The barbell at Expensify

In partnership with

Leadership in the US. Sales execution in LATAM.

Named with permission.

2 issues ago I made the argument for the barbell.

Last issue I priced it.

Today, a company that runs it, named with written permission.

Expensify.

Founded in 2008. Listed on Nasdaq. 15 million members.

The sales execution team sits in LATAM, hired through CloudTask and other partners.

The org

48 Account Executives.

Expensify scaled the team from 24 to 48 AEs after going public.

The AEs have now averaged more than 5 years of tenure. Expensify has worked with CloudTask for 8 years.

They sell to US customers during US hours.

They report to a sales leader in the US, and that leader owns the number.

Pay works like a sales team: base plus commission on won deals.

That last line matters.

A team paid on won deals is a revenue team, not a support desk.

Why a public company builds it this way

Expensify reports results every quarter. Every seat shows up in the numbers.

The strategic layer stays where the customers, the capital, and the product decisions are.

The execution layer sits where the same work costs less and the time zone matches.

Expensify also ships AI into its own product.

In June 2026 it launched an MCP integration connecting Expensify data with AI tools including ChatGPT, Claude, and Cursor.

It still hires people to sell.

That is the split from the last 2 issues inside 1 company.

Repeatable work goes to software.

Conversations go to people.

A meaningful part of that human execution layer sits in LATAM.

The test from last issue

Do the savings across the execution team cover the strategic hire?

We do not publish a client's compensation. Run the table from last issue against your own org.

The answer at Expensify is a sales team with 5+ years of average tenure and an 8-year relationship with CloudTask.

The trap

Reading Expensify as a cost story.

It is a management story.

A US leader owns the number. The LATAM team has a manager with time to coach. Commission points both locations at the same outcome.

Copy the org chart without the manager and you get 2 teams that each assume the other owns the result.

David Barrett, CEO of Expensify:

“LATAM has been a gold mine for talent. Our CloudTask hires understand our company culture and mission, and they connect with our customers in a way that drives high NPS and CX scores.”

We place both sides of this org.

US sales leaders on direct hire.

LATAM execution teams at a single all-in monthly rate.

Reply “ORG” with your next 5 hires. Include what each person will own and who they will report to.

I read every reply and send back the split: US direct hire, LATAM hire, or removed by AI.

Michael Sanchez
VP Sales, CloudTask

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