Measurable Advocacy Strategies: Elevating Customer Success Manager Performance

Jonathan Riftin


Director of Customer Success


Jonathan Riftin
Jonathan Riftin

Episode Summary

Today on the show we have Jonathan Riftin, the Director of Customer Success at Optimove.

In this episode, Jonathan shares his experience in implementing strategies to drive customer success manager (CSM) behavior towards advocacy and upsells.

He discusses the importance of setting compensation goals, streamlining processes, leveraging data, and empowering CSMs.

Tune in to discover how to elevate CSM performance and drive customer advocacy in your organization.

Mentioned Resources



Introduction and background of Jonathan Riftin00:01:24
Identifying the problem and the need for increased accountability00:04:53
Developing a plan and gaining buy-in from leadership00:08:31
Supporting CSMs to achieve upsell and advocacy goals00:13:53
Utilizing data to drive upsells and identify opportunities00:19:26
Managing the relationship between CS and account managers00:22:00
Key lesson learned: Focus on what you can control and be proactive00:25:05
Final thoughts and advice for CSMs00:26:44


[00:00:00] Jonathan Riftin: Basically, I would say two elements. One is observation of current processes that were somewhat not streamlined properly. So, for once, when we're talking about just getting reviews from our clients to increase our visibility due to crowd or other platforms, it wasn't working that well. I felt that we could drive more reviews if it was in our hands. It was mainly in our marketing department's hands and responsibility. By getting accountability, shifting the accountability to the customer success managers, I believe that we could drive better results. 

[00:00:42] VO: How do you build a habit-forming products? And you saw this different… Don't just gun for revenue in the door.

[00:00:48] Andrew Michael: This is Churn.FM, the podcast for subscription economy pros. Each week, we hear how the world's fastest growing companies are tackling churn and using retention to fuel their growth. 

[00:00:02] VO: How do you build a habit-forming products? We crossed over that magic threshold to negative churn. You need to invest in customer success. It always comes down to retention and engagement. Completely bootstrap, profitable, and growing. 

[00:01:14] Andrew Michael: Strategies, tactics and ideas brought together to help your business thrive in the subscription economy. I'm your host, Andrew Michael, and here's today's episode. 

[00:01:24] Andrew Michael: Hey, Jonathan, welcome to the show. 

[00:01:26] Jonathan Riftin: Hey, Andrew. How are you? 

[00:01:28] Andrew Michael: I'm great, thanks. For the listeners, Jonathan is the director of customer success at OptiMove, a customer-led marketing platform enabling you to run personalized multi-channel campaigns and deliver personalized experiences in real time. Jonathan has also previously founded a few startups and spent time at companies like Taboola and Google. My first question for you today, after seeing you spend time as a music critic in your early career, what in your opinion is the best album of all time? 

[00:01:57] Jonathan Riftin: Oh, wow. Okay, so the first thing that jumped to mind, I have to say that it's ‘OK Computer’ by Radiohead. 

[00:02:04] Andrew Michael: Okay, I've not heard that. I definitely have to have a listen. When I wrote this question, I was thinking to myself lately, I can't recall any albums that have been released. I think it's the way music has changed and Spotify. Back in the day, I remember listening to albums from start to finish and over and over and over again. 

[00:02:22] Jonathan Riftin: Yeah, so it's a pretty depressing one, but if you're going back to 96, that's a landmark. 

[00:02:29] Andrew Michael: Nice, nice. I'll definitely have to pull that up maybe and I'll again use Spotify probably just to listen but it's nice just to have something different every now and again to spark some creativity. Nice, so I gave a brief intro to a little bit about what Optimove does, but maybe if you want to just elaborate a bit for us, what is Optimove and specifically in your role, what are you responsible for? 

[00:02:52] Jonathan Riftin: For sure. So, the mission of OptiMove is basically to allow brands to have a more personalized and emotional connection with their audience. So we help marketers with B2C companies to enable them to engage better across multiple types of communication channels, email, push, SMS, what have you. And also give them great access to data so they can learn more about their audience and segment better.

[00:03:19] Andrew Michael: Very nice. Yeah, it's quite funny actually, like before I reached out to you, the first time I'd heard of Optimove was like a week ago or two weeks ago and then I started hearing about it from two or three other people. Maybe it was just subliminally, I was blocking it out, but I've seen this also gain quite a bit of popularity lately and I'm assuming you're going quite fast as well on your side.

[00:03:40] Jonathan Riftin: Yeah, so the company is over 12 years old, right? 

[00:03:44] Andrew Michael: It's not new as well, that's why I was surprised. 

