Director, GTM Systems & Applied AI

Checkr is looking for a strategic leader for its AI-driven GTM transformation. You are a long-term strategic thinker with a deep architectural mind - someone who understands the business motions of marketing, sales, and customer success to see where AI and systems architecture can fundamentally change how those teams operate.

Checkr is at the forefront of AI experimentation in GTM and has already brought the infrastructure live - with an AI-first sales platform, MCP architecture, and a strong data foundation. You’ll guide Checkr into the next phase of AI outcomes by bringing the vision for how our entire GTM technology ecosystem evolves, the prioritization of where to focus first, and the drive, clarity, and consistency to deliver real outcomes. As the Director, GTM Systems and Applied AI, you will report to the VP of Revenue Operations.

Responsibilities:

• Own the GTM systems architecture strategy: Partner with GTM leaders to define and evolve the systems architecture strategy across Sales, Customer Success, Marketing, Business Development, and Solutions Engineering - designing for scale, not just for today
• Lead AI transformation across GTM: Champion the shift toward an AI-first GTM infrastructure. Identify where AI agents, automation, and intelligent workflows can meaningfully change how marketing, sales, and customer success teams operate - from lead-to-cash to renewal and expansion
• Drive scale and optimization: Improving reliability, performance, and adoption of the systems already in place, while identifying the next wave of capabilities to build
• Protect and elevate the data foundation: Ensure data is clean, enriched, and consistently mapped across systems, with the governance and security protocols needed to protect it and make it trustworthy enough to fuel AI models and decision-making
• Align stakeholders and drive clarity: Define the systems architecture strategy to support rapid growth and scaling of our GTM teams 
• Manage and develop a high performing team of developers and engineers

What you bring:

• 10+ years experience working with fast paced companies and a proven track record of delivering high-impact, cross-functional projects
• 5+ years of experience leading and developing high-performing technical teams
• Deep architectural thinking: a demonstrated ability to design reliable, cohesive, well-documented systems that scale - not just point solutions
• Deep comprehension of the business motions across Marketing, Sales, and Customer Success, and the judgment to know where technology and AI can move the needle for each
• Hands-on, "AI-first" fluency: experience applying AI tools, agents, and automation to actual GTM workflows
• Experience managing a complex, multi-system GTM tech stack spanning CRM (Salesforce), marketing automation (Marketo, Hub Spot), and enrichment (ZoomInfo, Clearbit, Clay), and sales engagement tools
• Product-owner mentality with a focus on usability, design, and long-term maintainability
• Ability to work cross-functionally to gain consensus from multiple stakeholders and lead major change efforts
• Comfort operating at both altitudes - big-picture strategy and hands-on, in-the-details execution
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcome