Sr. Director, Sales

Rightsline • Boston, MA

3h

About The Position

The Sr. Director of Sales – New Logo will lead Rightsline’s new customer acquisition strategy and execution across Enterprise and Commercial segments. This role owns new-logo revenue growth, enterprise and commercial pipeline generation, and the scaling of a high-performance sales organization capable of driving Rightsline from ~$50M to $100M+ ARR. This leader will build a disciplined enterprise sales engine focused on complex, multi-stakeholder deals with long sales cycles, ensuring predictable execution, strong forecasting, and reduced “no decision” outcomes.

Requirements

• 5+ years of progressive B2B SaaS sales leadership experience, preferably in complex sales/ enterprise environments, preferably PE backed.
• 10+ yrs of B2B SaaS sales experience as an individual contributor capacity.
• Managed both individual and team sales quotas from $1M - $5M ARR.
• Deep expertise selling complex enterprise software with long sales cycles (ERP, CPQ, HCM, financial systems, rights/licensing, or mission-critical platforms).
• Demonstrated success building and scaling enterprise AE and SDR teams .
• Strong command of enterprise sales methodologies, value-based selling, and multi-stakeholder deal orchestration.
• Executive presence with the ability to engage C-suite and board-level stakeholders.
• Data-driven, operationally rigorous, and execution-focused leadership style.
• Thrives in fast-growing, metrics-driven organizations.
• Regular travel required (20–30%)

Responsibilities

• Own all new-logo revenue outcomes , including bookings, pipeline health, and forecast accuracy.
• Lead and scale a team of Account Executives (initially ~2-3), with responsibility to expand capacity over time.
• Build and scale a dedicated SDR organization aligned to enterprise and commercial account-based selling motions.
• Implement a rigorous enterprise sales methodology (e.g., MEDDICC) to drive qualification discipline, deal inspection, and predictable outcomes.
• Establish best-in-class enterprise sales processes including discovery frameworks, executive alignment, mutual action plans, and value-based selling.
• Reduce “no decision” outcomes by strengthening economic buyer alignment, business case development, and compelling event creation.
• Partner closely with Marketing to define ICP, target accounts, ABM strategies, and enterprise demand generation.
• Collaborate with Product, RevOps, and Customer Success to align enterprise GTM strategy, product positioning, and land-and-expand motions.
• Deliver accurate forecasts and pipeline reviews to executive leadership and the Board.
• Recruit, develop, and mentor top-tier enterprise grade sales talent while building clear career paths and performance standards.

Benefits

• Competitive Base Salary + Commission Opportunity
• Comprehensive Health & Wellness: A competitive benefits package covering health, dental, and vision to support you and your family.
• Building Your Financial Future: A 401K/RRSP Match Program to help you reach your long-term savings goals.
• Career Growth Opportunities: Continuous learning and career growth opportunities.
• flexible work hours
• birthdays off
• one-time home office allowance
• unlimited vacation time
• team socials
• happy hours
• career progression in a high growth environment

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed