Dara O'Toole
Madrid,Spain
Summary
Mid-Market and Enterprise SaaS Account Executive with 10+ years of experience driving revenue growth across UK&I, EMEA, North America and APAC markets. Consistent top performer with a proven record of exceeding quota in high-growth technology companies including Deel, SocialTalent, DocuSign and Indeed.
Specialises in complex consultative sales, strategic account expansion and self-generated pipeline creation, with 80–100% of revenue opportunities sourced through outbound prospecting and account development. Experienced in engaging C-suite and senior decision-makers across HR, Finance, Legal, Operations and IT functions, managing deal cycles from discovery through negotiation and close.
Track record includes 127% quota attainment against a $1.2M annual quota, 115% attainment at Deel, and closing deals worth up to $287K ARR. Passionate about helping organisations solve business challenges through technology while building long-term customer partnerships.
Overview
9
9
years of professional experience
Work history
Mid Market Account Executive
Deel
, Remote
2024.08 - 2025.12
- Managed a portfolio of Mid-Market customers across UK&I, North America and MENA, selling global payroll, Employer of Record (EOR), contractor management and workforce solutions.
- Achieved 115% annual quota attainment, consistently outperforming revenue targets in a high-growth SaaS environment.
- Delivered quarterly expansion quota attainment of 107% (Q1), 98% (Q2), 145% (Q3) and 112% (Q4).
- Generated 80%+ of closed revenue through self-sourced opportunities, leveraging strategic outbound prospecting, account mapping, executive networking and multi-threaded engagement.
- Closed the largest deal in territory worth $287,520 ARR, coordinating multiple stakeholders across HR, Finance, Legal and Procurement functions.
- Managed complex sales cycles of 3–6 months with an average deal size of $40K–$120K ARR.
- Led cross-functional expansion initiatives by identifying new buying centres and securing adoption across previously untapped departments, creating net-new revenue streams within existing accounts.
- Partnered with C-suite, HR, Finance and Operations leaders to design and implement global workforce strategies supporting international growth.
- Consistently delivered expansion revenue through strategic cross-sell and upsell motions across payroll, EOR and contractor management product lines.
- Represented Deel at executive customer and partner events through the company's strategic partnership with Arsenal Football Club.
Enterprise Account Executive
SocialTalent
Dublin, Remote
2022.07 - 2023.08
- Managed full-cycle enterprise sales across EMEA, North America, and APAC, selling talent development and learning technology solutions to enterprise organisations.
- Achieved 127% of a $1.2M annual quota, consistently exceeding revenue targets in a competitive SaaS market.
- Generated 100% of pipeline through outbound prospecting, owning the sales cycle from account identification to close.
- Achieved 145% quota attainment in the first quarter after ramp, the highest performance by a newly ramped Account Executive in company history.
- Closed the largest deal in the territory worth $185K ARR, managing complex, multi-stakeholder sales across HR, Learning & Development, and Talent Acquisition.
- Maintained an average deal size of $100K–€200K ARR across 90–150-day enterprise sales cycles.
- Executed account-based outbound strategies using LinkedIn Sales Navigator and Outreach to engage enterprise decision-makers.
- Built multi-threaded opportunities across global organisations, aligning talent and learning initiatives with strategic business objectives.
Account Executive
DocuSign
Dublin
2021.02 - 2022.06
- Managed a portfolio of approximately 300 UK & Ireland accounts, driving expansion and new business opportunities across existing customers.
- Achieved 117% annual quota attainment against a $360K annual quota.
- Generated 100% of pipeline through self-sourced prospecting and account development activities, owning opportunities from identification through close.
- Sold agreement cloud and digital transformation solutions to Mid-Market and Enterprise organisations across the UK & Ireland.
- Maintained an average deal size of $30K–£50K ARR with sales cycles ranging from 30–90 days.
- Built and executed strategic account plans to identify expansion opportunities, increase product adoption and drive incremental revenue growth.
- Conducted discovery, stakeholder mapping, commercial negotiations and executive presentations throughout the full sales cycle.
- Consistently partnered with executive decision-makers across Legal, Procurement, IT, HR and Operations functions to modernise document and contract workflows.
Partner Development Representative
DocuSign
Dublin
2019.04 - 2021.02
- Selected by senior leadership to pioneer the Partner Development Representative function across EMEA.
- Collaborated with DocuSign leadership to establish scalable partner-sourced pipeline generation processes and go-to-market strategies.
- Generated an average of 15–30 qualified opportunities per month through strategic partnerships, channel engagement and industry events.
- Developed relationships with technology and consulting partners to drive pipeline creation and accelerate revenue growth.
- Leveraged partner ecosystems to identify new business opportunities and expand market reach across EMEA territories.
- Consistently exceeded partner pipeline generation targets through proactive account planning and relationship management.
Market Development Representative
DocuSign
Dublin
2018.10 - 2019.04
- Generated pipeline through outbound prospecting into Mid-Market and Enterprise organisations across assigned territories.
- Developed territory plans aligned to market trends, customer success stories and marketing campaigns to maximise opportunity creation.
- Executed multi-channel outbound campaigns to increase brand awareness and generate qualified sales opportunities.
- Partnered closely with Account Executives to support strategic account penetration and pipeline growth.
Account Executive
Indeed
Dublin
2016.11 - 2018.06
- Achieved 104% of annual quota, delivering consistent performance against revenue targets.
- Consistently achieved quarterly targets, delivering results in five of six quarters within the role.
- Managed UK & Ireland territory, selling recruitment advertising and talent acquisition solutions to SMB and mid-market organisations, driving territory growth.
- Developed and executed outbound prospecting strategies, identifying and securing new business opportunities across UK & Ireland market, expanding client base.
- Sold consultatively to business owners, HR leaders and talent acquisition teams, aligning recruitment strategies with hiring objectives to meet client needs.
- Managed an average sales cycle of 90–120 days with average deal values of approximately £60K.
- Differentiated a premium solution in a highly competitive market through value-based selling and ROI-driven business cases.
- Built long-term customer relationships within a subscription-based model, driving customer retention and ongoing revenue growth.
- Conducted discovery meetings, product demonstrations, commercial negotiations and stakeholder presentations throughout the full sales cycle.
Education
Bachelor of Arts - Business And Management
National College of Ireland
Leinster08.2014
Skills
- Full-Cycle SaaS Sales
- New Business Acquisition
- Pipeline Generation
- Account Expansion & Cross-Sell
- Salesforce CRM
- LinkedIn Sales Navigator
- Outreach
- Forecasting & Pipeline Management
- Strategic Account Planning
- Executive Stakeholder Management
- Consultative & Value-Based Selling
- Commercial Negotiation
Websites
Languages
English
Timeline
Mid Market Account Executive
Deel
2024.08 - 2025.12
Enterprise Account Executive
SocialTalent
2022.07 - 2023.08
Account Executive
DocuSign
2021.02 - 2022.06
Partner Development Representative
DocuSign
2019.04 - 2021.02
Market Development Representative
DocuSign
2018.10 - 2019.04
Account Executive
Indeed
2016.11 - 2018.06
Bachelor of Arts - Business And Management
National College of Ireland