"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, everyone's in implementation mode — there's a clear structure, there's momentum, there's novelty. Year two is where you find out if the value is actually sticking or if the customer just hasn't gotten around to churning yet. What I'm wrestling with specifically is how to distinguish between accounts that are quietly disengaged versus accounts that are just stable and low-touch by nature. Our health scores help, but they're lagging indicators a lot of the time. By the time something looks yellow or red, the champion has already mentally moved on. The other piece is the renewal conversation itself. In year two, you're not selling on promise anymore — the customer has real data about what they got from the first contract. So if we didn't build a strong enough story around outcomes in year one, year two renewals get much harder to defend, especially when procurement gets involved and starts asking pointed questions.

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

For us, year two is really the test of whether the initial onboarding promise holds up. The honeymoon period is over — the customer has been through their first renewal, they've seen the product warts and all, and now they're deciding whether this is actually embedded in how they work or just something they're tolerating. The thing I'm most focused on at that stage is whether we have a real champion, someone inside the account who's actively defending the spend internally, not just a user who likes us. If we don't have that by year two, renewal gets uncomfortable fast.

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 adoption and is actually expanding — they've got new use cases, more seats, maybe a second team using the product. And the champion we built the relationship with in year one is now advocating internally without us having to prompt them. How far are we from that? Honestly it varies a lot by segment. Some accounts are exactly there — health scores are solid, QBRs are productive, we're talking about what's next. But there's a meaningful slice where we're still fighting for basic adoption, which at year two feels like we're behind. That's where I lose sleep. If we're heading into renewal conversations and the customer hasn't really embedded the product into their workflow, that's a difficult position to be in. The gap for us right now is probably less about the framework — we know what good looks like — and more about consistency across the book of business. Some CSMs are executing really well, others are still reactive. That variance is what I'm most focused on closing.

What would change your perspective on this entirely?

That's a fair question. I think if we consistently saw accounts that had low health scores at month 18 but still renewed — and renewed at expansion, not just flat — I'd have to rethink how much weight I put on the health score framework heading into year two. Right now I lean heavily on that, so evidence that it's not actually predictive would shake some assumptions. The other thing that would shift me is if I saw peer-validated data showing that QBRs don't actually correlate with retention in mid-market. We treat them as almost non-negotiable, but I don't have strong internal data proving causality versus correlation. If someone showed me rigorous analysis on that, I'd probably restructure how my team spends its time.

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

That's a fair question. I think people focus a lot on renewal rates and expansion ARR, but they don't ask enough about what's actually happening at the individual champion level by year two. By month 18 or 24, your original champion has often moved, gotten promoted, or shifted priorities. The real measure of a mature CS program isn't whether you hit your health score thresholds — it's whether you built enough relationships across the account that you can absorb that kind of change without the renewal being at risk. Multi-threading is something everyone nods at in year one, but by year two you find out whether you actually did it or just had a single great relationship that's now walked out the door. I don't hear researchers or vendors asking "how resilient is your account coverage when your champion leaves?" That feels like a more honest stress test of what good looks like at year two than any dashboard metric I've seen.

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 set up to deliver value at the complexity level our enterprise contracts require in year two, or whether we're essentially running the same playbook we used during onboarding. Year one is very structured — there's implementation, there's training, there's that initial QBR cadence — and then year two can feel like it just... coasts. The pressure I'm feeling from the board is around retention and expansion, and those two things require very different motions from customer success. Retention is about proving the platform is still earning its seat. Expansion is about finding the moments where a customer's business has evolved enough that there's a real upsell conversation. And I'm not convinced we have clear enough triggers for either. The other thing is that I came up through agency work, so I'm probably more attuned than most CMOs to how the vendor relationship can quietly degrade when the novelty wears off. The CSM who was super responsive in month three is now spread across a bigger book of business, response times creep up, and the customer notices — even if they can't articulate it. That's where NPS starts to erode before you ever see it in the renewal pipeline. So that's genuinely what I'm wrestling with right now.

