In this episode of Mastering CS: Candid Leader Insights, Irina Cismas talks with Cassandra Dehlot, Enterprise Customer Success Manager at Orca Security, an agentless cloud security platform. Cassandra explains how she structures her day around prioritization rather than urgency, why EMEA teams should wrap Q4 by early December, and how she uses the quiet weeks to plan the next half year.
She explains her approach to onboarding with milestones agreed from day one, how she treats success plans as the engine of adoption, and the AI workflows she built to automate follow-ups, update success plans, and spot risk and expansion signals in support tickets.
What You’ll Learn
- How an enterprise CSM structures the day to avoid getting lost in false urgency
- What good onboarding looks like when milestones are set at the four, six, and eight week marks
- Why success planning is the key to adoption and easier renewals
- Practical AI automations for follow-up emails, success plan updates, and support ticket analysis
- How to build a CS playbook for a new market by adapting what already works
- Why champions and early executive alignment matter in every industry
Key Insights & Takeaways
Prioritization protects you from burnout. Not everything is urgent. Start each day by reviewing your calendar and tasks and deciding what can wait.
In EMEA, Q4 ends in mid-December. Get renewals, upsells, and strategic engagements done by the first week of December so you are not firefighting at the end of the month.
Use Q4’s quiet time to plan ahead. Map out upcoming renewals, QBRs, and expansion opportunities for H1 before the new year starts, so you don’t miss critical signals.
Onboarding success is defined upfront. Agree on deliverables, KPIs, and milestones with the customer at the start, then track progress at four, six, and eight weeks.
Missed milestones are early warnings. If priority number one isn’t achieved by week four, step back and adjust before week eight.
Podcast transcript
Irina (0:06 – 0:42)
Welcome to Mastering CS, Getting Leader Insights, the podcast where we dive into the world of customer success with industry leaders. I’m your host, Irina Cismas, and today I’m joined by Cassandra Dehlot, Enterprise Customer Success Manager at Orca Security, an agentless cloud security platform. Cassandra, I’m really happy to have you here.
Thanks for joining! Before we dive in, you’ve worked across a few really different worlds, and you are now an enterprise CSM.
Paint us a picture of your day-to-day in cloud security. Who are your customers and what does the work actually look like?
A Day in the Life of an Enterprise CSM in Cloud Security
Cassandra (0:43 – 2:21)
Perfect. I will start with my customers. Cybersecurity is so broad that it touches any customer, regardless of their size or industry.
My customers are a big blend, from massive enterprises in the financial sector to education and healthcare, from big to a bit smaller, so I would say SMB. So it’s really broad and touches any segment.
What my actual day looks like, I guess, is like any CSM’s. It always starts with organizing and planning my day.
When you manage big customers across different industries, it’s always important to prioritize where you want to spend your time on a given day. So first things first: look at your calendar, look at your tasks, and prioritize what is most important and what can wait. I think as a CSM, it’s easy to get lost in the sense of urgency. You feel everything has to be done now, but the reality is that’s not the case. And if you don’t understand how to prioritize, you’re going to burn out really quickly. So step number one: understand your workload, prioritize, and that will help you plan your day accordingly.
When this is done, a big portion of my day is customer meetings: cadence calls, engagement reviews, or QBRs, depending on the company you work for and what you call them. Usually that takes about four to five hours in a given day.
And I always end my day with admin: summary emails, which I have now automated using AI, reviewing and updating success plans, and then looking at any outstanding tasks for the following day. That’s pretty much how my typical day looks, at a high level.
Q4 Planning Across EMEA
Irina (2:22 – 2:31)
And for the quarter, because we are almost reaching the end of the year, in case you are following the calendaristic.
Cassandra (2:31 – 2:31)
We are.
Irina (2:32 – 2:41)
We really are. What is the biggest priority? How are you going through Q4 planning? What does it mean for you?
Cassandra (2:42 – 4:37)
Obviously, the end of the year means the Christmas break. If you follow the January to December calendar, you know that Q4 is always shorter than the others across EMEA. In Europe, the DACH region, and sometimes even North Africa, which is the perimeter I’m covering, Q4 ends, I would say, mid-December. That’s honestly what anyone who manages this territory would tell you.
So the key for us is to get all renewals, all upsells, and all deep and strategic engagements done by the first week of December. The priority is to have everything wrapped up by then. That way, when customers go on holiday or things get slower, even internally, you’re not stretched and you’re not firefighting on the last day of the month. So that’s priority number one.
Now, as an enterprise CSM, I’m a firm believer in proactive forecasting. So once everything is wrapped up by the first week of December, I use the rest of the quarter to plan my H1 2027. What is it going to look like? Which renewals do I have that I haven’t started working on? Which QBRs should I be planning that I haven’t? Which customers should I be focusing my time on for the first half of next year? So for the rest of the quarter, Q4 becomes a big planning period for 2027, because before you know it, it’s already here.
