Episode 2 21:32 April 28, 2021
Leadership Development for Customer Success: Key Questions for CS Leaders

In this Episode

Customer Success Leaders serve four key audiences: their company, customers, team, and themselves. Each of them has different demands and different questions (some stated, some unstated) that they need answered.

Understanding this and being able to successfully answer these questions is a make-or-break leadership skill—one that is learnable as long as one focuses on it.

Here is an insightful conversation—between Marty Kaufman, Founder & Principal, Infinipoint, and Prithwi Dasgupta, CEO & Co-founder, SmartKarrot—as a lead-up to a one-of-its-kind, actionable leadership workshop series for Customer Success Leaders.


Hi, Good morning Marty


I’m very happy to have you here at Kaffeine and Karrots and you know we have been discussing something very interesting and like you and I discussed… it probably has value in sharing with the wider community as well so thanks for joining in … uh for everyone uh …you know I’m very happy to introduce uh Marty Kaufman to you.

Marty is the principal and founder of a customer retention consultancy called Infinipoint and uh he’s been doing customer-centric work for over 25 years now. In his current capacity works with a lot of customer-focused teams guides them, mentors them across the people, process, sort of technology spectrum…

So, he and I were discussing an initiative which really is his brainchild of.. handling this problem of CS leadership mentoring and CS leadership training very specifically in the community … uh.. and in the industry.

And we’ll discuss a little bit more in detail on why we feel… uh that is one of the key needs the industry faces and we’ll have a chat uh Marty around the same uh so whilst we were chatting about this and brainstorming this we felt you know it might be helpful to solicit feedback from the wider audience as well uh… many of you we will reach out to participate in this as well uh so without further ado Marty if I may uh you know I’ll kick off with my first question for you.


And then I’m sure you have a few for me as well and then we’ll just see how it goes from here uh so the obvious question is why do you feel… there is a need right now for something like this and if you could throw some light on you know what is it that we intend to do uh to address this and contribute to this
problem yep.

Yeah the good news is the need isn’t coming from something being horribly broken and often that is the big driver for you know identifying a need and putting a new initiative out there or something like that oh this is so broken that we have to fix…. fix it , and this is more of customer success as a discipline as a unique function within organizations has matured to the point where the people I work with the question is less about should we do this like do we need a customer success function?, and now pivoting more towards how do we get the most out of it? how do we prove that? how do we you know we believe in this capability?

But how do we really make sure that we’re …we’re optimizing that to… its ultimate degree and there’s many ways to do that but one of them that I keep coming back to.

And this is threaded throughout my whole background is you need excellent change-ready leaders to be able to move that forward to take it to the next level and to really get… the most value out of customer success um… and I should say upfront like I’ve come from a bit of a success background.

I don’t think of customer success as a team first. Ultimately customer success is an outcome that your organization is trying to achieve many people build a team around that and that’s fine uh both are excellent approaches however leadership is needed to whether you have an organization or not leaders that understand customer success how to drive it how to integrate it within the rest of the organization um …. the industry is ready for something like that now and so I’m kind of excited that the place where I’ve been working for the last 20 plus years um has finally grown up enough that it has its own name, disciplines are building around it and even uh leadership is even ready to take on a unique definition of what it means to be a leader in this context.

It’s an exciting time that’s why I’ve really wanted to jump into this and have been enjoying uh thinking about it and putting it together.

uh no absolutely and I think uh you know just adding on a little bit there so so… our take also; and what we have seen across the spectrum, Marty… is uh there are so many moving parts in this industry right so which is what sets it apart a little bit ,makes it a little bit more complex, and it’s in the limelight right now amongst all of these moving parts, and which is why need for strong leadership is probably higher … ;because things are still yet to be set there are a lot of fluidity in the industry on how do you approach things ,what is the best way to do it there are multiple you know- things to handle together which means you need strong leadership and and… ;if that falters the whole thing crumbles underneath so you may have the best technology, you may have the best processes, without the leadership it doesn’t bind together so our interest obviously although we are a technology-first firm ;but we are also a customer success customer centric organization ourselves ….and and we appreciate and see this day today.

So let me also ask you this specific to the leadership challenge right uh who do you you know …. think the leader actually serves?; and what are the constituents the leader serves?; and hopefully I’m queuing this up to allow you to also uh you know talk a little bit more about what the idea is on those specific workshops which you are intending to conduct.

Yeah, you cheated up well but I… I would also um there may be people listening who wonder why the question even has to be asked it’s obvious we serve the customer … that’s the whole purpose of the job we serve the customer more so than anybody else in the organization. It’s all about the customer and that’s our role um and if that’s your take you maybe end up being an excellent …excellent manager of a customer success function, but you’re probably not going to be an effective leader for your organization and in that way also for your customers and…….. for your team and so the direct answer to your question … I see I see three main audiences that uh a customer success leader really serves and has to be ready to deliver for. … uh..

