Greatest Hits Episode- Santiago Aparicio, Ontop- Transforming the future of work, Ep 192

For this week’s episode of Crossing Borders, we’re revisiting one of our greatest hits episodes featuring Santiago Aparicio, CEO, and Co-founder of Ontop.

The future of work is going to be remote and decentralized, according to Santiago Aparicio, Co-Founder and CEO of Ontop, a payroll software startup that allows companies to legally hire and pay anyone in the world. Santiago is a serial entrepreneur and sales passionate who believes in the influence of developing markets in defining the future of work.

After long nights working on Excel sheets back in his banking days, Santiago decided he wanted a change. He reached out to Felipe Villamarin, co-founder at Rappi, and joined the team as its seventh employee, which really helped him to become an entrepreneur.

I sat down with Santiago to talk about his experience as an entrepreneur, while Santiago shared the story of Ontop and their meteoric growth in their first fifteen months (actively operating in over 190 countries, transacting over $2M per month).

Fundraising and starting his first two companies

For Santiago, the next frontier as a salesperson was fundraising, which pushed him to build his first company, Fitpal, a fitness and wellness platform for gyms in Latin America. But after Covid hit, Santiago and his cofounder decided to launch a second company, this time focusing on something becoming increasingly popular: remote working.

Listen to this episode of Crossing Borders to learn how Ontop raised its initial money from founders of all over the region.

Building a sales engine for high growth

Santiago shares why the best salespeople are the ones that focus on the input instead of the output, and how finding the most predictable metrics in the sales funnel are the first steps to create a replicable process that allows a company to grow internationally.

Find out about Santiago’s advice on productizing a sales engine, how to hit network effect, and why you should focus on building something small instead of building something huge in this episode of Crossing Borders

Biggest lessons as an entrepreneur

Santiago offers advice on being kind, passing the ball to the team and being in constant pursuit of the best talent for Ontop. We also discuss the importance of staying grounded and not letting fame get in the way of creating a product that people will really love.

Check out Santiago’s story in this episode of Crossing Borders and find out why you should exercise kindness and the importance of having uncomfortable conversations within a company.

Outline of this episode:
[02:18] - About Ontop
[02:39] - Top line metrics from Ontop
[02:39] - Santiago’s background
[04:53] - On joining Rappi
[07:05] - Launching Fitpal
[08:48] - Santiago’s biggest lessons
[13:54] - Coming up with the idea for Ontop
[14:23] - Fundraising for Ontop
[17:13] - The crazy world of fundraising
[18:42] - On building a sales engine
[19:14] - The best salesman (or woman)
[21:00] - Predictable metrics
[23:52] - The big milestones
[27:33] - Being famous is not being successful
[28:13] - Advice for a younger Santiago
[31:06] - How to hit network effects
[32:48] - The importance of hard conversations
[34:11] - The future of work

Resources & people mentioned:
Santiago Aparicio
Fitpal
Ontop
Measure What Matters by John Doerr - Book
The Hard Thing About Hard Things by Ben Horowitz
Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott