John Sheffield

About John Sheffield

I’ve spent 20+ years in enterprise SaaS sales, but the last three have been the most interesting.At Yottaa, I built a services division from nothing: no budget, no marketing, no playbook. I led the sales strategy, designed the GTM motion, and built custom AI-powered sales infrastructure (Node.js command centers integrating Salesforce and Gong APIs, ICP health scoring, automated territory analysis) that replaced 3–4 dedicated headcount. The result: the company’s sole profitable business unit at $13.5M ARR, 100% organic logo retention through a forced platform migration, and an NRR trajectory from 69% to 101%.At Bazaarvoice, I built the enterprise acquisition function from scratch and led it for four years. 118% average quota attainment, a sales methodology (GPS) I created that’s still in use company-wide, and a systematic competitive campaign that won 49 of 50 target accounts after a DOJ ruling opened the market. Career theme: I get hired when the playbook doesn’t exist yet. I’ve built teams, created sales methodologies, productized free services into $2M+ ARR businesses, and operated as a one-person GTM engine using AI tools that most sales orgs haven’t adopted yet. I’m most useful when the situation is ambiguous and requires building, not just managing.

Experience

1. Vice President of Sales, Web Performance Services

   Yottaa

   May 2024 — Present

   Built and led Yottaa’s Web Performance Services division from inception — the sole profitable business unit generating 78.8% of total company revenue. Managed a portfolio of 70 enterprise accounts including Ralph Lauren, Bath & Body Works, and Kmart Group through a forced CDN platform migration and portfolio-wide contract repricing.• Achieved 100% organic logo retention in 2024 during forced migration from proprietary CDN to Fastly and simultaneous portfolio-wide repricing• Grew expansion revenue 5x year-over-year ($309K → $1.54M), driving annualized expansion rate from 3.4% to 14.5%• Improved raw NRR from 69% to 101% across 20-month tenure; posted first net-positive month January 2026• Built AI-powered sales operations infrastructure from scratch: custom Node.js command center integrating Salesforce and Gong APIs, CDN performance lookup tool, ICP health scoring system, and automated territory analyzer — replacing sales ops, enablement, and marketing functions with zero dedicated headcount• Managed $4.08M in structural contraction across 33 repricing events while outperforming rest of organization by nearly 2x (26.4% vs. 50.1% contraction)• Designed hunter/farmer team structure and personally managed 5 highest-complexity enterprise accounts as player-coach

Education

• Rhodes College

  Bachelor of Arts (B.A.), Philosophy