Senior Director of Revenue Enablement (Legal AI SaaS)

TL;DR

Senior Director of Revenue Enablement (Legal AI SaaS): Building a modern, high-velocity, AI-forward enablement function supporting global growth across Sales, Sales Development, Partners, and Customer Success with an accent on operational discipline, infrastructure building, and productivity programs. Focus on designing scalable field support models, data-driven reviews, AI-powered workflows, sales playbooks, and continuous learning to boost velocity, win rates, and retention.

Location: Open to candidates across Canada and the U.S. Hybrid work environment, with expectation for local hirify.globalns (Vancouver, Calgary, Toronto, Dublin, Sydney) to be in office minimum twice per week.

Salary: $198,200 to $297,200 USD (depending on region, experience, and skillset; eligible for variable pay).

Company

Global leader in legal AI technology empowering legal professionals and law firms to work smarter with increased access to justice.

What you will do

• Design full enablement operating model for multi-product GTM including field support, content strategy, AI-powered workflows, and continuous learning.
• Lead high-performing team shipping fast, measuring impact, and partnering strategically with frontline managers.
• Build data-driven review processes to evaluate programs, identify gaps, and improve productivity and conversion.
• Create onboarding and development programs to shorten ramp times and lift performance across segments.
• Diagnose and evolve sales processes using AI, voice analytics, and insights for real-time coaching and optimization.
• Partner with Product Marketing to build sales playbooks and training connecting positioning, messaging, and objections into winning habits.
• Stand up field support model with deal support, live coaching, and resources.
• Develop customer growth and retention playbooks with Customer Marketing and CS Ops.
• Own SKO strategy, design, execution including content and readiness materials.
• Lead enablement content strategy with LetterAI and AI-driven coaching via Hyperbound.
• Maintain expertise in products, buyers, customers, and industry trends.

Requirements

• Reporting to VP of Revenue Operations, build enablement as operational discipline diagnosing GTM issues and delivering productivity programs.
• Analytical, scrappy leader mobilizing cross-functional teams and building models, content, systems.
• Design scalable field support and playbooks; influence executives; partner with Product Marketing, Sales, CS, RevOps.
• 10+ years senior leadership in enablement at SaaS company ($400M+ ARR preferred).
• Experience driving SKO strategy and operational excellence tied to enablement outcomes.
• Track record hiring, developing top talent; build vision; solve problems in ambiguity.
• Analytical skills for quantitative metrics with Finance and RevOps.

Nice to have

• Bachelor's in business or related; MBA plus.
• Experience at SMB SaaS company.

Culture & Benefits

• Competitive salary with top-tier health, dental, vision insurance.
• Hybrid work with office expectation twice weekly for locals.
• Flexible time off encouraged at 20 days/year.
• EAP for counseling and resources.
• 401k matching and Child Education Savings.
• hirify.globalversary recognition at milestones.