Courtney O'Connell
Charlottesville,VA
Summary
I strive to be known as a strategic partner—both internally and externally—who gets results, solves problems, and wins with customers.
Rooted in ownership, teamwork, and curiosity, I aim to contribute meaningfully, lead when called upon, and communicate with intention to help motivate my teammates, and foster a culture of success.
Ideally, we’re doing all of this with a smile — building authentic relationships through thoughtful questions, active listening, and a positive, creative spirit.
Overview
11
11
years of professional experience
Work History
Senior Manager, Value Realization
Pluralsight
07.2023 - 07.2025
- Direct impact on the retention of over $32 million across 62 accounts in H1 2025, $120 million across 161 accounts in 2024 through data analysis, ROI delivery, and coaching of Customer Success and Revenue team members.
- Lead the effort to create new customer benchmarking for Customer Success best practices, playbooks, and engagement strategies.
- Spearheaded the creation and launch of a new Executive Engagement Program to connect executives with top customers, driving higher engagement, adoption, expansion opportunities, and renewals across the Enterprise and Strategic segments. This initiative contributed to the business surpassing its retention goals in Q4 2024.
- Led and managed strategic projects to enhance customer success processes, with a focus on customer health, engagement, user adoption, and net new growth. Notable initiatives included developing the Customer Journey framework, CSM Expansion and Retention Playbooks, and establishing Salesforce best practices.
- Worked cross-functionally with Customer Success, C-Suite, Operations, Pre-Sales, Marketing, Enablement, and other key teams to develop and implement strategic programs that drive revenue growth and customer success.
Senior Sales Director
The Block
07.2022 - 04.2023
- Led and managed team of 4-6 Account Managers and Account Management Associates for the $2.5mil growth business with a goal of 120% retention.
- Created and instituted new processes for Client Lifecycle including discovery, onboarding, risk and growth ID, negotiation and pricing, KPI’s and forecasting, leading to 9% jump in retention quarter-over-quarter.
- Executed quarterly account planning sessions with C-suite to provide transparency and collaborate for best outcomes in a dynamic market.
- Developed and implemented sales training for 4 new product lines to sell to new personas and new markets.
- Aligned cross-departmentally with engineering, operations, marketing and product to update sales processes, client engagement, product offerings, and integrate client feedback to future launches.
- Helped drive adoption of new tools on a daily basis (Salesforce, Salesloft and Chorus) through 1:1’s, team meetings
Sales Manager
Bloomberg Government
07.2021 - 05.2022
- Oversaw a sales team of 3 Account Executives and 4 Account Managers, hiring for a total of 10.
- Accountable for revenue and retention quotas, upsells, and cross-sells accounted for 30% of total net new revenue.
- Responsible for hiring, onboarding, and promotion of high-potential individual contributors.
- Lead efforts to restructure sales teams, new and existing territories, and sales strategies through collaboration with cross-functional teams to increase productivity and revenue captured; lead to a 30% increase in upsells and a shorter sales cycle.
- Created a new onboarding plan for AEs for a shorter ramp and faster initial sales after hire, decreased time from 6 months to 3 months to intial sale.
Manager, Client Service & Sales
Bloomberg Government
06.2019 - 07.2021
- Oversaw a team of 10 Account Managers and Senior Account Managers that owned the full renewal, upsell, and removal cycle.
- Lead the team to record organic growth of $600k (50% increase YOY) by coaching on opportunity identification, sales, and decision-making processes; the largest organic license upsell was $120k, and the largest cross-sale was $100k (data).
- Responsible for the strategy to retain and grow a $23M portfolio, comprised of transactional and complex clients.
- Effectively developed and implemented a strategic plan to increase the team’s retention from 68% to 82% by Year 2 that focused on performance expectations, new KPIs, client engagement mindset, and culture.
- Creatively resolved promotion limitations with stretch projects and responsibilities.
- Successfully handled multiple performance plans, promotions, and annual evaluations; grew the team from 7 to 10 members, and turned over 4 positions. A total of seven of my direct reports were promoted internally.
Account Manager, Senior Account Manager
Bloomberg Government
05.2017 - 06.2019
- Owned strategic client relationships throughout the lifecycle within a $2M+ portfolio of complex clients (consultancies, defense contractors, tech firms).
- Led the team in organic revenue growth ($150k, 150% to goal); provided referrals into three separate BUs, generating five leads and $100k in closed cross-sell revenue.
- Provided leadership and best practices for Account Managers to improve team culture and performance.
- Worked collaboratively with other leaders to impact the BU and influence product, data, S&S strategy.
Director, Strategic Accounts
TransPerfect Legal Solutions
03.2016 - 04.2017
- Owned and grew $4MM+ book of business by 25% through new and organic growth within portfolio
- Responsible for entire lifecycle from initial meeting, through sale and project management, invoice collection
- Assisted with marketing initiatives for unique client engagements and ROI
Account Manager, Account Executive
TransPerfect Legal Solutions
02.2014 - 03.2016
- Identified new and warm leads within a $2MM+ book of business through meetings and calls.
- Owned deals from prospecting through sale and collection phases
- Handled the highest volume of deals in the office, covering a global client base.
Education
Bachelor of Arts -
Colgate University
Hamilton, NYSkills
- Team leadership
- Revenue growth
- Customer success
- Client engagement
- Cross-functional collaboration
- Executive communication
- Process improvement
- Data analytics
Affiliations
- Director of Athletics Award
- Emerging Leaders Program, multiple organizations
- Avid Reader, Hiker, Restaurant Explorer
Timeline
Senior Manager, Value Realization
Pluralsight
07.2023 - 07.2025
Senior Sales Director
The Block
07.2022 - 04.2023
Sales Manager
Bloomberg Government
07.2021 - 05.2022
Manager, Client Service & Sales
Bloomberg Government
06.2019 - 07.2021
Account Manager, Senior Account Manager
Bloomberg Government
05.2017 - 06.2019
Director, Strategic Accounts
TransPerfect Legal Solutions
03.2016 - 04.2017
Account Manager, Account Executive
TransPerfect Legal Solutions
02.2014 - 03.2016
Bachelor of Arts -
Colgate University
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