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Strategic Sales Executive
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
Close the enterprise deals that define a category.
This role owns the full sales cycle for Syllo 's largest opportunities — AmLaw 200 firms and Fortune 500 legal departments running complex commercial litigation. Average deal size is $500K+ ARR with 6–18 month cycles. You will manage multi-stakeholder buying committees that include GC, CLO, CFO, and procurement, and you will close.
We are looking for an enterprise closer who has sold to legal buyers, runs a disciplined qualification process, and builds champion relationships that survive committee scrutiny. The market is real, the product is differentiated, and the demand is proven.
What you will do
Own the full enterprise cycle: From qualified opportunity through signed contract. You are responsible for the deal — discovery, demo, proof of concept, negotiation, close.
Sell to legal leadership: Build relationships and economic cases with GC, CLO, and CFO. Translate platform capability into matter economics and risk reduction.
Run MEDDPICC with precision: Maintain complete qualification records. Forecast is not aspiration — it is evidence.
Partner with Solutions Architecture: Coordinate technical evaluation and proof of concept. Own the relationship; share the technical depth.
Drive expansion: In a post-close world, the best AEs stay close to accounts and surface expansion signals. Expansion ACV is as important as new logo.
What you bring
Enterprise closing experience: You have closed multi-stakeholder deals at $1,000,000+ ARR with documented quota attainment for the last two years.
Legal buyer fluency: You understand how law firms and in-house legal departments make purchasing decisions — the politics, the committee, the budget cycle.
MEDDPICC discipline: You do not forecast deals you cannot qualify. You know the difference between a champion and a cheerleader.
Executive presence: You can hold a room with a Managing Partner or General Counsel. Concise, credible, direct.
ROI fluency: You can build and defend a value case to a CFO, not just a practitioner.
Experience and qualifications 7+ years of enterprise SaaS sales experience with closed deals 7 figure ARR deals.
Demonstrated quota attainment — at or above plan — for the last two full years.
Experience selling into legal, compliance, or regulated enterprise environments preferred.
Value Selling, MEDDPICC or equivalent qualification methodology required.
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: $175,000 + Commission and 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.
