RICHARD O’BRIEN
Broomfield,CO
Summary
Enterprise sales leader with 12+ years of experience driving multimillion-dollar revenue growth across AI, CCaaS, and SaaS platforms. Proven track record of closing $1M–$5M+ deals, exceeding quota up to 500%, and leading complex, multi-stakeholder sales cycles within Fortune 1000 and Public Sector organizations. Recognized for translating executive AI mandates into measurable business outcomes including cost reduction, automation, and operational scale. Strong background in strategic account development, C-level engagement, and partner-led GTM execution.
Overview
24
24
years of professional experience
Work History
Regional AI Sales Director
Talkdesk
Remote
10.2024 - 09.2025
- Led enterprise AI sales overlay across strategic accounts, contributing to record-breaking Q4 AI revenue performance
- Secured $600K+ ARR in new enterprise AI business within first quarter through consultative selling and executive alignment
- Positioned AI-driven CX solutions to drive automation, efficiency, and cost reduction across large enterprise environments
- Developed and implemented strategic sales initiatives to drive revenue growth.
- Led cross-functional teams to enhance collaboration and streamline sales processes.
- Mentored and trained sales team, fostering professional development and improving performance.
- Cultivated relationships with high-level clients, enhancing customer satisfaction and loyalty.
- Managed complex negotiations with key accounts resulting in long-term contracts that bolstered annual revenue figures significantly.
- Built relationships with customers and community to establish long-term business growth.
Enterprise Account Executive
Yellow.ai
Remote
10.2021 - 10.2024
- Closed $1M ARR enterprise deal (largest in company history), expanding into highest-billing account through multi-year growth strategy
- Secured 15+ new enterprise logos ranging from $300K–$3M in total contract value
- Built and managed multi-million-dollar pipeline across Fortune 500 organizations ($750M–$1B+ revenue)
- Drove AI platform adoption across customer service and operations, improving automation, efficiency, and scalability
- Collaborated with cross-functional teams to deliver tailored integrations of AI-driven solutions.
- Led negotiations on complex contracts, ensuring alignment with company goals while maximizing value for clients.
- Collaborated with internal teams to develop tailored solutions for complex client needs, resulting in increased revenue.
Senior Account Executive – Public Sector
Genesys
Remote
03.2020 - 10.2021
- Closed $5.1M statewide RFP deploying 1,800 agents across 26 agencies
- Achieved 505% of product bookings and 390% quota attainment
- Earned President’s Club (#6 NA, #7 Global)
- Led complex government sales cycles involving procurement, compliance, and multi-agency stakeholders
- Supported large-scale remote work and CX transformation initiatives during COVID across multiple states
- Led cross-functional teams to deliver tailored solutions, ensuring timely project execution.
- Increased account retention by building strong relationships with clients and addressing their needs promptly.
- Consistently met or exceeded monthly sales quotas through diligent prospecting efforts and effective closing techniques.
Lead Global Relationship Manager – SLED
Lumen Technologies (CenturyLink)
01.2019 - 03.2020
- Managed $10M+ enterprise account portfolio across healthcare, education, and government sectors
- Achieved 500%+ quota attainment in Q1 and 200%+ in subsequent quarters
- Led large-scale RFP initiatives involving infrastructure, networking, and cloud transformation
- Built executive relationships across CIO, CTO, and procurement stakeholders
Senior Enterprise Relationship Manager
Lumen Technologies
01.2018 - 01.2019
- Managed 150+ enterprise accounts while achieving 127% quota attainment
- Grew customer revenue from $1.5K to $12.5K monthly through strategic solution selling
- Closed multi-site enterprise contracts and expanded footprint across multiple locations
Lead Commercial Account Executive
Lumen Technologies
04.2015 - 01.2018
- Achieved consistent 100%+ quota attainment, including 116% annual performance
- Generated new business across enterprise networking, cloud, and telecom solutions
- Led complex sales cycles involving multi-location deployments and technical integrations
Business Development Manager
Baptie & Company
04.2014 - 04.2015
- Generated $1M+ in new business through strategic prospecting and executive engagement
- Managed full sales cycle from pipeline development to contract execution
Sales Manager
20/20 Tax Resolution
01.2002 - 01.2014
- Scaled revenue from $150K to $1M/month by leading and developing a 30-person sales team
- Reduced new hire ramp time from 4 months to 30 days through structured onboarding programs
- Earned multiple President’s Club and top performer awards
Education
Bachelor of Arts - History
Rhodes College
Memphis, TN05.1996
Skills
- Enterprise SaaS & AI Platform Sales
- Strategic Account Management
- $1M Deal Execution
- C-Level Engagement
- Public Sector / SLED Sales
- CCaaS & Customer Experience Transformation
- Pipeline Development & Forecasting
- Channel & Partner Sales (AWS, Genesys, etc)
- Consultative / Value-Based Selling
Accomplishments
- President’s Club – Genesys (#6 North America, #7 Global)
- 505% of product bookings | 390% quota attainment
- Closed $5.1M statewide public sector deployment (1,800 agents across 26 agencies)
- Closed $1M ARR deal (largest in Yellow.ai history)
- Built and managed $10M+ enterprise account portfolio
- Consistently exceeded quota across enterprise SaaS, AI, and telecom sales roles
Timeline
Regional AI Sales Director
Talkdesk
10.2024 - 09.2025
Enterprise Account Executive
Yellow.ai
10.2021 - 10.2024
Senior Account Executive – Public Sector
Genesys
03.2020 - 10.2021
Lead Global Relationship Manager – SLED
Lumen Technologies (CenturyLink)
01.2019 - 03.2020
Senior Enterprise Relationship Manager
Lumen Technologies
01.2018 - 01.2019
Lead Commercial Account Executive
Lumen Technologies
04.2015 - 01.2018
Business Development Manager
Baptie & Company
04.2014 - 04.2015
Sales Manager
20/20 Tax Resolution
01.2002 - 01.2014
Bachelor of Arts - History
Rhodes College