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Added 9 mins ago
SP
Senior Sales Director - Aerospace and Defence
Solace Power
Mount Pearl, NL
- Full-time
The Senior Sales Director – Aerospace & Defence will lead Solace Power’s sales and business development activities across the aerospace and defence market. This role is responsible for…
Added 9 mins ago
OP
Property Administrator
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Toronto, ON
- Full-time
Join us to accelerate your growth & development, prioritize wellness, build connections, and support the communities where we live and work.
Added 9 mins ago
CC
Scientist, Data Research
Cameco Corporation
Saskatoon, SK
- Full-time
Lead innovation initiatives from concept development and proof-of-concept through pilot execution, technology validation, and operational deployment.
Added 9 mins ago
T
Manager, Delivery Lead / Project Manager - Gen AI and Software Delivery
Toast
Montreal, QC
- $103,000 to $150,000 USD / year
- Full-time
…shipped, combining delivery discipline with AI-accelerated development practices so clients can move faster without sacrificing quality, security or trust. In this full-time role, you will…
Added 9 mins ago
AL
Customer Support Analyst - Bilingual (FRENCH)
AGDATA, LP
Cambridge, ON
- Full-time
Helping you save: you’ll have access to a Health Care Spending Account funded with employer contributions.
Added 9 mins ago
C
Strategic Sales Development Representative
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- Full-time
As one of our Strategic Enterprise Sales Development Representatives, you will:
Added 38 mins ago
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Business Development Representative
Alphabyte
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- Full-time
Book discovery calls for the Account Executive and hand each one over with a short written brief
Added 38 mins ago
AW
Data Analyst III
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- Contract
…business and external environment. Contribute to team capability development, including mentoring, documentation, training materials, and promotion of analytics and AI best…
Added 39 mins ago
Principal Product Manager - Billing & Platform
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…pricing, invoicing, payment methods, payment recovery, refunds and account changes. Decide what we build, in what order, and…
Added 39 mins ago
A
Senior Project Manager (Environment)
AtkinsRéalis
Toronto, ON
- Full-time
…resourcing, risk management, stakeholder coordination, and client account management and is at integration with the overall project…
Added 1 hour ago
UO
Clinical Research Coordinator, Clinical Neurosciences
University of Calgary
Calgary, AB
- Full-time
Under the direction of the Executive Director and Principal Investigator, the Clinical Research Coordinator utilizes knowledge of research methods in the detailed development, planning and…
Added 1 hour ago
LM
DIRECTOR OF INFORMATION TECHNOLOGY
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- Full-time
…the Group aims to accelerate its national and international…
Added 1 hour ago
CI
Office Manager
Community Inclusions Ltd
O'Leary, PE
- Full-time
As the Office Manager, you will work directly with the Executive Director and administrative clerk to fulfill financial duties & responsibilities, while overseeing and assisting with…
Added 1 hour ago
Customer Support Analyst - Bilingual (FRENCH)
a42f2e0b-2d4a-4df5-a7d9-43a8b36fe9f3
Cambridge, ON
Helping you save: you’ll have access to a Health Care Spending Account funded with employer contributions.
Added 1 hour ago
IT Investment Planning & Financial Strategy Manager
Innovation and New Technology
Winnipeg, MB
Reporting to the Executive Director, the IT Investment Planning and Financial Strategy Manager provides strategic leadership and expert advice related to IT investment planning, financial…
Added 1 hour ago
G&
District Sales Manager
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- Full-time
5+ years of experience in B2B sales, account management, or business development.
Added 1 hour ago
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Account Executive, Professional Liability Programs | Sage Advisor Resources Corp.
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AB · Edmonton, AB
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…an experienced insurance professional to join our team as an Account…
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Account Executive, Consumer Ticket Sales
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- Full-time
The Account Executive, Consumer Ticket Sales is responsible for driving new business through the sale of Edmonton Oil Kings Season Seats and Partial Plans. This role focuses on building…
Added 2 hours ago
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Customer Solutions Specialist
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NB · Grand-Sault/Grand Falls, NB
- Full-time
…Workplaces for Women and for having one of the Most Trusted Executive Teams, and included on TIME Magazine’s 2025 list of Canada’s Best Companies. These achievements speak to our commitment…
Added 2 hours ago
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South West Ontario Account Executive - Security Solutions
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- Full-time
Convergint is looking for a full-time, enthusiastic, results driven and forward-thinking Account Executive – Enterprise Solutions (Security Systems), to join our amazing culture in one of…
Added 2 hours ago
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Toronto, ON
- Full-time
…(RAP) reporting across Purpose & Sustainability and the broader Executive Office. The role is accountable for the integrity, governance and audit readiness of information used in external…
Added 2 hours ago
AG
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Allegis Global Solutions
Mississauga, ON
- $43 CAD / hour
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…It’s a career. It’s a community of people who invest in your development and empower you to blaze your own trail. Each of us is here to create real, measurable impact that moves needles. We…
Added 2 hours ago
SH
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Strengthen leadership capacity through development plans, stretch assignments and succession planning.
Added 2 hours ago
AG
Full-Cycle Engineering Recruiter II 6-Month Contract
Allegis Global Solutions
Mississauga, ON
- $43 CAD / hour
- Full-time
…It’s a career. It’s a community of people who invest in your development and empower you to blaze your own trail. Each of us is here to create real, measurable impact that moves needles. We…
Added 2 hours ago
RC
Gestionnaire de Comptes
Randstad Canada
Montreal, QC
- Full-time

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

Apply About employer

Applications open in a new tab.

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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