Why This Job is Featured on The SaaS Jobs
This Senior Principal Customer Success Manager role sits squarely in the strategic end of B2B SaaS, where outcomes are shaped as much by executive alignment and program design as by day to day support. Managing a small set of largest accounts signals work that influences how an established SaaS platform is adopted across complex customer organizations, with an emphasis on measurable value and long term partnership health.
For a SaaS career, the role offers repeated exposure to the operating mechanics that matter at scale: adoption strategy, renewal risk management, and expansion that emerges from successful implementations. The remit also builds durable cross functional fluency, translating customer priorities into product and engineering inputs and using business reviews to connect product capabilities to ROI narratives. Experience navigating multi stakeholder accounts tends to transfer well across enterprise SaaS categories.
This position best fits a practitioner who prefers consultative account leadership over transactional support, and who is comfortable setting an engagement cadence, synthesizing feedback, and influencing internal teams without direct authority. It aligns with someone who enjoys executive facing communication, structured planning, and using data and tooling to maintain visibility into account health.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
As a Senior Principal Customer Success Manager, you will be the lead advocate and strategic architect for Checkr’s most complex and highest-value partnerships. You will sit on our Strategic Accounts team, managing a select portfolio of our largest, household-name clients. You will work as part of a customer success team responsible for driving product adoption, growth, value, and partnership with our largest customers
Success in this role will be measured by your ability to deepen existing relationships through strategic alignment and by quickly earning the trust of key customer stakeholders. You will work alongside cross-functional professionals who succeed through collaboration, grit, and constant learning. You will also partner directly with the customer’s leadership team through polished communication and strong executive presence, allowing you to act as a trusted advisor and advocate while ensuring the overall health of your accounts.
What you’ll do
- Drive Customer Success: Develop a deep understanding of Checkr's products and strategically apply them to customer programs, ensuring alignment with their goals and driving positive business outcomes.
- Proactive Engagement and Planning: Lead a regular engagement cadence with customers and provide thought leadership and planning to optimize their use of Checkr's products and maximize their success.
- Executive Engagement: Lead Business Reviews and presentations that articulate product value, ROI, and future state.
- Build Trusted Partnerships: Cultivate strong, trust-based relationships with customers at all levels, acting as a strategic advisor and advocate for their needs.
- Champion the Voice of the Customer: Gather and synthesize customer feedback, effectively communicating it to internal teams (Product, Engineering, etc.) to drive product improvements and innovation.
- Facilitate Internal Collaboration: Collaborate seamlessly with internal stakeholders (Sales, Support, Engineering, Product, and Executives) to ensure customer goals are met, provide visibility into customer health, and escalate issues as needed.
- Account Health & Retention: Proactively identify potential risks within complex organizations—such as leadership changes or shifting business priorities—and develop plans to ensure long-term stability and retention.
- Support Account Growth: Partner with Account Management to identify and assist with expansion opportunities that arise naturally from strong customer relationships and successful product implementation.
What you bring
- 8-10 years of Customer Success or Account Management experience with a proven track record of managing high-value (multi-million dollar) accounts.
- Skilled at navigating organizations to maintain and expand relationships at all levels.
- Strong written and verbal communication skills, with the ability to present complex technical or regulatory topics to executive audiences clearly and professionally.
- Bias toward action and ability to extend influence to drive action without direct authority.
- A solid understanding of the mechanics of account growth and renewals within the strategic segment.
- Experience in a B2B software technology company. HR tech industry experience is a plus.
- Familiarity with applications like Salesforce, Google Apps, and basic analytics using tools like Google Sheets and Looker.
- Willing to travel domestically up to 20% as needed for customer-facing or internal team meetings.
- A solid understanding of the mechanics of account growth and renewals within the strategic segment.
What you’ll get
- 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
