Customer Success · Onboarding · Integration

Sydney Johnstone

Sydney
Johnstone

I turn complex products into confident customers — specializing in onboarding architecture, lifecycle design, and the cross-functional work that keeps users around.

Get in touch View experience

About me

Turning complexity
into clarity

I'm a Customer Success professional based in New York, NY, with a track record of building onboarding programs that actually stick. From high-volume factoring accounts to AI dispatch tools, I've helped users go from signed-up to fully productive — fast.

My work lives at the intersection of people and process: I design lifecycle journeys, write the SOPs that make them repeatable, and build the automations that make them scale. When something breaks down between a user and a product, I'm the one who figures out why — and fixes it.

I hold a B.A. in International Business from San Diego State University with a language emphasis in German and a minor in International Security and Conflict Resolution — which is a fancy way of saying I'm good at navigating complexity across cultures and contexts.

1,000+
Active accounts managed simultaneously at TruckSmarter
Day 1
Onboarding designed to get users to "aha" immediately, not eventually
0→1
Built SOPs, playbooks, and AI agent workflows from scratch

Work history

Experience

July 2025 — April 2026
Strategic Operations & AI Product Onboarding Lead
TruckSmarter
  • Spearheaded the "White Glove" experience for newly onboarded users, refining the post-onboarding journey to ensure immediate product proficiency and long-term user success
  • Authored a comprehensive library of SOPs and a "Best Search Practices" master document to standardize user education and internal team workflows
  • Engineered a tiered retention model by segmenting users into Week-over-Week cohorts, enabling personalized, data-driven outreach to at-risk accounts
  • Developed an automated Slack-integrated workflow to flag offboarding requests in real-time, enabling proactive "save" opportunities
  • Partnered with the Product team to synthesize user feedback on Dispatch and led beta tester recruitment for product launches
  • Established a "warm transfer" protocol with the Sales team to eliminate friction in the user journey for high-need onboards
  • Authored an extensive library of knowledge bases to build AI agents for optimized workflows
October 2024 — July 2025
Factoring Customer Onboarding Specialist
TruckSmarter
  • Managed a high-volume portfolio of 1,000+ active accounts as the primary post-onboarding lead for seamless factoring ecosystem transitions
  • Engineered a customized onboarding workflow that prioritized "ready-to-fund" users while maintaining automated engagement for long-lead prospects
  • Accelerated "Time to First Funding" through 1-on-1 technical guidance for initial invoice submissions, reducing payment turnaround times
  • Acted as technical liaison between customers and banking partners to troubleshoot fund disbursements and API payment issues, ensuring 100% liquidity access for clients
  • Cultivated long-term client retention through proactive relationship management as a dedicated subject matter expert for factoring services
August 2023 — January 2024
Carrier Success Specialist
Flock Freight
  • Sourced carriers for up to 10 assigned loads per day (partial, full, and shared truckloads) while supporting loadboard sourcing for the team
  • Managed a book of 50–100 accounts at any given time, booking up to 40+ loads per week
  • Used Salesforce to maintain carrier accounts and source loads matching preferred lanes
  • Collaborated cross-functionally to support carriers and enhance platform usage
August 2022 — August 2023
Digital Network Carrier Success Associate
Flock Freight
  • Filtered and managed 10–20 leads per day for platform onboarding using Salesforce
  • Grew and maintained carrier relationships to sustain platform usage and engagement
  • Trained carriers on platform usage, facilitated onboarding, and supported sales cycles
  • Worked closely with product teams to improve platform functionality for users
May 2022 — August 2022
Carrier Success Coordinator
Flock Freight
  • Supported regional specialists and managers in achieving sales targets by managing carrier needs post-booking
  • Implemented Project 44 for automated load tracking, improving communication efficiency and customer satisfaction
  • Gathered necessary paperwork from carriers throughout the load cycle to promptly process accessorial requests

What I bring

Skills

Onboarding & success

B2B SaaS onboarding Lifecycle design Time-to-value Retention strategy Churn prevention Cohort segmentation

Technical

Salesforce API troubleshooting Workflow automation Slack integrations AI agent building

Financial services

Factoring Invoice processing Fund disbursement Payment operations

Communication

SOP authorship Stakeholder engagement Customer education Cross-functional collaboration

Selected work

Projects & highlights

Onboarding architecture
"White Glove" Onboarding Program

Designed and led TruckSmarter's post-onboarding experience for new users — building the journey, the SOPs, and the "Best Search Practices" documentation that standardized how users learned the product from day one.

Retention & automation
Slack-Integrated Offboarding Workflow

Built an automated Slack workflow that flagged offboarding requests in real-time, turning potential churn moments into "save" opportunities with immediate, proactive outreach.

Lifecycle design
Week-over-Week Retention Cohorts

Engineered a tiered retention model at TruckSmarter that segmented users by WoW activity, enabling targeted, data-driven outreach to at-risk accounts before they churned.

AI & knowledge management
AI Agent Knowledge Base Library

Authored an extensive library of knowledge bases specifically structured to power AI agents — optimizing internal workflows and reducing manual overhead for the CS team.

Cross-functional
Sales "Warm Transfer" Protocol

Established a handoff protocol between Sales and CS at TruckSmarter, providing technical search-setup guidance at point of sale and eliminating friction for high-need onboards.

Fintech operations
Factoring Onboarding Workflow

Built a customized onboarding flow for 1,000+ factoring accounts that prioritized "ready-to-fund" users, accelerated Time to First Funding, and maintained automated engagement for long-lead prospects.

Let's connect

Get in touch

Open to new opportunities in Customer Success, onboarding, or operations. Based in New York — open to remote.

sydney.a.johnstone@gmail.com
LinkedIn ↗ (530) 574-5842