What an incredible session we had together! 🎉 Thank you to everyone who joined our recent webinar where I walked through exactly how I structure my day as a Principal CSM here at Gainsight — from morning priorities all the way through to how I'm using AI to prep, execute, and follow up on every customer interaction. If you missed it, here's a quick rundown of the highlights, and you can watch the recording here.
Key Highlights
1. Gainsight Home: Where My Day Starts
My first stop every morning isn't my inbox — it's Gainsight Home. I've customized it to surface exactly what I need to prioritize my day, and it helps me stay ahead of what's most important across my 6–8 strategic accounts.
Here's how I use it to kick off my morning:
- I review Calls to Action (CTAs) by due date — what's due today, what's due this week, and what needs my attention right now.
- I check my Staircase AI buckets to see what overnight signals came in: churn detected (a customer has explicitly signaled unhappiness or non-renewal) and churn risk (friction signals that aren't quite there yet but need watching).
- Before I have my first call of the day, I've already emailed every at-risk customer. Those responses trickle in throughout the day, and I'm ready to act.
- I also check who needs an EBR scheduled, whether my forecast needs updating, and whether any risk signals have hit accounts sitting in my renewal pipeline.
If you're in a mid-size or SMB segment, a lot of this same logic applies — you may just use the group send functionality to reach multiple customers at once rather than reaching out individually.
2. Meeting Prep: AI as My Research Partner
Once I've triaged my morning, I shift into meeting prep. I've got a few tools in rotation depending on the day.
Gainsight Copilot is my first stop for anything account-specific. I'll prompt it conversationally — "Give me a weekly update on this customer," "Help me prep for my call with Abbott today," or "What competitors should I be aware of heading into this renewal?" It works just like ChatGPT or Claude, but it's pulling directly from Gainsight data.
AI Cheat Sheet is another one I rely on heavily, especially for:
- Getting a fast contextual summary of background, contacts, and risk signals before a call
- Account transitions — if I'm newer to an account or covering for a colleague, it gives me everything I need in one place before I get on a call
I also review health scores and product adoption pre-call. Are they using Gainsight in a healthy way? What features aren't they leveraging? These become great talking points — it shows customers that I'm paying attention to their business, not just showing up to check a box.
And for those who've connected your LLM to Gainsight through the MCP (Model Context Protocol) — you can do all of this right from Claude or ChatGPT. The MCP pulls Gainsight data into your conversational chat so you can prep, build content, and act on signals without ever leaving your tool of choice.
3. Post-Meeting Actions: Closing the Loop
A great call is only as valuable as what happens after it. Here are the three things I do after every customer meeting:
1. Update Timeline and the Success Plan
AI follow-up drops the call recording and an AI-generated summary directly into Gainsight Timeline. From there, I generate the tasks, update the success plan, and add any notes worth capturing. You can also do this through the MCP — prompt it to summarize your call, generate CTAs, and post directly to Gainsight.
2. Log a CSQL
If a customer expressed interest in another product, needed more licenses, or dropped any buying signal, I create a Customer Success Qualified Lead right after the call. This opens a lead in the CRM for my sales counterpart to qualify, and there's a bonus structure tied to it — so it's in everyone's interest to move quickly.
3. Submit a Product Enhancement Request
If a customer flagged a product gap or a feature they need, I capture it while it's fresh. My tip: before submitting, push your customer to share the business impact behind the ask. How much time is it costing them? What's it blocking? That context makes a product investment request significantly more compelling.
4. The One-on-One Dashboard: My Manager Alignment Tool
Before my weekly one-on-one, I pull up my One-on-One Dashboard — a customized view built around my KPIs and responsibilities. I walk through it widget by widget with my manager so there are no surprises.
The four areas I focus on most:
- Health and product adoption — who's not green, and what's the get-to-green plan?
- Upcoming renewals with flagged risk — filtered by renewal date and ARR, with CTA updates ready before I walk in the door
- Stakeholder engagement — when did I last meet with each account? Who's been dark?
- Verified Outcomes — have I helped a customer close a meaningful, measurable success in the last 12 months?
If your manager is looking at different data than you, you can't have a real conversation. This dashboard closes that gap.
