Chief of Staff to the CEO — Finance & Strategy (Bilingual, Bogotá)

Cielo Travel · Safe Transfers Colombia

Bogotá, Colombia · Full-time · Hybrid: Zona T office + remote · Reports to: CEO

It's Tuesday morning. Our CFO needs September's numbers reconciled by Thursday. A strategic partner sent a due diligence questionnaire on Friday and nobody has opened it. The forecast has three assumptions no one has verified. And the CEO is boarding a flight.

Someone has to own all of it — precise, fast, bilingual, and discreet.

That's this role.

I'm Shawn Christopher Hiner Leamon, founder and CEO of Cielo Travel and Safe Transfers Colombia. This role reports directly to me, and I wrote this post myself.

Cielo Travel is a Bogotá-based travel technology company with two brands and a team of about thirty people. Safe Transfers Colombia is the country's English-first premium airport transfer service, trusted by hotels, embassies, corporate travelers, and international families, with more than 1,200 five-star reviews. Cielo.Travel is our tours and experiences brand. Underneath both runs the technology platform we built ourselves — instant pricing, automated dispatch, AI-native operations — designed to become the operating infrastructure for premium travel in Latin America.

We are preparing the company for its next stage of growth, and everything about how we run — the numbers, the documentation, the relationships with investors, partners, and advisors — has to be institutional-grade before we get there. This role sits at the center of that.

Right now, the numbers, the reporting, and the company's most important strategic projects live between me and our fractional CFO, squeezed in around everything else we run. That is the most expensive time in the company spent on work that needs one owner with a clear desk and a sharp model.

This role is that owner. You are my right hand on the numbers, the documentation, and the conversations that decide the company's next stage.

Two years in this role will teach you what ten years in a bank won't: how a real company gets built, run, and made ready for its most demanding investors and partners — from the inside, next to the person making the decisions. You'll work with the CEO and the CFO every day, with our lawyers and advisors every week, and on the projects that decide what this company becomes. And you'll be paid on the results, not on the hours.

Every month, the company's numbers — verified with our CFO, defined the same way every time, and turned into the update our investors and board actually read. You own the calendar, the accuracy, and the story the numbers tell.

The company's documentation, built to the standard a bank, an investor, or a strategic partner expects: corporate records, contracts, financials, technology documentation, all organized and current. You find the gaps before someone else's lawyer does, and you close them.

Unit economics, forecasts, and the model a professional analyst will take apart line by line. You build the version that survives that meeting.

The conversations and projects that decide the company's next stage — with investors, partners, and advisors. Research, preparation, materials, follow-ups, and the discipline that keeps nothing from falling through. Every conversation is logged; every loop is closed.

Competitive research, partner research, board materials, and the projects that don't fit anywhere else — usually the ones that matter most.

There is no ninety-day ramp. From the first week, the numbers go out on time and verified, the documentation gets organized to a standard a professional can review without basic questions, the model gets built and signed by our CFO, and every strategic conversation has its follow-up done. Success is simple to describe: the CEO stops being the bottleneck on the things that matter most, and it happens fast.

• Very good with numbers. Excel is home, and you build models people trust.
• Fast and organized. You work from a list, you close loops, and you don't need reminding.
• Discreet. You will handle confidential information every day, and you treat that as normal.
• Bilingual in a polished way. Professional-grade English and fluent Spanish.
• Hungry. You want the seat where results are visible and rewarded, early in a strong career.
• Comfortable with modern tools: spreadsheets, CRMs, and AI as a force multiplier.
  

• 2–4 years in investment banking, transaction services, consulting, private equity, or a startup finance role
• Strong Excel and financial modeling
• Fluent Spanish and strong professional English, written and spoken
• Based in Bogotá
• CV must be in English
  

This role is built for someone early in a strong career, not a twenty-year veteran, and the compensation reflects that: a fair base salary plus a meaningful success bonus tied to the outcomes of the strategic projects you drive. The base gets you started. The results are where you get paid. When the company hits the milestone, so does your bonus.

You will be hired by me, not by a committee, and I will be deliberate about it. Expect several rounds, and expect most of them to be tests of skill rather than conversations about personality: a financial modeling exercise with real numbers, a written analysis, a reporting exercise, and then real conversations with me. Skills get you to the final round; attitude and fit decide it. Reference checks before any offer. In return: clarity at every step, honest feedback, and no ghosting.

How we work

We work in English with investors and partners, and in Spanish with the team. Everyone posts a daily update and works one thing at a time. You report directly to the CEO.

Related titles: Chief of Staff · Finance & Strategy Associate · Corporate Finance Analyst · FP&A Analyst · Strategy Associate