Revenue Operations Lead

Checkbox TechnologyNew York, NY
$130,000 - $150,000Hybrid

About The Position

The Revenue Operations function is critical to Checkbox's future growth, responsible for both fine-tuning existing systems, playbooks, and strategies, ideating and codifying new ones, and being a detail-oriented project manager. This role is inherently cross-functional, supporting multiple functions and leaders, and driving change across the business. The ideal candidate loves executing and building process for scale, is obsessed with data and A/B testing, and exhibits intense levels of grit, determination, enthusiasm, and strategy. This role will partner with the existing Revenue Operations team to build a world-class operations function. The position reports directly to the Director of Finance and works closely with Senior Management and GTM leadership. Key outcomes include building and iterating systems, playbooks, and processes to improve GTM execution, owning data and outcomes, testing new strategies, codifying playbooks, owning the GTM tech stack, and partnering with finance on budgeting and compensation plans. The role also involves partnering with GTM Engineering to build durable systems for automation and utilizing AI to streamline processes. The successful candidate will be an excellent writer and orator, identify operational improvements, partner with product teams to enable sellers, and own all RevOps technology. They will also partner with Finance to manage Revenue team data and drive insights to hit targets, maintain CRM records, and deeply understand the Ideal Customer Profile (ICP) of in-house legal teams.

Requirements

  • 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
  • Proven to thrive in an entrepreneurial environment that absorbs rapid change and disruption
  • Comfortable shipping v1s quickly and rapidly iterating to solve evolving problems
  • Familiar with current AI tooling and can build AI workflows and automations
  • High character, consistently displaying integrity, high effort, and enthusiasm for the work
  • Believe in being unique, and that transparency and radical honesty sell better than perfection
  • Apply a strong analytical mindset to your work and leverage data to drive decisions
  • A learner and display a desire to learn the challenges facing legal teams, and opportunities for efficiencies and operational improvements
  • Creative, driven, and reliable
  • Willing to consistently go beyond the call of duty for the team, and to challenge the status quo to help Checkbox be better
  • Self-motivated, relentless, organized, and determined to overcome roadblocks
  • Demonstrated success in managing complex projects with multiple stakeholders
  • Demonstrated success in maintaining strong, long-lasting relationships and the ability to inspire trust and confidence in others
  • Outcome-oriented, adaptable, collaborative, memorable and personable
  • Take ultimate ownership over the success of your work
  • Enable your teammates to be more successful at Checkbox
  • Make every decision with an eye towards employee experience and ultimately driving performance

Nice To Haves

  • Bonus points for vibecoding

Responsibilities

  • 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
  • Manage strategic projects and build systems to connect GTM departments
  • Build automation and utilize AI to streamline existing processes and systems
  • 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

Benefits

  • Competitive compensation (OTE of 130-150k)
  • Health insurance, including dental and vision
  • 401K match
  • 20 days paid leave a year
  • Parental leave, including secondary carer
  • Hybrid working arrangements
  • Personal learning & development budget
  • Expense policy for small work-related items and salary sacrifice for larger items
  • Company wide social events (e.g., off-sites, boat parties, mansion stays, trips to Bali)
  • Transparent & open culture
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