5. AI-Powered Content Creation: Building Decks Without the Drag
A good chunk of my afternoon goes toward preparing for tomorrow's meetings. Before AI, building an EBR or steering committee deck could take hours. Now, I'm using the MCP with a custom branded skill I built from our best existing decks and content.
I prompt Claude to pull account data from Gainsight and structure it into a ready-to-use deck — and it comes out on-brand, personalized, and ready for review. It's not perfect out of the box; prompting is an iterative process. But it takes something that used to take half a day down to a fraction of the time.
I also use this approach to build product roadmap alignment decks — pulling a customer's open enhancement requests alongside what we're releasing and crafting a narrative around what's coming for them specifically.
6. The Rest of My Day: Staying Proactive
Beyond meetings and content, here's where else I spend my time:
- Support escalations — I have a great support team, but I'm the escalation point. I check in on active tickets and make sure communication with the customer stays open and moving.
- Product adoption reviews — proactively checking for dips, spikes, or underutilized features before customers flag them.
- Contact hygiene — 30 minutes a week (or live during a call when an org change comes up). Good hygiene means your automations, triggers, and AI outputs all work better. I block a Friday hour monthly for a full review.
Q&A Highlights
Q: I have 249 open CTAs. How do I keep these structured?
Filter by due date first, then ARR of the account, then CTA type — with risk always at the top. You can build custom views in your CTA dashboard so you're not scrolling through noise to find what matters.
Q: How do responsibilities differ across CSM segments?
At Gainsight, it's primarily driven by ARR. I'm weekly with most of my customers, while our mid-market team is monthly to quarterly. Strategic CSMs run thought leadership sessions and on-sites; other segments lean more on community resources, office hours, and scaled digital programs. The activities are similar — the frequency and personalization scale up or down.
Q: What are your EBR non-negotiables?
In my segment, the customer has to co-present. I require they share their roadmap and priorities before the meeting so I can tailor the entire EBR to what their executives actually care about. The joint success plan is non-negotiable — where are we against what we committed to, and where are we blocked? Adoption and usage trends round it out, with recommendations ready to go.
Q: How do you handle a touchpoint when the customer is green and nothing is burning?
Two moves: first, go through Gainsight happenings — webinars, field events, past recordings, things I've seen on LinkedIn that feel relevant to them. I build a quick slide through the MCP for this. Second, walk the success plan. There's almost always something that's shifted, and naming it out loud usually opens up a real conversation.
Q: Is the MCP an admin toggle?
Yes — it's admin-enabled on the backend, but before you flip the switch, go through your security review process. Once that's done, the setup is actually pretty quick. For CSM leaders and ops folks on the call: don't skip the security step.
Q: How do you manage contact hygiene across your book?
Account by account through the People tab, ideally right after a call or live during one when I hear about org changes. I also block a Friday hour monthly for a full pass — success plan updates, contact hygiene, weekly summaries. Put it on your calendar and protect it.
What I Want You to Take Away
- Start your day in Gainsight, not your inbox. Churn signals, CTAs, and EBR gaps don't send you a Slack message. You have to go find them.
- AI is a prompt game. Copilot, Claude, ChatGPT — they all need specificity to give you great output. Build your prompt library and iterate.
- Timeline quality drives AI quality. The better your notes and call sync, the better your Cheat Sheet, Copilot, and MCP outputs will be. Invest in your inputs.
- Post-meeting discipline is where the magic happens. Updating the success plan, logging the CSQL, submitting the product request — these aren't admin tasks, they're how you create long-term value for your customers and your business.
- Contact hygiene isn't glamorous, but it's foundational. Your automations, your AI outputs, your forecasting — all of it gets better when your data is clean.
Thank You! 🙌
A huge thank you to everyone who attended and brought such great questions to the session. The energy in the room was amazing, and I hope you walked away with at least one thing you can take back to your workflow this week.
If you have follow-up questions, drop them in the comments below or reach out directly. And don't forget — the recording will be available soon, so watch this space!
Until next time, keep operationalizing smarter. 🌟
Alexandra Helminski
Principal Customer Success Manager, Gainsight