The first is your organization or your company and yes that’s obvious but that is separate from needing to serve the customers of your company… so that’s the second audience you’ve got your company your customers and finally your team even if you start off as a team of one this idea that there is a function or an entity that’s purpose is customer success um that creates a third separate audience and each of those are going to have different demands, different questions they want answered um some stated some unstated; and so I that’s why I think it’s and you said this as well in teaming it up that’s part of the unique challenge is that uh… each of those is very unique but in the day-to-day, the leaders are dealing with all three of those simultaneously; and they are not asking the same things; and they are not all aligned and so getting clarity around that is a pretty key leadership skill and one that is it’s learnable as long as we’re focusing on it. And so um and I think that’s also another reason why I was um I’ve enjoyed our conversations about this the… folks that you all deal with the CEOs and the leaders of success and other client customer-facing functions- do you also notice that there’s I guess that the context matters right that it’s there’s a need for something that is unique for them just above and beyond…


Wherever their starting point was.

Yeah, 100 actually more than 100 percent and…. yeah it and it and it’s it’s….. also an opportunity I mean it’s a challenge uh for sure for leadership and customer success today.

Uh just by the burden of the expectation which is coming from the role from the CEO from the board uh and also like you mentioned from the team themselves. Just to give you an example, you know if I were to compare this to sales, and you are a sales leader now, it’s an evolved industry. You are hiring from the market, you are getting salespeople in some shape or form who understand fundamentals of selling, at least they may have to adjust to your style of selling; but it’s still an established function so when you look at just the team management aspects of this from a leadership standpoint, it’s still comparatively much more structured.

Now you compare that to customer success, you may get people from support, you may get from account management, from client services, from delivery, from product management, from sales, from pre-sales, and we have seen the entire spectrum now being part of your team.

Now your job as a leader suddenly is much more amplified; and you know the expectation is much more , so that’s the challenge I think why this becomes very important uh to address uh, Marty.

Yeah, now I like the point too that many people who are currently leading or are about to lead a customer success function, they’ve come from somewhere else they are experienced or tenured leaders in their own right. If this is not a job of untraining and retraining into something wholly new, but it’s a wonderful challenge of taking what they already know and layering in the context. So that they can take advantage of the great leadership skills they already have, and then build on that so that they’re able to serve these three audiences successfully.

Many of them can do one or two like I’ve worked with leaders who are fantastic in developing their teams, and you know career development, and or fantastic at managing upward through the executive team to get what they need and marshal the resources to uh to be successful and advocate for their function; but to have all three to have that and the client-facing piece where they are serving the paying customer….um.. on behalf of your entire organization and being accountable for that that the third piece is often unique and that’s why we want to want to think about all of them… um.. I don’t say it together all three are important, but they kind of need to be treated separately because those audiences are not again they don’t have the same demands of you as a leader so..

Yeah, well then, I agree again completely with you uh ,and like we discussed uh you know you said the three constituents obviously the paying customer uh right in the center, and then your organization’s interest, and then your team’s interest, and I know you and I discussed this and you know I’d recommend adding your self-interest as well.


Because that’s a significant component of this equation uh the skeleton in the closet is that it’s a 12 to 18 month you know lifespan in that role the industry is seeing right now, and it is because of all of these challenges which we mentioned that do you… know handle the complexities of handling a team which is so diverse as well as balancing out organizational expectations around retention, and then expansion, and growth, plus the customer challenges of you know adhering to their requirements needs creating value, showcasing value, and you know we can talk more and more around it; uh…. so you have to show value in your role as well which is a significant I think fundamental need for you to feel comfortable enough to able to do justice to the other three right so if that makes sense, Marty.

Well yeah, and being able to identify leaders who know why they do what they do, and why it matters to them, their passion, why they’re passionate about not just being a leader, but leading in this context for these customers on behalf of this organization that’s a powerful person like that, so your recommendation to add that sort of the fourth audience of yourself it really does tie those others together … um … so it’s a an excellent addition and one that is really central to almost all leadership development is you know understanding yourself as a leader, but even with customer success like…. that… asking yourself that question is … um is also unique like what is it about leading a customer success function that is so energizing, entertaining, or interesting to you or not, you know it may be that your leadership path is towards something that is uh um you know more focused towards where your preferences and needs are than uh than the current challenges of leading a customer success function.

Yeah no absolutely…. now uh.. so so you know you and I have chatted a little bit around this so I have some color; but for the rest may be good to also understand, what is it that you know you intend to recommend in it as part of this approach of participating in, and creating a sort of invitation-only work set of series of workshops with some select customer success leaders. How do you envision this you know playing out?

Um yeah, I guess I didn’t come right out and say like and this is what we want to do, so just uh to be clear I think there’s a there’s an opportunity here that I’m not going to individually fill but I want to help marshal the resources towards creating really high quality relevant leadership development …for for customer success folks, for customer success leaders, and one of the channels for that is um uh you know invitation only, again the reason for invitation only is to make sure that it’s the right cohort of people we can learn from each other uh that you know ..it it enhances the experience when we’re able to make sure that all the folks in the the room either virtually or or in real life are uh kind of rowing in the same direction, interested in in this topic in a similar way, um but but also being able to pull together the materials, the resources, the conversations that elevate the discussion of what it means to be a leader in the customer success context, and so as next steps will be interfacing with you know other consultants, practitioners, people who do just leadership development …and and pulling together a um I guess you can call it for some a curriculum, and for others a resource to to be able to elevate their practice of leadership in this context.