[00:03:46] Jonathan Riftin: It's not new. How could I not see it? Yeah, it's a little over a decade, but it was bootstrapped in Israel and only back in 2021 was a significant investment round from a growth fund in the US and since then it's been fueling the company to create more acquisitions in the space. In the past year, we acquired two companies and we're making our product more robust and just a better suite to help all the marketers use more and more channels and capabilities.

[00:04:19] Andrew Michael: Awesome. We've chatted a little bit about this over email, like what we would talk about today and the topic of driving behavior for CSMs came up and some different tactics that you can use to drive CSMs for more advocacy and upsells. You also mentioned that you had just gone through an exercise like this, Adopt 2Move, and I think today would be great if we can sort of unpack that process, what it looked like and how you went about enabling that. Maybe just getting started like at the very, very beginning what point did you decide this was something that needed to be worked on and why? 

[00:04:53] Jonathan Riftin: Great question. So initially, our teams were compensated by a very strong metric for retention. So retention of logos and retention of ARR. That's a classic API that any customer success team needs to have. One key issue that we faced was that, especially because our company works with more enterprise accounts, so the number of accounts per CSM is between 10 to 20. Therefore, the targets were more team-based, not personal-based. At the beginning, we wanted to increase the level of accountability for the metric and for the KPI so they would feel that it's more personal. So we were trying to think, how can we add metrics or KPIs that would drive a certain desired outcome but would also be more on a personal level and not on a team level? So that was one of our hypotheses. 

[00:05:54] Jonathan Riftin: The second one, we wanted to have…we understand that sometimes retention and churn are lagging indicators. There are metrics and there are things that you can do with your customers that could allow for retention and churn to have better results. A couple of these things is, first of all, just having your product being integrated into more channels and having your product selling more additional add-ons and having your clients utilize more of what you have to offer. So that's when we're looking at the app-sell angle, driving more add-ons and more opportunities to integrate. The second thing is, obviously with advocacy, is having your customers speak on their behalf. So whether it's providing reviews, referrals, doing case studies together, and that's something that once you get clients to do that, it's a great testament to your capabilities. And it sort of gives them accountability and the willingness to make things work with you, even if sometimes things are not 100%. 

[00:07:15] Andrew Michael: Very nice. Yeah, I think as well, if you think from the CSM's perspective, as you mentioned, if you have a good relationship and good rapport with the customer, it really enables them as well to be more willing and more likely to advocate, which is then also a good signal that the CSM is doing a great job working with their customer. And as you alluded to in the beginning, working with predominantly enterprise, it's difficult to find other metrics that you can focus on because the sheer volume is just not there to be able to say at an individual level, you are responsible for X, Y, or Z. But these are a lot more tangible and measurable at an individual level to understand, OK, if this customer, if you've been working with this customer, have they advocated for us and how are we driving up sales through the path and how are you working with it? So I'm interested then as well, you identified this was a problem internally, there wasn't enough accountability, you wanted to improve that. And obviously, the benefits of this increased accountability is more customer love and increase in NRR. Where did you go from there? What was the first step then when you started to decide, let's get this program up and running? What were the steps involved? How did you decide? What was it going to be even about? So why advocacy and upsells to begin with? 

[00:08:31] Jonathan Riftin: So obviously, the first conversation I had was with my boss, the chief customer officer of Optimum. At the beginning, she was a bit hesitant because we're really trying to draw a line between commercial conversations that customer success have and relationship building and product. We're really trying to avoid having the customer success managers talk these commercial conversations. And even now, these upsell opportunities, we're only alluding to opportunities and we're helping the CSM to drive these with account managers that are in charge of the commercial aspects of the account. So the first conversation was, I believe we need to have a change. And what is that change? So the number one is having the customer success being more responsible. 

[00:09:26] Jonathan Riftin:  Number two is like, okay, so if we want to change something, what is it that we want to change? Or what do we want to add to that mix of metrics? And obviously, these two are the first low-hanging fruits. So it's number one, getting the buy-in from your manager, from either the chief customer officer or VP customer success, and making sure they understand how that could contribute to the different actions of your team and how that drives the bottom line. Because when we're trying to talk about commercials like upsells, it is a revenue-generating activity. So that is something that is very persuasive when you go to your CEO and tell them, we want to improve our bottom line. These are the things, these are the different tactics we want to take. What do you think? Okay, how much is it going to cost me? Cost, obviously, we're talking about either bonuses or SPFs or what have you. 

