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Added 8 mins ago
GT
Technology Delivery Manager
Greater Toronto Airports Authority
Toronto, ON
- Full-time
Reporting to the Associate Director, Technology Delivery, the Technology Delivery Manager is responsible for leading the end‑to‑end technical delivery of digital solutions that enable…
Added 8 mins ago
P
Customer Service Manager
PolicyAdvisor
Oakville, ON
- $60,000 to $70,000 CAD / year
- Full-time
We are looking for a talented Customer Service and Operations manager interested in a high growth role at an early stage, well-funded startup. Our team is small, but growing, so your role…
Added 8 mins ago
R&
Program Manager
Robertson & Company Ltd.
Toronto, ON
- Contract
Our client is a top financial institution with significant North American holdings. They have operations across most major verticals, including institutional & corporate, wealth management,…
Added 22 mins ago
P
Country HR Manager - Canada
Prysmian
Vaughan, ON · Quebec, QC
- Full-time
…millions of lives every day. You’ll help support the energy and digital infrastructure that keeps communities, businesses, and industries moving…
Added 22 mins ago
Creator Manager
SALT XC
Toronto, ON
Salt is a North American marketing agency that creates connected experiences through creative, digital & media innovation.
Added 22 mins ago
TG
Senior Manager, Enterprise Risk Management
TMX Group
Toronto, ON
- $130,000 to $145,000 CAD / year
- Full-time
…senior leadership, independently challenging first-line business operations while integrating risk considerations into new products, initiatives, and third-party partnerships. Combining…
Added 22 mins ago
Security Manager
PACT
ON · Mississauga, Ontario
The Security Manager is responsible for leading the planning, coordination, and execution of security measures across construction activities. Working closely with Senior Project Manager…
Added 22 mins ago
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Senior Resource Manager
BIMM
Toronto, ON
- Full-time
Working closely with department leaders from Client Leadership, Operations, HR, Talent Team, and Finance, the Senior Resource Manager proactively identifies capacity constraints, staffing…
Added 22 mins ago
AE
Maintenance Manager
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Bolton, ON
- Full-time
Reports to: Senior Operations Manager/Director, Operations
Added 22 mins ago
S
ES-NU26-58 Administrative Assistant, IES
Springboard
Toronto, ON · Scarborough, ON
- Full-time
…documentation, timely data entry, and smooth day-to-day administration operations to support service delivery. The duties and responsibilities of this position includes but not limited…
Added 38 mins ago
GT
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GeoSpectrum Technologies, Inc
Port Coquitlam, BC
- Full-time
ISE is seeking an Operations and Project Coordinator to join our team!
Added 38 mins ago
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CSR
BMO
Surrey, BC
- Part-time
Offers advice and guidance on available digital and self-serve options with the goal of making it easy, simple, and fast to bank with BMO.
Added 38 mins ago
B
Customer Service Representative
BMO
Surrey, BC
- Part-time
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Added 38 mins ago
B
Personal Banking Associate, Winter 2027 (Co-op/Internship), Victoriaville - 4 months
BMO
Victoriaville, QC
- Full-time
Added 38 mins ago
A
Senior Director, Clinical Development Change & Transformation Lead
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Mississauga, ON · Canada - Mississauga
- Full-time
…strategy and roadmap set by Evinova's Clinical Development Digital Innovation & Transformation leadership, you will lead the day-to-day delivery: redesigning processes with functional…
Added 53 mins ago
S
ES-NU26-58 Administrative Assistant, IES
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Toronto, ON
- Full-time
…documentation, timely data entry, and smooth day-to-day administration operations to support service delivery. The duties and responsibilities of this position includes but not limited…
Added 53 mins ago
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Added 53 mins ago
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Richmond, BC
Join Amrize as a Procurement Manager and help construct what's next. If you're ready to put your skills to work on projects that matter - and build a career with a company that’s building…
Added 53 mins ago
E
Senior Product Manager, Ad Audiences
eBay
Toronto, ON
- Full-time
As the Senior Product Manager, Ad Audiences you will lead key advertising technologies within our stack and make them outstanding in delivering speed for advertisers. You will identify and…
Added 53 mins ago
KH
UKG Specialist
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Toronto, ON
- Full-time
…accurate data entry, reporting, and analytics to support HR operations and decision-making across the organization. The UKG Specialist will serve as the first point of contact for user…
Added 1 hour ago
LC
Conversion Optimization Manager, Growth (Fixed Term Contract)
Lightspeed Commerce, Inc.
Remote, Canada
- $85,000 to $105,000 CAD / year
- Full-time
- Remote
As a Conversion Optimization Manager, Growth, you’ll own the conversion rate optimization strategy for Lightspeed’s marketing websites, treating our digital experience as a product. You’ll…
Added 1 hour ago
W
Product Marketing Manager
WELLSTAR
Toronto, ON
- Full-time
Whether you are in research and development, administration, communications, operations leadership, or technology, joining us now is an opportunity to play a critical role in transforming…
Added 1 hour ago
EP
Commercial Property Manager
Edison Properties Winnipeg
Winnipeg, MB
- Full-time
Role Description The Commercial Property Manager is a full-time, on-site role based in Winnipeg, MB, responsible for overseeing the day-to-day operations of commercial properties within…
Added 1 hour ago
UC
Manager, Remote Services
Ukrainian Credit Union Limited
Toronto, ON · Greater Toronto Area, Canada
- Full-time
UCU is seeking an experienced, forward-thinking Manager, Remote Member Services to lead our full-service virtual branch, delivering personalized financial services, expert guidance, and…
Added 1 hour ago
L
Program Manager
LTM
Mississauga, ON
- Full-time
Program Manager | Strategic Financial Services Transformation | LTM FSTI

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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