And one of the approaches that I found really powerful that applies that layers onto, this in a really nice way is uh kind of a question-based approach to learning, and so instead of just putting topics out there uh really thinking about this as what are the key questions that a customer success leader has to either answer for their company, or the for the customer, and for their own team, and of course for themselves, and using that question format allows each of us to take a slightly different take on it.
So that might be able to customize if you know the questions that are coming at you, and not the tactical questions the real big strategic – what is the value of this function; why should we invest in it your company; may be asking you… your clients may be asking how do I know if I’m on track with what I’m supposed to be doing; that is a big question not a technical how-to and so being able to put this in a question context allows us to what we’re then teaching or learning together is how to answer those questions it makes it immediately applicable… back on the job uh makes the training transfer more easily, so it’s relevant, and and really puts some power behind the practice of leadership for customer success folks. So really excited about this next phase of you know pulling in more people as contributors, as learners in the cohort ,and uh and really dig in and see where we can take it.

No excellent, I think and… you know I’m glad you brought up the uh the questions part of it, Marty because that’s what attracted me and Smart Karrot to this initiative because you know, we as a technology platform deal with a lot of data, and you know we are seeing this trend of the data being now mined and queried, and intelligence sought from the data specifically to answer those questions, and if you tie it back to where is this coming from it actually comes from either the board asking a question, and then you go hunting – where is this I want the slice dice; I want to see a correlation between the number of touchpoints to whether your retention has happened or not ; so we see a lot of these asks out of the platform uh which we are able to address, and these are where it’s really a question-based system the same question applies also to your team performance; so you know is your team performing today?; where are they with their numbers?; What are their KPIs?; How are you tracking it?; Are you tracking their tasks? .. all of these have got a question mark at the end and they seek answers from the data in the system where we are aspiring to be as a technology solution to this industry is to sort of also over time start pre-empting those questions. Saying you know to your point the leadership, you know sort of guidance and coaching leads them to be asking the right questions across this entire spectrum in the hierarchy, but a lot of them may not you know so a solution should augment the leadership and really help them.

Also pre-empt some of these questions we know, you will be asked this so this is there no this is going to be required in this role, so this is there if you don’t ask for it you will never get it. With Smart Karrot, you have a better chance probably we will you know pull you or push you enough towards it so that’s our aspiration and that’s what interests me personally to also participate and learn from the cohort which you mentioned, uh you know what are these questions, because that’s our future.

Well I like the way you set that up, and I’ll um just to sort of further promote the idea that is part of what uh um why I’m excited to partner with you on this is the…Smart Karrot is not about the data right, it’s about the insights, and this whole concept of well the answer getting from a question to then data, intel, insights that you can actually take action on, um you’re aiming up here for the action and working backwards from it instead of starting from this enormous pool of data, and just wondering, what can be answered from the data um that’s always an interesting exercise, but it’s not the highest value activity.

And so I really appreciate how you all frame it of you know aiming for to provide leaders the insights they need to to do what they need to do, well that’s why I think we’re really aligned on this, and again there’s a readiness component that ….the the field of customer success is is now ready with both the intellectual readiness of people who have been in the job long enough, and know what they need, and uh and what it takes to be successful, but also having the tools behind it to make them really effective as leaders, and not just you know data analysts who happen to be leading a success function being able to give them real insights to answer these key strategic questions for their company, for their customers, for their teams, and ultimately themselves as well.

Absolutely no that’s a wonderful summary, Marty. And I think you know we have laid enough on the table hopefully to… you know let all the viewers who will eventually see this get a sense of what we are attempting, so we solicit you know feedback around this, you know what do you feel ,how do you think we should approach this uh we will reach out to a few of you who we know, and have a relationship with obviously one on one for the rest please feel free to reach out to either Marty or me…. uh we want to build the relationship with more of you as well and… truly try and help each other out as we you know navigate this very interesting, but uh admittedly complex problem the industry faces right now uh, Marty; anything else from you? uh Thank you so much for taking time out.

Yeah, no like I said it’s a .. it’s a passion area of mine that brings together several things that I’ve worked with throughout my career, and I look forward to this co-creation process both with you and the folks that hopefully reach out to you, and I to help craft it and then and then to be a part of it, but really looking forward to both the process and the product that comes out the other end.

Absolutely same here so yeah thank you so much and we’ll see you soon

now thank you Prithwi. Good luck; talk to you soon.

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Our Guests

Marty Kaufman

Marty Kaufman is the founder of Infinipoint - the customer retention consultancy. The common thread through his diverse background is helping organizations grow profitably by approaching customer success and retention as enterprise-wide goals and not merely team-based tasks. Marty has led, and advised leaders, in start-up organizations, Fortune 100 companies, and complex government agencies.

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Prithwi Dasgupta

Co-founder, SmartKarrot

Join Prithwi Dasgupta in his pursuit of Customer Success for All as he tracks the paths of trailblazers and unlocks founder insights. The Customer Success Intelligence Podcast is meant to spark conversation and ignite the CS community.

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