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Strategic Operations Leader

Chicago, Illinois

Company: tastytrade  
Role: Strategic Operations Leader 
Location: Chicago, IL – Hybrid (3 days/week in office) 

As Strategic Operations Lead, you'll work closely with the Head of Brokerage and Strategy and the rest of the tastytrade / IG Americas leadership team to optimize and streamline operations for the tastytrade family of companies. You will play a pivotal role in aligning the team's efforts with strategic priorities, help to accelerate the delivery of operational improvements and strategic initiatives, foster a culture of innovation and excellence, and work on a variety of special projects for the office of the Head of Brokerage and Strategy. This position offers a unique opportunity to influence business strategy, operational efficiency, and organizational development at the highest level. 

This role reports to the Head of Brokerage and Strategy and will work with and support efforts from the rest of the leadership team (Brokerage CTO, VP Operations, Heads of Delivery, Product, and Compliance). 

What You’ll Do:  

  • Serve as a trusted advisor and strategic partner to the Head of Brokerage and Strategy, helping to translate high level divisional strategy into tactical goals and their supporting initiatives, cascading those goals through the organization, setting priorities, and driving execution. 
  • Handle a stream of special projects for the leadership team to streamline operations, test new opportunities, and contribute to the IG Group global brokerage organization. 
  • Lead cross-functional initiatives to enhance operational efficiency, ensuring alignment across trading operations, product, compliance, risk management, and business functions. 
  • Develop and oversee mechanisms for tracking and reporting key performance metrics within the brokerage organization. 
  • Coordinate communications, planning, and decision-making processes to support the executive team and drive clarity across stakeholders.  
  • Act as a cultural steward, promoting diversity, inclusion, and a growth mindset throughout the organization.  
  • Identify and manage high-impact opportunities for improvement in processes, tools, and workflows to scale with a global brokerage.  
  • Collaborate with tastytrade and IG Group leadership to harmonize operational and business strategies.  
  • Represent the office of the Head of Brokerage and Strategy in internal and external engagements, communicating strategic priorities and progress. 
  • Drive initiatives to develop and retain top talent, cultivating leadership pipelines and operational excellence. 

Who You Are: 

  • Education: Bachelor's degree in Economics, Business, Finance, Accounting, or related field (or equivalent work experience). 
  • Experience: 7+ years of experience in managing projects within brokerage operations, trading operations, or financial services. While you don't necessarily need to have a deep technical background, you need to be familiar with brokerage workflows, regulatory requirements, and operational processes. 
  • Naturally Curious: You will need to rapidly absorb and contextualize information to quickly become conversant in new concepts, products, and market dynamics. 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 operational and regulatory concepts into straightforward language which everyone in our business can understand. 
  • Relationship Management: Proven ability to build and manage relationships with operations teams, executives, regulators, and external partners. 
  • Strategic Thinking: Strong bias for action, capable of setting priorities and executing in fast-paced, regulated environments. 
  • Detail Orientation: You'll be interacting with and externally representing a brokerage operation 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, market conditions, and regulatory requirements. 
  • Cultural Leadership: Passionate about fostering an inclusive, growth-oriented workplace.  
  • Problem-Solving: Structured thinker who balances short-term operational needs with long-term strategic 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 you're stuck. 
  • 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: 

  • Deep familiarity with trading, financial markets, and brokerage operations. 
  • Experienced in regulated industries, adept at navigating compliance, risk management, and regulatory landscapes.  
  • Background in operations, client services, or clearing and settlement processes. 

Company Perks + Benefits:    

  • Performance Bonuses    
  • Stock Purchase Options    
  • Medical/Vision/Dental Benefits  
  • 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 Range: $150,000 - $175,000
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.    

Location: Our office is in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars.  

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!  

 

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