[00:10:30] Andrew Michael: And then you laid that out as well in a plan and shared it with the chief customer officer as you mentioned as well. Having a focus on what the revenue impact can also be is a great way of doing that? What else went into this plan? Because I can imagine you didn't just go up to the chief customer officer and say, “Hey, we have a problem. This is what I think we should do.” How did you set that up initially, that presentation or whatever it was, to get the buy-in to go in this direction? What are some of the components you needed to pull in together to make a case for why now and why you should be the one to do this? 

[00:11:06] Jonathan Riftin: Basically, I would say two elements. One is observation of current processes that were somewhat not streamlined properly. So for once, when we're talking about just getting reviews from our clients to increase our visibility across G2crowd or other platforms, it wasn't working that well. I felt that we could drive more reviews if it was in our hands. It was mainly in our marketing department's hands and responsibility. By getting accountability, shifting the accountability to the customer success managers, I believe that we could drive better results. That's number one. Number two, I would say, is… getting data. I looked at the data of how many upsells and opportunities we actually had. Again, this comes into a process that we had, how actually we, like customer success, the CSMs, identified an opportunity and how they looked in the account managers. 

[00:12:10] Jonathan Riftin:  This was all half-baked within Slack environment and not really processed within our CRM platform, which we're using HubSpot for that matter. I thought that, first of all, there's an opportunity to fix that process. Second, there's an opportunity. The second opportunity is actually to drive more visibility into the revenue that the CSMs are generating from these opportunities. To go about that, I also looked into the data. I pulled up all the different upsells from the past year and tried to identify the roots of where they came, which ones came from CSMs, which ones came from other sources. Then I just showed them the numbers and I showed them, okay, this is what we had. I believe we could increase that if, A, we make it a better process and, B, we start compensating the CSMs for generating these opportunities. 

[00:13:10] Andrew Michael: Yes. Really diving into the data there and trying to understand where were the missed opportunities? How can we build a better case for this? You started out then, personally, you identified this problem. You built a business case. You got buying from the Chief Customer Officer. Now you need to go and roll this out and you need to figure out how are you going to actually deliver on those promises that are made and being able to increase upsells and advocacy. What were some of the first couple of things that you did in each of these areas to help the CSMs meet those goals? One was obviously setting compensation goals based on those targets. How else did this program then go about supporting CSMs to achieve those targets? 

[00:13:53] Jonathan Riftin: I believe that's pretty straightforward. You have to set the process in place. You have to write the playbook, have a Notion page about that, describe all the information, working closely with the CS operation manager, getting her to identify what are the different processes that need to happen between Slack, HubSpot, and different automations that need to happen in place. Make sure everything is clear. Rolling out to the team, maybe having a joint meeting about that. Obviously you need to get the numbers in place beforehand. You need to get the improvement of what is the level of compensation. We're talking about yearly bonus, SPFs, or whatnot. After having all this decision, then rolling it out to the team and explaining it. At the beginning, you have to set an example. You have to show, okay, maybe provide some templates for how to approach clients and ask them for reviews because sometimes it's not that intuitive for CSMs. Number two is, when it comes to the upsells opportunities, working alongside team leaders and empowering them to work with the CSMs in order to identify those and see how you translate a simple conversation like a weekly catch up with a client, how you translate things that they say on the conversation into an opportunity. 

[00:15:24] Andrew Michael: The compensation plan itself then, as you mentioned, that you need to get various approval, figure out what those levels and rates were without having to go into many specifics. If you want, you can be as specific as possible. How did you go about figuring that out and the breakdown of compensation? If previously it was all just based more on a team goal of NRR and now it becomes more on an individual basis, what did that look like for you and the team? 

[00:15:51] Jonathan Riftin: The easiest part is the decision that you're not going to change anything. You're going to stick with your existing limit quota, but you are going to play with the distribution. Let's just play with the numbers. If at the beginning your target was retention for AR and logos and assuming it was 80-20, all these numbers are not reflecting to what we have, but I'm just giving you an example. If it was 80-20, then you say, okay, I want to keep retention because it's important, but I'm going to limit it to, let's say, 60%. Now I have 40% I can play with either for advocacy activities or for the upsells. Let's say these two are equally important for me. Let's give 20% to one, 20% to the other, and you're still keeping within the premises, the limits of what you already had. Your CEO won't be like, “Oh no, no, you're asking for too much. I'm asking for the same. I'm just changing the distribution.” 

[00:17:04] Andrew Michael: How does the team respond to something like that? If they've been working in one specific way all along and all of a sudden the goalposts are shifting in terms of how they can score, how did you sell this to the team then? What was the way it was pitched there?

