Executive Assistant, tastytrade

$65-75k

+ Discretionary Performance Bonus: 8-12% of base salary based on individual and company performance + Stock Purchase Options

Concur

Mid and Senior level

Chicago

4 days a week in office

Options trading, futures & stock trading brokerage

Be an early applicant

Options trading, futures & stock trading brokerage

201-500 employees

FintechB2CTradingMobile

Be an early applicant

$65-75k

+ Discretionary Performance Bonus: 8-12% of base salary based on individual and company performance + Stock Purchase Options

Concur

Mid and Senior level

Chicago

4 days a week in office

201-500 employees

FintechB2CTradingMobile

Company mission

To help traders succeed through sophisticated technology, favorable pricing and exceptional customer service.

Job

Company

Role

Who you are

3–5 years of experience supporting executive-level leaders
College degree preferred
Brokerage 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, and SharePoint, 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
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!

What the job involves

We're looking for a sharp, highly organized Executive Assistant to provide high-level support to the Head of Brokerage and the Head of Brokerage - tastytrade
You'll be a trusted partner who keeps things running smoothly, anticipating needs, maintaining confidentiality, and managing competing priorities with ease in a fast-paced fintech environment
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 Brokerage, 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 team’s brand
Vendor & Finance Management: Manage 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

Our take

With the aim of "making investing fun”, Unicorn-verified tastytrade has amassed a following in the hundreds of thousands, delivering technology and support for "do-it-yourself" investors.

Founded in 2011, the company supplies not only a trading platform but trading education resources as well. It has launched dozens of podcasts and online video channels focusing on investment strategies and trading, as well as learning courses for those looking to get their start in the space.

Acquired by IG Group, a global player in trading, in 2021, tastytrade has since employed this added strength to scale up its business and expand into international markets. This increasing visibility - at a time when markets are especially unpredictable and its platform an invaluable asset - has enabled tastytrade to continue its upward momentum, reporting record demand in 2025. This strong performance highlights the growing importance of its platform in an ever-evolving market.

Freddie

Company Specialist at Welcome to the Jungle

Insights

23% employee growth in 12 months

Glassdoor (4.5)

Trustpilot (3.7)

Company

Funding (last 2 of 3 rounds)

Jun 2018

$20m

SERIES C

Jun 2013

$7m

EARLY VC

Total funding: $47m

Company benefits

3 Medical Plans Choice
Dental & Vision Benefits
Generous Paid Time Off
Paid Holidays - All Market Holidays Off
401(k) with Company Match
Generous Parental Leave
Disability Leave & Disability Insurance
Commuter Benefits
Pet Insurance
Wellness & Mental Health Programs
Performance Bonuses
Subsidized Engineering Training Program
Stock Purchase Options
Gym Membership Reimbursement
Charitable Donation Matching
Healthcare FSA
Two Paid Volunteer Days Off
Daily Catered Lunch
Fully-stocked Kitchen with Snacks and Drinks
Onsite Gym
Casual Dress
Sustainable Work Day
CTA stop a block away, Shuttle to/from Metra
Shared rooftop with greenery overlooking the city
West Loop Location - Chicago's Tech Center

Company HQ

Fulton Market, Chicago, IL

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