In this webinar, Irina Cismas, CMO of Custify sat down with Clare Knight from the Onboarding Lab and Jamie Moquin, Partner Success at Stellic, to discuss a critical question: when should Customer Success remain free, and when should services come with a price tag?
Summary Points
In this session, we explored how CS teams can balance free vs. paid services, set boundaries with Sales, and package value in a way that earns buy-in from both customers and leadership.
Key takeaways include:
- Define what belongs in CS vs. Professional Services to avoid scope creep.
- Charge for onboarding when it accelerates time-to-value or requires significant resources.
- Align with Sales to set clear expectations and avoid giving CS away for free.
- Use re-onboarding, consulting, training, and integrations as legitimate paid add-ons.
- Prove ROI with time and cost data; start simple and iterate.
- Keep frontline support, community, and evergreen education free.
Podcast transcript
Intro
Irina 0:01
Hello everyone, welcome. I’m Irina Cismas, Head of Marketing at Custify and I’ll be your host today. I’m super happy to see so many of you joining live for this session, and I will tell you what sparked this webinar.
Years ago I pitched an idea. I really believed it. I shared it with the team, brought it to leadership, only to get a polite no. Three months later a consultant pitched the same exact thing, but this time it was instantly approved.
Why? Because someone paid extra for that particular idea, and that stuck with me. In CS we give away so much value.
Ads, onboarding, QBR, strategic consulting, and it’s all bundled as support, but the moment there’s a price tag associated to it, the same work is taken more seriously. So today we are asking where do we draw the line between what’s free and what’s paid in customer success.
When does free become too expensive for us and for the customer?
And to help me unpack this, I’ve invited two brilliant customer success leaders. I’m talking with Clare Knight from the Onboarding Lab, who has worked with tons of teams on building high-impact onboarding that actually drives adoption, and on the other side is Jamie Moquin, Partner Success at Stellic, who has navigated the exact tension across CS, professional services, and strategic accounts. Jamie, Clare, thanks for joining me today.
Thank you. Thank you. A few housekeeping rules before we get started.
This session is being recorded, so you’ll get a replay, and if you have questions, drop them in the chat and we’ll try to take some as we go or during the Q&A at the end. And now, before we dive in, I want to get a quick buzz from everyone who is joining us live. I’m going to publish a poll. Give me one second.
Do you see it? Okay, so the poll is: does your CS offering include paid services or not? It’s basically yes or no, and for those of you who are voting yes, I’m curious about the distribution of the services that you have included.
We’ll give it a few moments so that everyone has a chance to participate. Also, for those who joined late, we want to see if your CS offering includes paid services or not, and if you could, drop them in the chat. While you are voting, I want to start the conversation and ask you, Jamie, why do you think so many companies default to giving CS away for free?
Where to Draw the Line: CS vs. Professional Services
Jaime 3:30
I think it’s driven by not spending the time to define, as an organization, what you want to support your customers in. Especially in the startup world or smaller organizations, CS usually comes later. It’s the last thing to be resourced.
It’s one of those “oh yeah, we have to do it,” and we don’t really know what we want it to be or how it aligns with who we serve. It’s an afterthought. Once they start, it gets difficult to get out of that. They haven’t defined it up front after implementation and onboarding.
What does that experience look like post-sale?
Irina 4:15
It seems like the distribution is about 50/50. For the ones who said yes, we do have paid services, contribute in the chat and let us know which those are. Clare, have you ever delivered high-value work but, because it was free, it didn’t land the way it should?
Clare 4:45
Yes. I’ve worked in a few different sizes of companies and a few different types of products, and it varies depending on whether it’s B2C or B2B, startup or enterprise, and whether it’s a complex product or not. It really depends on the type of user you have and what value they put on your time or the resource you’re providing.
I often find that if it’s a simpler product, a lot of people think, “I can just do this myself. Why pay for something extra?” even if you’ve validated the value you would provide or justified the cost. People assume, “I can charge for everything; it’s fine,” but you have to take some of these things into account. If it’s a simple product, they probably just want to get going with it and start using it. They don’t want to give you an hour of their time for a call, which is how we often justify charging. There are pros and cons, and you have to think through it strategically to make it worthwhile.
