Senior Product Support Specialist

We're looking for a

Senior Product Support Specialist

This role is Hybrid, 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 a Senior Product Support Specialist (Level 2), you will serve as a technical expert within Cornerstone's Global Customer Support organization, resolving complex product challenges and delivering advanced guidance that helps customers maximize the value of their Cornerstone solutions.

Working in a collaborative, AI-enabled support environment, you will leverage AI-powered tools, deep technical expertise, and advanced troubleshooting capabilities to resolve complex issues involving integrations, APIs, data, and product configurations. You will also serve as a trusted expert through our Pro Desk offering, providing personalized guidance that strengthens customer confidence, drives product adoption, and improves the overall customer experience.

This role offers the opportunity to expand your technical expertise, mentor fellow support specialists, and play a key role in delivering exceptional customer outcomes.

In This Role You Will...

• Own and resolve complex technical support cases involving integrations, APIs, data issues, and multi-module configurations, ensuring effective resolution and customer satisfaction.
• Deliver expert guidance through Pro Desk, leading scheduled one-on-one customer sessions to troubleshoot challenges, share product expertise, and help customers maximize the value of their solutions.
• Provide advanced real-time support through escalated live chat and phone interactions, resolving critical issues with urgency, professionalism, and a customer-first mindset.
• Leverage AI-powered tools and copilots to accelerate technical research, improve troubleshooting, draft and validate customer responses, and deliver efficient, high-quality support.
• Investigate and reproduce complex product defects, documenting technical findings, logs, reproduction steps, and customer impact to support engineering prioritization and resolution.
• Mentor and support Level 1 specialists by sharing technical knowledge, providing timely escalation assistance, and taking ownership of complex cases when needed.
• Collaborate with Engineering, Product, and internal support teams to resolve recurring technical issues, identify knowledge gaps, and improve support processes and documentation.
• Meet established productivity, customer satisfaction, and Pro Desk session quality expectations while continuously building technical expertise and improving the customer experience.

You've Got What It Takes If You...

• Have 3+ years of experience in technical support, SaaS product support, or a similar technical customer-facing role, with demonstrated experience resolving complex technical issues.
• Possess strong troubleshooting skills and hands-on experience working with APIs, integrations, SSO, system logs, data flows, and advanced software configurations.
• Are passionate about delivering exceptional customer experiences and helping customers successfully adopt and maximize the value of technology.
• Have excellent written and verbal communication skills, with the ability to explain complex technical concepts clearly to customers and colleagues.
• Are comfortable leveraging AI-powered tools, technical research platforms, and case management systems to improve troubleshooting efficiency and customer outcomes.
• Demonstrate strong collaboration and mentoring skills, with a willingness to share knowledge and help develop less experienced support specialists.
• Remain calm and solution-oriented during complex escalations, with strong attention to detail and the ability to document technical findings and customer interactions thoroughly.
• Are committed to completing required Pod Specialist certification within your first 45 days, maintaining certification with product releases, and continuously expanding your expertise across multiple Cornerstone products.

Our Growing Presence in Costa Rica

Cornerstone is excited to be building a new hub in Costa Rica as part of our continued investment in growing our global talent and capabilities. We are bringing together teams across a variety of functions, creating exciting opportunities for people to join us at the ground floor of this new chapter and help shape how we grow in the region.

We have invested in a new office in Costa Rica, with construction beginning soon, and we expect our presence and capabilities in the region to continue expanding over time. For those joining us now, this is a unique opportunity to help build something from the beginning, work alongside talented colleagues across Cornerstone globally, and be part of our longer-term growth in Costa Rica.

Employment Structure

As we establish our operations in Costa Rica and complete the process to operate under the country’s Free Trade Zone Regime, Cornerstone is partnering with Recluta, our local Employer of Record (EOR).

Our Culture

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

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