Revenue Operations Lead

Checkbox; New York (NY); Hybrid; USD 120,000 - 150,000; Full time

Benefits offered by this job

OTE 130-150k

Health insurance

401K matching

Paid leave (20 days)

Job summary

Checkbox is a Sequoia-backed technology start-up committed to enabling meaningful work through our no-code automation platform. We seek a Revenue Operations leader in New York to shape our GTM engine, own data-driven outcomes, and build scalable processes with AI-powered automation.

You will collaborate across Finance, GTM, and Product Marketing, reporting to senior leadership in a high-growth environment. Expect a hybrid work setup with a New York office presence and a strong focus on

Qualifications

• 3–5 years of experience in strategic operational roles within enterprise SaaS.
• Thrives in an entrepreneurial environment with rapid change and disruption.
• Able to ship v1s quickly and iterate to solve evolving problems.
• Familiar with current AI tooling and building AI workflows/automations.

Responsibilities

• Build and optimize GTM systems, playbooks, and processes.
• Own data, outcomes, and test new strategies responding to market trends and team performance.
• Codify playbooks, rules of engagement, and governance for revenue operations.
• Own the GTM tech stack and related automation initiatives.
• Collaborate with Finance on budgeting, compensation plans, and renewals.
• Partner with GTM Engineering to build durable systems for scalable automation.

Skills

Strategic ops

Data-driven

AI tooling

Cross-functional

Tools

CRM systems

Job description

Checkbox is a Sequoia-backed technology start-up with a mission to enable meaningful work for all. To achieve this, we built a no-code automation platform with the belief that the power of digital creation needs to be accessible to everyone, not just IT teams.

Seeing non-technical users surprisingly delighted when they use our technology to create in ways they never thought they ever could motivates us. Whilst our mission is big, our focus is sharp. Our customers today are primarily in-house legal departments from companies including SAP, BMW, Allianz, Elastic, Stryker, and Coca-Cola.

In 2024, we expanded our offering to not only help people do meaningful work, but manage it too. This came with the launch of our AI-powered Matter Management product, the “JIRA for lawyers”. This is part of our broader vision to be the “Legal Service Hub” for organizations, responsible for how legal work is raised, allocated, managed, and resolved. We believe that one day the Legal Service Hub will be as ubiquitous for legal teams as the CRM for commercial teams and we believe that Checkbox will be the market leader for this.

As a company, we are a tight-knit team of about 70 people across the United States, Australia, and Asia, made up of incredible high performers and Co-Founders in the Forbes 30 Under 30 list. Our culture is one of our superpowers. It's what people talk about when they join us, work with us, and leave us.

Read about what makes all of us a "Checkmate" here: https://www.checkbox.ai/core-values.

The Position

At Checkbox, we pride ourselves on simply first-class customer experience, from customer acquisition through customer retention. It is one of the things we’re known for, what we celebrate internally, and a key driver for our overall success as a company. Customers are our lifeblood and why we do what we do, so we hold a very high standard when it comes to bringing on the right customers that we can delight, feeling like they have not only partnered with the best technology, but the best team in the industry.

To deliver a first-class customer experience, you must also have a first-class go-to-market engine, including high-powered sales, marketing, and CS operations. The Revenue Operations function is critical to our future growth, responsible for both fine-tuning our existing systems, playbooks and strategies, ideating and codifying new ones, and being a detail-oriented project manager on a team with a lot of big-picture dreamers. This role is inherently cross-functional, as you’ll be supporting multiple functions and leaders, and driving change across the business.

You must love executing but also love building process to scale. You need to be obsessed with data, A/B testing, and proudly exhibit intense levels of grit, determination, enthusiasm, and strategy. You must be fearless and forceful to help us drive results and unlock new levels of growth. You’ll be partnering with our existing Revenue Operations team to build a world-class operations function.

In this role, you will own the following key outcomes:

• Build and iterate systems, playbooks, and process to help us execute GTM better
• Own the data and outcomes, and be creative to test new strategies and respond to market trends and team performance
• Help us codify and memorialize playbooks, rules of engagement, and more
• Own the GTM tech stack
• Partner with finance on budgeting, compensation plans, and more
• Partner with GTM Engineering to build durable systems that will be the foundation for agentic automation

This is not an easy job, but it will have a massive impact on Checkbox, be visible across senior leadership, and be one heck of a fun ride. Are you up for it?

In this position, you will

• Report directly to the Director of Finance and work closely with Senior Management and our GTM leadership to execute your role at the highest level
• Help us manage strategic projects and build systems to connect GTM departments
• Build automation and utilize AI to streamline existing processes and systems
• Be an excellent writer and orator
• Use your experience to identify key areas of operational improvement to deliver measurable business outcomes
• Partner with product managers and product marketing to enable sellers to best understand new features and how they impact our customers
• Show the care and attention to follow through on commitments and deliver outstanding results
• Own all RevOps technology, including identifying opportunities for new technology acquisition and track and manage technology renewals
• Partner with Finance to help own the Revenue team data, and use that data to not only drive insights but drive meaningful impact to help us hit targets
• Maintain accurate and up-to-date records of all sales activities and communications in the CRM and/or other relevant systems
• Dive deep into our ICP, in-house legal teams, to understand their business challenges, pain points and goals so you can properly lead our revenue operations

About you

• Minimum 3-5 years of experience or more in strategic operational roles, with a proven track record of building process and delivering results. Experience in enterprise business-to-business SaaS is essential
• You have proven to thrive in an entrepreneurial environment that absorbs rapid change and disruption
• You are comfortable shipping v1s quickly and rapidly iterating to solve evolving problems
• Are familiar with current AI tooling and can build AI workflows and automations, bonus points for vibecoding
• You are high character, consistently displaying integrity, high effort, and enthusiasm for the work
• You believe in being unique, and that transparency and radical honesty sell better than perfection
• You apply a strong analytical mindset to your work and leverage data to drive decisions
• You are a learner and display a desire to learn the challenges facing legal teams, and opportunities for efficiencies and operational improvements
• You are creative, driven, and reliable
• You are willing to consistently go beyond the call of duty for the team, and to challenge the status quo to help Checkbox be better
• You are self-motivated, relentless, organized, and determined to overcome roadblocks
• You have demonstrated success in managing complex projects with multiple stakeholders
• You have demonstrated success in maintaining strong, long-lasting relationships and the ability to inspire trust and confidence in others
• You are outcome-oriented, adaptable, collaborative, memorable and personable
• You take ultimate ownership over the success of your work. It matters to you to enable your teammates to be more successful at Checkbox, and you make every decision with an eye towards employee experience and ultimately driving performance
• Competitive compensation. We believe in comfortable compensation for our employees so that they can be as happy and productive as possible without any reservations. In this case, expect OTE of 130-150k
• Insurance coverage. We cover your health insurance, including dental and vision
• 401K savings. We match contributions to your 401K retirement savings
• Generous and flexible leave. We provide 20 days paid leave a year and parental leave, including secondary carer, with a culture of approving and encouraging time off as needed
• Hybrid working arrangements. Our New York team works out of an office a few days a week, and works from home as well. Enjoy the benefits of working from home, and working from our New York office when appropriate/required
• Personal learning & development budget. Continuous development and growth (#suckless) is one of our core values, and we believe in investing in our own home-grown leaders
• Expense policy. You can expense small work-related items and salary sacrifice larger items within reason
• Company wide social events. We have some wicked annual off-sites, past events include a massive boat party, a few days stay in a mansion in Australia’s wine region, and a week in Bali
• Transparent & open culture. Enjoy the benefits of an open culture where all questions and feedback are welcomed so we can be a better company day by day