Irina 6:04
I want to break this down and see what should always be free and what makes sense to charge for. I want to look from the customer perspective and from the company perspective. Since you have worked with different types of organizations, Clare, I want you to represent the customer voice. Which services do customers usually expect for free, and which do they expect to pay for when it comes to customer success? Let’s give examples: a B2B startup or a more mature B2C company.
Clare 7:15
Say you have a B2B product that is somewhat complex and needs a little hand-holding. In that scenario, it’s accepted and expected that someone will guide you through onboarding. You appreciate having support that is not just a support team; it is dedicated partnership. In that scenario, I’ve never seen pushback on a charge for onboarding, because the value is there. They want the time, interaction, and assistance. They want someone they can call directly and not have to go through a support team that they have never spoken to, where they have to find their ticket. They want someone they can call who knows the whole scenario, the history of the sales cycle, everything. There is a lot of value in that.
Pricing and Packaging Onboarding
Irina 8:11
You mentioned a complex product. How do you define “complex”? What falls into that?
Clare 8:34
In my experience, it’s something you can’t just log in to, make your own account, and start using. There are integrations that need to happen. You may have to onboard multiple users. There may be different permissions for different users. The list could go on, but I see it as something more involved than someone being able to sign up and start using a product.
Irina 9:06
For B2C products, are they used to paying for onboarding?
Clare 9:17
In my experience, no, and I think you would get a negative reaction. People signing up for B2C products are usually one person using their own money or a minimal budget from a manager. If you add an onboarding fee on top of that for a self-serve B2C product, it probably will not go down well. Often you do not have a direct link with an onboarding manager or a CSM in those scenarios, so there is a question about what this fee is. There are a lot of potential roadblocks and moments to annoy people, if I can use that.
Irina 10:15
Can you tie ARR to paid services? The higher the ARR, the more complex the product, so you need an onboarding fee or extra paid services in CS?
Clare 10:44
As a blanket rule, it is tricky, but if you have a higher average contract value, people paying that much will accept and probably expect a reasonable onboarding fee. It is not a recurring fee, whereas the contract will be, and in my experience high-value customers are not negative about onboarding fees.
Irina 11:19
From an organizational point of view, when companies formalize paid CS services, how do they decide what stays in customer success versus what gets built separately, Jamie?
Jaime 11:40
I’ll be honest, it’s not easy and there is some trial and error. I’ve been in models where you pay for a level of CS, and models where there is a base that everybody gets and certain things we charge for. The most important thing is to define your core values, who you are serving, and know your audience.
I have spent 20-plus years in the ed tech space, working with colleges, universities, K–12 school districts, and nonprofits, so understanding who they are and what they typically pay for matters. That is different from a B2B security company or a Fortune 500. You have to know their tolerance and what is expected in that marketplace, then define what is most important to you as an organization.
For retention, we looked at churn risks and decided what we must do to mitigate them, and we would do those for free, such as quarterly or monthly check-ins, tiered by account type. Thinking in services with a clear beginning and end helps, like onboarding. I would also argue that if they have some money in the game for onboarding, they tend to be more engaged.
Charging for things that move them along faster or provide value they cannot reach themselves can propel adoption. Many have infinite demands and finite resources. If we charge for something, we can help them adopt more quickly. Know who you are serving and what you must do to retain them. The rest you can decide to charge for or not.
Irina 14:37
We have some questions. Clare, how do you price onboarding depending on complexity, number of days versus a fixed package, and how do you manage if the onboarding cost gets high compared to the subscription? Jamie, feel free to contribute as well.
Clare 15:19
I’m trying not to say “it depends” to everyone, but when I started to figure out these packages, I took into consideration how much time, effort, and resources are spent on onboarding. “Complexity” is broad. It can mean getting your dev department involved for an integration, or custom work. Those things, as Jamie was alluding to, you should charge for. Anything custom should be chargeable.
