This is a hybrid in our Toronto Office, where we expect the candidate to work at least 3 days in the office.

The Position

Rightsline is seeking a highly motivated, experienced Sr. Enterprise Account Executive to drive new business acquisition within enterprise accounts across our target verticals in North America. Reporting to the Chief Revenue Officer, you will own the full sales cycle, from prospecting to close, and partner closely with Sales Engineering, Product, Marketing, and Customer Success.

Mission & Impact

This role is central to Rightsline's growth in the enterprise market. You will bring new customers onto a mission-critical platform trusted by global innovators like Disney, Amazon, Spotify, and the NFL, showing how our solutions support content rights, royalties management, and other workflows for IP-centric companies. Deals are strategic, multi-year, and involve senior executive buyers. Success is measured by consistent quota attainment, a healthy pipeline of qualified opportunities, and accurate forecasting.

What You Will Own

New Business Acquisition

• Own the full sales cycle from prospecting to close within Fortune 500 and enterprise accounts, selling high-value, complex solutions that require in-depth business and technical understanding.
• Create, qualify, and close new business by demonstrating how Rightsline supports content rights, royalties management, and other intellectual property workflows.
• Consistently build and maintain a robust pipeline of qualified opportunities to ensure sustained quota achievement.

Strategic Account Planning & Deal Execution

• Develop and execute comprehensive account strategies to penetrate, qualify, and close new business opportunities, engaging C-level and key executive stakeholders.
• Apply a rigorous sales methodology, such as MEDDICC or Challenger, to keep deals well-qualified, maintain deal momentum, and forecast accurately.

Cross-Functional Partnership & Market Insight

• Work cross-functionally with Sales Engineering, Product, Marketing, and Customer Success to ensure a seamless customer experience and successful solution implementation.
• Stay current on industry trends, the competitive landscape, and customer needs to position Rightsline as a strategic business partner.

What You Will Bring

• 5+ years of documented, consistent quota attainment in a full-cycle B2B SaaS sales role, selling into large enterprise accounts.
• Proven experience carrying an annual sales quota of at least $1M and managing deals with an average order value (AOV) of $250K or higher.
• Demonstrated success selling complex, multi-year contracts and solutions (SaaS, enterprise software, or equivalent) involving multiple stakeholders and long sales cycles (6-12+ months).
• Exceptional communication, presentation, and negotiation skills, with a track record of building trusted relationships with VP, SVP, and C-suite executives.
• Bachelor's degree or equivalent practical experience.

Preferred Qualifications:

• Hands-on experience with MEDDICC, Challenger, or a similar enterprise sales methodology.
• Experience selling into media and entertainment or other IP-driven industries; familiarity with rights, royalties, or licensing is a plus.
• Based in the Toronto area.

Our Core Values

At Rightsline, we look for these qualities in every hire, and we hold ourselves to them every day.

• Be Curious and Smart

Being smart isn't about having all the answers - it's about asking the right questions, seeking out new ideas, and never assuming you already know enough.

• Embrace Change

This industry moves fast and so do we. We don't resist change - we lean into it. That means staying flexible, letting go of what isn't working, and treating uncertainty as opportunity rather than obstacle.

• Show Up

Showing up means being present - not just physically, but mentally and emotionally. Your teammates count on you. Your customers count on you. We do our best work when everyone is fully engaged and accountable to each other.

• Get it Done

Ideas are easy. Execution is the job. We hold ourselves to what we commit to, push through the hard parts, and measure success by our actual accomplishments.

• Be Humble

Nobody here has a monopoly on good ideas. We listen more than we talk, share credit freely, and check our egos at the door. The best outcome matters more than whose idea it was.

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.