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

For us, the question at year two is really about whether the vendor has grown with us or is still treating us like a new logo. The onboarding honeymoon is over, our internal stakeholders have higher expectations, and the board is asking harder questions about what we're actually getting from this investment. The piece I need solved is proactive engagement — not reactive support. I want my CSM to know our business well enough to flag opportunities or risks before I have to raise them. That's the difference between a partner and a help desk.

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 stopped acting like we're still in implementation mode. They know our business well enough to bring ideas to us — not wait for us to diagnose problems and escalate. The CSM should be proactive, connecting what they're seeing across their customer base to what's relevant for our situation specifically. In terms of where we are today — it's mixed. Some of our SaaS relationships have matured into that kind of partnership. But there are a couple where we're still doing most of the work to drive value realization, which at $240k-plus contracts starts to feel like we bought software and also bought ourselves a part-time job managing the vendor relationship. The other thing I'd add is that "good" for me also means the vendor understands what I'm accountable to. I'm measured on NPS, on pipeline, on brand perception — so when a CSM walks in for a QBR, I want them to have thought about how their platform connects to those outcomes, not just feature adoption rates. That's the gap I see most often.

What would change your perspective on this entirely?

That's a fair question. I think if I saw strong evidence that proactive outreach from a CS team — not reactive ticket-closing, but genuine business reviews that actually connected to my pipeline and brand goals — consistently moved NPS at renewal, I'd weight it differently than I do now. Right now I'm somewhat skeptical that year two CS is anything more than relationship maintenance dressed up as strategy. The other thing that would shift me is seeing CS teams genuinely feed into the marketing motion — customer stories, peer validation, that kind of thing. When CS is just internally focused, it feels like a cost center. If I saw a vendor where the CS function was actively producing the kind of peer-voice proof that actually unsticks deals for me downstream, I'd view that investment very differently.

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

That's a fair question. I think the one that gets skipped is around what happens to the relationship when there's turnover on *our* side — not the vendor's. Everyone asks about CSM churn or vendor responsiveness, but when we've had leadership changes or team restructuring, the continuity of context on our end is just as fragile. A good CS team should have institutional memory that bridges those gaps, but most don't build for it. That's the piece I rarely get asked about directly.

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

Right now we're heading into year three with one of our larger platform vendors, and the honest question I'm sitting with is whether we're getting the same level of attention we got during the sales cycle. Year one had a lot of hand-holding — implementation support, executive check-ins, that kind of thing. Year two felt like it tapered off pretty noticeably. What I'm trying to figure out is whether the value we contracted for is actually being realized, or whether we've just gotten used to the tool and stopped asking hard questions about it. From a finance perspective, I want to see a clear customer success motion that ties back to measurable outcomes — not just usage stats, but actual business impact we can benchmark against what was promised in the contract. The headcount question is also in the background. If the platform is doing what it's supposed to, I'd expect to see some efficiency gains in the teams using it. We haven't had that conversation explicitly with the vendor yet, and that's probably something I need to push on.

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

For us, the core question at year two is whether we're actually getting the value we contracted for — and whether the vendor is being proactive about showing us that, or waiting for us to ask. We have a CS tool we renewed last year. Going into renewal number two, I want to know: what's the ARR impact, what's the headcount story, are we using the seats we're paying for? If the vendor can't walk me into that conversation with clean data, that's a problem. I don't want to be the one building the ROI case for their own product.

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

For us, "good" at year two means the system is running without us babysitting it, and my team isn't spending cycles on things the vendor should own. Adoption is solid, the data coming out is actually being used to make decisions, and we're not still arguing about integrations we thought were settled at go-live. How far are we from that? It depends on the vendor. We have one platform where we're reasonably close — the CS team is proactive, they flag issues before we do, and the QBRs have actual substance. We have another where year two looks a lot like year one: still escalating basic support tickets, still chasing the roadmap items that were part of the sales conversation. That gap is where I start thinking hard about renewal. The benchmark I keep coming back to is whether the tool is reducing headcount pressure or adding to it. If my people are managing the software instead of the software helping manage the operation, that's a problem I can quantify pretty quickly.