I like tiers of onboarding to cater for fluctuations. If something is becoming more work than normal, you can say it fits in a higher tier rather than the standard tier. In terms of number of days and whether it is a fixed package, it depends how long your onboarding is. Sorry, I said it depends. Onboarding length varies. I have worked in companies where onboarding was a month, and in companies where it has been three months. You would not charge per day for something that is three months, because that gets out of hand.
You have to weigh the workload and any custom work. You do not want onboarding to be more than the contract value, because it is very hard to convince the customer it is worth it unless you are doing something amazing, which you might be, but you still need to weigh it up.
I know this is hard to answer without context. I would say have tiers, have variation, allow yourself to adjust. It does not have to remain the same for every customer. Customers do not need to know how much other people are being charged. I would not vary it too much, but it should be relevant to the workload.
Jaime 17:46
I would add, do not over-engineer it. You can make it so complicated that it gets hard for the sales team to sell or price, and it gets complicated internally. Do a quick analysis of what you have done. Sometimes you will be under, sometimes over, and then adjust yearly or quarterly.
Depending on the sales process, the sales team will take one stab at scoping after listening to the customer, and we have all heard, “this will be an easy one.” Any time I hear that, I think, “oh no.” Get in front of the customer, or give Sales discovery questions that only Implementation really knows how to interpret, to get a deeper analysis. Your Implementation and Onboarding team knows the signals Sales might miss. Get CS engaged in the process, or provide Sales the right questions.
Clare 19:16
I am a big advocate for bringing onboarding representation into the end of the sales cycle to support that conversation and ensure the right information is there to price properly. I liken it to Apple Stores with Apple Geniuses as trusted experts. Bringing the onboarding representative into late-stage sales helps customers understand what they are paying for and sets the tone.
Irina 20:11
It sounds like both of you answered who decides if something should be chargeable. It should be a collaboration between Sales and CS. CS should assess onboarding time and what it means for a customer to be successful. Since it depends on the type of customer, pricing should also be flexible. We have another question. Michelle says their Sales team often offers CS time and services for free, leading to seemingly unlimited customer support. How do we reframe CS time? Where should we expect to charge for training or client support?
When Sales “Gives Away” CS Time
Jaime 21:38
There is no universal right or wrong. Some organizations decide to never charge because that is right for them, but you still have to be aware of where you spend your time. It is easy to get pulled into things that do not drive retention or expansion.
Leaders and ICs in CS should know what Sales is saying. If you are new, ask to watch a Sales demo. That step is often overlooked. Then give Sales precise positioning for onboarding and services. Customers hear what they want. Do not rely on “the customer said everything is included.” Go back to what was said and where expectations were set.
Have a clear, open dialogue. I have had strong relationships with Sales leaders by bringing them context: “the way this is phrased creates an expectation.” Once you show consequences, they adjust. Be specific with words. “Support” means access to our in-product support team, user community, and so on. You can always give more, but it is hard to take away. Make sure you are feeding Sales clear definitions. Avoid the “Sales did it again” tension. Be the leader and frame it as helping them turn wins into referenceable customers so they can expand the business. That is a win-win.
Irina 25:18
Another question: we are a small company and have an onboarding package. After onboarding is complete, the trained champion leaves. CS has to retrain or leave the client in jeopardy. Do you charge for that?
Champion Turnover & Re-Onboarding
Clare 26:02
We did this in a company where it was happening regularly and it impacted customer success every time. We created re-onboarding packages. It was a sped-up version of onboarding. We did not put them through the whole thing again, but the new champions were new to it, so we charged for it. We presented it as something they needed. Sometimes there was minimal handover, but our platform was a small part of the job, so they still needed support. We never had pushback on charging.
Timing matters. If the customer is healthy and successful, they want to maintain that level. If a customer is not using the product or is starting to churn, asking for paid training then might have a different result. Keep track of your champions. Have a close enough relationship that you do not find out a month after they have left. I know that is not always easy, depending on how many customers you have and how everything works, but it is important because it is a churn indicator if you start to lose champions.
