"What does great customer success actually look like at year two of an enterprise SaaS contract?"

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is what year two actually means for the relationship dynamic. Year one, there's energy — implementation, onboarding, early wins, everyone's paying attention. By year two, you're either embedded or you're furniture. And the risk is you become furniture without realizing it until renewal is three months out and your champion has gone quiet. For us specifically, I'm wrestling with how to keep health scores from becoming a lagging indicator. By the time a score drops, you've often already lost ground with the economic buyer. So I'm thinking a lot about what the leading signals are at that 12-to-18 month mark — are they expanding use cases, are they bringing in new stakeholders, are they showing up to QBRs with their own agenda versus just listening to ours. The other piece is champion stability. People move. Titles change. A customer can look perfectly healthy on paper and then their internal advocate takes a new role and suddenly you're starting from scratch on the relationship side. I don't have a clean answer for how to build redundancy there — it's something we're actively working through.

What's the most important thing you need to understand or solve here?

For us, it really comes down to whether year two is actually going well or just *looks* like it's going well on the surface. A customer can be quiet, not submitting tickets, not complaining — and you think you're fine. But their internal champion has changed, adoption has plateaued, and they're quietly evaluating alternatives. The thing I'm always trying to solve is: do we have leading indicators that are honest enough to tell us that story before it shows up as a churn conversation? Health scores are useful but they're only as good as the signals you put into them.

What does 'good' look like to you — and how far are you from that today?

For us, "good" at year two means the customer has moved past the initial use case they bought for and is actively expanding — either more seats, more modules, or they're starting to pull in adjacent teams. Health score is green across the three or four indicators I actually trust: product engagement, support ticket cadence, and whether we have a real champion who's still in the building. How far are we from that? It depends on the segment. Our stronger accounts at year two look pretty close to that picture. Where we fall short is the middle tier — accounts that renewed kind of quietly, without a lot of friction but also without a lot of momentum. They're not churning, but they're not growing either, and that's its own kind of problem because a single personnel change or a competitor conversation can tip them. The thing I'm honestly working on right now is making sure we have enough multi-threading in those accounts — not just one contact who likes us, but actual organizational stickiness. That's probably where the gap is most visible.

What would change your perspective on this entirely?

That's a fair question. I think if I saw consistent evidence that customers who had low health scores in year two still renewed at high rates because of factors we weren't tracking — relationship depth, organizational politics, budget inertia — I'd have to rethink how much I weight the quantitative signals. We put a lot of stock in product usage and engagement data, and if those turned out to be less predictive than we believe, that would change how I structure my team's priorities pretty significantly. The other thing would be if we found that our QBR cadence was actually creating noise rather than value for certain customer segments — that the ceremony of it was substituting for real relationship building. I don't have strong evidence of that right now, but it's something I think about.

What question are you not being asked that you wish someone would ask?

That's a fair question. The one I keep waiting for someone to ask is: "What does your CSM actually own at month 18 versus month 6?" Because the job description doesn't change, but the work completely does — and most organizations never formally acknowledge that shift or build for it. By month 18, your champion has probably changed roles or turned over, the original use case is either embedded or stalled, and you're essentially re-selling the value of the product to a new set of stakeholders. That's a fundamentally different motion than onboarding. If your CSMs are still running the same playbook they used in the first 90 days, you're going to feel it in your renewal numbers.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is whether our CS team is actually proactive or just reactive with a nicer dashboard. We're 22 months into a pretty significant platform contract, and I feel like the relationship has settled into a rhythm that looks healthy on the surface — QBRs happen, someone sends a usage report — but I'm not sure we're getting genuine strategic input anymore. The board pressure piece matters here too. I'm being asked to show that our martech investments are compounding, not just running. And when I look at what our vendor's CS function is actually contributing to that story, I'm not sure I can point to much beyond "they kept the lights on." That's not nothing, but it's not what I signed up for at renewal. So the real question I'm sitting with is: at year two, should the CS relationship look fundamentally different than it did at month six? Because right now it mostly doesn't, and I'm not sure if that's on us or on them.

What's the most important thing you need to understand or solve here?

