Strategic Operations Leader

tastylive•Chicago, IL

8d•Hybrid

About The Position

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).

Requirements

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.

Responsibilities

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.

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