Customer Success Director

RegScale is a continuous controls monitoring (CCM) platform purpose-built to deliver fast and efficient GRC outcomes. We help organizations break out of the slow and expensive realities that plague legacy GRC tools by bridging security, risk, and compliance through controls lifecycle management. By leveraging CCM, organizations experience massive process improvements like 90% faster certification times, and 60% less audit prep time. Today’s expansive security and compliance requirements can only be met with a modern, CCM based approach, and RegScale is the leader in that space.

Position:

We are seeking a Customer Success Director to own outcomes for RegScale's largest and most strategic accounts. This is a senior individual-contributor role - you will act as the most experienced voice in the Customer Success organization, serving as trusted advisor, escalation lead, and mentor across the team, while reporting directly to the VP of Customer Success.

You will carry a portfolio of our highest-value and most complex accounts, set the strategic playbooks the rest of the Customer Success team runs on, and represent the voice of the customer in senior cross-functional conversations with Sales, Product, Marketing and Services leadership.

This is a high-impact role for someone who thrives in a fast-paced startup, loves solving hard problems, and is passionate about making customers successful. If you're a relationship-builder who knows how to translate business goals into platform value, and you're ready to help shape the future of GRC, we'd love to meet you.

This position is fully remote with an option of being based in our Knoxville or DC area offices. Up to 30% travel to customer sites is anticipated.

Key Responsibilities:

• Own the end-to-end success strategy for RegScale's largest and most strategic Federal accounts, acting as executive sponsor and primary point of contact for C-level stakeholders.

• Serve as the senior escalation point for the Customer Success organization, stepping in on the most complex or highest-risk account situations.

• Lead customer-facing engagements such as Executive Business Reviews (EBRs), roadmap discussions, and renewal strategy for the strategic segment.

• Partner with the VP of Customer Success to set team-wide KPIs for adoption, retention, renewal, and expansion.

• Build and continuously refine the scalable playbooks and operating rhythms used by Customer Success Managers and Customer Success Engineers

• Provide informal mentorship and strategic guidance to Customer Success Managers and Junior Customer Success Managers on complex account situations.

• Represent the voice of the customer in senior cross-functional forums, driving product enhancements and process improvements.

• Partner with Sales on strategic renewals, expansion opportunities, and account planning for top-tier accounts.

• Own success delivery, account health scoring, and proactive risk and churn-mitigation strategy for the portfolio.

• Comfortable working directly in the platform to show capabilities, diagnose adoption barriers and recommend how customers should set up their compliance programs, such as control mapping, assessments, POA&Ms and continuous monitoring

• Understands how RegScale connects to the customer’s security stack (vulnerability scanners, asset inventories, ticketing, cloud providers) through APIs and integrations. Can work out whether an issue is a configuration, data or product problem before escalating.

Required Skills:

• Strong analytical and operational mindset; comfortable building and refining scalable processes from the ground up.

• Excellent executive-level communication, negotiation, and presentation skills.

• Deep understanding of SaaS business models, recurring revenue metrics, and customer lifecycle management.

• Solid understanding of security, risk, or compliance domains.

• Ability to translate platform capabilities into measurable business outcomes for senior stakeholders.

• Proficiency in tools like Salesforce, Jira, PlanHat (or similar customer success platforms), and collaboration tools.

• Experience administering or configuring a SaaS platform, working with APIs or integrations, or a technical certification (e.g., Security+, CISSP, cloud certifications)

Required Qualifications:

• 8+ years of experience in Customer Success, Account Management, or related customer-facing roles in a B2B SaaS company, including experience owning strategic or enterprise accounts.

• Background in governance, risk, and compliance (GRC), cybersecurity, or enterprise SaaS delivery.

• Demonstrated experience managing C-level relationships and leading executive business reviews.

• Familiarity with frameworks such as NIST RMF, FedRAMP, or CMMC strongly preferred.

• Bachelor's degree required; advanced degree or relevant certifications (CSM, PMP, CISSP, etc.) a plus.

• Experience working with U.S. Federal government agencies, programs, or contractors preferred.