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Chief of Staff - Technology

tastytrade.com Logo

tastytrade

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Location:
United States , Chicago

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Contract Type:
Not provided

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Salary:

120000.00 - 150000.00 USD / Year

Job Description:

As the Chief of Staff - Technology, you'll work closely with the tastytrade / IG Americas technology leadership team to optimize and streamline operations for the tastytrade family of companies. You will play a critical role in aligning efforts with strategic priorities, accelerating feature delivery, and fostering a culture of innovation and excellence during a transformational growth period for tastytrade.

Job Responsibility:

  • Serve as a trusted advisor and strategic partner to the regional CTO
  • Work on special projects for the technology leadership team to streamline operations, and test new opportunities
  • Lead cross-functional initiatives to enhance operational efficiency
  • Track and report key performance metrics within the technology organization
  • Help to coordinate communications, planning, and decision-making processes
  • Act as a cultural steward, promoting diversity, inclusion, and a growth mindset
  • Identify and manage high-impact opportunities for improvement in processes, tools, and workflows
  • Drive initiatives to develop and retain top engineering talent

Requirements:

  • 5-7+ years of experience in managing projects that involve software engineers
  • Familiar with concepts in software engineering or infrastructure space
  • Naturally curious
  • Exceptional written and verbal communicator
  • Proven ability to build and manage relationships with technical teams, executives, and external partners
  • Strong bias for action
  • Detail orientation
  • Comfortable with ambiguity
  • Passionate about fostering an inclusive, growth-oriented workplace
  • Structured thinker
  • Entrepreneurial mindset
  • Self-motivated
  • Highly responsive

Nice to have:

  • Familiarity with trading, financial markets, or brokerage technologies
  • Experienced in regulated industries, adept at navigating compliance and risk landscapes
What we offer:
  • Performance Bonuses
  • Stock Purchase Options
  • 401k Plan
  • 20 Paid Vacation Days
  • 10 Paid Sick Days
  • Gym Membership Reimbursement
  • Commuter Benefits
  • Pet Insurance
  • Wellness & Mental Health Programs
  • Charitable Donation Matching
  • Two Paid Volunteer Days Off
  • Daily catered lunch when in the office
  • Full kitchen with snacks and beverages
  • In-building gym
  • Shuttle to/from Metra

Additional Information:

Job Posted:
February 19, 2026

Employment Type:
Fulltime
Work Type:
On-site work
Job Link Share:

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