The Journey: #14 The Automated Advantage

When I started my Customer Success journey, we didn’t have AI. Heck, we barely had folders we could find.

No centralized hub.

No automation tools.

No "one-pager playbooks."

Just scattered docs, email threads, and sheer willpower.

We were running Enterprise accounts that demanded a “white glove” experience—personalized, proactive, and high-touch.

But we were doing it all manually. Every QBR deck? Custom. Every follow-up email? Written from scratch. Every onboarding plan? Pieced together on the fly.

And while it worked, it wasn’t scalable. It certainly wasn’t efficient.

It was held together by overachievers and caffeine.

Fast forward to today...

We have automations that can:

✅ Trigger workflows based on product usage

✅ Personalize communications at scale

✅ Track lifecycle stages and flag risk early

✅ Sync key data across platforms in real-time

✅ Let CSMs focus on strategy, not spreadsheet wrangling

The goal isn’t to remove the human. It’s to elevate the human.

How We Started Automating

We didn’t begin with sophisticated tech stacks or complex logic trees.

We started simple—with meaningful, human-centric workflows that moved the needle:

1. Onboarding Automation

• Welcome Email – Instantly greeted every new customer with a warm note from their assigned CSM.

• Prep Email – A one-stop message with everything they needed: booking link, kickoff survey, and a portal of onboarding resources.

• Post-Session Acknowledgement – Every milestone completed triggered a celebratory message acknowledging impact made.

• Mid-Onboarding Exec Alignment – 45 days in, an email from our exec to theirs to build relationship and proactively surface risks.

• Post-Onboarding Survey – A quick check-in asking “How did we do?”—capturing sentiment and readiness to move forward.

2. Adoption Automation

• No Engagement Trigger – 30 days of silence? The CSM received an internal alert with suggested next steps to re-engage.

• Adoption Win Email – When usage trends spiked, a personalized email highlighted success and teed up a strategic growth convo.

• Health Score Drop Alert – Behavioral dips automatically triggered a message to the customer: "We noticed a shift—how can we help?"

3. Renewal Automation

• 6-Month Renewal Survey – Asked customers directly: “Are you planning to renew?”—giving us time to address blockers.

• 125-Day Prep Email – Sent before entering the renewal window with everything the customer needed for a smooth discussion.

• Thank You & Align Email – Once renewed, a heartfelt note with an invite to align on goals for the next chapter.

These were simple automations. Lightweight. Easy to implement with our basic tech stack.

And yet—they created consistency, visibility, and scale without sacrificing the customer experience.

The Real Advantage?

You get to deliver the same white glove experience—without white knuckling it behind the scenes.

Automation doesn’t mean losing your personal touch.

It means systematizing your brilliance so it’s repeatable, reliable, and measurable.

Try This:

1. Identify 3 repetitive tasks you do each week—ask yourself, could this be templatized or triggered automatically?

2. Set up automated alerts for risk signals (declining usage, no logins, support tickets piling up).

3. Build one scalable onboarding template that personalizes itself based on customer segment.

Start small. Test it. Tweak it. Scale it.

That’s the Automated Advantage.