Customer Success Engineer @ Outreach

Chad
Rosser.

I sit at the intersection of deep technical expertise and genuine customer empathy — architecting CRM integrations, optimising AI workflows, and building things on the side because I can't help it.

See my work ↓ GitHub ↗ LinkedIn ↗ Email ↗
10+
Years in software
CSE
@ Outreach.io
GA
Georgia · Remote

About me

Technical depth.
Customer focus.

I'm a Customer Success Engineer at Outreach, where I serve as the technical backbone of the customer success motion. I manage a portfolio of 250+ enterprise and mid-market accounts representing $100M+ ARR — acting as the primary technical point of contact across the full customer lifecycle.

My background is a little unusual: I came up through customer success and QA engineering before landing in this role, which means I bring a rare combination of engineering instinct and customer empathy. I know how to find root causes, but I also know how to explain them to a VP of Sales at 9am on a Monday.

Outside of work, I'm building. Side projects, personal tools, websites — I enjoy the full arc from idea to something real and deployed.

🔗

Integration Architecture

CRM sync audits, Salesforce & Dynamics health reviews, scalable fixes that prevent problems before they compound.

📊

Risk & Retention

Identifying technical leading indicators of churn across a portfolio of 250+ accounts — and partnering with CSMs to get ahead of problems before they become conversations.

🛠️

Builder at Heart

Side projects, internal playbooks, audit frameworks — I ship real things, not just tickets.

What I do

Where I spend
my working hours

01

Integration Architecture

Proactively audit CRM integrations and integration health across Salesforce and Microsoft Dynamics environments — diagnosing data integrity issues that impact reporting, automation, and customer outcomes.

Salesforce MS Dynamics CRM Sync Data Integrity
02

Customer Lifecycle

Primary technical point of contact for 250+ enterprise and mid-market accounts representing $100M+ ARR — spanning onboarding, adoption, escalation, renewal, and expansion.

Enterprise Mid-Market $100M+ ARR Full Lifecycle
03

Risk & Retention

Identify technical leading indicators of churn before they surface in customer conversations. Partner with CSMs to mitigate exposure through targeted architectural improvements — not just account management.

Churn Prevention Risk Detection Cross-functional

Projects

Things I've shipped

All on GitHub ↗
Featured project
🎯

Chalk

A fantasy playoff pool manager where players pick their predicted Super Bowl matchup pre-season and manage those picks dynamically as teams are eliminated throughout the season.

In progress
Vanilla JS React / Next.js Supabase OAuth PWA
🔴
↗

Was There a Mass Shooting Today?

A public awareness website tracking mass shooting data in the United States.

Live
Web Data
🎬
↗

Joshua Ryan Dietz

Personal portfolio site built for a filmmaker based in Los Angeles — showcasing his work and presence as a director.

Live
Web Design
✦

More on the way

Always have something cooking. Follow on GitHub or check back soon.

Building

Writing

Thinking out loud

Mar 2026 Hello, World general

Résumé

Experience & background

Experience

Outreach May 2025 – Present
Customer Success Engineer · Remote
  • Manage a portfolio of 250+ enterprise and mid-market accounts representing $100M+ ARR, serving as the primary technical point of contact across the full customer lifecycle.
  • Conduct proactive CRM sync audits and integration health reviews across Salesforce and Microsoft Dynamics environments, identifying data integrity issues impacting reporting and automation.
  • Proactively identify technical leading indicators of churn risk, collaborating with CSMs to mitigate exposure through targeted architectural improvements.
  • Act as the technical bridge between Customer Success, Product, and Engineering — surfacing structured customer feedback into roadmap conversations and supporting renewals and expansions.
Outreach Oct 2021 – Feb 2024
Quality Assurance Engineer · Remote
  • Reduced manual testing time by 50% through automated test suites in Cypress and TypeScript, increasing test coverage by 25%.
  • Integrated automated regression testing into the CI/CD pipeline, reducing defect escape rate by 40%.
  • Increased testing efficiency by 30% through a hybrid approach, prioritizing high-impact manual testing while automating repetitive tasks.
  • Reduced defect resolution time by 25% by automating reporting and categorization via Jira integration.
  • Managed 12 product feature releases with zero critical defects in production.
Outreach Apr 2019 – Oct 2021
Technical Consultant
  • Collaborated with major enterprise clients to configure API integrations with Salesforce and Dynamics, reducing system integration time by 20%.
  • Designed and implemented a client-facing Postman process enabling bulk actions beyond native software capabilities, increasing client productivity by 25%.
  • Delivered tailored automation solutions that resulted in a 30% improvement in operational efficiency for client teams.
Outreach Jan 2018 – Apr 2019
Technical Support Engineer · Remote
  • Resolved 1,000+ client inquiries monthly, reducing ticket resolution time by 30% with a 90%+ customer satisfaction score.
  • Provided tier 1 and tier 2 support to enterprise clients on complex technical issues and API integrations.
  • Partnered with QA and engineering to prioritize and resolve escalated issues, improving retention and operational efficiency.
Coding Dojo Aug 2015 – Jan 2018
Code Instructor · San Jose, CA
  • Taught full-stack web development — JavaScript, Python, HTML/CSS, PHP, Ruby — to cohorts of up to 30 students, achieving 90% graduate completion rates.
  • 80% of students showcased portfolio projects to secure jobs in tech; 50% of graduates landed roles within 6 months of completion.
  • Received an average student satisfaction score of 4.8/5 across advanced workshops on async programming and debugging.
Stand-Up Comedian Sep 2010 – Sep 2015
Chattanooga, TN
  • Wrote jokes.
  • Performed said jokes.
  • People would applaud/boo accordingly.

Education

Dalton State College 2012 – 2014
B.B.A. · Management Information Systems

Core Strengths

CRM Integrations Salesforce Microsoft Dynamics API Configuration Integration Health Audits Churn Prevention Enterprise Account Management Technical Communication Cross-functional Collaboration Customer Lifecycle Postman JavaScript Python

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