Managing Director, Sales

Managing Director, Sales

Remote, USA

About the Role

Syllo is seeking a Managing Director, Sales to lead and scale our sales organization as we continue to expand the reach of our award-winning AI-powered litigation platform. Reporting to the EVP of GTM, this leader will own the performance of a team of 6 sellers, instill a rigorous value-selling and MEDDPICC discipline across the team, and play a key role in continuing to evolve Syllo's go-to-market strategy as we scale.

This is a great opportunity to join a dynamic and fast-growing startup and make a significant impact on the future of legal technology. If you are an experienced sales leader passionate about AI, value-based selling, and building high-performing teams, we would love to hear from you!

Responsibilities

• Lead, coach, and develop a team of 6 sellers, driving consistent achievement of individual and team sales quotas.
• Instill and reinforce a value-selling approach and MEDDPICC qualification discipline across every stage of the sales cycle.
• Own team-level pipeline generation, deal progression, forecasting, and reporting to the EVP of GTM.
• Continuously evolve and adapt Syllo's go-to-market strategy in partnership with executive leadership as the market and product evolve.
• Partner cross-functionally with Marketing, Product, and Customer Success to align messaging, surface market and customer insights, and inform the product roadmap.
• Recruit, hire, and onboard new sellers as the team scales.
• Represent Syllo's sales organization in strategic conversations with prospective enterprise clients, law firms, and legal departments as needed.
• Build and maintain scalable sales processes, playbooks, and enablement material to support consistent execution across the team.
• Develop and manage team pipeline and forecasting in HubSpot.

Qualifications

• 20+ years of experience in sales, with a strong preference for enterprise software/SaaS.
• Proven track record leading and developing sales teams around value selling and MEDDPICC methodologies.
• Demonstrated ability to adapt and evolve go-to-market strategy within a fast-growing, evolving environment.
• Strong cross-functional collaboration skills, with experience partnering across Marketing, Product, and Customer Success.
• Experience selling into the legal industry or legal technology a plus.
• Excellent communication, coaching, and organizational leadership skills.
• Qualified to work in and resident in the United States.
• Able to work in a remote environment.

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: $225,000 base, OTE $450,000, depending on experience.

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.

United States - Remote Pay Range

$210,000 - $250,000 USD