Chief of Staff - Technology

tastylive•Chicago, IL

4d•$120,000 - $150,000•Hybrid

About The Position

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.

Requirements

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.

Responsibilities

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.

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