Hugo Dempsey
Dublin
Summary
I've spent over 20 years+ helping organisations grow, from early-stage startups to global tech companies. I'm now at a point in my career where I want to bring that experience to something with a different kind of impact. The housing crisis in Ireland is real and urgent, and Habitat's combination of direct community action and longer-term systems change is exactly the kind of work I want to be part of.
Overview
24
24
years of professional experience
Work History
Fractional CRO / VP of Sales Ireland
Coupler.io
Dublin
04.2025 - Current
- Helping a product-led SaaS company build its first real sales function - defining commercial strategy, team structure, and messaging from scratch.
- The work is less about selling and more about building: the systems, culture, and processes that let a small team grow with limited resources.
VP & Head of Commercial, EMEA
Sprout Social
Dublin
09.2023 - 03.2025
- Led ~60 people across EMEA, responsible for ~$100M in annual revenue. Transformed the commercial model from reactive/inbound to outbound and value-led.
- +50% growth in Total Contract Value YoY; +500% growth in outbound pipeline; landed the two largest new-business wins in EMEA history.
Co-Founder & Chief Revenue Officer
Demoleap
Dublin
01.2019 - 09.2023
- Co-founded an AI-powered sales enablement platform. Took it from concept to VC funding and early enterprise revenue - raising £4.3M across pre-seed and seed rounds.
- Built the sales, marketing and customer success teams from zero. Personally closed the first 20 enterprise customers across the US and Europe.
- Startup life sharpened my ability to make the case for something new, operate with limited resources, and keep a team motivated under uncertainty - all directly relevant to voluntary board work.
Sales Director, UKI & Emerging Markets
Zendesk
Dublin
12.2017 - 01.2022
- Built Zendesk's first outbound mid-market and enterprise motion from scratch. Grew consistently at ~35% CAGR; 150% of quota in 2021.
- Closed major accounts including Ryanair, NHS, Siemens and Careem. Launched Zendesk's first vertical sales team (UKI FinTech).
Regional VP of Sales
Salesforce
Dublin
06.2008 - 12.2017
- Nearly a decade at Salesforce - growing from individual contributor to leading 24 AEs across Dublin and Tel Aviv. Scaled the territory from $10M to $100M+ ARR.
- President's Club 8 out of 9 fiscal years. EMEA Team of the Year FY17.
Bids & Tenders Manager
Dell Technologies
Dublin
08.2002 - 06.2008
- Six promotions in six years. Eventually led pursuit of large, complex high-value deals as a senior overlay - closing multiple contracts over $1M.
Education
Executive Leadership Programme - Business Management Practice
Stanford Graduate School of Business
01-2024
MSc - Leadership & Management Practice
UCD Michael Smurfit Business School
01-2018
Diploma in Sales Management - Sales Management
UCD Michael Smurfit Business School
01-2013
Skills
- Partnerships & fundraising strategy
- GTM design & execution
- Organisational scaling
- Commercial transformation
- Cross-functional leadership
- Stakeholder engagement
- Strategic planning
- Change management
- Revenue operations
- Team building & coaching
- International markets
- Data-driven decision making
Websites, Portfolios and Profiles
linkedin.com/in/hugodempsey
Timeline
Fractional CRO / VP of Sales Ireland
Coupler.io
04.2025 - Current
VP & Head of Commercial, EMEA
Sprout Social
09.2023 - 03.2025
Co-Founder & Chief Revenue Officer
Demoleap
01.2019 - 09.2023
Sales Director, UKI & Emerging Markets
Zendesk
12.2017 - 01.2022
Regional VP of Sales
Salesforce
06.2008 - 12.2017
Bids & Tenders Manager
Dell Technologies
08.2002 - 06.2008
Executive Leadership Programme - Business Management Practice
Stanford Graduate School of Business
MSc - Leadership & Management Practice
UCD Michael Smurfit Business School
Diploma in Sales Management - Sales Management
UCD Michael Smurfit Business School