Community Operations Team Lead

| Chicago
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Instawork is a mission-driven (and fast growing) company looking for top talent to help us scale our labor marketplace. Our team is composed of talented and dedicated individuals who are passionate about creating economic opportunity for businesses and skilled hourly professionals. Our headquarters is in San Francisco, with hub cities across the U.S., Canada, and India. Our company values are our North Star, guiding us as we craft impactful products and to be extraordinary colleagues to each other. 

We have been fortunate to be funded by some of the greatest technology investors supporting us on this journey, including: Benchmark (Bill Gurley), Greylock Capital, Y Combinator, and many more. Leveraging our accelerating growth, we will continue to grow our team and to expand globally in order to revolutionize the labor market.


  • Lead and develop a team of up to 8 Community Operations Specialists, responsible for their overall performance
  • Create performance goals for Community Operations Specialists, monitor weekly progress toward specific goals.
  • Collaborate with the Operations Coordinator to monitor the efficacy of the daily operations, and anticipate barriers to operational success.
  • Be the subject matter expert for all of Community Operations policies and procedures, preventing misinformation to external stakeholders by effectively monitoring communications and coaching specialists
  • Be the point of contact for escalation within the real-time operations and urgent issues with stakeholders
  • Manage the quality assurance program for Community Operations, performing weekly audits of specialists’ communications and reporting on quality assurance metrics
  • Monitor customer satisfaction of individual specialists and the team’s overall performance, weekly
  • Investigate low customer satisfaction scores and negative customer feedback, identifying the root causes and creating an action plan for current and future resolutions
  • Own proactively identifying opportunities to engage Instawork’s “power users” and top-quality customers
  • Improve team members’ productivity through weekly knowledge sessions and sharing insights on how to increase efficiency
  • Collaborate with leadership on Community Operations recognition and engagement initiatives, actively highlighting best practices and top performance within the team
  • Regularly communicate with senior leadership regarding the team’s performance, opportunities for improvement, and contribute to projects designed to enhance the customer experience.


  • 5+ years of experience working in customer support, preferably in the technology services industry
  • 2+ years leading remote or diverse teams, preferably in the technology services industry
  • Proven ability to provide urgent resolutions for high-priority issues and escalations
  • Experience handling complex or sensitive issues with stakeholders and follow-up documentation
  • Ability to expertly navigate complex tools and troubleshoot issues with internal and external products
  • Demonstrated success among all performance metrics, especially productivity and quality
  • Proven ability to motivate, influence, and work effectively with the organization’s stakeholders
  • Experience in mentoring new hires and contributing to their onboarding process
  • Proven ability to demonstrate organizational values and role model positive behaviors for a team
  • Experience with performance reporting and analytics is strongly preferred

Instawork Values

  • Bias for Action -- We are a growing team and an evolving product. We want a team of do’ers to drive the company forward, even if it means making decisions with incomplete information or being wrong.
  • Act Like an Owner -- Treat this company as though it is your own. Execute on the fundamentals, and act creatively to drive growth. Your ability to drive impact in any part of our company is only limited by your courage and conviction, not your job title.
  • Always Be Learning -- We are changing an entire industry. We strive to learn from each other and get better each day, week, and month, so that our team’s learnings can compound and we can all improve, together.
  • Empathy, Trust, Candor -- Empathy for our business partners and professionals means we put ourselves in their shoes. Empathy for our colleagues means we are always upfront and honest with each other, which comes from trust.

Founded in 2016, Instawork is the leading flexible staffing solution for local, hourly professionals. Its digital marketplace connects thousands of businesses and more than one million workers in the U.S., filling a critical role in local economies. Instawork helps businesses in food & beverage, hospitality, and warehouse/logistics industries fill temporary and permanent job opportunities in more than 25 U.S. markets. For more information visit

We value diversity on our team and firmly believe Instawork is stronger when we hire people who make their own unique contributions to our culture. We welcome all applicants and encourage candidates from underrepresented backgrounds to apply. 

To learn more about our company values, please visit:

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Technology we use

  • Engineering
    • C++Languages
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Chicago, IL

What are Instawork Perks + Benefits

Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Flexible Work Schedule
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
Happy Hours
Home Office Stipend for Remote Employees
Professional Development Benefits
Mentorship program
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