Sales Enablement Manager

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.

2. 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.

3. 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.

• 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