Customer Success That Grows With You – Not Against You.

Editor Notes

The Scoop

You’re scaling fast, but your Customer Success strategy feels like it’s held together by duct tape and hope. Sound familiar?

This week’s lineup:

• Discover the anti-playbook for navigating growing pains.

• Quick, high-impact plays that drive revenue, not just satisfaction.

P.S Still treating Customer Success as a cost center? Here's a wake-up call - companies increasing retention by just 5% are seeing profit jumps of up to 95%. Check out my LinkedIn post where I talk about it further.

Featured Article

Scaling Customer Success Without the Growing Pains

Picking up where we left off in navigating the ME ‘awkward phase’, here’s how to build CS infrastructure that grows with you – not against you.

Scaling Customer Success at a Medium Enterprise isn’t about adding more bodies or drowning in KPIs. It’s about ruthlessly prioritizing what actually moves the needle—and tossing the rest overboard.

Think of what I have outlined below as your anti-playbook for the “level-up” phase nobody warns you about. The one where your scrappy startup tactics crash into real grown-up problems: misaligned teams, leaky processes, and customers who suddenly expect enterprise-level handholding (but still want that “small company” vibe).

Let’s roll.

1. Scaling Operations Without Losing the Personal Touch

Challenge: As your customer base grows, it becomes increasingly difficult to maintain the personalised attention that made your customers fall in love with you in the first place.

Solution: Implement a tiered CS model. Categorise your customers based on factors like contract value, strategic importance, and growth potential. Provide high-touch, personalised service to your top-tier customers, while leveraging technology and automation for efficient support of your broader customer base.

2. Inadequate Investment in CS Technology

Challenge: You've outgrown your basic tools, but you're not quite ready for enterprise-level solutions. It's the CS tech equivalent of being too big for the kids' table but not quite ready for the adults' table.

Solution: Invest in a scalable CS platform that can grow with you. Look for solutions that offer features like customer health scoring, automated workflows, and advanced analytics, but with pricing models that work for MEs.

3. Lack of Clear CS Metrics and KPIs

Challenge: As your business becomes more complex, it's easy to lose sight of what really matters. You might find yourself drowning in data but thirsting for insights.

Solution: Define a focused set of CS metrics that align with your business goals. Prioritise metrics that give you actionable insights into customer health, product adoption, and revenue impact. My best advice - Keep it simple.

4. Misalignment Between CS and Other Departments

Challenge: As your organisation grows, departments can become siloed, leading to a disconnected customer experience. It's like each department is playing a different song, and the customer is stuck listening to the cacophony.

Solution: Foster cross-functional collaboration. Establish regular touchpoints between CS and other departments. Consider creating cross-functional teams focused on improving specific aspects of the customer journey.

5. Underestimating the Importance of Customer Education

Challenge: As your product evolves and your customer base diversifies, providing effective customer education becomes increasingly complex. You can't hold every customer's hand, but a sink-or-swim approach isn't the answer either.

Solution: Develop a scalable, multi-tiered customer education program. This should include self-serve resources, automated onboarding sequences, and reserved high-touch training for complex use cases or high-value customers.

Remember, these challenges are signs of growth, not failure. They're the growing pains that come with success. By anticipating these challenges and proactively addressing them, you can navigate the ME minefield and emerge stronger on the other side.

In my own words

Quick Tips

Quick Wins for Optimized Customer Success

Cut through with these battle-tested plays.

1. Tiered Support on Steroids
Stop spreading your team thin trying to please everyone equally.

• Segment customers by revenue impact, growth potential, and strategic clout

• Automate tier 3 support with chatbots, save human firepower for VIPs

• Personalize quarterly biz reviews for top-tier accounts
  

  Do this first: Ruthlessly categorize your top 20% accounts TODAY. Your CSAT scores will thank you by Friday.

2. Automation That Doesn’t Suck
Because your team didn’t sign up to be glorified FAQ bots.

• Deploy chatbots for password resets and invoice queries

• Create hyper-targeted email sequences (nudge: 70% of customers prefer self-service)

• Keep humans in the loop for escalations – tech should empower, not replace
  

  Do this first: Identify 3 repetitive tasks draining your team’s soul. Automate them by EOD.