And if you haven’t stopped to think about it proactively in Q4, you may end up missing some critical signs because you were so busy firefighting on existing renewals or existing customers. You may miss an expansion you didn’t work on in Q4 and should have spent a bit more time developing for next year. So a big portion of Q4 is getting everything done by the first week of December and then using that quiet time to plan H1 2027.
What Good Onboarding Looks Like
Irina (4:37 – 4:58)
Awesome. Now let’s go back to the beginning, because we switched a bit. Let’s talk about one of the most important parts and the foundation of customer success: onboarding. I’m curious, what does good onboarding look like for you?
What are you aiming for in the first few months? And I think the most important part, how do you know when you’ve got there?
Cassandra (4:59 – 6:34)
Yeah. So in my opinion, the biggest part of a good onboarding is to set the criteria from the get-go. I’ve done onboarding before as well.
I was an onboarding specialist at some point in my previous year’s role. And it’s very easy when you start an onboarding to get caught up by different initiatives as they come throughout this period that you called onboarding. So the success starts with being clear and aligned with the customer on within those four, six to eight weeks, what are the main deliverables you want to achieve to ensure you guys are good to go?
So it starts with that. Once you set those on and you are dead on timeline, KPIs, milestone, then it’s easy then to measure how the onboarding is going against those goals. So the success will as you go on through the four weeks mark, the six weeks mark and the eight weeks marks, where are you against those goals?
And that will determine how successful your onboarding is. That is my opinion. So this also helps you to reduce risk because let’s say you are four weeks in and then priority number one hasn’t been achieved.
Then it helps you to take a step back and say, okay, what do we need to revisit? So the next milestone is achieved or what do we need to change to ensure that they’re on track for week eight? So this is pretty much what I see how a good onboarding looks like and how healthy it looks like.
It’s defining based on the customer, sales handover, sticking to it and tracking success against those defined milestones at the start of the onboarding.
Driving Adoption Through Success Planning
Irina (6:35 – 7:03)
And once the onboarding ends, it’s the traditional adoption. How do you make sure that the customer is actually taking value from your solution and is basically rolling it out or blending it in? It’s in its own operations.
What makes your product sticky and what guarantees, I would say, an easier renewal conversation?
Cassandra (7:04 – 8:17)
Then that’s the two magic words, success planning, which is key if you want to make sure your solution sticks. So success plan needs to be defined with the customer. Is that internal solution for us to track success?
So if you think of the complex cloud solutions such as Orca that have different domain around compliance, cluster security, application security, the idea is to map a journey based on the customer use cases. And just as you go along, use the success plan to direct the customer on what they should be using against their goal in the platform to be successful. So it’s just success planning to ensure everything runs accordingly.
And the success plan needs to be constantly reviewed with the customer on the monthly or quarterly basis based on the size of the customer, sometimes even biweekly. And that’s ensure that not only the solution is correctly adopted, that we have measurable KPI that will be defined within the success plan. And this is continuously reviewed and aligned on and agreed upon with the customer.
So that’s pretty much how we do it. It’s all about success planning to ensure everything is rolled out and adopted as healthy as possible.
The CS Tech Stack
Irina (8:18 – 9:01)
At the beginning of our conversation, you mentioned that prioritizing and having a clear agenda is basically what helps you navigate the day. You need to be organized. You need to be prioritizing because otherwise everything is fire and you end up in burnout.
Now I’m curious, in order to maintain yourself so organized and structured, you need to have some systems and processes in place. What is the operational infrastructure behind all of this? What platforms are central to how CS actually runs at you guys?
Where do you start your day? Where do you, I would say, log in and try to make sure? How do you organize it?
Cassandra (9:02 – 10:40)
Number one is our CSP. It is the central customer success platform that we’re using. So this is where you can have the task assigned to you.
You can understand at a glance the health of your customer based on some key metrics. So you always start with that. Now, personally, I also leverage AI a lot in my day-to-day life.
So on the top of our CSP, I have also my own AI workflows that I have defined in line with how I work, which helps me to even be on the top of my task. So I’ve got a couple of skills project, depending on what you use, that is connected to key sources. You think of Slack, you think of Google Calendar, you think of any other source that you’re using, such as Queries, if you record your call.
And then everything will pretty much fit my AI model and then highlight some priorities I should be focusing on based on, I don’t know, some risk identified in my account or something that were mentioned on the call that I may have missed. And everything is then tracked in my own item tracker, action item tracker. And it will help using AI, prioritizing this is a high risk, this is a critical risk, this is a medium and low, and that’s also going to fit in the complement of the CSP, the tasks that I should be focusing on the day-to-day life.
That’s number one. And then obviously the second one is your CRM. So whether or not you use Salesforce or HubSpot, in our case we use Salesforce, is understanding if you look at your book of business, that will help you then to identify even further in terms of renewal and expansion, any renewal that you should be focusing on.
We also drive your priorities on account as you’re going through your day, weeks, and quarter.
AI Workflows That Cut Admin Time
Irina (10:42 – 10:49)
Tell me more about those AI use cases. How do you leverage it? What automations have you built on top of your current tech stack?
