Live Operations Specialist

Chicago, IL
As Instawork's Live Operations Specialist, you will help ensure that our Partners and Professionals have a magical day of experience and also help the operations team with fulfilling any urgent gigs. The right candidate is always looking to resolve problems with exceptional communication while building trust in the community and has a good sense of intuition. This is an hourly contract role with potential for full-time employment.


    • Manage real-time operations for gigs on the Instawork platform to provide our Partners and Professionals a positive experience before and during their gigs
    • Resolve urgent issues to ensure gigs are fulfilled, communicating with our customers by using various support platforms (email, chat, phone)
    • Communicate proactively with Professionals to ensure that they’re prepared for any gigs that day and also with Partners to ensure all of their day of needs are met
    • Help the operations team with fulfilling urgent gigs due to last-minute posting or cancellations
    • Be able to learn and master multiple internal systems 


    • Flexible availability and scheduling
    • Shift coverage may require early mornings, evenings and/or weekends with opportunity to work from home
    • 1+ years of experience
    • Ability to thrive in a fast-paced environment
    • Strong customer empathy and care for our customers
    • Enthusiastic and positive attitude
    • Resourcefulness
    • Strong writing and verbal skills
    • Bilingual English/Spanish is a plus


    • Bias for Action -- We practice high-velocity decision-making, despite encountering ambiguity frequently.
    • Act Like an Owner -- We have a strong ownership mentality, because of this, we work smart, hard, and long. Every person on the team has the potential to have a large impact.
    • Always Be Learning -- We learn rapidly and eagerly, from different teams within and outside the company. Respectful debate makes our organization stronger.
    • Empathy, Trust, Candor -- Being empathetic to our users and each other helps build trust in our community and company, and fosters successful decision-making.
About Instawork

Instawork's goal is to be the essential hiring engine for businesses across the globe. Our first step toward this goal is to become the "the Uber of Staffing” as our technology enables us to service needs of the massive gig economy. We are well positioned in the hospitality space (think catering companies, multi-location restaurants, hotels, event venues, golf courses) and looking to quickly expand our reach across the country and then the globe. 10% of Americans work in the hospitality industry and staffing is the by far the biggest struggle the industry faces for both the business and the worker. This presents a unique opportunity for a major disruption to the outdated job boards or help wanted signs in the window.

We are making a difference for thousands of businesses in multiple markets and currently looking for top-notch talent that want to change the way brick & mortar and large event venues utilize on-demand talent to fill staffing gaps. Essentially we are enabling gig workers to spend their extra time to make extra money to close the gap on their financial needs.

We’ve been fortunate to be funded by some of the greatest investors in Silicon Valley: Benchmark (Bill Gurley), Y Combinator, SV Angel, Crunchfund, Steve Chen (co-founder of YouTube), Mike Vernal (VP of Product at Facebook), among many more.