Sam Holstein

About Me

I'm Sam Holstein. I design and ship AI automations and agentic workflows that plug into real systems—CRMs, call platforms, content pipelines, and analytics. My work is reliability-first: measurable outcomes, guardrails, and production readiness over demos.

My approach is systems-first: map the workflow, define success, automate the stable steps, and add guardrails (human review, access control, monitoring, evals). I've shipped workflows that cut vendor spend, reduce cycle time from days to minutes, and remove hundreds of manual hours per month.

Earlier career chapters—product building, writing, entrepreneurship—taught me to turn complexity into usable systems and to explain the "why" behind decisions. That shows up in how I communicate architecture, tradeoffs, and failure modes today.

Milestones

Each season of my career has added a new lens—entrepreneurship, writing, and now AI systems work—that shapes how I partner with clients today.

2025

Recent

Director of Systems & AI — 1031X

Retired stalled vendor stack, replaced with internal automation; cut six-figure spend, unified call/CRM data, added call-to-CRM attribution, and reduced IVR changes from days to minutes.

2023

Marketing Ops & Systems Manager — 1031X

Rebuilt WordPress + HubSpot stack, increasing organic traffic 124% and conversion 370%; implemented CRM, funnel reporting, and early AI-assisted workflows.

2019

Published with Apress

Published a book with Apress, iPhone App Design for Entrepreneurs, to guide founders through building standout mobile products.

2017

Full-Time Writer

Began publishing long-form essays on Medium, growing an audience of 20K+ readers around entrepreneurship, creativity, and technology.

2013

EO High School Entrepreneur of the Year

Won the Entrepreneurs' Organization High School Entrepreneur of the Year award for Pufferfish Software's growth and impact. Read the profile.

2012

TEDx Speaker

Gave a TEDx talk about building technology as a teenage founder.

2011

Pufferfish Software

Founded Pufferfish Software to craft bespoke mobile and web products for schools, families, and small businesses.