Cassandra (10:50 – 13:11)
Yeah, so I will take five days back in understanding why I started to implement AI in my model. As I said at the beginning, customer success is a lot of tasks that you need to prioritize, but also to do, such as, I don’t know, follow-up emails or success plan updates. And all those things are, if you think about it outside of the success planning, are automated tasks.
Like your template, most likely follow-up emails look very similar, the content is just different. If you think about any QBR deck that you have, the core format would be quite similar, but the content would be different. So if you think at the core of all those tasks, you can find a way to automate all of these, and that’s where I started to see AI, is how can AI help me to reduce my admin time so I can then focus on more strategic tasks.
So a couple of workflows I’ve built, pretty straightforward or pretty simple actually, is automated my meeting follow-up emails, right? So at the end of the day, I’ve got my skill running, they will analyze my course call and summary, and then will draft in my Gmail inbox the summary of all of my meetings. So they will create one email for meeting with all the attendees, email subject, and then it’s just for me to review and send.
That’s one example. Every Friday, I have another skill that’s going to run through all my success plan, and then start drafting some key milestone and update the current one based on the content of the discussion with the customer. I’ve got another AI skill that will help me to make the identified risk faster.
There’s always one element that I feel customer success sometimes is missing, is support. So I’ve got this skill that analyze every week all of the support cases that some of my biggest customers have opened to identify trends, and that will also help me to understand, is there any risk? Because it could be that maybe there’s a feature that they haven’t understood, it could be that there’s something that is a requirement that they don’t tell us, but they tell support, but also expansion.
If they don’t understand something in the platform, or they’re asking for something that is already there and they don’t know, using AI to identify trends in support ticket can help you also to understand, oh, maybe there’s something we could delve into that could be an expansion opportunity, or just further adoption. So this is a couple of work that I have to help me plan my day, but also identify faster risk and expansion opportunities using AI.
Building the French Market Playbook at Procore
Irina (13:12 – 13:27)
I want to take you back for a second. At Procore, you were the first CSM for the French market, building the playbook for a brand new region from scratch. How did you actually approach that?
Where did you start? And what was the first thing that you’ve built?
Cassandra (13:28 – 15:18)
So the first approach there was to look at the other market that were mature at Procore, right? The US was heavily developed. So the first thing was to understand what worked well, which piece of the playbook that they already had was very successful, and then understand based on what I know about the French market, having been, obviously I’m French-native, but also I’ve worked constantly between French market and UK market, is how I can get what works already and just adapt it based on culture or maybe structure to the French market. That was number one. The second approach then was, now that I know what is working, let’s look at what wasn’t working in this same patch and see how I can maybe improve it to make it work in a new market, such as the French market.
That was step number two. Step number three was, when I was the first French CSM, they already had a little bit of French customer already established in the region. So now that I have all those, that’s how I called it, ready, then it was easy then for me to test it on my existing customer to see then how it can be adapted based on their feedback, their experience, to ensure that whatever I’ve built as a playbook then would be in line with what is the customer experience expectation.
So obviously the first playbook was, onboarding wasn’t one of them because they had the established onboarding team at the time, but the one that I’ve built was definitely around success planning. How can we show that whatever we build around success planning is solid, and then which step we should follow to ensure that we’ve got the KPI right, we’ve got the right stakeholder, we understand the different motion that they have within the business, and then we have a strategy that could be repeatable and implemented across pretty much any new customer that will come in.
Lessons That Carry Across Industries
Irina (15:19 – 15:34)
You’ve worked across cyber security, construction tech, and now back in the cloud security. Is there a habit, a way of thinking, or something you learned the hard way early on that still shows up in how you run accounts today?
Cassandra (15:39 – 17:21)
Yeah, first of all is regardless of the industry, you can only learn by engaging with your customer right. You can read everything you want from the product itself, you can assume, but for me the first thing is the more you speak to the customer the more you learn, and that’s something that is hard at the start, but in my opinion that’s one of the fastest ways to not only learn the customer in this new industry, but also the many use cases or challenges they are experiencing within the industry, but also using your technology and therefore help you to help more accordingly.
The second thing I’ve noticed across all industries is in the best of your abilities, build champions. I think champions is a very broad term, it can be used quite easily based on the type of people you’re talking to, but understanding who can advocate for you, for your platform, I think is something that still shows up on how I run my accounts. Identify a couple of champions, understand what they really care about, build a relationship, and ensure that whatever you do is in line with their goals they were constantly about for you.
And the number three, which is always hard I think from a CS perspective, is executive alignment. Once you understand who is the economical buyer and the decision maker, because sometimes the champion can be, as most of the time they are not, get some executive alignments as soon as you can, either with yourself or your manager or your C-levels, that’s something that it’s still across all industry hasn’t changed. It’s always a hard way to build this early on, but it also still shows up on how I run my account today.
Irina (17:22 – 17:40)
Cassandra, thanks for the conversation, I really enjoyed it, and thank you for taking the time to talk to us today. To everyone listening, thanks for tuning in.
Until next time, stay curious, keep learning, and mastering customer success.
