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Austen Tucker-Crowder

AI Enablement & Engineering Transformation Leader

Chicago, IL

austen@thearcades.mework.thearcades.megithub.com/Arcadesys
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Summary

AI enablement and engineering transformation leader, builder, program manager, and agile coach with 16+ years delivering customer-focused software. I build the operating systems, learning experiences, and decision-making practices that help teams adopt AI in their everyday work. An accessibility-first facilitator, I turn complex transformation work into usable tools, shared goals, and concrete next steps.

Key Accomplishments

  • Helped raise agentic-coding adoption from roughly 2% to 43% of merge requests; it was still climbing at departure
  • Led Devin adoption with goals and KPIs, including a game used to communicate the operating model
  • Led a March 2026 roadshow for product managers across three continents, introducing Cursor and agentic AI; attendees began producing prototypes afterward
  • Built Wavelength, an MCP-enabled operating artifact for tasks, RAID-log items, and program state
  • Within four days of arrival, facilitated an onsite that multiple attendees called one of their best
  • Reduced planning time by 50% at Arity via data-driven prioritization for 50+ engineers
  • Increased feature throughput by 400% at WorkTango during merger-driven agile transformation
  • Served as product owner for a Guaranteed Rate data-mining tool associated with $1.5B in locked loan volume

See the work:Case studiesProjects

Experience

ActiveCampaign

AI Enablement and Transformation

Chicago, IL · 06/2025–09/2026

  • Led AI enablement and transformation across engineering, product, and leadership, turning adoption goals into measurable, repeatable practice
  • Helped raise agentic-coding adoption from roughly 2% to 43% of merge requests; adoption was still climbing at departure
  • Led Devin adoption with goals and KPIs, using a game to communicate the operating model
  • Led a March 2026 roadshow for product managers across three continents, introducing Cursor and agentic AI; attendees began producing prototypes afterward
  • Built Wavelength, an MCP-enabled operating artifact containing tasks, RAID-log items, and program state
  • Coordinated cross-pillar AI transformation work, including outcomes and north-star metrics that supported ePMO governance and executive review
  • Built Claude skills and Langfuse evaluation prompts that supported daily operations and assessment of AI-agent response quality
  • Designed accessibility-first Cursor and agentic-AI learning experiences that gave participants room to build working prototypes
  • Within four days of arrival, facilitated an onsite that multiple attendees called one of their best
  • Created Worksites, intensive problem-solving sessions using board-game prototyping principles, and built operational tools for shared decisions and program visibility

Allstate

Senior Program Manager

Chicago, IL · 08/2023 – 02/2025

  • Led cross-functional teams to deliver key initiatives across the Allstate Family of Companies
  • Enhanced decision-making through robust metrics and streamlined project management tools
  • Championed agile practices and AI adoption by co-designing an AI training curriculum for the product department

Arity

Senior Scrum Master & Agile Coach

Chicago, IL · 06/2020 – 08/2023

  • Slashed planning time by 50% for quarterly planning for 50+ engineers
  • Mentored Scrum Masters, enabling three promotions and strengthening agile alignment within the org

WorkTango

Senior Scrum Master & Head of Agile PMO

Chicago, IL · 01/2019 – 06/2020

  • Spearheaded agile transformation during a merger, boosting feature delivery throughput by 400%
  • Redesigned workflows to double team velocity
  • Built a mentorship program within the technology organization to nurture future leaders

Guaranteed Rate

Scrum Master & Project Lead

Chicago, IL · 11/2015 – 12/2018

  • Rescoped a delayed initiative to deliver an MVP in two months, cutting production time by 75%
  • Acted as product owner for a data-mining tool associated with $1.5B in locked loan volume
  • Developed a measurement plan that streamlined app functionality and elevated user engagement

Earlier Experience

  • Chicago Housing Authority — Business Analyst & Scrum Master (2012–2015)
  • Technology Partnership Group — Business Analyst (2009–2012)

Community & Volunteer Work

Midwest FurFest

Operations Volunteer

Chicago, IL

Staff role at a registered 501(c)(3) running a 15,000-attendee annual conference. Volunteer coordination, on-site operations, and logistics at scale under a hard, immovable deadline.

Tools & Skills

AI & Automation: Claude Code, Cursor.ai, Langfuse, Glean, Agentic Development, LLM Evaluation, MCP Development, Claude Skills Development

Facilitation & PM: Jira, Digital.ai, Confluence, Airtable, Trello, Mural, Remote/Hybrid Facilitation, Offshore Coordination

Development: Next.js, React, Node.js, Python, Express, Bootstrap, Postgres, Amazon Lambdas

Tracking & Analysis: Google Analytics, Hotjar, Datadog, Grafana, Tableau

Communication: Video, Audio, and Graphic Production, Training Production, Professional Writing, Accessibility-First Design

Methodologies: Paper Prototyping, Constructivism, Kolb's Experiential Learning, Think-Pair-Share, MoSCoW, Rose/Thorn/Bud, Spotify Squad Health Check

Education & Certifications

  • Wabash College — B.A. in English, Rhetoric, and Teacher Education, 2007
  • Certified Scrum Master (CSM) — 2011–Present

Work with me

I help engineering and product organizations make AI useful in everyday work — through working tools, clear goals, and learning experiences that leave people with something they built. If that’s the problem on your desk, get in touch.

Email me Read the case studiesSee what I build