Katherine "Khaki" Hollingsworth
Raleigh,USA
Summary
Customer Experience leader with a proven track record of building and scaling cross-functional post-sales organizations—including presales, training, support, and consulting—to drive product adoption, customer health, and long-term retention across SMB to Enterprise clients. Experienced managing $100M+ B2B SaaS portfolios and leading high-performing teams with a consultative, data-driven approach. Skilled in developing usage-based engagement models, leveraging telemetry data and custom dashboards to identify risk and drive value. Adept at aligning CX strategies with GTM priorities, improving onboarding time-to-value, and transforming services programs into scalable profit centers. Thrive in fast-paced, high-growth environments focused on delivering measurable customer impact.
Overview
16
16
years of professional experience
Work History
Director, Customer Success & Inside Sales
LiveAction Software (Acquired by BlueCat)
Raleigh, NC
03.2024 - 04.2025
- Promoted in March 2024 to Director, overseeing both pre-sales Sales Development Representatives (SDRs) and post-sales Customer Success Managers (CSM) teams. Led the SDR team's transition to new Marketing leadership amid a company acquisition while maintaining focus on 2024 retention and cross-sell goals. Enabled the CSM team to generate $3M+ in pipeline in 2024 alone and achieve $1M+ in closed won business through strategic customer engagement and expansion initiatives.
- Developed and implemented a strategic customer segmentation framework and lifecycle plan, integrating telemetry data, CSM engagement, and journey milestones. Established a customer risk escalation and mitigation process ("SWAT") in collaboration with Professional Services and Engineering leadership to improve customer relationships.
- Partnered with Product and Support to launch a new Customer Portal for thousands of customer contacts, streamlining Salesforce contact data for better visibility into customer roles. In collaboration with Support, enhanced customer satisfaction by improving case escalation to CSMs, risk mitigation, and product feature request management.
Senior Manager, Customer Success & Inside Sales
LiveAction Software
Raleigh, NC
01.2023 - 01.2024
- Led and mentored a high-performing CSM team overseeing end-to-end lifecycle management, including renewals, of 600+ customers across the U.S. and Canada, driving $43.8M in ARR. Delivered weekly renewal forecasts and strategic insights to the CEO and executive leadership, informing retention efforts and growth strategies.
- Restructured the CSM team for regional alignment, improving collaboration, organization, and streamlining retention tracking. Implemented enhanced reporting mechanisms and repositioned CSMs as strategic partners to the account team, enhancing their role beyond renewals to provide proactive customer care.
- Quickly promoted to lead the Inside Sales SDR team within the first month, taking ownership of key initiatives including event follow-up for Cisco Live, the company's largest revenue-generating event, and cross-sell expansion campaigns. Despite three leadership changes in Marketing over the year, successfully maintained all initiatives, hired and onboarded an entirely new SDR team, developed a comprehensive training program, and led onboarding sessions to ensure seamless integration into the sales process.
Senior Manager, Customer Success Management - Enterprise
Citrix
Raleigh, USA
10.2021 - 02.2023
- Promoted to Senior Manager in October 2021, leading a team of 13 CSMs overseeing $130M+ in ARR from Citrix’s strategic enterprise customers, with expanded responsibility for Public Sector CSMs and customers.
- Coached the team to drive SaaS adoption, improve forecasting accuracy, and position add-on consulting and education services to support customer growth and satisfaction.
- Appointed to lead a cross-Success employee engagement workstream to establish Team Lead roles, collaborating with HR and presenting proposals to Success leadership to enhance career pathing and management development.
Manager, Customer Success Management - Enterprise
Citrix
Raleigh, USA
05.2020 - 09.2021
- Built and led a new Enterprise Customer Success team, guiding customers through the full lifecycle—from onboarding and cloud infrastructure setup to SaaS consumption growth and renewal.
- Coached the team to effectively identify risks, accurately forecast renewals, and uncover upsell/cross-sell opportunities while serving as the primary escalation point across internal departments.
- Selected and sponsored by Success/Operational leadership to pilot an adoption review process to mitigate customer risk, securing executive approval and driving cross-functional collaboration across Success, Sales, and support teams.
- Led the team through a major process and Gainsight overhaul (Lifecycle.Next program), managing account transitions and collaborating with Sales and Operations to scale the Success organization with minimal customer impact while improving internal organization.
Senior Manager, Customer Success & Renewals
Solarwinds
Morrisville, USA
03.2019 - 05.2020
- Managed Customer Success and Renewals teams supporting five acquired SaaS products (Pingdom, Loggly, AppOptics, Papertrail, and Librato) within the AppMan division, along with the ITSM Onboarding Premiere Service team.
- Led the Manila-based Renewals team, driving ~$10M in revenue while reducing churn and winning back recently canceled customers through targeted retention efforts and improved reporting visibility.
- Built and led a new Customer Success team focused on proactive engagement, onboarding, and retention for high-value customers, while driving upsell and cross-sell opportunities. Supported the POC selection of Totango, working with Engineering to integrate data, generate health scores, and scale customer engagement.
- Managed churn forecasting, downgrades, and win-back strategies for AppMan products, producing detailed reports and insights for leadership and executive forecasting meetings.
Manager, Client Success and Client Engagement Management – West
SiriusDecisions
San Francisco, USA
04.2017 - 02.2019
- Managed the Client Success team overseeing $24M in contract value, focusing on strategic account engagement and advisory services worth $14M on the West Coast.
