Director, GTM Systems & Applied AI

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

About Checkr
Checkr is building the data platform to power safe and fair decisions. Over 140,000 companies and millions of people rely on Checkr for AI verification in the moments that matter most: getting a new job, a new place to live, a car ride, childcare, even a date. Customers include Uber, Pennymac, Airbnb, Doordash, and Anthropic.

We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.

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, 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

Pay Transparency Disclosure

We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website .

On-target Earnings OR Base Salary range (San Francisco, CA)

$240,000 - $282,000 USD

What We Offer

• 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

At Checkr, we believe an in office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. 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.

Equal Employment Opportunities at Checkr

Checkr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance .

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