Chris Sidebottom

Legal Engineer • J.D., LL.M. • CIPP/US

Turning legal rules into working systems.

Denver, CO • ccrsidebottom@gmail.com • linkedin.com/in/chris-sidebottom • nova.chrissidebottom.com

Selected Work & Applied AI Systems

Nova — Legal Relationship & Governance Workbench FastAPI • SQLite • Python
nova.chrissidebottom.com
  • Interactive property graph workbench mapping multi-document contract stacks into typed relational schemas (Parties, PIs, Technologies, Instruments).
  • Engineered deterministic heuristic extractors with zero-shot LLM fallback to evaluate institutional governance rules (dual-faculty engagement, unexecuted assignment addenda, IP carveouts) across multi-document portfolios.
Fabric8r — Multi-Document Artificial Contract Synthesis Engine ReportLab • python-docx • NumPy
Benchmark Generation & Ground Truth Verification
  • Automated generator compiling realistic multi-document commercial stacks into native artifacts (born-digital PDFs, Word redlines, and degraded 110 DPI TIFF scans with affine shear and noise simulation).
  • Enforces a 6-word shingle similarity gate (pairwise Jaccard < 0.40) to prevent boilerplate collapse, outputting deterministic ground-truth answer keys (truth.json) with SHA-256 artifact verification for model benchmarking.
Rest8r — Deterministic Contract Consolidation & Restatement Engine Python AST Parser
Contract Restatements
  • Parses base agreements and cascading amendment hierarchies using Abstract Syntax Tree (AST) section resolution (matching hierarchical section addresses like Section 4.2(a)(ii)).
  • Automates the synthesis of fully restated contracts by executing structured replacement, insertion, and deletion transforms.

Experience

Faculty Consulting Program Director Dec 2025 – Aug 2026
CU Innovations, University of Colorado Anschutz • Aurora, CO
  • Inaugural director of the School of Medicine's faculty consulting program, launched January 2026, serving ~120 departments, divisions, centers, and institutes.
  • Wrote the program's agreement-classification, review-scope, and data-handling policies, and mapped them into Ironclad workflows.
  • Built a Power Automate integration with Ironclad's API that flagged incoming agreements for triage on adjustable keywords.
  • Served as triage point for misrouted agreements, routing out-of-scope contracts to Procurement, the Office of Grants and Contracts, and other University offices.
  • Carried ~60 agreements from intake to execution and served as escalation point for a four-person review team.
  • Diagnosed and escalated critical CLM automation defects where workflow notifications were triggering legally operative communications (offers, acceptances, voided-signature notices) at premature milestones.
  • Drafted novation, ratification, and assignment templates for the program's legacy-agreement transition.
Senior Marketing Support Manager Nov 2023 – Jun 2025
DIRECTV • Remote
  • Designed and implemented the company's first standalone OneTrust collection points for email-preference self-service, enabling a full marketability lifecycle, including re-entry.
  • Researched the legal frameworks within CAN-SPAM and state statutes to create customer-data-rehabilitation procedures built within the production data environments.
  • Directed a $2 million internal budget to increase Legal, Service, and Marketing communication reach, leading to a 118% year-over-year increase in marketing-consented audience.
  • Led a pilot enabling email-address validation at the service-center agent level, with an anticipated five-year benefit of $7 million.
  • Reviewed marketing campaigns for compliance with CAN-SPAM, CCPA, TCPA, and emerging AI rules.
Email Marketing Manager Apr 2022 – Oct 2023
Frndly TV • Denver, CO
  • Created the company's first Data Subject Request procedure from scratch, establishing intake, verification, fulfillment, and documentation protocols aligned with CCPA.
  • Drafted a Privacy Impact Assessment ahead of upgraded app listings on Amazon, Apple, and Roku storefronts.
  • Designed a privacy-compliant A/B testing framework connecting deidentified customer behavior with aggregated app activity, enabling product decisions without individual profiling.
  • Ran all outbound email for a live TV streaming service, roughly 200 million emails a year, and improved delivery from 88% to 99% while tripling volume.
  • Designed and led training for all new hires on email policies and customer data and privacy best practices.
Founder & Principal Attorney May 2017 – Dec 2021
Law Office of Christopher Sidebottom • Aurora, CO
  • Guided ~12 early-stage businesses and startups on entity formation, intellectual property, and privacy compliance.
  • Drafted, reviewed, and negotiated privacy policies, data processing agreements, and terms of service for digital platforms and streaming services.
  • Negotiated eSports and e-commerce contracts for streaming clients: IP licensing in and out, promotions, privacy, and identity.
  • Built FCC-compliant sponsored-content disclosures with creators and influencers.
  • Appeared as local counsel in first-party insurance litigation, from pre-trial management through mediation and arbitration.
Research Counsel Jul 2015 – May 2017
University of Colorado, Office of University Counsel • Aurora, CO
Embedded with the Technology Transfer Office (now CU Innovations), Anschutz Medical Campus
  • Brought in after negotiations had gone badly to lead a 10-year, $100 million multi-institution research agreement to mitigate the risk of gestational diabetes; moved it to execution, and it was in its fourth year of research as of 2020.
  • Personally negotiated over 1,100 agreements a year (MTAs, NDAs, SRAs, and more) and built a system for prioritizing the office's ~2,300 annual contracts.
  • Negotiated confidential-information, data-use, data-access, and research data-sharing agreements for compliance with HIPAA, FERPA, COPPA, and contractual restrictions.
  • Developed negotiation and protection strategy for over $3 million in sponsored research on downstream software tools.
  • Presented on the Defend Trade Secrets Act to attorneys and constituents across the University.
Earlier Experience
  • Guild of Metallic Content, eCommerce Operations Specialist (part-time), 2019 – 2020: stopped competitors copying designs from product photos by moving production to resin-printed internal geometries a photograph can't reproduce; learned the process from scratch.
  • Inside Out Creative, Digital Marketing Specialist, 2021 – 2022: email marketing and web builds for B2C and B2B clients.
  • LSU AgCenter, Office of Sponsored Programs and IP, Intern, 2012 – 2013: built an intake system for material transfer agreements; evaluated patent and technology licenses.
  • Office of the Louisiana Attorney General, Criminal Appellate Section, Summer Extern, 2013: drafted two published advisory opinions and most of an appellate brief.
  • Louisiana Supreme Court, Chambers of Justice John L. Weimer, Summer Law Clerk, 2012.

Education

LL.M., International and European Intellectual Property and Business Law • Université Jean Moulin Lyon 3 • 2014 (assez bien)

J.D. and Diploma in Comparative Law • LSU Paul M. Hebert Law Center • 2014

B.A., Philosophy, minor in Economics, cum laude • Wabash College • 2011

Credentials

CIPP/US, International Association of Privacy Professionals (IAPP) • 2025

Bar Admissions: Colorado (2016, inactive) • Illinois (2015, inactive)

Tools & Technologies

Legal Tech & CLM: Ironclad (workflow design, API, schema modeling) • Microsoft Power Automate • OneTrust CMP

AI & Systems: Relational Property Graphs • AST Section Resolution • Heuristic Extractors • LLM Benchmarking • Local Model Orchestration

Languages & Core: Python • SQLite / SQL • C#/.NET (architecture) • HTML/CSS • Git • DNS and email authentication (SPF, DKIM, DMARC, BIMI)

Also

Co-created and hosted Mile High Fight Night, a biweekly Denver eSports tournament broadcast (2018 – 2020). Produced internet radio for Doowopradio.com (2017 – 2019). General Manager, WNDY 91.3 FM (2010 – 2011).