Irina 28:25
Jamie, the next question is from Benjamin. He is interested in language: onboarding, training, consultancy, support. What do clients value most? Sectors are different. What do you see most in ed tech?
Jaime 28:56
The most confusing one is mixing implementation or onboarding with training. They are different. Onboarding or implementation is setup: getting things ready to go, optimizing the system for business needs and use cases. That is onboarding, and it typically has a finite date. Training never ends if you want customers to continue using your product. Re-engagement and turnover mean ongoing training.
In CS and tech, avoid certain words. You would not say to a customer, “I am coming in to do a QBR.” You talk about value and outcomes. If you move into ed tech, learn the vocabulary. Academic institutions do not go by quarters. They have different calendars. Translate terms. Implementation can feel never-ending in some sectors, so “onboarding” can create a cleaner transition to monthly trainings and the user community.
Define your terms and know your audience. The fastest way people trip up moving into ed tech is not knowing the vocabulary. There are resources like The Chronicle of Higher Education. Internationally, principles still translate. Use their language or they will not listen.
Irina 32:05
How do we present paid services so they feel like added value, not a cost? Should they be presented as a package in Sales, along the way, or split with Sales communicating the price and CS providing the value? If it depends, give some examples.
Packaging & Selling Paid Services
Clare 33:22
A big learning for me was building the internal relationship with Sales and Marketing. You have to give them specific context. Explain what is in it for the customer and for the salesperson, such as commission. You cannot just create something and say, “go sell that,” because they will not. I also had to stop Sales from discounting services or waiving the onboarding fee to close deals. That undervalues what we do.
There is a psychological principle called the endowment effect, which suggests that if something has a price attached, people are more invested in it. If someone discounts it without our input, we know they will not be as invested. Make it easy for the Sales team to know what they can and cannot do, what they should and should not say, and what the packages are.
In my experience, building a world-class onboarding experience starts with Marketing and Sales. You do not want a full sales cycle and then, at the end, the salesperson says, “and then you are going to be onboarded, and it is going to cost this much.” That does nothing for building trust or excitement. The relationship piece is key.
Jaime 35:33
In the sales process, define what you charge for at the initial sale. You can package an enhanced tier that includes Professional Services hours per year and a PS catalog. Then, as a CSM, you can say, “you already bought this,” which avoids new budget approvals. Maybe it includes passes to your annual conference or an annual on-site.
When introducing a paid service later, I do not call Sales back in. CS has the relationship, and these needs emerge organically. “You cannot move forward because you lack resources. We can set this up or consult one-on-one, and there may be a charge.” If Sales mentioned optional services early, it is not a surprise. Price it with a finite start and end.
We also sold credits or hours. Projects cost credits. Customers received a yearly allotment. As a CSM, that is great: “let’s start this; it will not cost extra. It is in your ARR.” In ed tech, they ask for money once a year. Bundling sets them up for success. Understand your base.
Onboarding Qualified Leads (OQLs)
Clare 39:01
One small addition: onboarding qualified leads. Like CS qualified leads later in the lifecycle, if onboarding is really slick and you have iterated on it, tracking expansion identified during onboarding elevates the team. It is powerful data and highlights value.
Irina 39:47
What is the definition? I know MQL, SQL, and CSQL, but this is the first time I am hearing onboarding qualified lead. Can you expand?
Clare 40:01
We may have made it up in our previous company, but it helped to be measured on. It gave the team something to work toward. They were not necessarily selling. It might be passed to CS or account management, but if they ran a successful onboarding and identified expansion or referrals during onboarding, that increased revenue. We also measured CSAT and an onboarding success score, but we wanted metrics highlighting onboarding’s value. When onboardings were poor, those onboarding qualified leads were not there.
Irina 41:12
If someone wants to start charging for a service tomorrow, where do they begin, Jamie?