- Selected by the CFO to contribute to company-wide initiatives, regularly presenting retention progress, customer insights, and reporting analytics to the C-Suite while collaborating with Business Operations and Sales leaders to enhance client onboarding, renewals, and data integrity.
- Recruited, trained, and developed a high-performing client engagement team, leading analyst-led workstreams, driving sales opportunities, and enhancing the client experience to improve retention and account growth.
Global Customer Delight Manager
AdRoll
Dublin, Ireland
01.2016 - 01.2017
- Led the global Customer Delight team, managing 58% of AdRoll's customer base and 15% of revenue while implementing strategies that drove +90% CSAT.
- Established the first support Quality Assurance process, overseeing evaluations, QBRs, and performance management for direct reports and outsourced teams.
- Developed customer engagement tools, optimized Zendesk reporting, and collaborated with Growth, Marketing, and Product to enhance self-serve retention and reduce churn.
Team Lead
AdRoll
Dublin, Ireland
08.2014 - 01.2016
- Managed a global vendor program with 25+ agents across India and Poland, collaborating with leadership to upskill support teams, launch incentives, and implement QBRs for performance assessment.
- Led the localization of Help Center content into six languages, overseeing translation, QA, and imagery while hiring and training an internal team of eight localized agents across multiple regions.
Sr Delight Specialist
AdRoll
Dublin, Ireland
07.2013 - 07.2014
- Selected as the first Delight ambassador to establish AdRoll's EMEA headquarters in Dublin alongside new executive leadership.
- Build and led the EMEA Delight team, hiring language specialists, facilitating training, and preserving company culture across departments.
Delight Specialist
AdRoll
San Francisco, USA
06.2012 - 06.2013
- Managed high-volume customer inquiries across multiple channels, acting as a liaison between customers and internal teams to relay product feedback and resolve issues.
- Launched and optimized online advertising campaigns, ensuring budget fulfillment, inventory efficiency, and troubleshooting escalations with Engineering.
Account Manager
Groupon
Chicago, USA
06.2011 - 05.2012
- Managed a portfolio of 125+ priority merchant accounts in a Top 5 U.S. market, Atlanta, GA, generating +$7.2M in revenue within 10 months.
- Led 415+ successful marketing campaigns and served as the primary merchant contact, ranking in the Top 10% of Account Managers with a 9.0 NPS.
Project Manager
BrightSpot I.D.
Austin, USA
01.2011 - 06.2011
- Managed client projects for Sunni Brown, one of Fast Company’s 100 Most Creative People and a 2011 Long Beach Conference TED Talk speaker, including Disney, Abbott, DELL, and SXSW Interactive.
- Oversaw project timelines, contracts, proposals, and invoices for events, workshops, and educational videos.
Marketing, Sales Enablement and Worldwide Industry Paid Intern
Initiate Systems
Austin, USA
03.2009 - 08.2009
- Managed intra-office website, sales tools, and customer research to support Sales and Marketing alignment
- Analyzed Marketing performance and oversaw material distribution for trade shoes, e-commerce, and direct mail.
Education
Bachelor of Arts - Business Major; Communications Minor
Lake Forest College
Lake Forest, IL12.2010
Skills
- Customer Retention & Churn Mitigation
- Scalable Customer Success Programs
- Strategic Leadership & Stakeholder Management
- Data-Driven Decision Making & Forecasting
- Customer Experience & Engagement Optimization
- Revenue Growth & Expansion Strategies
- Cross-functional Collaboration with Sales, Marketing, & Product Teams
- Salesforce, Gainsight, Totango, Tableau
Accomplishments
- LiveAction (acquired by BlueCat), Director of Customer Success & Inside Sales, Q1 2024, CEO Award
- SiriusDecisions, Senior Manager, Customer Success & Renewals Manager, Q3 2019 Employee Spotlight Award
- SiriusDecisions, Manager, Client Engagement - West, Quarterly all company recognition award for the Sales organization in Q2 2018.
- AdRoll, Global Customer Delight Manager, SMB’s Century Club manager winner in Q3 2016.
References
References available upon request.
Timeline
Director, Customer Success & Inside Sales
LiveAction Software (Acquired by BlueCat)
03.2024 - 04.2025
Senior Manager, Customer Success & Inside Sales
LiveAction Software
01.2023 - 01.2024
Senior Manager, Customer Success Management - Enterprise
Citrix
10.2021 - 02.2023
Manager, Customer Success Management - Enterprise
Citrix
05.2020 - 09.2021
Senior Manager, Customer Success & Renewals
Solarwinds
03.2019 - 05.2020
Manager, Client Success and Client Engagement Management – West
SiriusDecisions
04.2017 - 02.2019
Global Customer Delight Manager
AdRoll
01.2016 - 01.2017
Team Lead
AdRoll
08.2014 - 01.2016
Sr Delight Specialist
AdRoll
07.2013 - 07.2014
Delight Specialist
AdRoll
06.2012 - 06.2013
Account Manager
Groupon
06.2011 - 05.2012
Project Manager
BrightSpot I.D.
01.2011 - 06.2011
Marketing, Sales Enablement and Worldwide Industry Paid Intern
Initiate Systems
03.2009 - 08.2009
Bachelor of Arts - Business Major; Communications Minor
Lake Forest College
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