Director, GTM Systems

Checkr, Inc.

San Francisco (CA)

On-site

USD 240,000 - 282,000

Full time

11 days ago

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Benefits offered by this job

Learning & development allowance

Competitive cash and equity

Medical, dental, vision coverage

Fertility / adoption support

Flexible PTO

Monthly wellness stipend

Relocation stipend

Job summary

Checkr, Inc. in San Francisco, CA seeks a Director, GTM Systems to architect the Sales, Marketing and Customer Success tech stack and drive AI-first transformations across the GTM workflow.

Lead a cross-functional team, align stakeholders, and deliver scalable systems built on Salesforce, Marketo, HubSpot, ZoomInfo, Clay, and more; report to the VP of Revenue Operations and collaborate across hub locations (SF, Denver, Nashville, Santiago). In-office presence 3+ days per week.

Qualifications

10+ years experience in fast-paced companies delivering cross-functional projects.
5+ years leading and developing high-performing technical teams.
Deep architectural thinking for scalable, cohesive systems.

Responsibilities

Own the GTM systems architecture strategy across Sales, CS, Marketing, BDR, and Solutions Eng.
Lead AI transformation across GTM with AI-first workflows and automation.
Drive scale, reliability, and adoption of existing systems while defining the next capabilities to build.
Protect and elevate the data foundation with governance and security for AI models.
Align stakeholders and drive clarity to support rapid growth of GTM teams.
Manage and develop a high performing team of developers.

Skills

GTM architecture

AI-first workflows

Cross-functional leadership

Multi-system integration

Stakeholder alignment

Team management

Tools

Salesforce

Marketo

HubSpot

ZoomInfo

Clearbit

Clay

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

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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