Dylan Moneypenny

• Owned full sales cycle for mid-enterprise accounts generating $25M–$4B revenue.
• Sold solutions to Directors, VPs, and C-level stakeholders in IT, Security, Finance, and Legal sectors.
• Achieved $530,000 ARR in FY2025, exceeding ramp quota by 161%.
• Maintained average ACV of $285,000 with deals up to significant values.
• Shortened sales cycle by 40% through enhanced discovery techniques and MEDDPICC methodology.
• Consistently built and maintained $1,300,000 pipeline coverage at 4x.
• Secured five new logos, including two Fortune 1000 companies.

• Owned end-to-end sales cycles in mid-enterprise territory, engaging multi-stakeholder committees, including C-suite and VPs.
• Surpassed quota by over 110% through strategic outbound prospecting and executive alignment.
• Executed renewal and expansion strategies, enhancing customer lifetime value via upselling and cross-selling initiatives.
• Represented Rapid7 at industry and partner events, fostering pipeline creation and executive relationship development.
• Utilized Salesforce and Clari for effective pipeline management, assessing deal risk and ensuring accurate forecasting.
• Supported team members with deals, contributing to collaborative success and team performance enhancement.
• Participated as a panel member during interviews to evaluate prospective team candidates.

• Led and scaled a team of 7–10 AEs, owning hiring, onboarding, coaching, and performance management.
• Supported and influenced the close of six- and seven-figure deals, including $768K, $480K, and $472K transactions.
• Delivered accurate weekly forecasts to Head of Sales, maintaining strong pipeline visibility and rigor.
• Drove adoption of MEDDICC, standardizing deal qualification, reviews, and forecasting.
• Built and operationalized end-to-end sales playbooks to improve prospecting, discovery, and close rates.
• Led ongoing rep development through weekly 1:1s and team enablement sessions.

Team Performance (6 straight quarters above goal):

• 125% | 137% | 169% | 122% | 163%