Stephen E. Dockray
Boston,MA
Summary
Customer Success and SaaS sales professional with 9+ years of experience driving net-new revenue, renewals, and expansions across high-performing software organizations including LoopNet (CoStar), Apryse, and ServiceNow. Strong background in prospecting, discovery, and closing new business, paired with managing multimillion-dollar enterprise portfolios. Known for building pipeline, navigating complex buying groups, and converting customer outcomes into long-term ARR growth.
Overview
10
10
years of professional experience
Work History
Account Executive
LoopNet
Boston, USA
08.2025 - Current
- Own full-cycle sales process for net-new advertisers, from prospecting and discovery through close
- Build and manage outbound pipeline targeting property owners, brokers, and developers
- Close subscription and advertising revenue by aligning LoopNet solutions to leasing and visibility goals
- Present ROI-driven proposals and negotiate contracts with senior decision-makers
- CoStar Group, NASDAQ: CSGP
Senior Enterprise Customer Success Manager
Apryse
Boston, USA
01.2023 - 08.2025
- Managed portfolio of 15 enterprise accounts totaling $9.6M in ARR across financial services, manufacturing, pharma, and retail
- Achieved 200% of annual expansion target through strategic upsell and cross-sell initiatives
- Generated expansion pipeline through proactive discovery, stakeholder mapping, and use-case identification
- Partnered with Sales on net-new opportunities within existing enterprise organizations
- Led complex renewals and negotiations, consistently maintaining 95%+ retention
Customer Success Manager
ServiceNow
Greater Boston, USA
07.2017 - 12.2020
- Owned commercial outcomes for a $5M+ enterprise book of business including renewals and expansion
- Drove net-new and expansion revenue by identifying whitespace across departments and workflows
- Supported Sales-led new business motions through technical discovery and executive alignment
- NYSE: NOW
Account Executive
EverQuote
Cambridge, USA
06.2016 - 06.2017
- Closed net-new insurance partners through high-volume consultative sales
- Managed full sales cycle in a quota-driven environment
- Prospected, pitched, negotiated, and closed SMB and mid-market accounts
- NASDAQ: EVER
Education
Bachelor of Arts - Political Science & Economics
University of Massachusetts Boston
Skills
- Net-New Logo Acquisition & Full-Cycle Sales
- Enterprise Account Management & Expansion
- Renewals, Upsell & Cross-Sell Strategy
- Prospecting, Discovery & Value-Based Selling
- Executive & C-Suite Stakeholder Engagement
- Forecasting, Pipeline Ownership & CRM Management
- Salesforce
- HubSpot
- Gainsight
Websites
Timeline
Account Executive
LoopNet
08.2025 - Current
Senior Enterprise Customer Success Manager
Apryse
01.2023 - 08.2025
Customer Success Manager
ServiceNow
07.2017 - 12.2020
Account Executive
EverQuote
06.2016 - 06.2017
Bachelor of Arts - Political Science & Economics
University of Massachusetts Boston