Stephen Smith
Tigard,Oregon
Summary
Customer Success Leader focused on the intersection of operational excellence and revenue growth. Expert at designing scalable post-sales ecosystems that secure over $300 million in quarterly renewals while maintaining a 110% net revenue retention. Specialist in leveraging AI-driven insights and Gainsight architecture to eliminate operational friction, reduce manual overhead by 70%, and transform the CS function into a predictable, high-margin growth engine.
Overview
7
7
years of professional experience
Work History
Manager, Customer Success Operations
Trimble Inc
03.2024 - Current
- Architected and scaled a global Customer Success Operations department from the ground up, establishing a four-pillar functional model (Digital, Enablement, Systems, and Data/BI) to support a 120+ person global organization.
- Elevated brand advocacy and sentiment by architecting a Closed-Loop feedback system, achieving a world-class 66 NPS and 80% CSAT; leveraged real-world qualitative insights to identify friction points, resulting in a 25% increase in referral-based pipeline.
- Operationalized the retention engine for $1.2B in annual renewals, maintaining a consistent NRR of 110%+ through the development of real-time churn-risk modeling and executive-level Domo dashboards.
- Engineered a global organizational turnaround by standardizing workflows across North America and EMEA, eliminating regional silos and unifying disparate post-sales motions into a single, high-performance operational framework.
- Spearheaded the enterprise-wide migration to Gainsight, deprecating legacy CRM processes and automating 70% of manual administrative tasks through the deployment of strategic Playbooks and Success Plans.
- Pioneered an AI-First CS workflows by integrating LLMs and custom GPTs to automate sentiment analysis and predictive insights, accelerating the transition from reactive account management to proactive, data-driven advocacy.
- Forged cross-functional partnerships with Finance and Sales Ops to design and implement complex commission structures and data-governance protocols, ensuring 100% alignment on source of truth metrics.
- Institutionalized a culture of continuous enablement, launching a comprehensive 4-week onboarding program and monthly Global Enablement Hours that reduced time-to-productivity for new hires by 40%.
Director of Customer Success
ResellerRatings
06.2022 - 03.2024
- Engineered a 40% surge in renewal rates by architecting new success frameworks, driving $1M in incremental YoY revenue.
- Built and scaled a high-performance CS department designing the entire talent acquisition strategy, onboarding workflow, and professional development programs.
- Optimized onboarding velocity by 100%, leveraging HubSpot automation and Playbooks to compress the client lifecycle from 60 to 30 days for 150+ accounts.
- Launched a cross-functional upsell channel in collaboration with Sales and Marketing, generating $500K–$600K+ in new annual revenue.
- Achieved a 120% increase in product engagement via strategic activity-led initiatives, resulting in a 30% retention lift and a 50% improvement in customer ROI.
- Pioneered AI-driven standardization using HubSpot and LLMs (ChatGPT/Bard) to automate workflows and developed custom product-led dashboards for real-time health monitoring.
Customer Success Manager
eSolutionsFirst, Freddie Mac
02.2021 - 06.2022
- Architected a post-sales success framework that drove a 40% increase in renewal rates and maintained a 95% client retention rate across a portfolio of 45+ enterprise tech accounts.
- Directed a cross-functional team of 25 (Success & Talent Acquisition), implementing rigorous management cadences and performance metrics that secured $10M+ in new revenue.
- Scaled business units through strategic onboarding, resulting in a 70% revenue surge within the first 6 months and a 30% increase in YoY growth through executive-level relationship cultivation.
- Optimized the Tech Stack (Salesforce/Beeline) to automate pipelines and playbooks, transforming raw data into actionable insights that identified $1M+ in hidden upsell opportunities.
- Owned the MSP/VMS vendor ecosystem, serving as the primary executive contact for high-value accounts including Freddie Mac and Pontoon.
- Strategized with C-Suite leadership to bridge organizational talent gaps and lead cross-departmental initiatives, ensuring 90%+ customer satisfaction through proactive issue resolution.
Services Procurement Specialist
Allegis Global Solutions, Fannie Mae
05.2019 - 02.2021
- Managed client satisfaction, ensuring a high level Directed a $1M+ expansion revenue stream by transforming client satisfaction into a proactive sales engine through strategic relationship management.
- Governed a 200-client portfolio, serving as the executive liaison for high-stakes communications, conflict resolution, and long-term account health.
- Orchestrated complex project lifecycles on 6-month cadences, overseeing vendor selection, SOW formation, and work classification for budgets up to $1M per project.
- Institutionalized a QBR/MBR framework to drive Trusted Advisor status, ensuring strict adherence to cost, quality, and delivery KPIs across all enterprise accounts.
- Led a high-growth internal culture by coaching and mentoring 10 junior team members, accelerating their professional development and functional expertise.of customer service resulting in $1M+ in additional sales.
Education
Bachelor of Science -
Central Michigan University
Skills
- Strategic Operations: Global CS Strategy, Revenue Operations Alignment, NRR/GRR Optimization, Churn Mitigation Frameworks
- Organizational Architecture: Multi-region Team Scaling (Global), Cross-functional Leadership, Resource Allocation, Change Management
- Customer Journey Mapping: Digital-Led Strategy, Automated Success Playbooks, Lifecycle Stages, Health Score Development
- Financial & Data Governance: Renewal Forecasting, Incentive & Commission Design, Data Integrity, Executive Reporting
- Enablement & Training: Curriculum Design, Onboarding Optimization, Product-Led Growth Strategy, Knowledge Management
Other Customer Experience
- Camp Director, Camp Tannadoonah, 05/01/18 - 05/01/19
- Residence Hall Manager, Northwestern Michigan College, 08/01/17 - 05/01/18
- Director, Cheley Colorado Camps, 05/01/17 - 08/01/17
- Assistant Director, Cheley Colorado Camps, 05/01/14 - 08/01/16
Technical Ecosystem
- Customer Success Platforms: Gainsight, Totango, ChurnZero.
- Data Visualization & BI: Domo, Tableau, Power BI, SQL.
- CRM & Sales Ops: Salesforce, HubSpot, Clari, Salesloft.
- AI & Operational Efficiency: LLM Integration (Gemini, NotebookLM, ChatGPT), GEMS.
- Automation: Zapier, Workato.
- Collaboration & Enablement: Gong/Chorus, Highspot, Guru, Slack, Jira.
Timeline
Manager, Customer Success Operations
Trimble Inc
03.2024 - Current
Director of Customer Success
ResellerRatings
06.2022 - 03.2024
Customer Success Manager
eSolutionsFirst, Freddie Mac
02.2021 - 06.2022
Services Procurement Specialist
Allegis Global Solutions, Fannie Mae
05.2019 - 02.2021
Bachelor of Science -
Central Michigan University