The Great Planning Retro: Build for Change, Not Perfection

Planning cycles start with rigor. Sales compensation and RevOps leaders enter the cycle with clear goals, executive alignment, and thoughtful modeling behind them. The intent is strong. The assumptions are documented. The plan is built carefully and collaboratively.

Yet, go-live isn’t the finish line. 

The rigor continues as edge cases surface. Manual fixes creep in. Field feedback reveals complexity that didn’t show up in the model. The challenge isn’t designing the plan. It’s adapting as reality sets in.

In a recent webinar, we hosted a candid “planning retro” with the following industry experts to unpack what actually happens after go-live and how modern teams are evolving their approach:

• Kayla Giese, Revenue Operations Lead, StackAdapt
• Johnny Kerins, Sr. Director, North American Sales Operations & Strategy, FranklinCovey

Three themes emerged from the conversation: 

1. The best teams design for change, building flexibility into their plans from day one. 
2. They strive for simplicity, knowing that clarity drives adoption and trust. 
3. And they start earlier than ever, aligning on assumptions and documenting decisions before pressure builds.

The teams improving year over year aren’t logging the plan and moving on. They’re revisiting it, pressure-testing it, and refining it as reality unfolds.

Here are our experts’ learnings. 

How did planning go last year? 

Kayla: I wasn't with StackAdapt for last year's fiscal planning, but I think the team had been working on so many improvements throughout the year based on what they learned last fiscal year. I was able to benefit from those learnings during this planning cycle.

Overall, planning felt a lot more intentional and data-led than some planning cycles I've been a part of in the past. But it was also more complex. 

We introduced a lot of changes. Historically, we operated on a quarterly planning model, which can be very reactive. We made the decision to move to a bi-annual planning model. This allowed us to think further ahead and focus on being more thoughtful with headcount capacity planning, quota durability, book balancing, and better alignment between RevOps and Finance. 

It was nice to see those efforts pay off. Overall, I think the planning cycle went really well. 

The trade off is that there were a lot of changes happening at the same time. There's always some thrash for the field, as well as the internal RevOps team, when you have comp changes, process changes, and tooling changes at the same time. 

So, while the lift felt a bit heavier, we built stronger foundational logic into the plan.

What advice would you give other leaders that want to roll out multiple changes at once without being too disruptive to their teams? 

Kayla: Make sure to sequence the introduction of those changes. We had a lot of changes at once. And while they were changes for the field, they were also changes for us. 

There were things that we didn't foresee or plan for. Questions came up that we weren’t expecting. Consider introducing just one change at a time. And the internal team should start planning for those changes as early as possible, so that when they finally make their way to the field, there’s a seamless rollout. But I think it's also one of those things where there's just never enough time in the day. 

What was different about this year’s planning cycle? 

Kayla: The biggest change was moving from quarterly to biannual planning. That's a change that the team had been talking about doing for a while. 

We did it because there's so much that goes into planning. It's such a time suck for RevOps and for the field. Moving to biannual planning allowed us to free up some time while also reducing the volatility that comes with more frequent cycles. 

Another change is that we had a much more structured process for headcount and capacity planning that we tried to get ahead of prior to any quota setting exercises.

To plug CaptivateIQ, we introduced its territory planning tool for the first time, which allowed managers to experiment with changes to their books of business. For example, how can we even out capacity? Can we get a clearer view of the current state of the team? 

Sometimes you're going off of qualitative feedback, like what reps feel. But having data to tell us where we can shift each book of business naturally informs headcount planning. It's not just saying, “We need this many more heads.” We’re understanding what we can do with the team we have and then optimizing that as much as possible before asking for net-new headcount. 

And then the last one is that we've improved our quota logic. In the past, we had account-level quota assumptions which can sometimes have an adverse effect on reps. Having done quarterly processes, we had so much feedback around what the numbers were, what the quotas looked like. We continued to improve our logic and move towards portfolio-based quotas that reward over-performers and raise expectations for underperformers.

[BLOCKQUOTE
| Quote: Ultimately, we continue to be more prescriptive with all the numbers and quotas that we're putting out there. It’s always a work in progress.
| Author: Kayla Giese
| Title: Revenue Operations Lead, StackAdapt
]

Johnny: We tackled two things differently this year, compared to last year. First was how we documented assumptions. There's a lot of assumptions that go into the planning process, whether that's through book building or quota setting. We found that we would revisit conversations we had in the past and realize there was no source of truth. We didn’t know where some of those assumptions or numbers came from. 

So, we prioritized relentless documentation. As tedious as it can feel at times, it’s super important to make sure that we’re all grounded on where we are and where we’re going. 

Second, I would say, “the earlier the better,” was huge for us. We are on a true annual planning cycle with slight iterative processes throughout the year.

