How To Join

Oak St. is a small firm building its technology from first principles: the data estate, the research platform, the trading path, and the security around them. Joining now means owning a piece of that build outright, working next to the people who set the standards, and being accountable for what you ship.

Click here to apply.

Career Development

Every engineer at Oak St. works with the founding partners directly and sees the whole system, not a slice of it. We fund the learning that the work demands, from conferences and courses to time to read the papers, and we promote on demonstrated judgment rather than tenure.

Choose Your Path

I am an engineer interested in at the office.

Viewing 6 of 12 openings

technology leadership
Chicago
Apply for this position by email
: Owns the firm's technology from first principles: the research platform, the trading stack, the data estate, the security posture, and the people who...
Base salary
$250,000
Accountable for
Architecture, budget, vendors, and launch accountability
Location
Chicago
Responsibilities
Set and defend the reference architecture across research, production trading, data ingestion, cloud, and security.
Own the technology budget end to end, including the $2.9M hiring ramp and every vendor and colocation contract.
Hire, structure, and lead the 12-person launch team; define on-call, change control, and incident response before the first live order.
Act as the accountable executive for launch readiness, regulatory technology obligations, and third-party diligence.
Required
15+ years in software engineering with at least 7 years leading technology at a systematic trading firm, market maker, or exchange.
Has personally taken a trading platform from greenfield to live capital, including exchange connectivity, risk gateways, and post-trade.
Deep fluency in Linux systems, networking, distributed systems, and at least two of C++, Rust, Python, Java.
Experience managing budgets above $3M and vendor portfolios covering colocation, market data, cloud, and security tooling.
Bachelor's degree from an Ivy League university, MIT, Stanford, Caltech, Carnegie Mellon, or an international peer (Oxford, Cambridge, Imperial, ETH Zürich, IIT) strongly preferred; graduate degree in computer science, mathematics, statistics, physics, or electrical engineering preferred
Preferred
Prior CTO, Head of Technology, or Head of Trading Systems title at a quantitative fund with more than $1B AUM.
Published work, patents, or open-source leadership in low-latency systems, storage engines, or schedulers.
Experience with SEC, CFTC/NFA, or FCA technology and recordkeeping examinations.
Apply by email · subject line “Application – Technology Lead / Chief Technology Officer – <Last name, First name>”
technology leadership
Chicago
Apply for this position by email
: Designs the platform that every other engineer builds on: service boundaries, data contracts, identity, observability, and the integration patterns...
Base salary
$200,000
Accountable for
Reference architecture, standards, and integration
Location
Chicago
Responsibilities
Author and maintain the reference architecture, coding standards, and the internal RFC process.
Design integration between the research platform, the order management system, the risk gateway, and the data lakehouse.
Review every significant design across the team and hold the line on simplicity and operability.
Required
12+ years in software engineering including 5+ years as a principal or staff engineer accountable for a multi-team platform.
Demonstrated ownership of architecture at a trading firm, exchange, or high-throughput financial data business.
Expert in distributed systems, event-driven architecture, schema evolution, and API design; strong in Python and one systems language.
Bachelor's degree from an Ivy League university, MIT, Stanford, Caltech, Carnegie Mellon, or an international peer (Oxford, Cambridge, Imperial, ETH Zürich, IIT) strongly preferred; graduate degree in computer science, mathematics, statistics, physics, or electrical engineering preferred
Preferred
Experience standing up platform engineering at a fund launch or a spin-out.
Working knowledge of FIX, binary exchange protocols, and market-data normalization.
Formal methods, performance modelling, or capacity-planning background.
Apply by email · subject line “Application – Enterprise / Platform Architect – <Last name, First name>”
infrastructure and reliability
Chicago · 2 openings
Apply for this position by email
: Builds and runs the physical and network layer: colocation cages, cross-connects, low-latency switching, compute fleets, and storage, with the...
Base salary
$165,000 each
Accountable for
Colocation, network, compute, storage, and operations
Location
Chicago
Responsibilities
Design, procure, and operate colocation and office infrastructure, including exchange cross-connects and market-data feeds.
Run the network: L2/L3 design, multicast, precision timing (PTP), firewalls, and out-of-band management.
Own hardware lifecycle, capacity, monitoring, and the 24×7 operations rota with the SRE team.
Required
8+ years in network and infrastructure engineering with 4+ years in a trading, exchange, or market-data environment.
Hands-on with Arista/Cisco/Juniper, multicast market data, PTP/GPS timing, and colocation operations at CME, Equinix, or equivalent facilities.
Strong Linux administration and automation (Ansible/Terraform, Python).
Bachelor's degree in computer engineering, electrical engineering, or computer science from a top-tier program; CCIE, JNCIE, or equivalent preferred.
Preferred
FPGA or kernel-bypass (Solarflare/Onload, DPDK) experience.
Prior responsibility for a production trading network during a major market event.
Apply by email · subject line “Application – Network / Infrastructure Engineer – <Last name, First name>”
infrastructure and reliability
Chicago · 2 openings
Apply for this position by email
: Owns the cloud estate and the reliability practice: infrastructure as code, Kubernetes, observability, SLOs, and incident response for research and...
Base salary
$175,000 each
Accountable for
AWS, Kubernetes, infrastructure as code, observability, and reliability
Location
Chicago
Responsibilities
Build and operate the AWS footprint with Terraform and Kubernetes; enforce least-privilege identity and network segmentation.
Define SLOs, alerting, and on-call; run incident response and blameless post-mortems.
Automate deployment, secrets management, backup, and disaster recovery, and test them regularly.
Required
7+ years in SRE, platform, or infrastructure roles with 3+ years running production Kubernetes at scale.
Expert in AWS, Terraform, and at least one of Go or Python; deep understanding of Linux internals and networking.
Track record of measurable reliability improvement (SLO attainment, MTTR) in a regulated or financial environment.
Bachelor's degree in computer science or a related field from a top-tier program; AWS Professional or CKA/CKS certification preferred.
Preferred
Experience with hybrid colocation-plus-cloud topologies and cost governance.
Security engineering exposure: SIEM, EDR, identity federation.
Apply by email · subject line “Application – Cloud / Site Reliability Engineer – <Last name, First name>”

