The PositionReporting to the Chief Revenue Officer (CRO), the Sr. Director, Account Management will lead Rightsline's revenue expansion organization across Strategic and Enterprise customers. This leader owns commercial growth within the existing customer base, including upsells, cross-sells, multi-product expansion, migrations, and Net Revenue Retention (NRR), while building and mentoring a high-performing Account Management team.
Mission & ImpactDrive sustainable growth and customer value through repeatable account expansion strategies, executive relationships, and strong cross-functional execution. Success will be measured primarily by Net Revenue Retention (NRR), supported by expansion ARR, multi-product attach rate, renewal performance, forecast accuracy, and executive engagement.
What You Will OwnRevenue Expansion & Account Strategy- Own all commercial outcomes within the existing customer base, including upsells, cross-sells, multi-product expansion, and migrations.
- Deliver NRR targets through structured expansion plays including whitespace mapping, discovery, and multi-product attach strategies.
- Develop and scale Account Management playbooks covering account planning, negotiation frameworks, and renewal workflows.
Executive Relationships & Customer Retention- Strengthen executive relationships with key customer stakeholders and serve as an escalation point for commercial risk.
- Collaborate closely with Customer Success to align renewals and customer outcomes with commercial expansion opportunities.
Cross-Functional Growth & Team Leadership- Partner with Product, Revenue Operations, and Marketing to drive expansion campaigns, product adoption pathways, and industry-specific plays.
- Build, lead, and mentor a high-performing Account Management organization focused on Strategic and Enterprise customer segments.
Success Metrics- Net Revenue Retention (NRR) - primary metric
- Expansion Annual Recurring Revenue (ARR) from upsells and cross-sells
- Multi-product attach rate
- Gross Revenue Retention (GRR) / renewal rate, in partnership with Customer Success - secondary metric
- Forecast accuracy and pipeline discipline
- Executive relationship depth and engagement coverage
What You Will Bring- 10+ years of progressive Account Management or commercial leadership experience in B2B SaaS.
- Proven track record of owning NRR and expanding accounts through structured growth frameworks.
- Deep experience navigating enterprise deals, multi-product selling, and complex negotiations.
- Ability to build and scale high-performing Account Management teams across segments to $100M+ ARR.
- Experience working closely with Customer Success, Product, Marketing, and Revenue Operations in high-growth environments.
- Ability to thrive in metrics-driven, execution-focused environments.
- Availability for regular travel (20-30%).
Preferred Qualifications:- Experience working in a private equity-backed B2B SaaS business.
Compensation & Benefits- Competitive compensation and health and dental benefits.
- 401(k) / RRSP match program.
Our Core ValuesAt Rightsline, we look for these qualities in every hire, and we hold ourselves to them every day.
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.
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.
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.
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.
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 TodayIf you want to join a company that strives for a mission, purpose and making an impact, we encourage you to apply today.
