Senior Sales Enablement Specialist

Who you are

• You are a segment enabler who thrives in a high-volume, fast-moving sales environment. You understand that Velocity selling wins on speed, repeatability, and consistent execution across short cycles, and you build the playbooks, talk tracks, and quick-hit training that help reps convert faster. You do not wait to be told what to build. You look at the calls, the pipeline data, and the conversion metrics, and you come to the table with recommendations. You own outcomes for your segment, not just the delivery of sessions
• 3+ years of experience in sales enablement, high-velocity or SMB sales, or a related learning and development role
• Experience designing and delivering training for high-volume, transactional sales teams
• Familiarity with velocity or SMB sales motions and the metrics that drive them
• Knowledge of instructional design principles and adult learning theory
• Strong facilitation and presentation skills across all levels of the organization
• Comfort with tools such as Gong, Letter AI and Salesforce
• Ability to analyze engagement and performance data to drive program improvements
• Strong project management skills across multiple concurrent workstreams
• Experience in a SaaS or technology company
• Experience enabling multi-product attach or cross-sell motions
• Proficiency with generative AI tools (Claude, ChatGPT, or similar) for content development and ideation
• Experience in legal tech or a comparable regulated industry
• Relevant sales or enablement certifications

What the job involves

• We are currently seeking Senior Sales Enablement Specialist, Velocity to join our Revenue Enablement team in the United States or Canada. This role reports to the Senior Manager, Sales Enablement and is the dedicated enabler for our Velocity segment across new business and customer sales
• The Revenue Enablement team at Clio equips our sales and customer success organizations with the knowledge, skills, tools, and processes they need to drive revenue growth and deliver exceptional client experiences. We design and deliver onboarding and ongoing programs, run a center of excellence operating model, and partner closely with Sales, Marketing, Product Marketing, and Revenue Operations to turn product launches into field-ready execution. We are a team that runs on curiosity, data, and a genuine commitment to helping people do their best work
• Own enablement for the Velocity segment across new business and customer sales, covering both dedicated reps and their managers
• Own measurable rep outcomes for the segment, including 90-day conversion rate, multi-product attach, and time to ramp
• Build repeatable playbooks, objection handling, and product positioning tuned for short, high-volume sales cycles
• Run a consistent Gong review rhythm on Velocity calls to surface coaching themes, objection patterns, and content gaps
• Design and maintain role-play and certification content grounded in real Velocity conversations
• Coach front-line Velocity managers on reinforcing trained behaviors so enablement lands in the field
• Tailor product and multi-product enablement to the Velocity buyer and deal profile
• Use generative AI tools to accelerate content creation, role-play design, and iteration at the pace the segment demands
• Deliver a regular segment health readout covering what is working, what is not, and the top unmet needs
• Partner with Sales Onboarding, Product Marketing, and Revenue Operations to keep proof points and playbooks current
• Other duties as required

Benefits

• Specialized learning and development programs and access to an in-house performance coach
• Equitable compensation for your contributions, regardless of gender, race, or any other identifying factor
• Access to pay transparency on all of our global roles
• Company equity for applicable employees
• RRSP-matching in Canada, 401k in the US, and pension plans in Ireland
• Hybrid model – striking the right balance between the benefits of in person connectivity that in office brings, and the flexibility of remote
• Flexible paid time off (4-week minimum with opportunities for personalization based on individual needs and achievements)
• Parental leave options for birthing and non-birthing parents
• A $500 contribution to your child’s RESP
• Various health, dental, and vision benefits for you and your family, including an Employee and Family Assistance Program
• Virtual and In-person Wellness Programs to support mental and physical health
• Paid time for volunteering through our Clio Gives program
• $2000 annual counseling benefit for CAD Clions