[00:17:22] Jonathan Riftin: Luckily, it's quite an easy sell because you're basically telling them, okay, if before you are under a team KPI, now it's on you. What we gave them at the beginning wasn't such an achievable goal, something that they can do that we felt they can do. By projecting this, they felt like, okay, I can make this work and I can make sure that that X% bonus at least in my pocket, even if the team doesn't meet the team KPI for this year. 

[00:18:06] Andrew Michael: So moving in much more ownership then onto the individual themselves, them being able to be responsible for their outcome. I can definitely see that as being a big driver, especially for the more motivated in the team as well, which is essentially who you want to be pushing and getting excited. You developed that. You had a good plan in place now. And then the activities that you started working with the team, you mentioned as well, like on the advocacy front, really supporting them with how to talk about advocacy, how to get customers talking about these things. On the upsell side, you mentioned working with team leaders and in the very beginning, you also talked about the data that you looked at in terms of how you were going to drive these upsells forward. Was there any process where you worked with the data team internally at OptiMove trying to understand, okay, what are these key drivers that are leading towards upsells? What are sort of the key mechanisms we need to be focused on? How did you determine these actions that the team would need to be focused on? And is maybe the metric just purely did the customer upgrade or are these more focused on activities that generally lead to upgrades? So maybe introducing a new add-on or trying a new feature within the product. How is that structured? 

[00:19:26] Jonathan Riftin: I would say that there are a couple of ways that you can handle this. Number one is getting the data in terms of reviewing all your clients, what they have, what they're missing, so where are the opportunities. And then sorting by, let's assume that you have a client that's like a big one, that's paying you X amount, and they're not using a really easy low-hanging fruit add-on that there's no reason why they won't use. You start with those, as opposed to clients that are more on a limited budget and approaching them with additional opportunities. Maybe they would want it, but they just don't have the budget for it. So it just would create not a pleasant conversation with them. So number one is surfacing the data. And that's obviously you need maybe a product analyst for that. You need your BI reports or your CS ops to help you gather this information. 

[00:20:31] Jonathan Riftin: Number two is looking at the conversations that the CSMs already had, looking past the conversations that they already had with their clients in the past year or so. And at the time, whenever there was some sort of an opportunity, they would loop in the account manager and kind of like a thread on Slack. So trying to identify those, see what actually translated into a CRM opportunity on HubSpot, which is where our account managers live. And I literally counted them, almost manually trying to pull different reports, going back and forth and identifying what actually translated into a cell and what didn't. And obviously, the things we do now, I believe every playbook that you release as a customer success leader is a product in and of itself. It's an MVP. We're starting now. We're already starting to see results. And obviously, we'll iterate based on success, whether we see that the targets are too low or too high. And then we'll just change accordingly, maybe the distribution even. 

[00:21:45] Andrew Michael: Very nice. And how long has it taken to roll this out just to get a sense of context of the time it takes to get so from initial idea? This is the problem to the point now where you're at where you're starting to see some results and being able to iterate then? 

[00:22:00] Jonathan Riftin: I believe it takes like a quarter or two. You need at least one quarter because you need to start from beginning of quarter or beginning of the year, depending on your fiscal year. And you need to plan in advance. So I would give it like, depending on how big your company is, it's one quarter for planning and getting the buy-in and approvals, one quarter for laying out the foundations and then release. So between two to three.

[00:22:31] Andrew Michael: Two to three quarters. And looking back now, it's always a lot easier in hindsight to be critical of our actions. Is there anything you would have done differently with the program? Anything you would advise people to avoid doing when thinking about setting something like this up?

[00:22:47] Jonathan Riftin: I wouldn't say avoid, but whenever it comes to compensation and these personal level metrics, there are a lot of edge cases that you would face. What if the add-on was discussed before the program started, but only now it started? Do I open an opportunity or not? If the account manager was part of the call where we discussed this, is it on the CSM? So there are a lot of edge cases that you need to think before rolling it out. and it's good to have those in writing. 

[00:23:31] Andrew Michael: And that's an interesting one. Actually, you mentioned the relationship then between the CS and account manager because how does that look like at OptiMove? Are they responsible account managers for upsells and for renewals or are they just focused on the initial sale with customers? Because then I can imagine the relationship between the CS and the account manager could get a little bit complicated with a program like this. 

[00:23:55] Jonathan Riftin: Yeah, it's always complicated between sales and CS. But to your question, account managers are only responsible for renewals and upsells, not for new deals. And it's not a zero-sum game. So there isn't really a fight for the source. The playbook is here to streamline the operation and to make sure that the revenue that is generated by the CS team would be recognized. 

