Summary
Overview
Work History
Education
Skills
References
Timeline
Generic

Matthew Espinosa

La Grange Park,IL

Summary

Accomplished sales executive with a proven track record of driving new logo acquisition, expansion revenue, and customer retention across regional markets. Experienced in leading high-performing teams, including Sales Directors and Enterprise Account Executives, with a strong focus on operational excellence and strategic execution. Adept at coaching frontline teams, optimizing sales methodologies, and aligning cross-functional initiatives to support scalable growth. Trusted advisor to executive leadership, contributing to go-to-market strategy, market forecasting, and organizational planning. Recognized for fostering strong customer relationships and leveraging market insights to inform continuous improvement across products, processes, and solutions.

Overview

9
9
years of professional experience

Work History

Director, Enterprise Sales

Culture Amp
Chicago, IL
01.2025 - Current
  • Executed sales strategies to drive revenue growth across diverse markets.
  • Managed hybrid sales team, focusing on new logo acquisition and revenue expansion.
  • Created and led strategic sales trainings.
  • Presented sales forecasts for strategic planning.
  • Worked cross-functionally to drive execution
  • Monitored market trends and competitor activities to adjust sales strategies effectively.

Director, Enterprise Account Management

Culture Amp
Chicago, IL
02.2024 - 01.2025
  • Led team of 8 Enterprise AEs focused on retaining and growing North American clients
  • Analyzed market trends to uncover opportunities for business growth and innovation.
  • Identified process improvement opportunities to enhance customer retention strategies.
  • Utilized CRM tools for tracking leads, managing pipelines, and generating reports.
  • Managed financial forecasting for future sales activities based on historical performance data.

Director, Enterprise Sales

Upwork
10.2022 - 06.2023
  • Led team of 32 Enterprise Account Executives and 4 Sales Managers to support Fortune 500 clients.
  • Retained and expanded 150+ accounts, generating over $100 million in gross sales value.
  • Transformed sales strategy to consultative engagements achieving 28%+ QoQ revenue growth.
  • Established structured pipeline system, producing over $85 million in new opportunities at a 37% close rate.
  • Developed comprehensive sales strategies covering account growth, accurate forecasting, and quota attainment.
  • Implemented standardized forecasting methodology, achieving 98% accuracy for ten consecutive quarters.
  • Negotiated contract prices to optimize profitability and enhance sales agreements.

Sr. Sales Manager, Enterprise Sales

Upwork
04.2020 - 10.2022
  • Led recruitment, training, and coaching of seven Enterprise Account Managers, consistently achieving quotas for three years.
  • Secured $8M in revenue with 37% year-over-year growth.
  • Transformed 14 accounts into top performers, exceeding $1M annually in TTM GSV.
  • Sustained a 96% client retention rate by aligning Upwork's value propositions with client strategies.
  • Managed a $46M pipeline, achieving a 38% average close rate.
  • Conducted collaboration sessions to guide sales representatives in prioritizing their book of business by TAM.
  • Piloted a forecasting model adopted by the Enterprise Sales Team.
  • Enhanced efficiency between sales and support functions, reducing churn by 12% and boosting opportunity size by 15%.

Director, Sales

PowerReviews
Chicago, IL
11.2016 - 04.2020
  • Led a team of 9 Account Executives targeting eCommerce brands with revenues exceeding $500M.
  • Achieved 110% of annual quota by optimizing opportunity size and shortening sales cycles.
  • Mentored sales representatives, resulting in top-of-funnel pipeline growth exceeding individual quarterly goals by over three times.
  • Reduced sales cycle by 20% while increasing average Annual Contract Value (ACV) by 17% through proactive relationship management.
  • Managed revenue streams by establishing sales targets and implementing effective go-to-market strategies.
  • Facilitated collaboration among client success, product, and sales teams to enhance conversion rates and streamline processes.

Education

BA - Corporate Communications

Northern Illinois University
DeKalb, IL
01.2007

Skills

  • Sales strategy
  • Financial forecasting
  • Market analysis
  • CRM utilization
  • Contract negotiation
  • Performance management
  • Data-driven decision-making
  • Revenue growth
  • Cross-functional collaboration
  • Pipeline management
  • Consultative selling
  • Negotiation expertise

References

References available upon request.

Timeline

Director, Enterprise Sales

Culture Amp
01.2025 - Current

Director, Enterprise Account Management

Culture Amp
02.2024 - 01.2025

Director, Enterprise Sales

Upwork
10.2022 - 06.2023

Sr. Sales Manager, Enterprise Sales

Upwork
04.2020 - 10.2022

Director, Sales

PowerReviews
11.2016 - 04.2020

BA - Corporate Communications

Northern Illinois University

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