Head of AI-Driven GTM Systems & Architecture

Checkr; San Francisco (CA); On-site; USD 240,000 - 282,000; Full time

Benefits offered by this job

100% medical, dental, and vision

Learning and development allowance

Competitive cash and equity

Relocation stipend may be available

Flexible PTO

Monthly wellness stipend

Job summary

Checkr is seeking a Director, GTM Systems to shape the next era of AI-enabled revenue operations. You will define the systems architecture across Sales, Customer Success, Marketing, and Solutions Engineering, balancing scale with usability and reliability.

Lead AI-first transformation, drive adoption of an integrated GTM stack (Salesforce, Marketo, HubSpot, ZoomInfo, Clearbit, Clay), and build a high-performing team delivering measurable outcomes for revenue growth.

Qualifications

• 10+ years experience in fast-paced companies and delivering cross-functional projects.
• 5+ years leading and developing high-performing technical teams.
• Deep architectural thinking to design scalable, cohesive systems.
• Understanding of Marketing, Sales, and Customer Success motions.
• Hands-on, AI-first fluency in GTM workflows.
• Experience with a multi-system GTM tech stack (CRM/Marketing/Enrichment).
• Product-owner mindset focused on usability and maintainability.
• Ability to drive consensus across stakeholders.
• Comfort with both big-picture strategy and hands-on execution.
• Bias for action and ownership to deliver outcomes.

Responsibilities

• Own the GTM systems architecture strategy across Sales, Customer Success, Marketing, Business Development, and Solutions Engineering.
• Lead AI transformation across GTM, introducing AI agents and automation to workflows.
• Drive scale, reliability, and adoption of existing systems while planning next capabilities.
• Protect and elevate the data foundation with governance and security protocols.
• Align stakeholders and define strategy to support rapid GTM growth.
• Manage and develop a high performing team of developers and engineers.

Skills

Cross-functional leadership

Strategic thinking

AI-first mentality

Architectural thinking

Stakeholder alignment

Change management

Tools

Salesforce

Marketo

HubSpot

ZoomInfo

Clearbit

Clay

Sales engagement tools

Job description

Checkr is seeking a Director, GTM Systems to shape the next era of AI-enabled revenue operations. You will define the systems architecture across Sales, Customer Success, Marketing, and Solutions Engineering, balancing scale with usability and reliability.

Lead AI-first transformation, drive adoption of an integrated GTM stack (Salesforce, Marketo, HubSpot, ZoomInfo, Clearbit, Clay), and build a high-performing team delivering measurable outcomes for revenue growth.