Location: Nosara, Costa Rica (preferred) or Remote with travel

Reports To: Senior Leadership

Build More Than Financial Systems: Help Build the Future of Regenerative Real Estate!

Shift Living is a regenerative real estate development company on a mission to redefine how communities are conceived, built, and experienced. We believe the built environment should not simply minimize harm, it should actively regenerate people, communities, and the natural world.

Our flagship project, Shift Esperanza, is a 108-acre master-planned regenerative community in Nosara, Costa Rica: one of the world's premier destinations for wellness, nature, and conscious living. The community will ultimately comprise 285 residences, a vibrant commercial village, hospitality offerings, wellness amenities, and thoughtfully designed public spaces that foster connection, health, and belonging.

Unlike traditional developers that compete primarily on location or product, Shift Living is creating an entirely new category of real estate. Our long-term vision is to develop regenerative communities around the world that deliver exceptional environmental, social, and financial outcomes.

Shift Living is founded by Blesso Properties, an award-winning real estate and hospitality firm founded by Matthew Blesso in 1998. Over three decades, Blesso has developed internationally recognized projects across New York, Panama, and Costa Rica that have received numerous design awards, set pricing records, and earned widespread industry recognition.

Today, Shift Esperanza is fully entitled, fully capitalized, under construction, and already generating strong home sales. We are now assembling the leadership team that will help build not only this project, but the visionary company that will scale the concept globally.

Why This Opportunity? 

Most Controller roles are about maintaining financial systems, this one is about helping build an extraordinary company! 

As one of the early finance leaders, you'll work directly with executive leadership across virtually every aspect of the business, from real estate development and hospitality operations to investor reporting, treasury management, capital planning, and strategic decision-making. 

You'll have the opportunity to design scalable financial systems, strengthen organizational infrastructure, and help shape the financial foundation of a company with global ambitions. 

Most importantly, we view this position as the natural leadership pathway toward a future Chief Financial Officer role as Shift Living expands into multiple projects and markets. While advancement is earned through performance, we are intentionally looking for someone with the capability, ambition, and leadership potential to grow alongside the company. 

Highlights include: 

• Join a company building one of the world's most ambitious regenerative real estate platforms.

• Work alongside experienced entrepreneurs, developers, investors, and executive leadership.

• Help build scalable financial systems at the forefront of AI implementation.

• Gain broad exposure to development finance, investor relations, hospitality, treasury, and strategic planning. 

• Profit-sharing potential tied to the success of current and future developments.

• Build a career with meaningful long-term growth while contributing to projects that generate lasting environmental, social, and financial impact. 

About the Role: 

The Controller will lead accounting, financial reporting, treasury oversight, tax coordination, compliance, and financial operations across our businesses in Costa Rica (70%), Panama (20%), and the United States (10%). 

This is a hands-on leadership role requiring both technical excellence and an entrepreneurial mindset. You'll serve as a trusted financial partner to executive leadership, providing accurate reporting, building scalable systems, strengthening internal controls, and delivering the financial insights necessary to support a rapidly growing organization. 

The position currently manages a small accounting team, with responsibility expected to grow significantly as the company expands. 

Key Responsibilities: 

Financial Leadership: 

• Lead accounting operations across all company entities and jurisdictions. 

• Oversee monthly, quarterly, and annual financial reporting. 

• Manage consolidated financial statements and intercompany accounting. 

• Maintain strong internal controls, accounting policies, and financial governance.

Development Finance: 

• Oversee project accounting for real estate development, including budgets, cost tracking, capital expenditures, and development reporting. 

• Support executive leadership with financial modeling, forecasting, and strategic analysis.

• Coordinate lender reporting, debt compliance, construction draws, and investor reporting. 

Asset Management 

• Serve as owner’s oversight in overseeing financial asset management of hospitality assets in Panama. 

Treasury & Tax: 

• Manage treasury operations, cash flow forecasting, liquidity planning, and banking relationships. 

• Coordinate tax compliance and planning with external advisors across Costa Rica, Panama, and the United States. 

• Ensure timely regulatory filings and financial compliance. 

Team Leadership: 

• Lead, mentor, and develop the accounting team. 

• Build scalable financial processes, systems, and standard operating procedures.

• Foster a culture of accountability, accuracy, continuous improvement, and operational excellence. 

Who We're Looking For: 

We're seeking a builder, not simply an accountant.

The ideal candidate enjoys creating order from complexity, embraces ownership, and understands that great finance leaders help shape the future of a business rather than simply report on its past. 

You likely bring: 

• Bachelor's degree in Accounting, Finance, or a related field. 

• CPA or equivalent professional designation strongly preferred. 

• 7+ years of progressive accounting or finance leadership experience. 

• Experience in multi-entity and multi-currency organizations. 

• Experience within real estate development, construction, hospitality, or similarly complex project-based businesses preferred. 

• Strong treasury management, cash flow forecasting, and financial controls experience.

• Knowledge of U.S. GAAP; familiarity with Costa Rican and Panamanian accounting is an advantage. 

• Experience working directly with lenders, investors, auditors, and external tax advisors.

• Entrepreneurial mindset and already well versed in AI. 

• Fluency in English and Spanish. 

• Exceptional integrity, judgment, discretion, and organizational skills. 

• Most importantly, you're someone who wants to build something meaningful. 

How to apply 

Send your resume and a short video (maximum 4 minutes) to talent@shiftliving.com responding the following questions: 

• What about this role excites you. 

• What are your super powers? What makes you special and why do you feel you would be a better fit than other applicants we might receive? 

• What do you hope to be doing in 5 years? 

• Tell us about a financial system you've built or improved from scratch. 

• Tell how you have been innovative or entrepreneurial in your past roles. 

Why Shift Living? 

We believe the future of real estate isn't simply greener buildings. 

It's healthier people. 

Stronger communities. 

More meaningful human connection. 

And developments that regenerate the places they inhabit rather than merely occupy them. If you're looking for another accounting position, this probably isn't the right opportunity. 

If you're excited by the idea of helping build a category-defining company from the inside, and growing into a future financial leadership role as that vision becomes reality, we'd love to meet you!