Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.
We are currently seeking a
Director of Revenue Enablement
to join our
Revenue Operations team. This role is open to candidates
across Canada and the U.S.
What your team does:Revenue Operations drives growth by supporting our revenue‑generating and revenue‑retaining teams. We work closely with Channel, Sales, Marketing, Finance, Customer Enablement, and Customer Support to provide insights and recommendations, improve the efficiency of the GTM motions, and enable GTM teams to be innovative and self‑sufficient.
Who you are:Reporting to the VP of Revenue Operations, the Director of Revenue Enablement is responsible for building a modern, high‑velocity, AI‑forward enablement function that supports Clio’s global growth across Sales, Sales Development, Partners, and Customer Success. This leader treats enablement as an operational discipline, not a training function. They diagnose where the GTM system is breaking, build the infrastructure to fix it, and deliver programs that directly improve productivity, velocity, and conversion.
The right leader is fast, analytical, and deeply scrappy with real range. They operate as an organizational leader who can mobilize cross‑functional teams to drive impact, and as a doer who jumps in to build the model, the content, and the systems themselves. They design field support models that scale and turn complex ideas into clear, actionable guidance that Sales and CS can execute immediately. They can build playbooks from zero and translate ideas from marketing in a succinct and efficient manner.



They have a point of view on what outstanding looks like in a multi‑product environment and know how to operationalize it.
They will influence executive‑level decisions, partner tightly with Product Marketing, Sales Leadership, Customer Success, and RevOps, and pioneer AI‑driven enablement programs that scale globally.
What you’ll work on:
Design the full enablement operating model for a multi‑product GTM including field support structure, content strategy, AI‑powered workflows, and continuous learning.
Lead a high‑performing team that ships fast, measures impact, and acts as a strategic partner to frontline managers.
Build a data‑driven review process that evaluates program effectiveness, identifies gaps, and continuously raises the bar on productivity and conversion.
Create onboarding and continuous development programs that materially shorten ramp and lift performance across every segment.
Continuously diagnose and evolve the sales process by defining the skills, knowledge, tools, and process changes needed to increase velocity and win rates, leveraging AI, voice analytics, and behavioral insights to surface win‑loss patterns and inform real‑time coaching and optimization.
Partner closely with Product Marketing to build original, high‑quality sales playbooks and training programs that connect positioning, messaging, discovery, objections,



and pitches into winning habits across front‑line teams.
Stand up a real field support model that provides reps with timely deal support, live coaching, and targeted resources to remove friction.
In partnership with Customer Marketing and CS Ops, build customer growth and retention playbooks that improve GRR and NRR across segments.
In partnership with Corporate Events, own the full SKO strategy, design and execution, and refinement and delivery of a high‑quality program including content, executive presentations, run of show, and all readiness materials that move the GTM org forward.
Own the enablement content strategy using LetterAI and lead all AI‑driven coaching through Hyperbound, providing hands‑on support and a clear plan for maximizing both tools to ensure the field is fully trained, confident, and ready to execute.
Serve as a go‑to subject‑matter expert by maintaining deep expertise in Clio’s products, buyers, and customers, while staying current on industry trends, best practices, and emerging technologies in revenue enablement.
What you may have:
Bachelor’s degree in business or a related field. MBA is a plus
10+ years of experience in a senior leadership role leading enablement teams at a SaaS company.
Experience at a company of $400M+ ARR (preferably an SMB SaaS company).
Experience driving SKO strategy, design and execution.
Proven track record of driving operational excellence and outcomes that are tied to specific enablement programs.
Track record of hiring, developing, and retaining top talent to build high‑performing teams.
Strong ability to build future vision and activate d

📌 Director, Revenue Enablement (Toronto)
🏢 Clio
📍 Toronto