Advanced Technical Support Specialist

Advanced Technical Support Specialist

Heredia, Costa Rica

About Cornerstone

Cornerstone believes human potential grows exponentially when AI works in service of people. Global Customer Support is where that promise is kept — one customer, one case, one conversation at a time.

At Cornerstone, we’re passionate about helping organizations unlock the full potential of their people. Our customers rely on our technology to develop talent, build skills, and drive business success. Delivering exceptional customer experiences is at the heart of everything we do.

Our Global Customer Support team plays a critical role in bringing that commitment to life. We are relentlessly customer-obsessed, focused not only on resolving issues but also on building trust, driving engagement, and ensuring customers realize the full value of their Cornerstone solutions. We believe every customer interaction is an opportunity to make a meaningful difference, strengthen relationships, and help our customers succeed.

We’re looking for individuals who share our passion for delivering exceptional service, embrace innovation and AI-powered technology, and take pride in making every customer interaction count.

The Role

As an Advanced Product Support Specialist (Level 3), you will serve as a technical authority within Cornerstone’s Global Customer Support organization, providing deep product expertise to resolve our most complex technical challenges and improve the overall effectiveness of our support teams.

Working in a collaborative, AI-enabled support environment, you will leverage advanced troubleshooting capabilities, AI-powered insights, and strong partnerships with Engineering and Product teams to identify root causes, resolve critical issues, and proactively address emerging customer challenges. Rather than managing a traditional case queue, you will focus on the most complex, high-risk, and aging cases where your expertise can make the greatest impact.

You will also play a critical role in developing technical capabilities across the team, strengthening product knowledge, and ensuring our customers receive exceptional support that builds confidence, drives engagement, and maximizes the value of their Cornerstone solutions.

In This Role You Will…

• Serve as the technical authority for your assigned product area, proactively identifying and taking ownership of the most complex, high-risk, and aging support cases to drive timely and effective resolution.
• Lead advanced technical investigations, performing in-depth root-cause analysis to identify underlying product defects, configuration challenges, and integration issues.
• Partner closely with Engineering and Product teams to validate defects, ensure accurate reproduction steps, and support prioritization and resolution through established defect management processes, including OneList.
• Leverage AI-powered tools, customer sentiment insights, and support analytics to identify recurring issues, improve troubleshooting effectiveness, and proactively address opportunities to enhance the customer experience.
• Own technical knowledge development for your product area, identifying knowledge base gaps, contributing to certification content, and leading technical deep-dive sessions to strengthen team capabilities.
• Mentor and coach Level 2 support specialists, using case quality insights and Level AI performance data to identify development opportunities and improve technical problem-solving across the team.
• Provide technical expertise on critical customer escalations, partnering with escalation management teams, including DEEP, to validate solutions and ensure accurate, effective resolution.
• Partner directly with the Pod Director to identify technical risks, improve support processes, and strengthen overall pod performance, including case aging, backlog health, defect quality, and customer satisfaction.

You’ve Got What It Takes If You…

• Have 5+ years of experience in advanced technical support, SaaS product support, or a similar technical role, with deep expertise in complex enterprise software environments.
• Possess advanced troubleshooting and root-cause analysis skills, with demonstrated experience resolving complex product, integration, configuration, and data-related challenges.
• Are recognized as a trusted technical expert who can confidently diagnose complex issues, validate solutions, and guide others through challenging technical situations.
• Have experience collaborating with Engineering and Product teams to investigate defects, document technical findings, and drive effective issue resolution.
• Are comfortable leveraging AI-powered tools, support analytics, and customer sentiment data to identify trends, improve technical support quality, and drive operational improvements.
• Demonstrate strong mentoring, communication, and knowledge-sharing skills, with the ability to develop technical capabilities across a team and influence others without direct authority.
• Are proactive, collaborative, and customer-obsessed, with a strong sense of accountability and a commitment to delivering exceptional customer outcomes.
• Are committed to completing required Expert-tier certification within your first 90 days, maintaining deep expertise in your primary product area, and expanding your knowledge across related Cornerstone solutions.