Chief of Staff - Technology

JobsCloseBy Editorial Insights

tastytrade is seeking a Chief of Staff: Technology in Chicago, in office three days a week, to partner with the IG Americas technology leadership team to align strategy, accelerate delivery, and drive operational excellence during a transformational growth period. Reporting to the regional CTO, you will translate strategic goals into actionable plans, lead cross functional initiatives across engineering, product, compliance, and the new business operations team, and track key metrics while coordinating communications and decision making. You will also serve as a cultural steward who promotes inclusion and a growth mindset. The ideal candidate has five to seven years guiding tech projects with software engineers, exceptional written and verbal communication, and a proven ability to thrive in ambiguity while delivering impact. Nice to have trading or regulated industry exposure. To apply, share concrete examples of strategic impact and cross functional wins, and tailor your resume to show how you turn concepts into prioritized work.

Company Name: tastytrade
Role: Chief of Staff – Technology 
Location: Chicago, IL (In-office 3 days/week)

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. Reporting to the regional CTO of IG North America, you'll also collaborate closely with the Brokerage CTO, Head of Product Delivery, and Head of Design to execute on high-priority projects and drive organizational transformation.

This is a high-growth role designed for someone who thrives in ambiguity and sees opportunity in complexity. You'll have significant influence shaping how the technology team works, connecting cross-functional initiatives, and driving clarity on critical priorities. Your impact will come from being the strategic partner and force multiplier that helps the technology leadership team move faster and execute more effectively.

What You'll Do:

• Serve as a trusted advisor and strategic partner to the regional CTO, helping to translate 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. 
• Help to coordinate communications, planning, and decision-making processes to support the technology team and be 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 of experience in managing projects that involve software engineers. Although you don't necessarily need to have a software engineering or infrastructure background, you need to be familiar with concepts in the space. 
• Naturally Curious: You will need to rapidly absorb and contextualize information in order to quickly become conversant in new concepts and technology. You'll also need the humility to quickly and honestly acknowledge when you're out of your depth. 
• Communication: Exceptional written and verbal communicator, skilled at distilling complex material and concepts into straightforward language which everyone in our business can understand. 
• Relationship Management: Proven ability to build and manage relationships with technical teams, executives, and external partners. 
• Strategic Thinking: Strong bias for action, capable of setting priorities and executing in fast-paced environments. 
• Detail Orientation: You'll be interacting with and externally representing a technology function and organization which holds itself to high standards. Building and maintaining credibility within this team will require precise attention to detail and an exacting standard of quality in your work product. 
• Adaptability: Comfortable with ambiguity, quick to adapt to evolving challenges and opportunities. 
• Cultural Leadership: Passionate about fostering an inclusive, growth-oriented workplace. 
• Problem-Solving: Structured thinker who balances short-term needs with long-term goals. 
• Entrepreneurial Mindset: Skilled at identifying and capitalizing on business-aligned opportunities. 
• Responsibility: You must be self-motivated, capable of working from loose concepts at times, and getting work done in an extremely efficient fashion. You are someone who knows how to politely knock on doors and how to kick them in when appropriate. 
• Highly Responsive: Our team is globally distributed and travels frequently, so you'll need to be comfortable with both synchronous and asynchronous communication and willing to flex your working schedule accordingly. 

Nice to Haves 

• Familiarity with trading, financial markets, or brokerage technologies. 
• Experienced 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 
• Office located in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars 

Salary Range: $120,000 - $150,000 
The actual salary offered will be based on the candidate's 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. Founded in Chicago by the creators of thinkorswim, acquired by London-based IG Group in 2021, we combine startup innovation with the backing of a global fintech leader with 50+ years of experience.  
 
From our headquarters in Chicago's Fulton Market, our team builds award-winning trading platforms, produces live financial education content daily, and creates technology that makes complex markets accessible. tastytrade is our retail brokerage for self-directed investing and trading, with tastylive providing content to educate our customers. tastyfx is the fastest-growing forex broker in the US. tastycrypto provides self-custody digital wallets for decentralized finance. 
 
We're a lean, collaborative team that values autonomy, pragmatism, and impact. Whether you're building technology, creating content, serving customers, or supporting operations, you'll work alongside people who are passionate about disrupting traditional finance and genuinely care about helping traders succeed. Our culture rewards initiative, embraces experimentation, and measures success by the value we create for our users.  
  
tastytrade | tastylive  | tastyfx | tastycrypto  
1330 W Fulton Market, Chicago, IL 60607  
 
*Don't 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!