Diana Pfeil

Head of AI

Boulder, Colorado, United States12 yrs 5 mos experience

Key Highlights

  • 2-time AI startup CTO with extensive leadership experience.
  • Expert in guiding startups through AI and ML implementation.
  • Strong background in operations research and mathematical modeling.
Stackforce AI infers this person is a B2B SaaS and Healthtech expert with a focus on AI and ML strategies.

Contact

Skills

Core Skills

Coaching & Mentoring

Other Skills

Machine LearningOptimizationMathematical ModelingOperations ResearchResearchMatlabRStatisticsPythonAlgorithmsData AnalysisApplied MathematicsStatistical ModelingLaTeX

About

I help startup leaders - especially in B2B SaaS and healthtech - figure out what AI to build, and how to actually get it shipped. As a 2-time AI startup CTO, ex-Amazon engineer, and MIT PhD, I’ve seen how teams get stuck: burning months chasing hype, unclear on priorities, unsure which tools or frameworks to trust—or building features that never see the light of day. Now I partner with founders and tech leads to actually ship high-impact GenAI and ML features. Whether you're starting from zero or knee-deep in experiments, I help you find the right direction, move faster, and avoid wasted time. I bring clarity, momentum, and get-after-it energy, so your AI work delivers value your board, investors, and customers can see.

Experience

Attesto

Head of AI

Aug 2025Present · 8 mos

Indecollective

Member

May 2025Present · 11 mos · Denver, Colorado, United States

  • IndeCollective is a private community where top consultants, coaches, and fractional leaders tap into the proven playbooks, far-ahead mentors, and supportive community, and modern tools to build high-impact businesses and more balanced lives.
  • I'm passionate about working with Series-A+ startups in the areas of Machine Learning and AI strategy and execution.

Sunbeam consulting

Founder | Advisor | Fractional Head of AI | Coach

Jan 2024Present · 2 yrs 3 mos · Colorado, United States

  • Fractional CTO and ML/AI Advising services for startups.
  • https://www.dianapfeil.com/advising/

Techstars boulder

Mentor

Jul 2023May 2024 · 10 mos · Boulder, Colorado, United States

  • Lead mentor to Techstars Boulder startups in the security and travel tech space.
Coaching & Mentoring

Pex

2 roles

CTO

Promoted

Mar 2022Oct 2023 · 1 yr 7 mos

  • Pex is the leader in digital rights technology, providing solutions to identify music and rightsholders for licensing, content management, compliance, and anti-piracy. Pex is backed by $50M+ in venture funding.
  • Led 70+ person engineering team at Pex, focusing on
  • providing strategic direction for the team
  • building a wonderful work environment for engineers to drive effective hiring and retention
  • technical soundness for Pex’s industry-leading ML/AI-powered tech
  • operational excellence including fast iterative execution
  • Represented Pex at hearings for the US Copyright Office, speaking on the topic of using AI for identification and attribution of copyrighted works.

Head of R&D

May 2021Mar 2022 · 10 mos

  • Led a 15-person ML research team at Pex. Teams focused on ML for audio data, and building industry-leading content identification algorithms to power identification for audio, image, and video data.

Paypal

Staff Data Scientist

Jul 2020May 2021 · 10 mos

  • via Honey acquisition, continuation of ML-focused role at Honey

Honey (joinhoney.com)

Data Scientist / Data Science Manager

Mar 2019Jun 2020 · 1 yr 3 mos · Boulder

  • Founding member and leader of risk team to launch Buy Now, Pay Later fintech product. Iterated on credit risk models using non-traditional data. Delivered model risk management process including a fair lending regulatory component.
  • Contributed and advised on machine learning projects across Honey, including automated content extraction from the web, fraud detection, building of a canonical product catalogue, and the Honey rewards program.

University of colorado denver

Adjunct Prof of Business Analytics

Jan 2016May 2016 · 4 mos · Denver, CO

  • Taught a Big Data Predictive Analytics Practicum course to Business Analytics masters students. Designed all course content, lectures, and a practicum project.

Lumo

CTO

Jul 2015Jan 2019 · 3 yrs 6 mos

  • We're a predictive technology company working on machine learning for air travel.
  • First member of engineering team for the travel tech startup funded by NASA SBIRs and venture funding. Hired and led engineering team, including full time, contract engineers, and an offshore team.
  • Prototyped and built Lumo’s core machine learning engine to predict FAA actions and flight delay. Built and operated Lumo’s REST APIs, and oversaw the web and mobile apps.
  • Engaged with customers and investors, and oversaw all short term and strategic technology and infrastructure decisions. Stack included AWS, Python, and Kubernetes. React Native for mobile.

Opttek systems, inc.

Senior Optimization Analyst

Jul 2012Jun 2015 · 2 yrs 11 mos · Boulder, CO

  • Projects included developing models to predict customer churn for a large SAAS provider, improvements to the core algorithms in OptTek’s simulation optimization engine, basic research in clustering, and prototyping and developing a tool for exploratory data analysis of large scale simulations.

Amazon.com

Software Development Engineer

Jan 2005Jul 2006 · 1 yr 6 mos

  • Worked in the machine learning group on projects such as:
  • behavior based search, a system which mined anonymized customer behavior data to suggest highly relevant search results
  • developed a generic key value store used by dozens of Amazon teams. This was a precursor to AWS NoSQL stores such as SimpleDB and later Dynamo

Education

Massachusetts Institute of Technology

PhD — Operations Research

Jan 2011Present

University of California, Berkeley

B.A. — Mathematics and Computer Science

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