10+ years in B2B SaaS leading knowledge, support, and onboarding, with the automation built in-house to back it up.
I organize chaos where customer signals, operations, and how people actually learn software all meet. For 10+ years I've built the systems that get customers to value faster and keep them there.
Plenty of CX and ops leaders can read a dashboard. I write the code behind it. At Entrata I built a 4-agent AI pipeline in Python and GitHub that pulls patterns from customer data, surfaces where people get stuck, and routes the findings to close the gap before it compounds.
The approach is always the same. Find where customers get stuck, trace it back to where it could have been prevented, fix it there, and build something that doesn't need reinventing next quarter.
Production pipelines I build in Python and GitHub, with real version control behind them. At Entrata, 4 specialized agents cut standard article updates 62% (8 hours to 3, across 80% of the work) and dropped complex drafting from 14 hours to 90 minutes. That's 8+ hours per cycle back to the team.
Governing content at scale. 3,500+ help articles across 60+ product lines, release-aligned publishing, KCS methodology, and content signal scoring. The library my team runs deflects 60% of support tickets traceable to documentation.
Building the teams and systems that get customers to value fast. At Canopy I grew an onboarding org from 1 to 30, cut onboarding from 3-4 months to 30-60 days, and put 900-1,000 customers a year through a repeatable program.
Curriculum, LMS configuration, and certification programs designed from learning objectives through measurable outcomes. At Qualtrics, Experience Basecamp generated $1.6MM over 24 months and reached 250K employees.
Available for consulting engagements, fractional leadership, and full-time roles. Get in touch →
Where customers actually get stuck. I read the tickets, the signals, and the content gaps before touching a tool.
Back to where the problem could have been prevented. The fix usually lives upstream of where the pain shows up.
At the source. Often that means building the automation, the content system, or the SOP that closes the gap for good.
So it doesn't need reinventing next quarter. KPIs and feedback loops keep it honest after I'm gone.
A Zendesk knowledge base at 3,500+ articles across 60+ product lines. Manual updates ate the team's time, and self-service was hard to measure.
ApproachBuilt a 4-agent AI pipeline in Python and GitHub. Ran the Zendesk Copenhagen to Lotus migration, rebuilt the taxonomy, applied KCS methodology, and stood up a Jira content workflow with clear SLAs. Self-service rose 25% year over year.
ResultStandard updates 62% faster (8 hrs to 3) • complex drafting 14 hrs to 90 min • 60% ticket deflection
No structured onboarding ecosystem. New customers were left to figure out the product on their own, driving early churn and overwhelming support.
ApproachGrew the onboarding org from 1 to 30 and built the stack from scratch: Knowledge Base, LMS, video library, and 2 certification programs. Put 900-1,000 customers a year through a repeatable program.
ResultOnboarding 3-4 months to 30-60 days • 40% churn reduction • 30% onboarding efficiency
Instructor-led training couldn't keep pace with customer growth across global markets. They needed an on-demand education model that could.
ApproachBuilt and launched Experience Basecamp on Skilljar, digitizing 70+ courses on guided pathways and creating a certification program customers could complete on demand.
Result$1.6MM revenue over 24 months • 130% of expansion targets • 250K employees reached
"Kyle's analytic skills helped us identify inefficiencies to target as a management team. His ability to break down complex data sets and concepts and make them easily accessible to senior leadership helped build consensus and a clear path forward. His unique blend of strong work ethic with a bit of fun make him a joy to work with."
Aaron Bestic Operations Leader, McMaster-Carr
"Kyle is the person you want in the room when there's a complex problem to solve. He has a natural ability to break things down, analyze the data, figure out the smartest path forward, and then roll up his sleeves and get to work. He's resourceful, sharp, and doesn't shy away from ambiguity. In fact, he thrives in it."
Michelle Overdevest Product Marketing, Canopy