The core question for me is whether the vendor is still actively invested in our success at year two, or whether we've quietly moved to the back of the line now that the contract is signed and the implementation high has worn off. Year one tends to have a lot of hand-holding and attention. Year two is where you really see the true nature of the relationship — are they proactively bringing us insights, or are we the ones always initiating? That's the tell. From a CMO standpoint, I'm also watching how our customer success metrics translate into something the board actually cares about — retention health, NPS trajectory, whether we can credibly turn this vendor relationship into a case study or reference. Those things compound over time, but they only happen if the partnership stays active.

What does 'good' look like to you — and how far are you from that today?

For us, "good" at year two means the vendor has essentially become part of our operating rhythm — they're not waiting for our QBR to flag a problem, they're surfacing things before we have to ask. And on the marketing side specifically, that means they're helping us build the case internally, not just delivering dashboards I have to translate for the board. How far are we from that? It depends on the vendor. We have one relationship that's actually close to that standard — the CSM understands our NPS goals, they know our renewal cycle, they flag usage gaps proactively. But that's more the exception than the rule. The more common pattern is that year two feels like a slower version of year one — same onboarding energy is gone, and what replaces it is just... account maintenance. The board pressure piece matters here too. When I'm being asked to justify every platform spend against pipeline or retention outcomes, I need my vendors to help me make that argument — not leave me to construct it myself from raw data. That's probably the biggest gap right now.

What would change your perspective on this entirely?

That's a fair question. I think if I saw a vendor genuinely treat year two as the starting point for innovation rather than the maintenance phase — meaning they're bringing us net-new capability, not just keeping the lights on — that would shift how I think about the whole relationship. Right now most of what I experience at the two-year mark is a lot of renewal conversation and not enough "here's what we're building with you next." The other thing that would change my view is seeing CS teams actually connected to business outcomes in a way I can report upward. If a CSM walked into a QBR with something I could put in front of my board — not just usage metrics, but something tied to retention lift or revenue influence — that would change how I resource and prioritize those relationships on our end too.

What question are you not being asked that you wish someone would ask?

That's a fair question. The one I'd push back and raise myself is around *who actually owns the customer relationship* at year two — and I don't mean contractually, I mean day-to-day. Because from where I sit, there's often real ambiguity between customer success and account management on the vendor side, and that plays out in ways that affect whether we renew or not. By year two we've usually burned through the enthusiasm of the initial implementation, the executive sponsor on their side has moved on to something else, and we're left interfacing with a more junior CS person who's juggling thirty other accounts. Nobody really asks whether that transition was designed intentionally or just happened by default. And for me, that's where a lot of value either compounds or quietly erodes.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now we're actually heading into year two with a couple of our larger SaaS vendors, and the question I keep coming back to is whether we're getting what we paid for — not just in terms of features being live, but in terms of measurable impact on our operations. Year one is mostly implementation noise. You're standing things up, training people, working through integration issues. By year two, I expect the vendor to be proactive about showing me we made the right call. What I'm finding is that some of them go quiet — the sales energy disappears and the customer success contact is mostly reactive. For a manufacturing environment like ours, headcount efficiency is a big part of the ROI story. If I can't point to something concrete when the renewal conversation comes around — reduced manual effort, better throughput on a process, something I can benchmark — that contract is going to get scrutinized hard. So what I'm wrestling with is really: whose job is it to build that case, mine or theirs?

What's the most important thing you need to understand or solve here?

The renewal conversation. By year two, we're past the honeymoon period — the implementation dust has settled, the internal champion who pushed for the tool has either proven it out or moved on to something else, and I need to know whether this thing is actually moving the needle on the metrics we cared about when we signed. For me specifically, that comes down to headcount and throughput. Did we reduce labor in the workflows this was supposed to touch, or did we just add a new tool on top of existing headcount? If I can't get a clear before-and-after on that, the renewal conversation gets harder.

What does 'good' look like to you — and how far are you from that today?

For us, "good" at year two means the vendor basically disappears from my calendar in a good way — the tool is embedded, the team isn't calling me with problems, and we can point to something measurable that justifies the spend. Not a dashboard full of activity metrics, but actual before-and-after on a specific workflow or headcount decision. Where we are today is somewhere in the middle. The platform we're on is functional, adoption is reasonable, but the CS team still shows up to QBRs with utilization stats rather than anything tied to our cost structure or output. I keep waiting for someone to walk in and say "here's what this is worth to you in your environment" — and that hasn't really happened yet.

