Investment Compliance Technical Lead

We’re an AI services firm that helps companies figure out where and how to use AI. We’ve bootstrapped Casper Studios to roughly 40 people, worked with 30+ clients, and done deals with some of the largest companies, PE funds, and model providers. We’ve also 4x’d revenue in the last few months.

The reason comes down to how we work with clients. Before we build anything, we listen, understand the business, and help them figure out the highest-leverage way to get started on their AI journey.

We're looking for someone who sits at the intersection of investment compliance expertise and technical architecture. You'll lead a project for a trillion-dollar AUM asset manager, transforming how they manage Investment Management Agreements (IMAs) - a massive corpus of PDF documents that define how each client's portfolio can be managed.

Today, the firm's teams manually search these documents and copy critical terms into spreadsheets or trading systems. The same rule can appear across an IMA, an amendment, an email, and other systems - creating slow work and genuine risk that staff use outdated terms, miss amendments, or apply the wrong rules to a client portfolio.

You'll build the semantic and data foundation that turns this into a structured, searchable, deterministic compliance system. Think: rules that understand effective dates, preserve amendment history, trace back to source clauses, and can be tested like code.

This is a role for someone who owns outcomes, bridges business and technical domains, and wants unusual amounts of responsibility early.

• Assess the landscape: Map how restrictions, benchmarks, exceptions, and remediation requirements are currently expressed across IMAs, amendments, and CRIMS configurations

• Define the semantic model: Design the canonical vocabulary, schema, and rule composition model that represents restrictions, thresholds, and exceptions consistently - with effective dating, versioning, and provenance baked in

• Resolve ambiguity: Work directly with legal, compliance, and investment stakeholders to interpret guideline language and turn it into unambiguous, computable rules

• Model the hard parts: Structure limits, ratings, benchmarks, breaches, remediation actions, and effective-date logic - the full complexity of investment mandates

• Design traceability: Ensure every rule traces back to its source clause and interpretation, with auditable change control

• Prototype and guide implementation: Build the initial platform, establish rule validation and scenario-testing practices, and set the technical direction for the team

• Technical Architecture & Implementation

  • Rules engine or decision-modeling experience: Drools, DMN, Camunda, Open Policy Agent, or similar

  • Temporal / versioned data models: You've modeled data that changes over time and needs to be queried as-of a given date

  • Knowledge graphs or semantic modeling: RDF, OWL, ontology design - you know how to represent complex relationships and enforce logical consistency

  • Audit trails and provenance: You've built systems where every data point knows where it came from

  • Contract or document extraction: You've worked with clause extraction, taxonomy design, or converting unstructured legal text into structured data

  • Property-based or scenario-based testing: You know how to validate rule logic deterministically

• Investment Compliance Expertise

  • You've coded investment guidelines into pre- or post-trade compliance rules on platforms like Charles River (CRD), Aladdin, Sentinel, or Bloomberg AIM

  • You understand the asset management workflow: holdings, benchmarks, credit ratings, breaches, remediation - and what portfolio managers and compliance officers actually need

  • You've worked with IMAs and mandates: You know how investment restrictions are written, what ambiguity looks like, and how to resolve it

  • You're comfortable mapping business rules to technical logic - and explaining the tradeoffs to both lawyers and engineers

• Agency & Communication

  • High agency: You frame ambiguous problems, state your assumptions, and push work forward without being managed

  • Strong writing: You can turn a long, meandering client call into a clean set of tickets - and write clearly enough that legal stakeholders trust what you've built

  • Client-facing at a senior level: You can talk shop with their engineers and give their executives clarity

Most people land on one side of a line. Strong compliance experts can read an IMA but can't model a temporal rules engine. Strong engineers can build the platform but don't know what a "negative covenant" or "rating-based restriction" actually means. We need both - plus the judgment to design a system that legal, compliance, and engineering teams can all trust.

Someone who needs clean requirements and heavy supervision won't thrive here. Neither will someone who builds something that falls apart when you ask "what was the rule on this portfolio six months ago?"

• You've converted legal or regulatory text into computable rules

• You're T-shaped: deep in one area (rules engines, data modeling, or investment compliance) and rounding out the rest

• You've built something that required traceability, auditability, and deterministic logic - not just "it works on the happy path"

• Fully remote, US/Canada based, with occasional client travel. We have team members across North America and internationally, mostly overlapping North American time zones. Work when and where you want, as long as the work gets done

• Compensation calibrated to your location and seniority - we'll talk comp and align on specifics early

• 🏥 Medical, Dental, and Vision Coverage: Comprehensive health benefits to keep you and your family healthy.

• 🌴 Flexible PTO: Take the time you need to relax and rejuvenate.

• 🚑 Health FSA/HSA: Manage out-of-pocket health expenses effectively.

• 🏥 Life Insurance: Providing peace of mind for you and your loved ones.