Strategic Sales Executive

Syllo; Oregon; Hybrid; USD 175,000 - 350,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

Vacation and holidays

Equity options

Fitness class reimbursements

Job summary

Syllo is hiring a Strategic Sales Executive to own the full enterprise sales cycle for AmLaw 200 firms and Fortune 500 legal departments. You will close multi-stakeholder deals with average ARR $500K+ and navigate complex committee structures, including GC, CLO, and CFO.

You will run MEDDPICC with precision, forecast with evidence, and coordinate with Solutions Architecture on proofs of concept. A 7+ year track record in enterprise SaaS sales is expected.

Qualifications

• 7+ years of enterprise SaaS sales experience with 7 figure ARR deals and quota attainment above plan.
• Experience selling into legal, compliance, or regulated enterprise environments preferred.
• Value Selling, MEDDPICC or equivalent qualification methodology required.
• Bachelor's degree required.

Responsibilities

• Own the full enterprise cycle from qualified opportunity through signed contract.
• Sell to legal leadership (GC, CLO, CFO) and build economic cases.
• Maintain MEDDPICC qualification records and ensure accurate forecasting.
• Coordinate technical evaluation with Solutions Architecture and manage the relationship.
• Drive expansion and surface expansion signals post-close.

Skills

Enterprise SaaS sales

MEDDPICC

Forecast discipline

Executive stakeholder management

Quota attainment

Education

Bachelor's degree

Tools

MEDDPICC

Job description

Strategic Sales Executive

Location: Remote, US

Department: GTM — Sales

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

• You have closed multi-stakeholder deals at $1,000,000+ ARR with documented quota attainment for the last two years.
• You understand how law firms and in-house legal departments make purchasing decisions — the politics, the committee, the budget cycle.
• You do not forecast deals you cannot qualify. You know the difference between a champion and a cheerleader.
• You can hold a room with a Managing Partner or General Counsel. Concise, credible, direct.
• 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 base / $350,000 OTE (uncapped) 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.

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.

United States - Remote Pay Range$175,000—$350,000 USD