SuccessHacker

SuccessHacker We help CSMs and Customer Success teams know the best practices that drive success and how to apply them to the real challenges Customer Success pros face.

We’ve created a comprehensive training program trusted by CSMs from companies around the globe. SuccessHACKER is a Customer Success advisory firm focused on education, coaching, recruiting, consulting and Success Hacking services.

06/02/2026

AI in CS is evolving quickly, but not everyone is using it the same way. How would you describe your relationship with AI in your role right now?

How do you use AI in your CS work?

👍 Task-based tool
❤️ Strategic partner
😂 Honestly, both
😮 Still figuring it out

If you're looking to get more out of AI in your CS role, we built a practical system for using it across the workflows that actually drive retention and expansion. Link in the comments!

Special launch pricing through June 17: 50% off with code AI4CS.

Last week, we launched the AI for Customer Success program from SuccessCOACHING.This isn't a tips course or another prom...
05/28/2026

Last week, we launched the AI for Customer Success program from SuccessCOACHING.

This isn't a tips course or another prompting guide. It's a working system built on the workflows where CS credibility is actually on the line.

Your Customer Success team is already using AI on renewal narratives, EBR prep, and executive communications. The real question is whether what they're sending is actually defensible… or just sounds like it is.

This program is the system that answers that question.

It’s built on five key workflows every CSM works in and anchored in your real accounts. Output scoring, validation discipline, and confidence calibration are built into every deliverable, so you know what's going out and you can stand behind it.

If your team is using AI on customer-facing work, this is the system that makes it defensible.

Launch pricing through June 17: 50% off with code AI4CS.

05/27/2026

What if the best place to start with AI isn't the flashiest use case, but the task you dread most?

Usage reporting. QBR prep. Data analysis. These are the workflows eating hours out of your week that AI is genuinely good at. Now, what used to take four to five hours can be done in under 30 minutes, and built into repeatable skills your whole team can use.

In May’s CS Mastermind session, AI Augmentation in Post-Sales: Exploring Where Humans and Technology Meet, panelist Rachel Jennings-Keane explains the benefits of using AI in your workflow, and how it can genuinely make your day more manageable and enjoyable.

During this live, online event, the panelists discussed:

👉Post-sales activities best suited for AI augmentation

👉How AI can help identify risk and opportunity earlier

👉Preventing AI from undermining customer trust

👉Measuring success when AI is part of the workflow

And more!

Watch the full replay, read the transcript, and get the key takeaways at the link in the comments ⬇️

Meet the host:

🌟 Andrew Marks, Founder and CRO at SuccessHACKER

Meet the Panelists:

🎙Bertil Weil, Customer Success Leader

🎙Lorenzo Serva, Director of Customer Success at Sumo Logic

🎙Rachel Jennings-Keane, Principal Customer Success Manager at Backstory

05/26/2026

How confident is your AI? Most professionals using AI can’t tell the difference between a high-confidence claim and one the model invented because it seemed plausible. And there’s real risk when customer and executive trust gets eroded by deliverables that didn’t hold up to scrutiny.

In this video, you’ll learn about the problematic AI confidence gap and get practical techniques that will change how you evaluate and trust AI output from this point forward.

What's covered:
→ Why AI doesn't signal uncertainty (and why that's a design feature, not a bug)
→ The difference between "it sounded right" and "I can defend every claim in this document."
→ The confidence calibration prompt you can run on any AI tool today

Learn more at the links in the comments ⬇️

ai

We just released Claude for Customer Success, a full open-source set of agents, skills, and cookbooks based on our 12+ y...
05/22/2026

We just released Claude for Customer Success, a full open-source set of agents, skills, and cookbooks based on our 12+ years of curriculum, frameworks, research, articles, webcasts, and operational methodologies. ✨Link to repository in comments.

05/21/2026

When Marketing, Sales, and CS operate from the same definition of value, everything gets easier. Deals close faster, customers get what they were promised, and renewals stop being battles.

What's made the biggest impact on cross-team alignment? 👇

👍 Shared outcome data

♥️ A defined value framework

😲 CS feedback loops to Sales

Introducing AI for Customer Success from SuccessCOACHING.This is not another AI tips course. It’s a working system built...
05/20/2026

Introducing AI for Customer Success from SuccessCOACHING.