3. Customer Whisperer Network
Turn your biggest fans into growth co-pilots.

• Recruit 8-10 key accounts for quarterly advisory sessions

• Pay them in early feature access and executive facetime

• Weaponize their feedback to kill useless product features
  

  Do this first: Slide into your top-spender’s DMs with a “Shape Our Future” invite. 83% acceptance rate guaranteed.

4. Knowledge Base or Bust
Your support team isn’t a 24/7 answering machine.

• Document every recurring question like it’s the Holy Grail

• Embed training videos in onboarding emails (cuts “how-to” tickets by 40%)

• Let power users create peer-to-peer troubleshooting guides
  

  Do this first: Audit last month’s tickets. The top 5 pain points become your KB launchpad.

5. Feedback Loops That Actually Close
Stop collecting surveys that gather digital dust.

• Map feedback to specific teams: product gripes → engineers, billing issues → finance

• Share raw customer voice clips in all-hands meetings

• Update customers publicly on how their input changed your roadmap
  

  Do this first: Add a “You Spoke, We Listened” section to your next newsletter. Watch NPS pop.

6. Tech Stack Tetris
No more Franken-systems that make your team want to quit.

• Demand integrations or walk away (looking at you, clunky CRM plugins)

• Negotiate modular pricing – pay for what you use now, scale later

• Bonus points: Tools with built-in customer health scores
  

  Do this first: Declare amnesty on unused software licenses. Slash your stack by 30% minimum.

7. Metrics That Matter
Ditch vanity metrics for the holy trinity of CS: Retention, Expansion, Advocacy.

• Calculate customer health scores using product usage + support ticket sentiment

• Track how CS-driven upsells impact quarterly revenue

• Ruthlessly sunset metrics that don’t tie to board-level goals
  

  Do this first: Replace “first response time” with “expansion conversations initiated.” Watch priorities shift.

8. Cross-Departmental Jedi Mind Tricks
Break down silos before they break your customer experience.

• Host monthly “day in the life” swaps between CS and engineering

• Embed CS metrics in sales comp plans (suddenly, everyone cares about churn)

• Make product teams attend 5 customer calls weekly
  

  Do this first: Hijack next week’s leadership meeting with unedited customer complaint audio. Watch action happen.

The Bottom Line
This isn’t a choose-your-own-adventure game. Start with tiered support – it’s the foundation everything else builds on. Then pick 2-3 other tips that plug your biggest leaks.

Pro Tip: Measure impact in 90-day sprints. If a strategy isn’t moving the needle by day 45, scrap it. Your playbook should evolve faster than your customers’ needs.

Events

Save The Date

CX Symposium 2025
📅 Date: April 2-3, 2025
📍 Location: Hunter Valley, Australia
🌐 Website: https://ashtonmedia.com.au/symposiums/customer-360-symposium/cx-symposium/

TSIA World INTERACT 2025
📅 Date: April 29 - May 1, 2025
📍 Location: Orlando, Florida, USA
🌐 Website: https://www.tsia.com/conference

X4 Summit 2025
📅 Date: March 18-20, 2025
📍 Location: Salt Lake City, Utah, USA
🌐 Website: https://www.qualtrics.com/x4summit/#overview

Deep Dive

What We've Been Reading

Would You Do That to Your Mother?: The "Make Mom Proud" Standard for How to Treat Your Customers by Jeanne Bliss

Priority is Prediction: Seven Principles to Guide Enterprises Toward Better Decisions and Greater Outcomes by Greg Kihlstrom

What We've Been Listening Too

Voice Of Customer Truth: Why Customers Really Leave by Doing Customer Experience Right with Stacy Sherman

7 Ways To Break Organizational Silos; The Silent Killer Of Customer Experience by The Intuitive Customer

What We've Been Watching

Should Customer Success Use the Same CRM as Sales?