About
AI GTM Engineer & Enablement Leader
I build the systems, not just the content.
Hi, I'm Evan. I have eight years of experience across healthcare, SaaS, and enterprise software, spanning the full commercial motion, seller onboarding and ramp, sales methodology and skills coaching, manager enablement, channel readiness, and the product enablement that makes complex platforms sellable. I started in the seat, as an SDR and eventually an AE, so I build for how reps actually sell, not how the organization wishes they did. Now my work is AI-native: designing, shipping, and driving adoption of GTM agents, plugins, and knowledge infrastructure that sales and customer success teams use in the flow of work. Equal parts builder and enabler. I engineer the tooling, then make sure the people using it know how and why.
Experience
Eight years across the full commercial motion.
Oct 2025 – Present
Spring Health
AI GTM Engineer & Enablement Lead
Launched a pilot network of GTM AI agents that act as an embedded chief of staff for enterprise sellers, delivering personalized guidance inside the seller workflow. Design and ship internal AI capabilities end to end with Claude plugins and skills, Guru knowledge agents, and automated launch pipelines that cut manual asset production time by more than 50%. Own the source-of-truth knowledge infrastructure GTM teams depend on.
AI agent network for enterprise sellers>50% cut in asset production timePreviously Product Enablement LeadFeb 2025 – Oct 2025
Dropbox
Enablement Partner, Global Field Operations & Sales Strategy
Designed and delivered global revenue enablement for Sales, Account Management, and Channel across North America, EMEA, and APJ, covering Core, Sign, Dash, and Reclaim.ai. Built the field motion for Dropbox Dash and ran a recurring Blitz Week that generated net-new pipeline, scaling from $1.2M to $2.3M to $3.1M over three consecutive quarters.
$3.1M quarterly Blitz Week pipelineGlobal scope: NA, EMEA, APJWinning by Design Provocative SellingDec 2022 – Mar 2025
HST Pathways
Head of Sales Training & Enablement
Led training and enablement for the full Revenue org, closing 2024 at 102% of bookings plan. Built the company's first AI roadmap for GTM, launched a companywide LMS that reduced ramp time, and embedded modern sales methodology that improved close rates org-wide. Developed deep fluency in HIPAA, SOC 2, and HITRUST to set messaging apart with healthcare buyers.
102% of 2024 bookings planFirst company AI roadmap for GTMFour product launches, two new service lines2021 – 2022
Provi
Sales Training & Enablement Lead
Scaled sales readiness through rapid growth with custom content that improved field efficiency and cut average time to first order from 30 days to 15. Designed new hire onboarding, partnered with Product and Marketing on GTM strategy, and supported the SevenFifty merger through due diligence and post-merger integration.
Time to first order cut 30 → 15 daysSevenFifty merger integration2020 – 2021
PatientPop (now Tebra)
Inside Sales Training & Enablement Manager
Rolled out Gap Selling as the core methodology, driving a 20%+ increase in average deal size. Ran monthly onboarding for SDRs, AEs, and Field Sales that cut ramp time by more than 25%, and maintained enablement continuity through the Kareo merger that formed Tebra.
+20% average deal sizeRamp time cut >25%2018 – 2020
Compeat (now Restaurant365)
Sales Trainer | Account Executive | SDR
Fastest promoted SDR in company history, from SMB to enterprise prospecting, into a full-cycle closing role across a seven-state Midwest territory, and finally into Sales Trainer. This is where it started: in the seat, learning how reps actually sell.
Fastest promoted SDR in company historyFull-cycle AE before moving into enablement
Skills
Core capabilities.
AI & Agent Engineering
GTM agent design and orchestration, Claude Code, Claude plugins and skills, ChatGPT agents, Guru knowledge agents, prompt engineering, Salesforce integration, workflow automation, AI adoption roadmaps.
Revenue Enablement
Launch and product enablement, onboarding and ramp design, persona playbooks, competitive positioning, live and AI role plays, LMS content creation and administration.
GTM Partnership
Product, Product Marketing, and Sales alignment, sales methodology rollouts, frontline manager coaching, channel enablement, global program delivery.
Methods & Domains
Challenger Sale, Winning by Design, Gap Selling, value-based selling, behavioral healthcare and SaaS, HIPAA, SOC 2, HITRUST.
Education: University of Wisconsin–Madison (Business Management) · Edgewood College (Clinical Psychology & Spanish) · NASM Certified Personal Trainer
Work with Evan