This is not another AI tips course. It’s a working system built on the five CS workflows that drive retention and expansion, anchored in your real accounts, with validation discipline built into every deliverable.

Here's what makes it different.

Most AI training simply teaches prompting. The SuccessCOACHING AI for Customer Success program teaches you not only how to craft solid prompts, but more importantly, what to do with the output: how to score it, validate it, and turn it into a customer-ready deliverable that holds up under scrutiny. Because the risk isn’t that your team isn’t using AI. It’s that there’s no consistent standard for what goes out to customers.

The five workflows covered: renewal risk assessment, EBR and QBR prep, executive communications, escalation response, and expansion positioning. Every CSM on your team works in all five. Every one carries credibility consequences.

You'll finish the program with a personal CS AI Playbook that includes prompt chains, exemplar library, audience-persona templates, and scoring thresholds. And it’s all built on your real-life accounts.

For CSMs: move faster on work that drives revenue. Stop re-prompting and start producing deliverables that hold up.

For CS leaders: get a consistent quality standard across your team on the outputs that reach customers, and the visibility to know they're defensible.

Special launch pricing through June 17: 50% off with code AI4CS.

🌟 LIVE CS MASTERMIND 🌟Tune into the next in the CS Mastermind series, AI Augmentation in Post-Sales: Exploring Where Hum...
05/18/2026

🌟 LIVE CS MASTERMIND 🌟

Tune into the next in the CS Mastermind series, AI Augmentation in Post-Sales: Exploring Where Humans and Technology Meet. Host Andrew Marks and a panel of CS leaders will dive into the balancing act of utilizing AI while maintaining human touch.

📅 THIS WEDNESDAY, May 20, 2026

⏰ 11am PT / 2pm ET

During this free online learning event, the panelists will discuss:

👉 Post-sales activities best suited for AI augmentation

👉 How AI can help identify risk and opportunity earlier

👉 Preventing AI from undermining customer trust

👉 Measuring success when AI is part of the workflow

And more!

Join us this Wednesday to learn effective strategies for navigating the intersection of data and human relationships, and where AI can enhance efficiency and insight without eroding trust, judgment, and empathy.

Link in the comments below 👇

Meet the Panelists:

🎙Bertil Weil, Customer Success Leader

🎙Lorenzo Serva, Director of Customer Success at Sumo Logic

🎙Rachel Jennings-Keane, Principal Customer Success Manager at Backstory

This is your 🚨 LAST CHANCE 🚨 to take advantage of our Spring 2026 Sale!The best CSMs aren't waiting to figure out revenu...
05/14/2026

This is your 🚨 LAST CHANCE 🚨 to take advantage of our Spring 2026 Sale!

The best CSMs aren't waiting to figure out revenue skills on the job. They're training for it now, and this spring, that training is on sale.

Get 20% off of our ✨ Value-Based Selling Training Program OR the Customer Success Complete Training Bundle (which includes Value-Based Selling + the full CS Foundations program)! ✨

Use promo code SPRING20 to save! Offer expires TOMORROW, MAY 15, so don’t wait!

Link in the comments below 👇

The future of post-sales work depends on striking the right balance between automation and human connection. Check out t...
05/13/2026

The future of post-sales work depends on striking the right balance between automation and human connection.

Check out the next in the CS Mastermind series, AI Augmentation in Post-Sales: Exploring Where Humans and Technology Meet. Host Andrew Marks, along with a panel of CS pros, will dive into how to navigate the intersection of data and human relationships in your organization.

During this free, online learning event, the panelists will discuss:

🔷 Post-sales activities best suited for AI augmentation

🔷 How AI can help identify risk and opportunity earlier

🔷 Preventing AI from undermining customer trust

🔷 Measuring success when AI is part of the workflow

And more!

Join us live on May 20 at 11am PT / 2pm ET to learn how you can use AI to automate your role without damaging the trusted relationships you’ve developed with your customers.

Link in the comments below! ⬇️

Meet the Panelists:

🎙Bertil Weil, Principal CSM Leader - Global Major Accounts at Cloudflare

🎙Lorenzo Serva, Director of Customer Success at Sumo Logic

🎙Rachel Jennings-Keane, Principal Customer Success Manager at Backstory

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