# UPSIDE Insurance Services jobs and careers

> 0 open roles at UPSIDE Insurance Services as of October 23, 2026. Source: https://www.thejobsmap.com/company/upside-insurance-services

UPSIDE Insurance Services is an independent insurance brokerage built on over 20 years of industry expertise. Under the leadership of Drew and Kyndle Cottrell, we’ve grown rapidly—expanding our team, refining our processes, and setting a new standard for how insurance should be delivered. We specialize in serving business owners through commercial insurance and personal insurance solutions, with a commitment to providing service that’s truly out of this world. Our growth is fueled by a relentless focus on client relationships, market expertise, and delivering solutions that protect what matters most. We’re here to Insure Your Universe.

## Key facts

| | |
|---|---|
| Open roles | 0 |
| Headquarters | United States |
| Founded | 2018 |
| Employees | 1 to 10 |
| Industries | Finance, Financial Services, Insurance |
| Website | https://upsideins.com |

## Leadership

- Drew Cottrell, Owner

## Common questions

### Is UPSIDE Insurance Services hiring right now?

UPSIDE Insurance Services has no open roles listed as of October 23, 2026. Roles appear here as soon as they are posted on UPSIDE Insurance Services's careers site.

### Where is UPSIDE Insurance Services headquartered?

UPSIDE Insurance Services is headquartered in United States and was founded in 2018.

### Who leads UPSIDE Insurance Services?

Drew Cottrell, Owner, is at the top of UPSIDE Insurance Services's org chart.

### How do I apply for a job at UPSIDE Insurance Services?

Pick a role on UPSIDE Insurance Services's TheJobsMap page and select Apply. Every listing links to the original posting on UPSIDE Insurance Services's own careers site, so you apply directly with the employer.