We started conversations earlier, specifically at the macro, executive level, to understand the intention of next year. This really allowed us to have more time to work through the big problems that we want to tackle, and also the small nuances or unexpected changes that come out through the planning cycle. 

[BLOCKQUOTE
| Quote: The great thing about the planning process this time was that there were no last-minute decks, no last-minute phone calls. What was actually within our control, from a decision-making process, had been aligned on so early that those parts of our planning process went really well.
| Author: Johnny Kerins
| Title: Sr. Director, North American Sales Operations and Strategy, FranklinCovey
]

How will you measure the effectiveness of your plan this year? 

Kayla: It's going to be a mix of quantitative and qualitative metrics. Quantitatively, we want to understand how we're performing against plan. Are we performing against our company target? What does quota distribution look like? We want to make sure we understand what that attainment looks like before we go into our H2 planning. 

What are the takeaways that we can solve in our next cycle, based on those learnings? We’ll compare every assumption we made in our model to reality. Whether it be rep ramp assumptions, growth assumptions, we’re constantly cross checking against what's actually happening.

Qualitatively, we need to get as much feedback as possible. We just received feedback from our planning survey that we shared with field managers. There were so many great insights in there. Some things went well that I wouldn't even have thought were important to them, which is a great learning to ensure we continue to prioritize those elements in the process.

Of course, insights on areas we can improve. Every manager has different priorities when they're going into planning or things that they focus on. Certain data points were really helpful to some and not others. There were things they wish they had that would have helped them make decisions. 

And, how does our team feel? How many manual changes are we making? How many new processes are popping up through this first half while this plan is in place? It's an ongoing evaluation of how we're doing.

Johnny: Being six months into an annual plan is an interesting point of view to have when you're looking to measure success.

We're looking at lagging indicators, such as productivity, retention rates, renewal rates, and churn, in order to understand if our assumptions were correct. Where are we leaning in more positively? Where are we actually lagging behind where we want it to be? 

And then as we're starting the conversation for our next planning cycle, we're also looking into leading indicators. How is our pipe health looking? What is our capacity planning looking like? What does our ramp health look like? 

We’re at sort of a crossroads of leading and lagging indicators to understand if this annual plan is actually working, and what we need to introduce into our next plan. 

From a qualitative perspective, reducing the noise is basically all we're trying to do. Hit financial goals and reduce the noise. 

[BLOCKQUOTE
| Quote: If people are focusing on the jobs they're hired to do, qualitatively we count that as success.
| Author: Johnny Kerins
| Title: Sr. Director, North American Sales Operations and Strategy, FranklinCovey
]

What other best practices would you share? 

Kayla: I have two key themes that come to mind. That’s not to say that we always accomplish these, but they’re good goals to strive for.

First, I’d recommend designing your plan for change. Hiring shifts, account churn, territory changes, all of these things are inevitable. And I think the best teams plan for that level of disruption. You can build in buffers or flexibility within your plan so that you aren't constantly solving for exceptions.

Second, fight for simplicity. I think a simple plan that managers can understand will perform much better than a complex plan that feels perfect on paper.

There’s always a balancing act. There are a million things we want to change and optimize, but is it going to be best for the field? Are they going to understand all these changes? Are they going to be able to keep track of them?

It’s not to say that things should necessarily be simple for RevOps, but I do think it’s our job to make things feel simple for the field.

Try to take a step back and look at your entire plan from different perspectives, whether that’s cross-functional teams that will be impacted, your field, or team leadership, and ask yourself: how can you make it feel as simple as possible?

Simplicity also improves adoption and trust. If you're sharing numbers and things feel overly complex, you start to lose trust from the field. But if it’s something they can understand, they can get behind the logic. It becomes very clear when you’re transparent about the assumptions that were made.

Johnny: One of the things that we found to be successful was creating a phased communication rollout plan. So instead of taking the plan, doing all of this work, and then going to the field and just saying, “Here's exactly what we decided on. Good luck,” we involved different stakeholders throughout the entire process.

That started with executive alignment and worked its way down to second-line leaders to make sure that not only did they understand the why behind things, but also reviewed the actual execution of the plan.

Then we moved to a second phase with direct sales managers so that they could do the same thing. It allowed them to vet our work, build confidence in the plan, and feel ownership because they were part of the process. Lastly, we went to the entire field after that.

And so with a phased communication approach, each iteration built alignment and buy-in. The field felt like they were involved and it wasn't throwing everything at everyone all at once.

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For more insights, watch the on-demand webinar, “The Great Planning Retro: What Really Happens After Go-Live.” 

If you’re interested in participating in one of the Multiplier Q&A features, reach out to us at multiplier@captivateiq.com.