# Remote Year funding: rounds and investors

> Remote Year has raised $17M across 2 rounds since 2016. Investors include Highland Capital Partners and Lightbank. Every round with its source.

Source: https://millionrounds.com/company/remote-year (Millionrounds; every figure on the page links to its filing or article)

United States · [Funded startup](https://millionrounds.com/companies)

# Who invested in *Remote Year*

2 rounds we have observed, with the 2 investors named in them. Every figure came from a named source, and where the company reported a raise to the SEC itself, that is shown beside it.

Consumer Services Travel & Hospitality

Funding summary Updated 26 Oct 2026

**$17M** raised across 2 rounds since 2016, from 2 sources

**$12M** Round **$5.0M** Round

- **Latest round:** Round, $5.0M Oct 2019
- **Led by:** Lightbank
- **Biggest round:** $12M Round · Oct 2016
- **Investors:** 2 (1 led)

See who backed them

## The funding story

Each circle is a round, placed by date and sized by amount. The line above is the running total.

2017 2018 2019

**$12M** Round

**$5.0M** Round

- **First round:** Round, $12M
- **Biggest round:** $12M
- **Between rounds:** 3 years

## The rounds

- **Oct 2019** Round **$5.0M** *1 new* *1 returning* [Lightbank](https://millionrounds.com/fund/lightbank) Lead [Highland Capital Partners](https://millionrounds.com/fund/highland-capital-partners) Reported by Pulse2 SEC filing: $7.0M sold, first sale Aug 2019
- **Oct 2016** Round **$12M** *1 new* [Highland Capital Partners](https://millionrounds.com/fund/highland-capital-partners) Reported by FinSMEs

## Founders and team

From the SEC filings it signed: 3 on the team.

- **Gregory Caplan** Executive Officer, Director i
- **Sam Matthew** Executive Officer i
- **Sam Pessin** Executive Officer i

On the board, as filed i *Craig Driscoll* *Earl Grossman* *Eric Ong* *Mike Mauceri*

## Who was in which round

The busiest backers across the latest rounds. A filled square is a round they joined; a dark one, a round they led.

**Round** 2016 **Round** 2019 [Highland Capital Partners](https://millionrounds.com/fund/highland-capital-partners) [Lightbank](https://millionrounds.com/fund/lightbank) L

## Everyone who backed them

[Highland Capital Partners](https://millionrounds.com/fund/highland-capital-partners) VC firm **2** rounds

[Lightbank](https://millionrounds.com/fund/lightbank) VC firm **1** round, led 1

Missing a round, or an investor who was in one? [Tell us](https://millionrounds.com/corrections?slug=remote-year).

## Quick answers about Remote Year

### Who invested in Remote Year?

Remote Year's investors include Highland Capital Partners and Lightbank. Lightbank led its latest round.

### How much has Remote Year raised?

Remote Year has raised $17M across 2 rounds since 2016.

### When did Remote Year last raise?

Remote Year's most recent round was an Undisclosed round of $5.0M in Oct 2019, led by Lightbank.

### What was Remote Year's biggest round?

Remote Year's largest round on record is $12M (Undisclosed round), in Oct 2016.

### Who backed Remote Year first?

Remote Year's first round on record, in Oct 2016, was backed by Highland Capital Partners.

### What stage is Remote Year at?

Remote Year's latest named round is an Undisclosed round, in Oct 2019.

### Where is Remote Year based?

Remote Year is based in the United States.

### Who led Remote Year's rounds?

Lightbank led the Undisclosed round in 2019.

## Companies like Remote Year

In the same sector, and raised in the last eighteen months.

[**Rosie** $7.0M · Oct 2026](https://millionrounds.com/company/rosie)[**Chariot Claims** $23M · Oct 2026](https://millionrounds.com/company/chariot-claims)[**Stride** $16M · Oct 2026](https://millionrounds.com/company/stride)[**Intellivisa** $3.0M · Oct 2026](https://millionrounds.com/company/intellivisa)[**Dextr AI** $6.7M · Sept 2026](https://millionrounds.com/company/dextr-ai)[**Spotnana** $77M · Sept 2026](https://millionrounds.com/company/spotnana)

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