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Rightsline

Sr. Director, Sales

Reposted 13 Days Ago
Be an Early Applicant
In-Office or Remote
Hiring Remotely in Chicago, IL, USA
Senior level
In-Office or Remote
Hiring Remotely in Chicago, IL, USA
Senior level
Lead new-logo enterprise and commercial customer acquisition, build and scale AE and SDR teams, implement disciplined enterprise sales methodology (e.g., MEDDICC), drive predictable forecasting and pipeline health, collaborate cross-functionally on GTM, and recruit and mentor sales talent to double ARR from ~$50M to $100M+.
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Since 2012, Rightsline has been revolutionizing rights and royalties management with its leading IP Commerce SaaS platform. Trusted by global innovators like Disney, Amazon, Spotify, and the NFL, our solutions empower rights holders to maximize portfolio value, reduce risk, and increase profitability. Serving industries from media and entertainment to life sciences, our scalable platform combines advanced analytics, business process outsourcing, and decades of expertise to tackle the most complex rights and royalties challenges.


With over 300 employees across multiple regions, including the United States, Canada, the United Kingdom, and India, Rightsline fosters a dynamic, collaborative environment where innovation thrives. We’re passionate about creating smarter solutions, encouraging personal growth, and celebrating creativity. Join a team that offers competitive benefits, a supportive workplace, and the opportunity to lead the future of intellectual property management.

Welcome to a world of less data entry and more data integrity. Welcome to the Rightsline reality!

 

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.

Status: Full-Time Opportunity – Our recruitment team is actively seeking candidates for this open position.
**Hiring Remotely - Open to East and Central US applicants. 

 What you will do:

  • 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.

Success Metrics:

  • New-logo Enterprise ARR attainment
  • Optimize SQL to SQO conversion (hand off from SDR to AE)
  • Align SDR targets with Account Executive goals
  • Reduce ramp to quota and increased efficiency in sales cycle durations
  • Pipeline coverage ratio (4–6× quota)
  • Increase Win rate on strategic, enterprise and commercial segments 
  • Sales cycle progression and late-stage conversion
  • Reduction in no-decision outcomes
  • Forecast accuracy and deal inspection rigor
  • AE and SDR ramp productivity and retention

What you will bring to the role

  • 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%)

Compensation

  • Competitive Base Salary + Commission Opportunity: At Rightsline, we offer a competitive package that reflects the unique skills, experience, and certifications you bring to the role. Your starting point within this range will be determined by your niche expertise, collaborative initiative, and specialized skill sets you bring to our team. In addition to these variables, we also take into consideration internal equity and regional labour markets to ensure our offers remain fair, balanced, and aligned with our evolving team’s needs.
  • 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.

The Rightsline Advantage

At Rightsline we encourage inclusiveness, purpose and innovation. We offer flexible work hours, birthdays off, one-time home office allowance, unlimited vacation time, team socials, happy hours and career progression in a high growth environment. 

  • Rightsline was the very 1st cloud-based rights and contract management platform, so we’re used to innovation. We’re also used to incredible growth if you’re into that sort of thing. 😉
  • You will become part of an amazing culture with a supportive executive team, smart colleagues who truly care, and a global team that’s been rocking this virtual collaboration thing since before anyone had ever heard the term COVID19.
  • You’ll often hear “Yes, let’s try that!” and then have the chance to execute your ideas.
  • You will grow more here than you would at any other company. That’s a promise.
  • A People First Company - 4.2 rating on Glassdoor

 

Our 4 Stage Recruitment Process

  1. Review - We review applications and screen based on a variety of criteria
  2. Phone - Candidates will be screened via a quick 20-minute Zoom meeting to discuss the role opportunity
  3. Interview - We will conduct 2 stages of interviews
  4. Offer - We will make an offer to the candidate that we feel would excel most in the role. 

**Please be advised that only those candidates selected for interviews will be contacted, and references will be requested for those candidates selected in the final interview stage.**

 

Equal Employment Opportunity

Rightsline is an equal opportunity workplace. All candidates will be afforded equal opportunity through the recruiting process. We do not discriminate against any employee or applicant for employment because of race, color, sex, age, national origin, religion, sexual orientation, disability, gender identity and/or expression. We are dedicated to growing a diverse team of highly talented individuals and creating an inclusive environment where everyone feels empowered to bring their authentic selves to work.

 

If you are contacted for an interview and require accommodation during the interviewing process, please let us know.

 

 

Apply Today

If you want to join a company that strives for a mission, purpose and making an impact, we encourage you to apply today.

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