Rightsline

Senior Director, Sales

Rightsline

full-time

Posted on:

Location Type: Remote

Location: Massachusetts • United States

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Job Level

Senior

Tech Stack

ERP

About the role

  • 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.

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%).
Benefits
  • 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.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
B2B SaaS salesenterprise sales methodologyMEDDICCvalue-based sellingdeal inspectionpipeline managementquota managementsales forecastingaccount-based sellingenterprise software sales
Soft Skills
leadershipmentoringexecutive presencecollaborationcommunicationdata-driven decision makingoperational rigorexecution focusstrategic thinkingadaptability