Ryan Oakley
Nashville,TN
Summary
Quota-carrying Account Executive with experience driving net-new revenue, building pipeline, and closing complex B2B technology deals across mid-market and enterprise organizations. Background selling SaaS and technical solutions to IT leaders combined with 10+ years inside global technology organizations. Proven ability to run full sales cycles, win competitive deals, and build trusted relationships with executive and technical stakeholders. Experienced in remote, high-growth environments and collaborating with BDRs, marketing, and customer success teams to consistently exceed revenue targets.
Overview
11
11
years of professional experience
Work History
Senior Account Executive
Advantage Technical
07.2025 - Current
- - Drive net-new business development by selling IT and engineering workforce solutions to enterprise and mid-market organizations.
- - Execute targeted outbound strategies to penetrate new accounts and expand into previously untapped market segments.
- - Built and managed active pipeline within Salesforce, tracking deal progression and forecasting revenue performance.
- - Closed a strategic partnership with the largest healthcare organization in the United States, creating a long-term enterprise account.
- - Collaborate with internal recruiting and delivery teams to accelerate hiring timelines and improve client outcomes.
- - Maintain a curated network of technical talent to improve response speed and increase win rates in competitive deals.
Account Executive
Payscale
12.2024 - 05.2025
- - Managed the full SaaS sales cycle from outbound prospecting through contract negotiation and close.
- - Achieved 105% of sales quota through consultative discovery and value-driven product demonstrations.
- - Built and advanced pipeline across mid-market and enterprise HR and finance leaders.
- - Delivered tailored platform demonstrations aligning customer compensation challenges with Payscale’s SaaS solution.
- - Partnered with SDRs and marketing teams to convert inbound and outbound leads into qualified opportunities.
- - Maintained accurate pipeline and forecasting in Salesforce, supporting leadership visibility into deal progression.
Program Leader
Cisco
08.2022 - 04.2024
- - Led global initiatives supporting technical workforce enablement across distributed teams.
- - Managed strategic vendor partnerships to deliver cybersecurity training and enablement programs at scale.
- - Produced executive-level communications and business cases to secure alignment for new security initiatives.
Business Operations Manager
Cisco
09.2020 - 08.2022
- - Directed organizational OKR alignment initiatives improving cross-team execution and operational transparency.
- - Managed a multi-million-dollar cybersecurity training partnership, optimizing vendor performance and program ROI.
- - Delivered enablement programs that strengthened internal technical expertise and sales readiness.
Project Manager | Enablement Manager | Customer Success Manager
Cisco
01.2015 - 01.2020
- - Managed relationships with 90+ enterprise customers, identifying opportunities to expand adoption of Cisco technologies.
- - Delivered global enablement programs across multiple regions supporting customer success and technical teams.
- - Developed playbooks and operational frameworks used across global customer success organizations.
Business Development Specialist
ServiceSource (Concentrix)
12.2014 - 05.2017
- - Supported outbound sales programs for global technology clients through improved messaging and campaign strategy.
- - Coached sales teams on outreach tactics to increase engagement and opportunity conversion.
Education
Bachelor of Arts - Business Administration
Middle Tennessee State University
Murfreesboro, TN12.2011
Skills
- Full-Cycle SaaS Sales
- Mid-Market Account Executive (200–2,000 employees)
- Net-New Logo Acquisition
- Outbound Prospecting & Pipeline Generation
- Consultative Solution Selling
- Product Demonstrations & Technical Discovery
- Contract Negotiation & Closing
- Salesforce Pipeline & Forecasting
- Executive Stakeholder Engagement
- Cross-Functional Sales Collaboration
Websites
Timeline
Senior Account Executive
Advantage Technical
07.2025 - Current
Account Executive
Payscale
12.2024 - 05.2025
Program Leader
Cisco
08.2022 - 04.2024
Business Operations Manager
Cisco
09.2020 - 08.2022
Project Manager | Enablement Manager | Customer Success Manager
Cisco
01.2015 - 01.2020
Business Development Specialist
ServiceSource (Concentrix)
12.2014 - 05.2017
Bachelor of Arts - Business Administration
Middle Tennessee State University