Customer Success · Onboarding · Implementation

Sydney Johnstone

Sydney
Johnstone

I help companies build the onboarding and lifecycle systems that turn new signups into customers who actually stay. Most of the work is cross-functional: connecting product, CS, and marketing so users don't fall through the cracks after the sale.

About me

Turning complexity
into clarity

Customer Success professional based in New York. I've built onboarding programs for high-volume factoring accounts and AI dispatch tools, environments where users have no patience for a slow ramp and support can't absorb the slack.

I build lifecycle programs, write the SOPs that make them repeatable without me in the room, and connect the automations that handle volume without adding headcount. When users hit a wall with a product, I find which wall it is and fix it.

B.A. in International Business from San Diego State, with a German language emphasis and a minor in International Security and Conflict Resolution. In practice, that was four years studying why communication breaks down when the stakes are high, and how to close the gap. That's still most of what I do.

1,000+
Active factoring accounts I managed at once at TruckSmarter
Day 1
Onboarding built to get users productive in their first sessions
0→1
SOPs, playbooks, and AI agent workflows I built from scratch

Work history

Experience

July 2025 — April 2026
Strategic Operations & AI Product Onboarding Lead
TruckSmarter
  • Ran the "White Glove" onboarding experience for new users, rebuilding the post-signup flow so users reached proficiency in their first sessions instead of weeks later
  • Wrote the SOPs and the "Best Search Practices" master doc the team used to teach users and train each other
  • Built a retention model that sorted users into week-over-week cohorts, so outreach went to the accounts actually at risk instead of everyone
  • Set up a Slack workflow that flagged offboarding requests the moment they came in, which gave us a shot at saving accounts before they left
  • Worked with Product to turn Dispatch user feedback into changes, and recruited the beta testers for launches
  • Set up a "warm transfer" handoff with Sales so high-need users didn't get dropped between teams
  • Wrote the knowledge bases that powered our internal AI agents
October 2024 — July 2025
Factoring Customer Onboarding Specialist
TruckSmarter
  • Managed 1,000+ active accounts as the main post-onboarding contact, moving users into the factoring product
  • Built an onboarding flow that pushed "ready-to-fund" users to the front while keeping slower prospects warm on automation
  • Cut Time to First Funding by walking users through their first invoice submission one-on-one
  • Sat between customers and banking partners to fix disbursement and API payment problems, so clients always had access to their money
  • Was the go-to person for factoring questions, which kept clients around
August 2023 — January 2024
Carrier Success Specialist
Flock Freight
  • Sourced carriers for up to 10 loads a day (partial, full, and shared truckloads) and backed up the team's loadboard sourcing
  • 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
  • Worked across teams to support carriers and get them using the platform more
August 2022 — August 2023
Digital Network Carrier Success Associate
Flock Freight
  • Filtered and managed 10–20 leads per day for platform onboarding using Salesforce
  • Built and kept up carrier relationships to keep them active on the platform
  • Trained carriers on the platform, ran their onboarding, and supported the sales cycle
  • 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 hitting sales targets by handling carrier needs after booking
  • Rolled out Project 44 for automated load tracking, which cut down back-and-forth and kept customers informed
  • Collected carrier paperwork through the load cycle so accessorial requests got processed quickly

What I bring

Skills & Certifications

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

Certifications

Introduction to Data Analytics
IBM · Coursera · May 2024
Verify ↗

Selected work

Projects & highlights

Onboarding architecture
"White Glove" Onboarding Program

Built TruckSmarter's post-onboarding experience for new users: the flow itself, the SOPs, and the "Best Search Practices" doc that set how everyone learned the product.

Retention & automation
Slack-Integrated Offboarding Workflow

A Slack workflow that flagged offboarding requests the moment they came in, so the team could reach out and try to save the account before it left.

Lifecycle design
Week-over-Week Retention Cohorts

A retention model that sorted users by week-over-week activity, so outreach went to the accounts actually at risk instead of the whole list.

AI & knowledge management
AI Agent Knowledge Base Library

The knowledge bases behind our internal AI agents, structured so the agents could handle routine CS work without a person in the loop.

Cross-functional
Sales "Warm Transfer" Protocol

A handoff between Sales and CS that gave high-need users their search setup at the point of sale, so nothing got dropped between teams.

Fintech operations
Factoring Onboarding Workflow

An onboarding flow for 1,000+ factoring accounts that moved "ready-to-fund" users first, cut Time to First Funding, and kept slower prospects warm on automation.

Endorsements

References

Dan Kao
CEO, TruckSmarter
Former manager
Read letter ↗

Let's connect

Get in touch

Open to roles in Customer Success, onboarding, or operations. Based in New York, open to remote.

Connect on LinkedIn