Ryan Cunningham
Castle Rock,CO
Summary
Dynamic sales leader with over 15 years of experience in executive roles, specializing in scaling SaaS revenue and developing high-performing teams. Achieved $1.5 million in annual recurring revenue within two years at Zing through a robust multi-channel go-to-market strategy. Proven track record of implementing effective forecasting and pipeline management practices that enhance deal predictability and reduce sales cycles. Former President & Co-Founder of ClearConnect, successfully grew a technology marketplace to $5 million ARR by creating repeatable sales processes and mentoring distributed sales teams.
Overview
24
24
years of professional experience
Work History
Chief Revenue Officer
Zing
01.2022 - Current
- Company Overview: SaaS platform delivering websites and digital marketing to SMBs
- Scaled ARR from $0 to $1.5M in two years by architecting a repeatable SaaS sales model and multi-channel go-to-market strategy.
- Built and led a high-performance sales organization, instituting rigorous forecasting, pipeline reviews, and sales tech stack integrations that improved predictability and shortened sales cycles.
- Designed compensation and enablement programs that increased close rates and long-term retention.
- SaaS platform delivering websites and digital marketing to SMBs
President & Co-Founder
ClearConnect
01.2015 - 01.2022
- Company Overview: B2B telecom and SaaS-enabled marketplace
- Founded and grew the largest B2B cable brokerage to $5M ARR with over 1,000 monthly new customers.
- Recruited, coached, and retained a distributed sales team, driving consistent quota achievement and multi-year revenue growth.
- Built strategic carrier partnerships and automated sales processes to scale efficiently.
- B2B telecom and SaaS-enabled marketplace
Area Vice President
DexMedia
01.2012 - 01.2015
- Directed 250-person regional sales force, pioneering digital marketing adoption and achieving record digital revenue growth.
- Implemented disciplined sales process and data-driven forecasting to increase retention and reduce churn.
Regional Vice President & Earlier Roles
Cbeyond
01.2002 - 01.2012
- Rose rapidly from Outside Rep to RVP, overseeing five major markets and $350K in monthly recurring revenue.
- Drove double-digit year-over-year growth and designed new CRM-based sales operations.
Education
B.A. -
California State University, Fullerton
01.2000
Skills
- Sales Leadership
- SaaS sales model
- Team Development
- Data-Driven Forecasting
- Pipeline Management
- SaaS Go-to-Market Strategy
- Strategic Partnerships
- High-Performance Cultures
- Customer Acquisition
- Customer Retention
Websites
Timeline
Chief Revenue Officer
Zing
01.2022 - Current
President & Co-Founder
ClearConnect
01.2015 - 01.2022
Area Vice President
DexMedia
01.2012 - 01.2015
Regional Vice President & Earlier Roles
Cbeyond
01.2002 - 01.2012
B.A. -
California State University, Fullerton
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