Managing Director, Sales

Managing Director, Sales Location: Remote, USA Department: GTM — Sales 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. About Syllo Syllo is a fast-growing software company in the legal space that offers an AI-powered litigation workspace that enables lawyers to safely harness the power of language models. We offer an award-winning agentic AI solution for conducting automated review of documents in litigation and investigations. After spending years developing our cloud-based application, Syllo's applications are now being used by a wide range of legal professionals – from the largest law firms in the world to the most prestigious law schools. We are a lean, fast-moving, and multi-disciplinary startup led by exceptional lawyers and engineers who joined Syllo from AmLaw 100 law firms and technology companies like Google and Palantir. We hold each other accountable to achieve ambitious goals in a timely way while treating one another with respect and understanding. If you're a sales leader excited about AI and passionate about being part of a remote team that seeks to transform the legal practice, this is the job you've been looking for! 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: Competitive base salary + 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. United States - Remote Pay Range $210,000 — $250,000 USD