What would change your perspective on this entirely?

That's a fair question. If I saw consistent, documented evidence that a vendor's CS function actually correlated with measurable retention and expansion outcomes — not anecdotes, not a case study they cherry-picked — I'd pay more attention to it. Show me the cohort data. Show me that accounts with high CS engagement renew at materially better rates than accounts that don't, and that the delta justifies the cost embedded in my contract. The other thing that would shift my thinking is if a CS team could demonstrate they've reduced our internal headcount burden. Right now my team spends time on things the vendor should own — troubleshooting, pulling reports, managing integrations. If CS actually absorbed that work reliably, that's real value I can put a number on.

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

That's a fair question. I'd say — what does the vendor actually do with the data they're collecting on how we use their product? By year two, they know our workflows, our weak spots, our usage patterns. And I'm not sure that ever gets discussed in a meaningful way during these renewal conversations. It just feels like an area where we should probably be more deliberate as buyers.

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 "success" even means at year two versus year one. Year one, everybody's still in honeymoon mode — the CSM is attentive, the exec sponsor is engaged, the implementation team is still visible. Year two is when you find out if the relationship actually has legs. What I'm wrestling with specifically is the expansion conversation. We sell multi-year agreements, and the backlog quota is real — my reps are measured on it. So if a customer isn't growing their usage or adding seats by month 18, that's a problem for my number, not just a CS metric. The question I'm always asking is whether our CS team is actually positioned to surface those expansion signals early enough for sales to act on them, or whether we're just finding out at renewal that the account has gone flat. The other piece is reference-ability. A happy year-two customer who'll get on a call with a prospect or do a case study is genuinely one of the most valuable things we have. I don't have a strong view yet on the best way to systematically build that, but I know when it's not happening because my reps are scrambling to find social proof late in a deal cycle.

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 implementation is done, the executive sponsor who championed the deal has probably moved on or lost interest — and now you're asking whether this thing actually lives in the workflow or just sits there. The thing I want to know is: are we expanding, or are we defending? Because if my CS team is spending year two just fighting to hold the contract flat, that's a problem for my renewal number and frankly for my own comp on any backlog quotas I'm carrying. What I need to understand is whether the platform has actually driven enough measurable value that the customer can articulate it — ideally in their own words — because that's what turns a renewal into an expansion conversation, and eventually into a reference I can use with a new prospect.

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 expanding — they're not just renewing, they're buying more seats, adding modules, something. If we're flat at renewal, that's almost a yellow flag even if we technically kept the account. Where we are today... we're closer than we were 18 months ago, but CS and Sales still have some friction around who owns the expansion conversation. That's probably our biggest gap right now. The handoff is cleaner at year one, but by year two it gets murky — CS thinks Sales is going to swoop in, Sales thinks CS has been cultivating the relationship. So deals slip. I don't have a strong view on the metrics side of what "great" looks like quantitatively — that varies a lot by segment and contract structure — but directionally, I want CS to be generating pipeline, not just managing satisfaction scores.

What would change your perspective on this entirely?

That's a fair question. If I saw consistent, documented evidence that a CS team was actually driving measurable expansion revenue — not just "relationship health" — that would shift how I think about it. Right now CS at year two feels more like a retention function than a growth function in most of the vendors we work with. The other thing that would change my view is better peer-validated proof. If I'm hearing from other VP-level buyers at companies like ours that a specific CS model genuinely moved the needle on adoption and expansion, that carries weight. Case studies written by the vendor don't do much for me — but a peer telling me at a conference or on a reference call, that lands differently.

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

That's a good one. I'd say... nobody really asks about what happens to the CS relationship when the rep who sold the deal is long gone and the customer feels like they're starting over from scratch. Year two is often right when that transition friction shows up. The CSM inherited the account, they weren't in the original conversations, and the customer's expectations were set by someone who promised the moon to close. So now CS is playing defense instead of driving value. That's a real breakdown point that I don't think gets enough attention in these conversations.