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

Requirements

• 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

Benefits

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive cash and equity compensation, and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend
• In office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location.