Director, GTM Engineering

Checkbox Technology • New York, NY

41d • Hybrid

About The Position

At Checkbox, we pride ourselves on delivering a first-class customer experience—from acquisition through retention. It is one of the things we’re known for, what we celebrate internally, and a key driver of our success.

To deliver this at scale, we are evolving beyond traditional Revenue Operations into a GTM Engineering function—a systemized, AI-powered engine that drives predictable, scalable growth.

The Director of GTM Engineering and Revenue Operations is a critical role responsible not just for optimizing our GTM motion, but for designing and building the systems, automation, and intelligence that power it.

This role is inherently cross-functional. You will partner across Sales, Marketing, Customer Success, Product, and Finance to architect a modern GTM operating system—combining data, automation, and AI to continuously improve how we acquire, convert, and retain customers. Importantly, you must be a detail-oriented project manager (on a team with a lot of big-picture dreamers) to help us bring big vision to reality.

You must love executing—but more importantly, you must love building systems that execute without you.

You need to be obsessed with data, experimentation, and leverage AI to unlock new levels of efficiency and growth. You must be fearless and forceful to help us drive results, challenge the status quo, and build a world-class GTM engine.

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

Requirements

• 5+ years of experience in strategic operational or RevOps roles within enterprise B2B SaaS
• You think like a builder and systems designer, not just an operator
• Experience with GTM tech stacks (CRM, automation, analytics tools), AI tools and workflows is a must
• You apply a strong analytical mindset and use data to drive decisions
• You are creative, strategic, and excited about transforming how GTM teams operate
• You are self-motivated, organized, and relentless in overcoming roadblocks
• You thrive in fast-paced, high-growth, and ambiguous environments
• You have experience leading or mentoring others and want to grow as a people leader
• You are an excellent communicator and collaborator
• You take ownership and care deeply about outcomes and team success
• You challenge the status quo and look for step-change improvements, not incremental gains

Responsibilities

• Build and iterate GTM systems, playbooks, and processes to improve execution and scalability
• Own the data, insights, and revenue intelligence layer, using experimentation and AI to drive decisions
• Codify and memorialize playbooks, workflows, and rules of engagement across the funnel
• Partner with sales leadership to drive enablement across AE and BDR teams
• Own the GTM tech stack, including designing and implementing AI-powered workflows and automation
• Partner with Product and Product Marketing to enable sellers with clear, effective GTM execution
• Partner with Sales Leadership to deliver training, coaching, and development
• Partner with Finance on budgeting, compensation plans, and forecasting models
• Partner with SLT to build revenue models, targets, and strategic plans
• Report directly to the Global SVP of Revenue and work closely with Co-Founders, Senior Management, and GTM leadership
• Help manage strategic projects and act as a connector across departments
• Be an excellent writer and communicator
• Dive deep into our ICP (in-house legal teams) to understand their challenges, pain points, and goals
• Identify key areas of operational and systems-driven improvement to deliver measurable outcomes
• Build and implement AI-driven workflows to improve productivity across the GTM funnel
• Own all revenue technology, including evaluation, implementation, and optimization
• Lead and develop the Revenue Operations team into a GTM Engineering function
• Maintain high data integrity across CRM and all GTM systems

Benefits

• Competitive salary & equity – We believe in employee ownership and comfortable compensation for our employees so that they can be as happy and productive as possible without any reservations. In this case, expect an OTE of around $180,000 made up of base salary, paid monthly. In addition, there will be an opportunity for equity.
• 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 (paid as cash if unused) 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 11-50 employees