Fire & Flower Inc.
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…supervising staff, assisting cashiers, delivering a consistently high customer service level, cash management, administrative duties, setting alarms, and keeping the front of house clean…
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Retail Experience Lead
Fire & Flower Inc.
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…supervising staff, assisting cashiers, delivering a consistently high customer service level, cash management, administrative duties, setting alarms, and keeping the front of house clean…
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Added 1 hour ago
Prepared Foods - Clerk Department Second Deli
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Elmsdale, NS
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Added 1 hour ago
TS
General Manager – HVAC Distribution
TalentSphere Staffing Solutions
Kelowna, BC
- Full-time
…and play a key role in its next stage of growth. The General Manager for their Kelowna operation will have significant influence across sales, operations, financial performance, customer…
Added 1 hour ago
C
Operations Manager
Confidential
Barrie, ON
- $85,000 to $100,000 CAD / year
- Full-time
A growing service-based organization is seeking an experienced Operations Manager to oversee multi-site field operations. This role is responsible for ensuring safe, compliant, and…
Added 2 hours ago
IS
Customer Success Manager - Quebec
InnovMetric Software Inc.
QC
- Full-time
By joining our team as a Customer Success Manager, you will be responsible for proactive customer engagement, personalized guidance, and cross-functional collaboration to support customer…
Added 3 hours ago
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Front End - Clerk Sales/Service - Tier II SW
Safeway Canada
Brandon, MB
- Full-time
Responsible to support the front end manager in the overall operation of the front end department including providing management and leadership to Front End staff . Ensure operational…
Added 3 hours ago
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Assistant Store Manager
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Montreal, QC
- Full-time
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Added 3 hours ago
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Hotel Manager
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Added 5 hours ago
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Talent and Business Operations Manager, Stores
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- Full-time
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Added 6 hours ago
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Senior Partnerships Manager - Toronto
Teamtailor
Toronto, ON
- Full-time
You'll report to our Team Manager of Partnerships and work closely with the global Partnerships team, as well as regional Sales, Marketing, Customer Success, and leadership teams across…
Added 7 hours ago
CO
IT Technician I (FT, Permanent)
City of Dawson Creek
Dawson Creek, BC
- Full-time
…The position is responsible for service desk activities, user onboarding and offboarding, Microsoft 365 support, technology asset management, and the configuration and maintenance of…

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Nov 26, 2026
Posting language: English
Posted: Oct 27, 2026

Original job description

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

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.

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.

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

Own the global sales enablement strategy, readiness programs, messaging, content, and technology stack, building an AI-first model that uses connected agents and systems to support seller workflows. Measure enablement performance against revenue outcomes, use data to identify gaps, and report results and investment priorities to executive leadership.

Requirements

Requires at least five years in a high-performance B2B technology sales organization, including at least three years as a quota-carrying individual contributor, plus demonstrated success building measurable sales enablement programs. Candidates should have hands-on experience with AI and LLM workflows, strong sales process and coaching expertise, familiarity with modern GTM tools and content or learning systems, and be based in or willing to relocate to Toronto.

Skills

Sales Enablement
Enablement Strategy
Sales Readiness
AI Workflow Automation
Claude and LLM Tools
Sales Coaching
Sales Methodologies
Messaging Strategy
Content Strategy
Revenue Analytics
Salesforce
Gong
Snowflake
Prompt and Agent Governance
Change Management
Communication and Presentation

Benefits

Medical Insurance
Vision Insurance
Dental Insurance
RRSP
Life Insurance
Accidental Death and Dismemberment Insurance
Long-Term Disability Insurance
Gender-Neutral Parental Leave
Stock Options

Visa sponsorship

Not detected in the job text

Keywords

Sales Enablement
B2B Technology
SaaS
IT Service Management
Artificial Intelligence
Claude
MCP
AI Agents
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
Revenue Operations
Sales Readiness
Sales Coaching
Sales Methodology
Go-to-Market Strategy
Content Management
Learning Management Systems
Sales Kickoff
Ramp Time
Win Rate
Sales Cycle
Prompt Engineering
Workflow Automation
Performance Analytics

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