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Salary: USD 240,000 - 0 / annual
Checkr is a data platform powering safe and fair decisions through AI verification. The company serves over 140,000 companies and millions of people, with customers including Uber, Airbnb, DoorDash, and Anthropic. Checkr is recognized on the Forbes Cloud 100 2025 list and is a Y Combinator 2024 Breakthrough Company.
As Director of GTM Systems & Applied AI, you will lead Checkr's AI-driven go-to-market transformation, reporting to the VP of Revenue Operations. This is a strategic leadership role focused on architecting and evolving the GTM technology ecosystem to leverage AI and systems thinking at scale.
Key responsibilities include:
- Own the GTM systems architecture strategy across Sales, Customer Success, Marketing, Business Development, and Solutions Engineering, designing for scale and future growth
- Champion the shift toward an AI-first GTM infrastructure, identifying where AI agents, automation, and intelligent workflows can meaningfully transform how teams operate—from lead-to-cash through renewal and expansion
- Drive scale and optimization of existing systems while identifying the next wave of capabilities to build
- Protect and elevate the data foundation, ensuring data is clean, enriched, and consistently mapped across systems with proper governance and security
- Align stakeholders and drive clarity around systems architecture strategy to support rapid GTM scaling
- Manage and develop a high-performing team of developers and engineers
You bring 10+ years of experience at fast-paced companies with a proven track record of delivering high-impact, cross-functional projects. You have 5+ years leading and developing technical teams. You possess deep architectural thinking—designing reliable, cohesive, well-documented systems that scale. You understand the business motions of Marketing, Sales, and Customer Success, with judgment about where technology and AI create real impact. You have hands-on AI-first fluency and experience applying AI tools, agents, and automation to GTM workflows. You've managed complex, multi-system GTM tech stacks spanning CRM (Salesforce), marketing automation (Marketo, HubSpot), enrichment tools (ZoomInfo, Clearbit, Clay), and sales engagement platforms. You operate comfortably at both strategic and tactical levels, with a product-owner mentality focused on usability and long-term maintainability. You work cross-functionally to build consensus and lead major change efforts with urgency, resilience, and ownership.
