Principal Customer Success Manager

Checkr Trust and Checkr Insurance are fast-growing businesses inside Checkr, serving insurance carriers, marketplaces and other verticals that touch our everyday lives. Demand is building, our customer base is expanding, and we're scaling toward $100M. We're looking for a Customer Success Manager who can help us get there by turning strong customer relationships into deep adoption, durable retention, and meaningful expansion.

You will own a portfolio of strategic accounts and be accountable for:

• Adoption
• Retention
• Expansion
• Executive alignment
• Long-term value realization
  
  

This is a proactive, commercially minded CSM role. You'll be the trusted partner our customers rely on and the owner of outcomes across your book of business. You'll join a team with momentum, playbooks to build on, and room to make them better as we scale. As the business grows, so will the opportunities for you, with real room for personal and career growth.

What You'll Do

Own Strategic Accounts End-to-End:

• Serve as the primary post-sale owner for high-impact, high-visibility customers
• Drive executive-level alignment on business goals and measurable outcomes
• Ensure customers move from contract to meaningful production usage quickly

Drive Adoption & Commercial Growth:

• Identify underutilization and remove barriers to deeper adoption
• Surface expansion opportunities tied to customer workflows and risk exposure
• Partner closely with Sales on renewals and strategic growth motions
• Be accountable for retention and expansion revenue across your portfolio
• Use AI tools to work smarter and scale your impact across accounts

Translate Product Into Business Impact:

• Understand customer workflows well enough to connect product capabilities to operational and financial outcomes
• Lead quarterly business reviews that demonstrate ROI and strategic value
• Turn performance data into actionable insights that shape customer strategy
• Leverage AI to turn data into insights
• Bring the voice of the customer to Product and leadership through structured feedback

Help Us Scale:

• Apply and refine our segmentation, engagement models, and risk signals as the customer base grows
• Strengthen repeatable frameworks for onboarding, renewals, and expansion
• Contribute to the processes and best practices that let the team support more customers without losing quality
• Raise the bar on what great customer partnership looks like as we grow

What You Bring:

You likely have:

• Experience managing a book of enterprise accounts in Customer Success, Strategic Account Management, or a similar post-sale role in B2B SaaS
• Experience owning enterprise or high-growth accounts with meaningful revenue responsibility
• A track record of driving both retention and expansion
• Comfort working with executive stakeholders as well as customer technical teams
• Experience in a high-growth environment
• Curiosity about AI and a habit of experimenting with it in your workflows
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through change, and take ownership of outcomes

You don't need a technical background or a history in a technical account management role. You do need to be sharp and technically comfortable enough to:

• Learn our product and data deeply and explain it clearly to customers
• Work with customers' teams to understand their workflows and what's slowing adoption
• Speak confidently with product and technical stakeholders
• Work in tools like Zendesk, Salesforce, Google Apps, Lovable, and Claude, and BI tools like Looker and Omni

Behaviorally, You:

• Take full ownership of revenue and outcomes
• Push customers forward when momentum slows
• Balance empathy with accountability
• Stay calm and effective in a fast-moving, high-growth business
• Prefer building scalable systems over maintaining the status quo

People describe you as gritty, commercially sharp, resilient, and proactive.

Why This Role:

• You'll play a direct role in scaling a high-growth business toward $100M
• You'll work with sophisticated customers solving complex trust and safety problems
• You'll have real, visible commercial impact on retention and expansion
• You'll help shape how Customer Success scales as the business grows
• You'll have room to grow your own career, with expanded scope and new opportunities as the company grows

This role is demanding. It requires urgency, discipline, and ownership, and it's highly rewarding for someone who wants to grow with a business that's winning.