What would change your perspective on this entirely?

That's a fair question. If a vendor could show me clean before-and-after data — headcount held flat while throughput went up, or a measurable reduction in process exceptions — that would move me. Not a case study written by their marketing team, but something a peer CFO at a comparable manufacturer actually signed off on. The other thing that would shift me is if the customer success motion stopped feeling like relationship management and started looking like operational accountability. Right now most of what I see from vendors at year two is check-in calls and QBRs that recap usage stats I already have. If someone came in and said "here's where you're leaving value on the table and here's the remediation plan with a timeline," that's a different conversation entirely.

What question are you not being asked that you wish someone would ask?

That's a fair question. I'd probably want someone to ask how we evaluate whether the vendor's customer success team actually understands our business at year two versus year one. In year one there's a lot of hand-holding and onboarding energy. By year two I want to know if the CSM can walk into a conversation with me and talk about our specific manufacturing environment, our headcount constraints, where we're trying to take costs out. If they're still giving me generic best-practice decks, that's a signal. We're not a SaaS company, we're a manufacturer in Detroit. The CSM who figures that out and adjusts is worth renewing with. The one who hasn't figured it out by month eighteen is a problem I start factoring into the renewal conversation.

Tell me what's top of mind for you on this topic right now — what are you wrestling with?

Right now the thing I keep coming back to is: who actually owns the customer relationship at year two? Because in year one, sales is still close — you closed the deal, you're doing handoffs, there's energy around it. By year two, it's fully in CS's hands, and the quality of that experience is really uneven. What I'm wrestling with is that the CS team's incentives don't always line up with mine. I'm measured on net new and expansion, and if a customer is just... quietly plateauing — not churning, not growing — that's not a win for me. But CS might consider that account healthy. So there's this gap where accounts sit in a gray zone and nobody's really pushing them forward. The other piece is that year two is when you start seeing whether the promises made during the sale actually held up. And when they don't, that's when renewal conversations get hard and expansion is off the table entirely. I don't have a clean answer for how we bridge that right now.

What's the most important thing you need to understand or solve here?

For us, year two is really the proving ground. The honeymoon is over — the customer has lived with the product through real workflows, real edge cases, and real organizational change. What I need to understand is whether the CS team is actually staying close to the right stakeholders, because the economic buyer who signed the deal is often not the same person using the product day-to-day. If CS is only talking to the champion and the champion leaves, we're exposed at renewal. The other piece, honestly, is whether the value story is getting built out in a way I can actually use. Case studies, peer-validated ROI — that stuff matters enormously when I'm trying to expand the footprint or protect the contract in a competitive situation. Year two is when you should have enough data to tell that story convincingly.

What does 'good' look like to you — and how far are you from that today?

For us, "good" at year two means the customer is already talking to someone else in their network about us. They've hit the outcomes we sold them on, their power users are active, and when renewal comes up it's not a negotiation — it's a formality. Ideally they're generating case studies or willing to be a reference, because that kind of peer validation moves deals faster than anything my team can put in front of a prospect. How far are we from that? Closer on some accounts than others. The ones where our CS team stayed tight through implementation tend to hit that mark. The ones where there was a lot of handoff noise in month three or four — those are still catching up. I'd say we're getting there on maybe 60% of our book, which isn't bad, but it's not where I want it.

What would change your perspective on this entirely?

That's a good question. Probably if I saw a CS team actually drive a meaningful expansion without sales being involved at all — like, they sourced it, they closed it, they owned the whole motion. That would shift how I think about where CS sits in the revenue org. Right now my instinct is that CS is a retention and reference function, and the real growth at year two still runs through my team. But if the data started showing that accounts with heavy CS engagement were expanding faster than the ones my reps were actively working, I'd have to rethink how we're dividing the coverage model.

What question are you not being asked that you wish someone would ask?

The expansion motion at year two. Everyone asks about retention and health scores, but nobody asks how CS and sales are actually coordinating on upsell at that point in the contract. In my experience, that handoff is where a lot of revenue gets left on the table — CS either doesn't flag the opportunity early enough, or they flag it and there's no clear owner. I'd love to see more research on what that coordination actually looks like in practice at different company sizes.