Jesse Urry
Senior Account Executive @ Webware.ai
About
Your everyday Senior Account Executive who’s passionate about helping businesses grow through SaaS while shattering quotas in the process! Over 8 years of strategic sales experience, hitting 300 - 500% of quota consistently across multiple organizations, recognized as the Top Account Executive in 2019, 2020, 2021 and again in 2023, 2024, and 2025. Known for solution-based and value-based consulting while helping organizations drive significant revenue growth and optimizing processes for maximum efficiency. I prefer to work 7 days a week and am comfortable operating across all time zones. A wise man once said that if you love what you do, you’ll never work a day in your life and I couldn’t agree more.
Canada
Toronto
Management Consulting
Cold Calling, Excellent Communication, Pre-Owned Vehicle Sales, New Vehicle Sales, Consultative Selling, Full-Cycle Sales, Objection Handling, Relationship Management, Strategic Prospecting, SMB Sales, Mid-Market Sales, Contract Negotiation, Meddpic, Bant, Sandler Selling System, Challenger Sales, Discovery, Value based selling, Solution based selling, Pipeline management
Experience

Senior Account Executive
• #1 Account Executive company-wide / Top Revenue Producer Award (2023, 2024, 2025) • Closed over $3M+ in ACV in 2025 against a $780K quota (385% attainment) • Achieved 500%+ of monthly quota, setting a new company record • Closed over 500 deals total in the SMB / Mid Market Space • Increased closed ACV by $1M+ year-over-year, three consecutive years • Consistently top performer across revenue, close rate, and deal velocity • Trusted to handle highest-value opportunities and complex deal cycles • Hit quota every month during entire tenure

Account Executive
• Set company prospecting record for most demos set and sales accepted opportunities. • Set company record for ACV closed by an Account Executive during ramp. • Achieved 177% of quota in first month on the floor. • Closed $625k in ACV within first 6 months in role (Ramp). • Ranked top AE across pipeline conversion and closed revenue in a high-velocity transactional environment. • Promoted to Senior Account Executive in 6 months based on performance.

Senior Account Executive (SMB + Mid-Market)
Direct Auto Canada
• #1 Sales Representative nationwide for three consecutive years (2019–2021) • Led new logo acquisition strategy across high-revenue dealership groups throughout Canada • Closed consistent $60K–$120K ARR net-new contracts • Built executive-level relationships with owners and leadership teams • Developed and presented ROI-driven business cases • Owned full-cycle revenue generation across inbound and outbound channels • Drove year-over-year revenue growth within assigned territory through disciplined outbound prospecting and strategic account expansion

Business Development Representative
Direct Auto Canada
• Generated $1.2M+ in qualified pipeline within first 120 days through outbound prospecting • Set company record for cold call appointments booked during ramp • Built structured multi-touch outbound campaigns converting cold outreach into revenue opportunities • Promoted to Account Executive within 4 months based on performance

Executive Sales Consultant / Business Development
Edmonton, Alberta, Canada
• Drove new business growth through high-volume outbound prospecting, appointment setting, and referral generation. • Set monthly and quarterly prospecting record for most appointments booked. • Managed full-cycle sales from outbound prospecting, appointment setting, discovery, negotiation and close. • Recognized as Top Salesperson of the Month and Quarter based on unit sales. • Cross-collaborated with finance and operations teams to ensure deals were structured, approved, and finalized efficiently. • Built and maintained a strong personal pipeline through disciplined follow-up and relationship management. • Delivered a consultative buying experience in a high-pressure, commission-driven environment.

Oil and Gas Specialist
BROCK CANADA is a leading industrial services provider, supporting large-scale infrastructure and energy projects across the country. At Brock, I committed to the grind — working extended shifts and as many days in a row as possible — building the foundation of the relentless work ethic I now bring into sales. My time here sharpened my discipline, mental toughness, and team-first mindset — all critical traits that continue to drive my performance in high-pressure, results-driven environments. Built for the field. Refined for the boardroom. This is where my hustle started.
Jesse Urry's Contact Information
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