[00:24:28] Andrew Michael: And sorry, maybe I misphrased as well. The sales team themselves, are they responsible for renewals and upgrades or are they just focused on the first sale? 

[00:24:36] Jonathan Riftin:So the sales team is split between account executives who manage new business and account managers who deal with existing business. 

[00:24:46] Andrew Michael: So there's definitely sort of that relationship that needs to be figured out and understanding when thinking about a program like this, especially in a place like OptiMove. 

[00:24:56] Jonathan Riftin: Yeah

[00:24:57] Andrew Michael: Very cool. What's one thing that you know today about churn and retention that you wish you knew when you got started with your career? 

[00:25:05] Jonathan Riftin: One thing, I need to think about it. Well, for starters, it's not always in your control. Maybe you're optimistic and you think that I can change everything, I can bring back accounts, I can reactivate, I can save fires. But sometimes it's just different issues and different problems that are really outside of your – could be outside of your limit as a CS, as a relationship manager with the company or even with sometimes it's outside of the product. Sometimes it's a political issue that's internally. So focus on what you can control and try to be as proactive as possible. And then you could sleep well at night knowing that you're 100%. 

[00:25:56] Andrew Michael: Yeah, it's interesting you say that because we had a recent episode with Zev Tillett. I believe you know him as well. And this was one of the key points that he highlighted. He sort of said, there's the things that matter and there's the things that are in your control. And when those two overlap, like that's where you want to be spending most of your time. You want to be spending your time on things that matter and things that you can control. And maybe early on in your career, you might spend on your time on a lot of things that don't matter or you worry about too many things that are outside of your control. And when you can get that balance right between the two, that's sort of the sweet spot where you want to be focusing most of your time and energy.

[00:26:30] Jonathan Riftin: Yeah, that's a great insight.

[00:26:32] Andrew Michael:Very nice. Jonathan, it's been a pleasure having you on the show today. Is there any final thoughts you want to leave the listeners with anything you'd like to share on how they can keep up to speed with your work or any final notes on what we've discussed today?

[00:26:44] Jonathan Riftin:I, you know, just one advice for all the CSMs out there. I believe, as we said earlier, be proactive. Always think one step ahead and never assume that someone else is going to do the job for you. Just go ahead and do it. And that's, you know, maybe a basic career advice, but it always works also for CSMs who wants to progress in their career and for anyone else.

[00:27:09] Andrew Michael: Very nice. Yeah, I was actually going to mention that as well in the beginning. Is it like in companies? It's not very often that people do come to you with like, here's a problem. Here's the solution. We need to go out and fix it. And it's generally the people that do those sorts of things like yourself are the ones that sort of move very, very fast within organizations and progressing their careers because you want problem solvers. And as you mentioned, like never assume that just somebody else is going to do it or it's going to fix itself on its own, especially in early stage startups. And as you're growing and think like it's just a million different problems and million different directions and having people that are proactive to help and solve those, I think it goes a long way. 

[00:27:44] Jonathan Riftin: Yeah, I agree. 

[00:27:45] Andrew Michael: Jonathan, thank you so much for joining. I wish you best of luck now going forward. Excited to hear as well how this rollout goes now and wish you best of success with it as well. So thanks for joining. 

[00:27:57] Jonathan Riftin: Thank you very much. It was a pleasure. 

[00:27:58] Andrew Michael: Cheers.

[00:27:59] Jonathan Riftin: Cheers. 

[00:28:01] Andrew Michael: And that's a wrap for the show today with me, Andrew Michael. I really hope you enjoyed it and you were able to pull out something valuable for your business. To keep up to date with Churn.FM and be notified about new episodes, blog posts and more, subscribe to our mailing list by visiting Also, don't forget to subscribe to our show on iTunes, Google Play or wherever you listen to your podcasts. If you have any feedback, good or bad, I would love to hear from you and you can provide your blunt, direct feedback by sending it to Lastly, but most importantly, if you enjoyed this episode, please share it and leave a review as it really helps get the word out and grow the community. Thanks again for listening. See you again next week.


Jonathan Riftin
Jonathan Riftin

The show

My name is Andrew Michael and I started CHURN.FM, as I was tired of hearing stories about some magical silver bullet that solved churn for company X.

In this podcast, you will hear from founders and subscription economy pros working in product, marketing, customer success, support, and operations roles across different stages of company growth, who are taking a systematic approach to increase retention and engagement within their organizations.


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