Sales Enablement Specialist
Filevine
Chicago, IL · $110k–$130k a year · Posted October 9, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about sales jobs
- Best cities for sales jobs #1 New York (2,774 openings)
- Best cities for sales pay after cost of living #1 Santa Clara ($175k)
- Most requested AI skills in sales jobs #1 AI tools in daily work (4.1%)
- AI tools named most often in sales jobs #1 Gong (0.93%)
- Employers with the most sales jobs #1 Charter Communications (389 roles)
How AI is used in this kind of work
Among retail salespersons, AI is already used for a large share of the tasks. Measured exposure for retail salespersons: 32% (high).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
Say which you have and which you want to build. We use it to match you to jobs like this one.
About the job
About Filevine
Filevine is a Legal AI company delivering Legal Operating Intelligence for the future of legal work. Grounded in a singular system of truth, Filevine brings together data, documents, workflows, and teams into one unified platform, where modern legal work happens with clarity and consistency.
Powered by LOIS, the Legal Operating Intelligence System, Filevine connects context across every matter to transform legal operations from reactive to proactive. LOIS reads, understands, and reasons across your data to surface insight, automate complexity, and give professionals the clarity and confidence to see more, know more, and do more. Fueled by a team of exceptional collaborators and innovators, Filevine’s rapid growth has earned AI awards and recognition from Deloitte and Inc. as one of the most innovative and fastest-growing technology companies in the country.
The Role
You will own how new Business Development Representatives (BDRs) learn to sell at Filevine, from their first day through ongoing skill development. You’ll run our monthly onboarding program, build the training curriculum, manage our mentor program, and use performance data to improve all three. Your goal is to get BDRs productive faster and keep them improving.
What You’ll Do
Onboarding
Run a two-week onboarding program for each monthly BDR cohort, combining live sessions (in person and virtual) with self-paced learning in GTM Buddy.
Build and update curriculum covering our tech stack (Salesforce, Gong, Nooks, ZoomInfo, Sales Navigator, 6sense, GTM Buddy), sales methodology, writing and communication skills, professionalism, and product and persona knowledge.
Set clear expectations and success metrics for every new hire, and track progress against them through the first 90 days.
Coach new BDRs on live calls and give feedback using Gong and other engagement tools.
Ongoing Training & Enablement
Design coaching programs that improve SQL-to-SAL conversion.
Lead 1:1 and group coaching, performance clinics, and short, targeted enablement sprints.
Partner with AE Enablement on certifications and training by vertical, persona, and product line.
Develop new cadence strategies for practice areas and product launches.
Mentor Program
Own the BDR Mentor Program: selecting and training mentors, running weekly check-ins, and tracking results.
Set program standards and hold mentors accountable for measurable mentee improvement.
Measurement & Improvement
Report on ramp time, training NPS, call quality, and qualification metrics.
Use performance data to refine content and delivery, and keep completion and engagement high.
What Success Looks Like
BDR ramp time decreases, and new hires contribute pipeline sooner within their first 90 days.
SQL-to-SAL conversion for ramped BDRs increases.
Training satisfaction scores (NPS) are consistently high.
Mentors and mentees report clear, positive impact.
Sales, Product, and Marketing Enablement see you as a trusted partner.
Qualifications
Must-Have Experience
3+ years in Sales Enablement, BDR/BDR training, or sales leadership (preferably in SaaS).
Experience developing and facilitating training programs for inbound and outbound sales.
Strong instructional design skills and experience with adult learning principles.
Deep understanding of B2B SaaS sales tools (e.g., Salesforce, SalesLoft, Gong, GTM Buddy).
Exceptional facilitation, coaching, and communication skills.
Bonus Points
Prior experience in a quota-carrying BDR or AE role.
Familiarity with legal tech or complex, multi-persona sales cycles.
Experience designing certification paths and persona-based enablement strategies.
Background in instructional design or learning & development.