Director of Revenue Operations (North America)
United States (Remote or New York, Hybrid) | Full-time Permanent
The Company
Checkbox is a Series A technology start-up with a mission to enable meaningful work for all legal professionals. To achieve this, we built a no-code automation platform based on the belief that the power of digital creation should be accessible to everyone, not just IT teams.
Seeing non-technical users delighted when they create in ways they never thought possible motivates us every day. While our mission is big, our focus is sharp. Our customers today are primarily in-house legal departments at companies including SAP, BMW, Allianz, Elastic, Stryker, and Coca-Cola.
In 2024, we expanded our offering to not only help legal teams do meaningful work, but manage it too. This came with the launch of our AI-powered Matter Management product, often described as the “JIRA for lawyers”. It forms part of our broader vision to become the Legal Service Hub inside organisations, responsible for how legal work is raised, allocated, managed, and resolved.
We are a tight-knit team of around 70 people across the United States, Australia, and Asia. Our culture is one of our superpowers and is consistently highlighted by those who join, work with, and grow at Checkbox. Learn more about our values here: https://www.checkbox.ai/core-values
The Position
At Checkbox, we pride ourselves on delivering first-class customer experience from acquisition through retention. It is one of the key drivers of our success.
To deliver a first-class customer experience, we must also operate a first-class go-to-market engine. This includes high-performance Sales, Marketing, and Customer Success operations.
The Director of Revenue Operations is a new and critical role for Checkbox. You will be responsible for fine-tuning existing systems, building and codifying new playbooks, and operating as a detail-oriented project leader within a high-ambition team.
This role is inherently cross-functional. You will support multiple leaders, drive change across departments, and lead our Revenue Operations function to the next level.
This is not an easy job. It is highly visible, deeply impactful, and central to how we scale.
Key Outcomes You Will Own
- Build and continuously improve GTM systems, processes, and playbooks
- Own data integrity, reporting, and performance outcomes
- Codify rules of engagement and scalable operational frameworks
- Drive enablement across AE and BDR teams
- Own and optimise the GTM technology stack
- Partner with Finance on budgeting, forecasting, and compensation plans
- Work with senior leadership to build models and set targets
In This Role, You Will
- Report directly to the Global SVP of Revenue
- Work closely with Co-Founders, Senior Leadership, and GTM leaders
- Lead strategic cross-functional projects
- Dive deep into our ICP and in-house legal customer landscape
- Identify and implement operational improvements that drive measurable outcomes
- Partner with Product and Product Marketing to enable sellers on new features
- Partner with Sales leadership on training, coaching, and development
- Own revenue technology acquisition, renewals, and optimisation
- Lead and coach the Revenue Operations team
- Partner with Finance to drive insight-led decision-making
- Maintain CRM accuracy and operational discipline
About You
- 5+ years of experience in strategic operational roles within enterprise B2B SaaS
- Proven track record of building processes, scaling teams, and delivering results
- Demonstrated leadership capability and desire to coach others
- Strong analytical mindset with data-driven decision making
- High integrity, high effort, and strong ownership mentality
- Thrives in fast-paced, entrepreneurial environments
- Comfortable managing complex cross-functional initiatives
- Proven ability to build trusted relationships across stakeholders
- Self-motivated, organised, and resilient
- Passionate about driving operational excellence and team performance
Compensation & Benefits
- Competitive salary and meaningful equity
- Comprehensive health insurance including dental and vision
- 401K with company match
- 20 days paid leave annually with unused leave paid out
- Paid parental leave including secondary carer
- Hybrid working model in New York or remote flexibility
- Personal learning and development budget
- Expense policy and reasonable salary sacrifice options
- Annual company off-sites and team events
- Transparent, open culture where feedback is welcomed
