Freelance Remote Sales Enablement Jobs (NOW HIRING)

Sales Enablement Manager

Location: Remote, USA

Department: GTM - Sales

About Syllo

Syllo is defining the Litigation AI category. We are the first unified platform designed to autonomously manage the entire litigation lifecycle end-to-end. Founded in 2019 by a team of litigators and engineers, Syllo enables legal teams to securely harness the power of AI across any matter, regardless of complexity or scale. Our technology supports Fortune 500 companies and AmLaw 200 firms managing their most complex litigation portfolios. Awarded ILTA Transformative Project of the Year and ALM eDiscovery Technology of the Year for 2026, we are the market leader in enterprise-grade litigation AI. Backed by top-tier VCs, we are at a clear inflection point - the team has doubled in the last six months and growth is accelerating.

About the role

Build the system that makes every rep on the team dangerous faster.

This role owns sales enablement at Syllo - the onboarding programs, training curricula, playbooks, and tools that allow the GTM team to ramp faster, qualify better, and close more consistently. You sit between Sales, Marketing, and Product, translating market intelligence and product capability into content and coaching that changes what reps do on Monday morning.

Syllo's sales motion is complex. The buyer is a sophisticated legal professional. The product has technical depth. The competitive landscape is evolving. The Enablement Manager is the person who ensures that every rep - regardless of tenure - can tell the Syllo story credibly, qualify a deal rigorously, and run a discovery conversation that earns a second meeting.

We are looking for someone who has built enablement programs at enterprise SaaS companies, measures success in rep performance rather than content volume, and treats every training session as a behavior change problem, not a knowledge transfer exercise.

What you will do

• Own onboarding: Design and run the new hire onboarding program for AEs, BDRs, and SEs. A rep finishing onboarding should be able to run a discovery call and tell the Syllo story without coaching.
• Build and maintain playbooks: Develop the qualification playbook, discovery framework, competitive battle cards, and objection handlers the team uses in the field. Keep them current.
• Run ongoing training: Design and deliver recurring training sessions tied to specific skill gaps, product updates, or competitive developments - not a monthly all-hands slide deck.
• Measure rep readiness: Define and track the metrics that distinguish a rep who has completed training from one who has actually changed behavior. Certifications, call scoring, and pipeline quality all count.
• Partner with Sales leadership: Align the enablement roadmap to the Sales Director's priorities. Enablement that does not serve the business need is noise.
• Equip the full GTM team: Support AEs, BDRs, and SEs with differentiated content and skills development appropriate to each role and sales stage.

What you bring

• Enablement program design: You have built onboarding and ongoing training programs for enterprise B2B sales teams - from competency framework through delivery and measurement.
• Sales process fluency: You understand MEDDPICC, discovery methodology, and enterprise sales cycles from the inside. You cannot design a qualification playbook without having lived the sales motion.
• Content development: You write clearly and compellingly. Playbooks, battle cards, and objection handlers from you are actually used - because they reflect how good reps think, not how marketing writes.
• Adult learning methodology: You design training for behavior change, not knowledge transfer. You know the difference and it shows in your programs.
• Cross-functional influence: You align Sales, Marketing, and Product around the enablement roadmap without direct authority over any of them.
• Measurement discipline: You track metrics that connect to revenue outcomes - ramp time, pipeline conversion, win rate - not training completion rates.

Experience and qualifications

• 4-6 years in sales enablement, sales training, or a GTM-facing role at a B2B SaaS company.
• Demonstrated experience building and measuring enablement programs for enterprise sales teams.
• Proficiency with enablement tools (Highspot, Seismic, Gong, or comparable) and CRM platforms.
• Experience with MEDDPICC or a comparable qualification methodology required.
• Legal tech or professional services domain experience is a strong advantage.
• Bachelor's degree required.

Total rewards and benefits

At Syllo, we believe in taking care of our team so they can focus on building the future of legal tech.

Compensation: $160,000-$190,000 + equity options.

Benefits: Medical, dental, vision, and voluntary insurance options. Vacation, sick leave, and paid holidays. Access to benefit counselors and fitness class reimbursements.

Growth: Annual learning and development budget and real career growth in a fast-scaling organization.

Equal opportunity employer

We celebrate diversity and are committed to creating an inclusive environment for all employees. We provide a fair and accessible hiring process. If you require accommodations during the application or interview stage, please let us know.