+4 Positions

Recruiting Security: Emails from genuine Oak St. recruiters always come from the @oakst.vc domain. Oak St. does not engage search firms for these roles, does not conduct interviews through messaging applications, and never asks for banking information or any payment as part of the recruiting process. If something seems off, or you are contacted by an unexpected third party, write to security@oakst.vc.

Additional Opportunities: See the Internships section for the summer program.

How to apply

Write to careers@oakst.vc. There is no form and no portal; every email is read by a person.

Subject line

Exactly this format, so the application routes to the right reviewer:Application – <Position title> – <Last name, First name>for example “Application – Trading Systems Engineer – Nakamura, Aiko”

Include

Résumé or CV as a single PDF, file name Lastname_Firstname_CV.pdf
A cover note of no more than 300 words in the body of the email (no attachment)
Links to any public work: repositories, papers, talks
Your earliest start date and any visa or relocation considerations

Rules

Send one email per position. Multiple positions in one email are not reviewed.
Write from a personal address you control; the domain of that address is recorded with the application.
Do not send compressed archives, executables, or links to file-sharing services; those messages are discarded unread.
Every application receives an acknowledgement within five business days. Oak St. does not conduct interviews through messaging applications and never asks candidates for payment of any kind.

Pay

Base salary planning figures are shown per role. Total compensation adds employer-paid benefits, a discretionary annual bonus tied to firm and individual performance, and, for senior roles, participation in the firm's long-term incentive plan. Oak St. budgets deliberately above the national medians reported by the U.S. Bureau of Labor Statistics for these occupations.

Application data is processed under the Candidate Privacy Notice (available from privacy@oakst.vc).

Interviewing

Interviewing is how we get to know each other. Expect a conversation about your work in depth, a technical exercise close to the job itself, and time with the people you would work with every day.

Compelling candidates tend to:

Uphold high standards
Analyze rigorously
Communicate clearly and concisely
Thrive on collaboration
Demonstrate intellectual curiosity

If you want to learn more about our approach to interviewing, our guide to preparing for an interview can help you put your best foot forward.

A typical process is an application review, a phone conversation, one or two technical interviews held remotely, a half-day on site in Chicago with the team, reference conversations, and an offer. Depending on the role we may ask for a code sample or a short written design. We try to complete the whole process within four weeks.

Internships

We take a small number of interns each summer in Chicago. Interns work on real projects with a named engineer as reviewer, join the team's design reviews, and present their work to the whole firm at the end of the term.

Find Your Internship

Internship postings for summer 2027 open in October 2026. Until then, send an expression of interest by email using the format below.

Software Engineering Intern
Chicago · Summer 2027, 10 weeks · $12,000 per month
Work inside the trading-systems or platform team on a scoped project that ships: replay tooling, a connectivity adapter, or a piece of the risk gateway, with a named engineer as your reviewer.
Data Engineering Intern
Chicago · Summer 2027, 10 weeks · $12,000 per month
Build and validate an ingestion pipeline or a data-quality monitor for one dataset end to end, from raw feed to point-in-time tables researchers can use.
Infrastructure Intern
Chicago · Summer 2027, 10 weeks · $11,000 per month
Automate a piece of the estate: provisioning, observability, or timing and network telemetry, with the SRE and network engineers.

See more info

Benefits

Our people are at the heart of everything we do. We design our benefits to help you care for yourself and those closest to you.*

Healthcare
Medical, dental, vision, and mental-health coverage for you and your dependents, with the firm paying the full premium.
Retirement
A 401(k) with a firm contribution that does not depend on yours, vesting from day one.
Family
Paid parental leave for every new parent, and support for fertility, adoption, and surrogacy.
Time Off
Paid time off that people are expected to take, plus the exchange holidays.
Amenities
A Wolf Point office with firm-provided meals, a fitness allowance, and quiet space to think.
Reimbursements
Equipment, home-office, learning, and conference budgets that support the work you do.

*Benefits are described in summary; the plan documents govern, and offerings vary by office and applicable local law.

Our benefits are the same for every full-time employee from the first day, in every office.