Paul Drayton

About Paul Drayton

I don\'t just sell — I win. And the numbers prove it.Over 15+ years, I\'ve built a career doing one thing exceptionally well: closing complex, high-stakes SaaS deals inside Fortune organizations. At Twilio, I\'ve generated $14M+ in ARR while averaging 138% quota attainment across four consecutive years — hitting 157% in 2025. That\'s not luck. That\'s discipline, obsession, and a relentless drive to compete at the highest level.I specialize in multi-threaded enterprise sales cycles where the deals are large, the stakeholders are many, and the competition is fierce. I sell to CIOs, CTOs, and C-suite executives across Healthcare & Life Sciences, Financial Services, Retail, and Technology — building ROI-driven business cases tied to digital transformation, contact center modernization, and customer experience initiatives.My approach is rooted in MEDDPICC and Challenger Sale methodologies — I qualify hard, challenge the status quo, build consensus across complex buying groups, and close with conviction. I bring both tactical sharpness and strategic vision to every deal, whether I\'m navigating a 9-month competitive displacement or driving expansion ARR within an existing Fortune account.Core Strengths:$14M+ ARR closed | 138% avg quota attainment | 157% peak attainment Fortune enterprise sales — Healthcare, Financial Services, Retail, Technology MEDDPICC & Challenger Sale | Executive alignment & C-suite selling CPaaS, UCaaS, Cloud Contact Center, SD-WAN, Cybersecurity & Infrastructure Salesforce CRM | Outreach | HubSpot | Contract negotiation & closing 70% self-sourced pipeline — I create opportunities, I don\'t wait for themI thrive in fast-paced, high-performance sales cultures alongside other top producers. If you\'re building an enterprise sales team that demands results — let\'s connect.

Experience

1. Enterprise Solutions Specialist

   Twilio

   Jan 2020 — Present · Atlanta, GA, US

   Selling CPaaS and cloud contact center platforms — Twilio Flex, Programmable Voice, and SIP Trunking — exclusively into Fortune enterprises across Healthcare & Life Sciences, Financial Services, and Technology. Territory spans the Southeast and West Coast. Generated $14M+ ARR over four years, averaging 138% quota attainment — peaking at 157% in 2025 YTD and ranking #1 in region. Closed a $1.4M ARR agreement with a national healthcare provider modernizing patient communication infrastructure using cloud contact center technology. Secured a $900K multi-year SaaS deal enabling omnichannel customer engagement for a Fortune 500 financial services organization, displacing an incumbent after a competitive 9-month cycle. Led enterprise migration to Twilio Flex supporting agents for a global technology company — a multi-phase, multi-year platform transformation. Drive 70% of pipeline through self-sourced prospecting, engaging CIOs, CTOs, VP Customer Experience, and Operations leadership across Fortune accounts. Apply MEDDPICC and Challenger Sale methodologies to maintain deal control, compress timelines, and deliver clean forecasts on six- and seven-figure agreements.

Education

• The University of Georgia

  Bachelor of Science, Economics

Skills

• Cisco Technologies
• Sales Management
• Burglar Alarm
• Surveillance
• Salesforce.com
• Virtualization
• Routers
• Cisco Switches
• Ibm Servers
• Sales Operations
• Storage
• Cisco
• Access Control
• Channel Partners
• Ip
• Cctv
• Dell Poweredge Servers
• Hp Proliant
• Networking
• Problem Solving
• Direct Sales