Sam Caldwell

SC

Looking for a job

Sam Caldwell

@samcaldwell

Customer Success Manager at Datadog who managed a $10M+ portfolio and drove a $4M TCV agreement.

At Datadog, I managed a $10M+ portfolio across 30 Mid-Market and Enterprise accounts, aligning the observability platform with customer KPIs and technical priorities.

I drove retention and expansion, including a $4M TCV agreement and $500K in year-over-year portfolio growth. I also used AI- and MCP-enabled workflows to reduce QBR and usage-review preparation by 6x.

At Oracle, I handled full-cycle sales across Oracle Cloud Infrastructure and adjacent cloud solutions, exceeded quota every quarter, and partnered with engineers on infrastructure and integration solutions. Earlier, I managed digital programs and client engagements in nonprofit and web technology environments.

Experience

Work history, roles, and key accomplishments

DA

Customer Success Manager – Key Accounts

Jan 2023 - Jan 2026 (3 years)

Owned a $10M+ portfolio across 30 Mid-Market and Enterprise accounts, driving retention and expansion. Achieved 100-221% quarterly attainment and led the organization with 280% Product Attachment attainment in Q3 2024.

Strategic Account Management Customer Retention and Growth Executive Stakeholder Management QBR and Success Planning Forecasting Consultative Discovery Value Based Selling Account Growth Cross Functional GTM Alignment Commercial Negotiation Customer Adoption Cloud Architecture AWS Solution Design Technical Discovery Application and Data Modernization Cloud Concepts IT Vendor Management Solution Evaluation Platform Selection Vendor and Partner Collaboration Technical Stakeholders Cross Functional Solution Planning Business and Technical Requirements Alignment Data Fabric Enterprise Integration Oracle Ecosystem API Concepts And Standards Data Flow and System Connectivity SaaS and Cloud Platforms Observability Data Driven Operations Salesforce Datadog OCI Tableau Metabase Observability Platforms CRM and Analytics Tooling ChatGpt Claude AI Driven Reporting And Analytics Workflow Automation MCP tools AI Assisted Research Data Driven Account Planning Usage and Adoption Analysis

OR

Account Executive – Cloud Venture West | Business Development

Jan 2021 - Jan 2023 (2 years)

Owned full-cycle sales across Oracle Cloud Infrastructure (OCI) and adjacent cloud solutions for high-growth Bay Area accounts. Exceeded 100% of quota in every quarter and contributed to team onboarding and cross-functional sales initiatives.

Full cycle Sales Oracle Cloud Infrastructure Cloud Solutions Consultative Discovery Stakeholder Management Technical Stakeholders Cloud Infrastructure SAP Data Integration Technical Resource Architecture Alignment Quota Exceedance Team Onboarding Cross Functional Sales Council Leadership

VR

Marketing Manager, Web Design & Content Management

Various Roles

Jan 2019 - Jan 2021 (2 years)

Managed digital programs, client engagements, and operational initiatives across nonprofit and web technology environments. Directed a $10K/month Google Ads program and supported expansion of a nonprofit organization into a new market.

Digital Programs Client Engagement Operational Initiatives Google Ads Project Lifecycle Client Communication Research Audit Performance Analysis

Education

Degrees, certifications, and relevant coursework

UG

University of Georgia

Bachelor of Business Administration, Marketing

Earned a Bachelor of Business Administration in Marketing from the University of Georgia in 2019.

Tech stack

Software and tools used professionally

Tableau

Metabase

Oracle

Datadog

Google Ads

Oracle Cloud Infrastructure (OCI)

ChatGPT

AWS

Availability

Looking for a job

Location

United States

Authorized to work in

Salary expectations

74k+ USD

Job categories

Customer Success Manager Account Executive Marketing Manager Web Designer Content Manager

Skills

Strategic Account Management Customer Retention Customer Expansion Enterprise SaaS Full cycle Sales Consultative Selling Value Based Selling Success Planning Executive Stakeholder Management Commercial Negotiation Forecasting Cloud Architecture AWS Oracle Cloud Infrastructure (OCI)Application Modernization

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