Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets.
We started from scratch by building a completely cloud-native clearing and custody system designed for today's complex, global market. Our platform is fully integrated with central clearing houses and exchanges to support billions in trading volume per day. We've agonized about our data model abstractions, created horizontal scalability, and crafted thoughtful APIs. All so we can provide a best-in-class experience for our clients.
By combining highly-skilled product and engineering talent with seasoned finance professionals, we're building the essentials to compete in today's fast-paced markets.
The Team:
The mission of the Clear Street Active team is to provide best execution for every asset class in every market. Active is currently building a new, state-of-the-art, cloud-based trading platform providing high-performance traders access to liquidity venues across multiple asset classes, cutting-edge charting capabilities, and sophisticated order handling with the flexibility to service both the active trader and institutional workflows.
The Role:
You will own the reliability and quality bar for an AI copilot embedded in an trading platform used by sophisticated investors
You will design and build evaluation systems that measure correctness, safety, latency, and regression risk across market analysis, portfolio/risk reasoning, and trading workflows (including order placement)
You will develop and maintain benchmarks: curated “golden sets,” scenario suites, stress/adversarial cases, and continuously refreshed market/regime-based test corpora
You will build automated quality gates and regression workflows that block releases when key metrics degrade
You will partner with engineering and product to define safe tool/action contracts (deterministic previews, confirmations, auditability) and ensure predictable assistant behavior
You will own model improvement loops tied to evals: data collection/labeling strategies, error taxonomy, prompt/tooling changes, and when appropriate, fine-tuning or preference optimization to measurably improve benchmark performance
You will design and operate monitoring + incident response for AI: telemetry, alerting, RCA, and “fix-forward” processes
You will develop a deep understanding of trading concepts (margin, shorting, portfolio margin, risk, execution) and how to express them accurately and understandably to users
Tech Stack: Rust, TypeScript, Postgres, React (Web), React Native (Mobile), observability/telemetry tooling, LLM APIs + model serving, eval/training pipelines
Requirements:
- At least Eight (8) years of experience shipping production software; strong proficiency with any programming language
- Strong knowledge of computer science fundamentals, testing methodology, and systems design
- Experience building evaluation frameworks, test harnesses, and benchmark suites for complex systems (LLMs/agents/search/retrieval/ranking/recommenders)
- Experience running model improvement cycles: dataset curation, labeling/QA, offline experimentation, and deploying changes with measurable impact on benchmarks
- Ability to define metrics, build measurement pipelines, and drive engineering/product decisions from data
- Comfort working across the stack: debugging model/tooling failures, instrumenting services, and partnering with frontend/product on UX patterns that improve safety and trust
- High degree of self-motivation and willingness to jump into unfamiliar areas to solve problems
Bonus:
- Experience with fine-tuning, preference optimization, distillation, or prompt/compiler-style techniques for improving tool-use reliability
- Experience creating domain-specific benchmarks and adversarial suites (e.g., “known-bad” scenarios) for high-stakes applications
- Deep experience with trading across asset classes, margin types, etc.
- Experience with Rust and performance-sensitive services
- Experience designing incident response and SLOs for ML/AI systems
We Offer:
The Base Salary Range for this role is $200,000 - $350,000. This range is representative of the starting base salaries for this role at Clear Street. Where a candidate falls in this range will be based on job related factors such as relevant experience, skills, and location. This range represents Base Salary only, which is just one element of Clear Street's total compensation. The range stated does not include other factors of total compensation such as bonuses or equity.
At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.
Our top priority is our people. We're continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We are proud to be an equal opportunity employer and put in the effort to make such a workplace a daily reality. #LI-Remote
Skills Required
- At least eight (8) years of experience shipping production software
- Strong proficiency with any programming language
- Strong knowledge of computer science fundamentals, testing methodology, and systems design
- Experience building evaluation frameworks, test harnesses, and benchmark suites for complex systems (LLMs/agents/search/retrieval/ranking/recommenders)
- Experience running model improvement cycles: dataset curation, labeling/QA, offline experimentation, and deploying changes with measurable impact on benchmarks
- Ability to define metrics, build measurement pipelines, and drive engineering/product decisions from data
- Comfort working across the stack: debugging model/tooling failures, instrumenting services, and partnering with frontend/product on UX patterns that improve safety and trust
- High degree of self-motivation and willingness to jump into unfamiliar areas to solve problems
- Experience with fine-tuning, preference optimization, distillation, or prompt/compiler-style techniques for improving tool-use reliability
- Experience creating domain-specific benchmarks and adversarial suites for high-stakes applications
- Deep experience with trading across asset classes, margin types, etc.
- Experience with Rust and performance-sensitive services
- Experience designing incident response and SLOs for ML/AI systems
What the Team is Saying
Clear Street Compensation & Benefits Highlights
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Healthcare Strength — Health coverage across medical, dental, and vision is described as strong, with multiple notes on good coverage and reasonable costs. Feedback suggests FSA/HSA and mental-health options complement the core plans.
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Wellbeing & Lifestyle Benefits — Day-to-day perks such as commuter benefits, lunch stipends/free meals, stocked kitchens, and office events are consistently highlighted, especially in hub offices. Feedback suggests these tangible perks add meaningful everyday value.
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Leave & Time Off Breadth — Vacation, paid holidays, and sick time are portrayed as solid, with recent updates indicating well-regarded PTO. Feedback suggests time-off policies are workable and appreciated.
Clear Street Insights
What We Do
Clear Street’s mission is to give every sophisticated investor access to every asset, in every market, through a unified platform built for speed, transparency and scale. We give our clients the technology, tools, and service once reserved for the largest institutions, rebuilt with modern infrastructure. Our single, cloud-native, end-to-end capital markets platform powers investor growth today and is transforming how they can interact with markets tomorrow. For more information, visit https://clearstreet.io.
Why Work With Us
Clear Street has thoughtfully cultivated a team that combines problem-solving engineers with financial industry experts across clearing platforms, compliance, and more. The company is focused on building a team that is motivated to tackle fintech innovation and create a collaborative work culture for everyone.
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Clear Street Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.
