Senior Site Reliability Engineer, tastytrade

Linux Systems & Application Observability

$180-200k

+ Stock Purchase Options & Discretionary Performance Bonus: 15-20% of base salary based on individual and company performance

Python

Java

Linux

Ruby

Prometheus

Flow

Grafana

Senior and Expert level

Chicago

3 days a week in office (West Loop, IL)

Options trading, futures & stock trading brokerage

Be an early applicant

Options trading, futures & stock trading brokerage

201-500 employees

FintechB2CTradingMobile

Be an early applicant

$180-200k

+ Stock Purchase Options & Discretionary Performance Bonus: 15-20% of base salary based on individual and company performance

Python

Java

Linux

Ruby

Prometheus

Flow

Grafana

Senior and Expert level

Chicago

3 days a week in office (West Loop, IL)

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

Hands-on experience designing fault-tolerant, self-healing distributed systems — not just describing the patterns, but having shipped them
Deep understanding of one or more: distributed systems, Linux systems, cloud-native architectures, containerization
Experience running gap analyses on observability/telemetry systems: identifying what's not instrumented, not alerted on, or not visible until it's too late
A track record scaling systems under real production load, including capacity planning and architectural bottleneck identification
Hands-on experience with OpenTelemetry, Prometheus, and Grafana, with the ability to instrument services directly
Strong Linux internals and networking fundamentals, including TCP/IP, UDP/multicast, packet capture, and flow analysis
On-call experience on production systems and comfort building a blameless post-incident review process
Working knowledge of SLOs and error budgets as a tool, not the job description; HashiCorp Nomad, Consul, or Vault experience is a strong plus
Strong programming skills in a language such as Python, Ruby, Java, or similar
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

What the job involves

As our first Senior Site Reliability Engineer, you'll harden the systems behind order execution and market data delivery — designing for fault tolerance, closing gaps in our telemetry, and making sure our HashiCorp Nomad-based service fabric scales cleanly as trading volume grows
You'll work embedded alongside our infrastructure and application engineering teams, contributing directly to our Ruby, Java, and Elixir services.
This is a rare opportunity to shape a practice and a culture from day one, on a platform where every order, quote, and position has to be right, because real client capital is on the line.
Build self-healing, fault-tolerant infrastructure and internal tooling that automates repetitive operational work and reduces toil for Platform and Application teams
Run gap analysis across our observability stack to find blind spots in telemetry, logging, and alerting coverage, then close them so failures surface before customers feel them
Own scalability work across our HashiCorp Nomad service fabric: capacity planning, load testing, and identifying architectural bottlenecks before they become incidents
Extend our observability stack (Prometheus, Honeycomb, OpenTelemetry) with the instrumentation needed to actually see the failure modes above
Set SLOs and error budgets with multi-window burn-rate alerting for critical brokerage flows, once the fault-tolerance and telemetry foundation is in place
Mentor engineers across teams to build a culture of site reliability champions so the practice outlives any one person

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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