Jaime 41:29
Define what you are offering, the value, and the why. If it is a new upsell service, do a teaser. Offer a small snippet to introduce it, then offer it to select customers who might want it or have the funding. Build use cases and testimonials.
Decide if you start with new customers versus current ones. Legacy customers are hardest to transition to paying for services they had before, so you might offer to new customers first. Or have CSMs identify customers who have mentioned wanting it and start the conversation. You may charge a different price for current versus new customers.
Concrete Paid Services to Offer
Irina 43:12
Let’s give concrete examples of paid services for those who do not have them. Onboarding is one. What else? If needed, break onboarding into services too.
Jaime 43:52
Training. Most customers expect some level of free training, like a help center or a monthly webinar, but private, custom, or on-site training is paid. Professional Services or consulting, such as redesigning customer flows or journeys, is paid. Data work is often paid, such as annual maintenance or new integrations.
Clare 44:44
Some of those fit into onboarding as well, like integration setup. Anything that is a “do it for you” service could be offered for a fee so the customer does not have to do it. Re-onboarding, as mentioned, when there is turnover, is valid and can be charged repeatedly if turnover continues. I would not slice onboarding into too many pieces. Create one onboarding package that includes training, education, and assistance with implementation, such as integrations and data transfers. That is the easiest way to communicate it to customers.
Proving ROI for Onboarding
Irina 46:01
You mentioned an onboarding ROI calculator. That helps justify cost or investment. What are the key inputs?
Clare 46:32
It is still being built, but one section is simply charging for onboarding. Many companies do not, and it highlights missed revenue. Another is resource time. There is the onboarding manager, the CSM, Support, Engineering for integrations, and custom building. When you add up the hours and cost, it can add up quickly, and you can end up losing money. It is a hidden cost.
When you calculate this, you see the impact of streamlining, such as the timeline and people involved. It is hard to figure out, which is why I am building the calculator. The goal is to help leaders understand the impact of not investing in or improving onboarding. Individual contributors can talk about it forever, but without leadership buy-in nothing changes. Numbers help win buy-in.
Irina 48:52
Did we lose Jamie? I think we lost internet. She will probably come back. I want to end by asking you: looking back, what is one thing you wish you had done differently when it comes to pricing onboarding?
Clare 49:27
I wish I had done it sooner. I was trying to make it perfect. My advice is to start simple. Do not overcomplicate and try to create the perfect package. Start with an onboarding fee that is simple, easy to implement, and approved internally. Outline the main pieces that come with it and iterate. We were scared to get it wrong, but it does not really matter. The longer you wait, the less reason there is not to do it.
Irina 50:25
Jamie, you are back. We were wrapping up with the question: what is one thing you wish you had done differently when it comes to pricing CS work?
Jaime 50:49
Sorry about that. We have storms rolling through, so I got kicked out. One thing I would do differently is not overcomplicate it. At first, I tried to define every type of service and nail down the price for each. I would put things in buckets instead. Look historically at what caused churn and ask if doing X would have made a difference. Start there, then go from there. You can complicate this extremely.
What Should Remain Free
Irina 51:42
We have talked about what to charge for. What should remain free?
Jaime 52:05
Frontline customer support where a customer can get questions answered or access information. Do not charge for that. I also think user communities should never be charged for. Strong communities help each other and reduce the day-to-day load on CSMs.
Irina 52:44
Clare, what is your take?
Clare 53:02
I agree. I would add any form of education that you have available, whether that is a help center, video content, or other ongoing materials. If a customer is proactively learning, do not charge for that. It is good for adoption.
Irina 53:31
Thank you both. We discussed what should be free, what should be paid, how to communicate it, when to say it, and how to team up with other teams to smoothly set expectations with the customer. Thank you both for taking the time to talk to us today. For those of you thinking about how to scale your CS operations without increasing headcount, by adding the right tools and processes, reach out to us, because Custify can help. As promised at the beginning, we will send the recording shortly, and we hope to see you at the next webinar in the second half of October, but more on that soon. Until next time, stay safe and take care. Thank you!
