Tastylive
Strategic Operations Leader
$150,000 – $175,0001w ago
Calendar & Scheduling: Own executive calendars end-to-end — coordinating meetings, protecting priorities, and handling senior interview logistics. Meeting Support: Keep meetings sharp and productive. Prep materials, capture decisions, and track action items so nothing falls through the cracks. Communications: Serve as a professional first point of contact for the Head of People, thoughtfully managing incoming correspondence — exercising sound judgment to respond, prioritize, or escalate with the right context and appropriate urgency. Executive Materials: Create polished presentations, reports, and documents that reflect the People brand Vendor & Finance Management: Manage HR vendor contracts and invoices, process expense reports, and assist with budget oversight Confidentiality: Handle sensitive and market-sensitive information with the utmost discretion and professionalism Events & Culture: Organize company events, off-sites, and team activities that reflect our unique fintech culture Proactive Support: Anticipate needs and solve problems before they escalate—staying two steps ahead
3–5 years of experience supporting executive-level leaders College degree preferred HR Administration experience a plus but not required Exceptional organizational skills with the ability to juggle multiple priorities Strong written and verbal communication skills Proficient in Microsoft Office Suite, Concur, SharePoint, and Workday—and quick to pick up new tools Self-directed, with sound judgment and strong decision-making skills Professional, personable, and highly discreet Flexible and adaptable, including occasional after-hours availability
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 Office located in the West Loop - Chicago's growing center of tech, great cuisine, and high-end bars
Salary Range: $65,000 - $75,000The actual salary offered will be based on the candidate's level of experience and qualifications. Discretionary Performance Bonus: 8-12% 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!