Senior Director Professional Services

We're looking for a

Senior Director Professional Services - Costa Rica

This role is Hybrid, Costa Rica

The opportunity
Cornerstone is seeking a Costa Rica-based Senior Director to lead Professional Services across the Americas and build Costa Rica into a strategic delivery hub within our global Services organization. This leader will own regional performance across Services Sales and Delivery while establishing the local team, leadership structure, operating model, and culture required to scale customer value.
This is a builder-operator role with full accountability for the existing Americas Services business and the creation of new capacity in Costa Rica. The leader must strengthen today’s operation while transforming how we sell, staff, govern, and deliver services—without compromising customer commitments, commercial performance, delivery quality, or team engagement.
What you will own
• Lead the Americas Services business. Set regional priorities and operating plans across Services Sales and Delivery, with accountability for bookings, pipeline conversion, revenue, margin, utilization, capacity, delivery predictability, customer experience, and talent.
• Build and scale the Costa Rica organization. Create the workforce plan, organization design, leadership structure, recruiting and onboarding approach, operating rhythms, and culture needed to establish a high-performing Professional Services team in Costa Rica.
• Operate one integrated regional model. Define how Costa Rica and the broader Americas organization work together across pursuit support, scoping, solution design, staffing, delivery, knowledge management, governance, and escalations.
• Improve customer outcomes and time-to-value. Raise the standard for implementation planning, executive sponsorship, risk management, customer communication, adoption, and value realization. Ensure teams manage to business outcomes—not simply project completion.
• Strengthen commercial discipline. Partner with Sales and Customer Success to improve services attach, scope quality, estimation, pricing, contracting, expansion identification, and the conversion of bookings into predictable revenue and successful delivery.
• Build a scalable delivery ecosystem. Integrate regional teams, global Centers of Excellence, and delivery partners through clear roles, quality standards, capacity plans, handoffs, and accountability. Use partners strategically while protecting the customer experience and Cornerstone’s delivery standards.
• Modernize delivery with AI and automation. Apply AI, digital workflows, reusable assets, and knowledge management to increase consultant leverage, implementation speed, consistency, quality, and operational efficiency.
• Develop leaders and a high-performance culture. Coach managers, build succession and critical capabilities, attract and retain strong talent, and create an inclusive culture grounded in customer ownership, accountability, learning, and collaboration.
• Lead through change. Provide clarity, transparency, and stability as the organization evolves. Make thoughtful tradeoffs, address performance directly, and maintain momentum across a geographically distributed team.
• Represent Services with customers and executives. Build credibility with senior customer stakeholders, lead critical engagements and escalations, and influence cross-functional decisions across Sales, Customer Success, Support, Product, Partners, Finance, and People teams.
What success looks like in the first 12 months
• A clear Costa Rica strategy, organization design, leadership structure, workforce plan, and phased build roadmap are approved and underway.
• The Costa Rica team is recruiting, onboarding, and ramping against plan, with defined capability, quality, productivity, and engagement measures.
• The established Americas organization has clear priorities, stronger leadership routines, and stable customer and business performance through the transition.
• Services Sales and Delivery operate with improved scoping, forecasting, capacity planning, handoffs, and accountability for customer outcomes.
• Regional dashboards and operating reviews provide reliable visibility into bookings, revenue, margin, utilization, backlog, delivery health, customer risk, quality, and talent.
• Customers experience more predictable implementations, faster time-to-value, clearer executive engagement, and fewer avoidable escalations.
• AI-enabled workflows and reusable delivery assets demonstrate measurable gains in speed, consultant productivity, consistency, or quality.
• A stronger leadership bench and connected regional culture are taking hold across Costa Rica and the broader Americas team.
What you bring
• Services leadership at scale. Substantial leadership experience in enterprise software, SaaS, cloud, or technology-enabled Professional Services, including ownership of a regional or comparably complex delivery business.
• Builder and transformation experience. A track record of establishing a new delivery location, scaling a regional capability, or materially transforming a Services organization while maintaining active customer and financial commitments.
• Commercial and operational fluency. Strong command of bookings, pipeline, revenue, margin, utilization, capacity, backlog, forecasting, quality, and customer experience—and the ability to convert data into timely action.
• Customer-outcome orientation. Demonstrated success improving implementation predictability, time-to-value, adoption, executive alignment, and customer outcomes in complex enterprise environments.
• Organizational leadership. Experience leading distributed, multicultural teams; building capable leaders; managing organizational change; and creating accountability across locations and functions.
• Cross-functional influence. The credibility and judgment to align senior stakeholders across Sales, Customer Success, Support, Product, Partners, Finance, and People teams without relying solely on formal authority.
• Partner ecosystem experience. Experience using systems integrators or delivery partners to extend capacity and capability, with disciplined governance for quality, economics, enablement, and customer experience.
• Digital and AI mindset. Practical experience applying AI, automation, knowledge management, or digital delivery methods to improve Services productivity and customer value.
• Executive presence. Strong communication, decision-making, and customer leadership skills, including the ability to navigate high-stakes engagements and ambiguity with clarity and composure.
Location and travel
This role must be based in Costa Rica and will play a visible role in building Cornerstone’s local organization and culture. The position requires the flexibility to work across Americas time zones and travel periodically for customer, team, and leadership engagements.

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.

Check us out on LinkedIn, Comparably, Glassdoor, and Facebook!