Cory Benton
Lake Forest
Summary
Dynamic and forward-thinking Customer Success Executive with a decade of experience scaling teams, transforming customer journeys, and driving bottom-line impact for fast-growing SaaS companies. Known for building world-class CS orgs that blend proactive service with strategic insight, resulting in loyal customers, energized teams, and sustainable growth. I bring a hands-on, people-first leadership style, deep roots in restaurant tech, and a mindset grounded in performance, culture, and fun.
Overview
15
15
years of professional experience
Work History
VP, Customer Success
SpotHopper
03.2022 - Current
- Lead a 100+ person global Customer Success & Operations org at a leading restaurant SaaS platform, aligning teams across onboarding, support, AM, and loyalty
- Drove KPIs that matter: improved NPS from 10 → 45, boosted gross margins from 50% → 85%, and held customer churn below a 1% monthly rate
- Scaled the CS team by 85% in a single year, launching new roles and functions aligned to customer outcomes.
- Rolled out key systems (Dialpad, HubSpot, Gainsight, Salesforce) to streamline workflows and elevate the customer experience.
- Credited with scaling CS organization by 85% in 2022 with added headcount in Onboarding, Account Management, Operations, and Sr. Manager/Director level leadership
- Built a culture praised by the CEO for its professionalism, energy, and collaboration—with 99% employee retention to prove it.
- Experience implementing key software tools such as Dialpad/Gainsight/Litmos/HubSpot Service/Salesforce
- Maintained a 99% employee retention rate across all of CS while limiting spend and COS
Sr. Director - Account Management
Tebra
07.2020 - 03.2022
- Led enterprise AM org focused on billing companies and multi-site healthcare clients.
- Doubled the team size while exceeding ARR expansion targets by 300%.
- Achieved 110% NRR and 99% retention—driven by tailored engagement strategies and a customer-first mentality.
- Designed and executed President’s Club trips and cross-functional growth programs.
- Achieved and maintained an NPS score of 80
Director - Customer Success
Kareo
10.2017 - 06.2020
- Oversaw 100+ indirect reports and 7 managers across Onboarding, VIP Support, Engineering Support, and Retention.
- Saved $1.4M annually through smart resource allocation (U.S. → Costa Rica), while maintaining a 90% CSAT.
- Championed data transparency with dashboards and KPIs that empowered CS and leadership teams alike.
Manager - Onboarding & Clinical Sales
Kareo
01.2014 - 09.2017
- Created and led Onboarding for Kareo’s flagship product line.
- Designed onboarding playbooks focused on converting free users to paid subscribers—generating $1M annually.
- Piloted go-to-market strategies that laid the foundation for long-term growth.
Customer Success Team Lead
Kareo
12.2011 - 02.2014
- Kareo’s first CS Coach; quickly promoted to Team Lead.
- Designed the company’s early Salesforce reporting structure and helped launch its Culture Council.
Football Coach
Purdue/Italy
01.2011 - 12.2011
- Graduate-Assistant football coach at Purdue University 2009-2011
- Offensive Coordinator and Player for Bologna, Italy IFL Warriors (NFL Europe)
- Coached team to an undefeated season and Italian Super Bowl appearance
Education
Bachelor of Science - Organizational Leadership
Purdue University
05.2009
Masters of Science - Education: Curriculum & Instruction
Purdue University
05.2011
Skills
- Leadership
- Revenue Expansion
- Customer Retention
- Client Onboarding
- Executive Communication
- Client Relationship Management
- Team leadership
- Relationship building
- Decision-making
- Critical thinking
Hobbies and Interests
Youth sports coach - high school varsity football and 10u girls softball, #girldad
Timeline
VP, Customer Success
SpotHopper
03.2022 - Current
Sr. Director - Account Management
Tebra
07.2020 - 03.2022
Director - Customer Success
Kareo
10.2017 - 06.2020
Manager - Onboarding & Clinical Sales
Kareo
01.2014 - 09.2017
Customer Success Team Lead
Kareo
12.2011 - 02.2014
Football Coach
Purdue/Italy
01.2011 - 12.2011
Masters of Science - Education: Curriculum & Instruction
Purdue University
Bachelor of Science - Organizational Leadership
Purdue University
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