Chief of Staff Technology

Company Name: tastytrade Role: Chief of Staff – Technology Location: Chicago, IL (In-office 3 days/week) What You'll Do Serve as a trusted advisor and strategic partner to the regional CTO, translating high-level divisional strategy into tactical goals and their supporting initiatives, cascading those goals through the technology team, setting priorities, and driving execution. Work on special projects for the technology leadership team to streamline operations and test new opportunities. Lead cross-functional initiatives to enhance operational efficiency, ensuring alignment across engineering, product, compliance, and the newly formed business operations team. Track and report key performance metrics within the technology organization. Coordinate communications, planning, and decision-making processes to support the technology team and serve as a liaison to other business stakeholders. Act as a cultural steward, promoting diversity, inclusion, and a growth mindset within the technology team and throughout the organization. Identify and manage high-impact opportunities for improvement in processes, tools, and workflows to scale with a global brokerage. Drive initiatives to develop and retain top engineering talent, cultivating leadership pipelines and technical excellence. Who You Are Experience: 5-7+ years managing projects involving software engineers; familiarity with engineering concepts is required. Natural curiosity and humility to absorb new concepts and admit when out of depth. Exceptional written and verbal communication skills, with the ability to distill complex material into straightforward language. Proven ability to build and manage relationships with technical teams, executives, and external partners. Strong bias for action, capable of setting priorities and executing in fast-paced environments. Detail orientation and commitment to high standards of quality. Adaptability to ambiguity and evolving challenges. Cultural leadership passion for fostering an inclusive, growth-oriented workplace. Structured problem‑solving that balances short-term needs with long-term goals. Entrepreneurial mindset to identify and capitalize on business‑aligned opportunities. Self‑motivated, efficient work‑style, comfortable with both synchronous and asynchronous communication, and flexible schedule. Nice to Haves Familiarity with trading, financial markets, or brokerage technologies. Experience in regulated industries, adept at navigating compliance and risk landscapes. Company Perks + Benefits Performance Bonuses Stock Purchase Options 401k Plan 20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!) 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 Salary $120,000 - $150,000. The actual salary offered will depend on your level of experience and qualifications. Discretionary Performance Bonus: 15-20% of base salary based on individual and company performance. About IGNA + tasty: IG North America is home to tastytrade, tastylive, tastyfx, and tastycrypto—a family of brands built to democratize trading and empower individual investors. From our headquarters in Chicago’s Fulton Market, our team builds award‑winning trading platforms, produces live financial education daily, and creates technology that makes complex markets accessible. *Don's meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they have every single qualification. Our team is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role, but your experience doesn’t align perfectly, we encourage you to apply anyway. You may be just the right candidate for this or other roles! #J-18808-Ljbffr