Iterative Sales Planning With Kayla Giese and Johnny Kerins

Even the cleanest annual plan will encounter real-world complexity that no model could fully anticipate. Accounts transition. Contracts shift regions. Hybrid roles blur ownership lines. New goals emerge mid-quarter. 

The question isn’t whether change will happen. It’s how confidently and consistently you respond when it does.

The teams that navigate this well don’t chase perfection at the start of the year. They design for iteration. They document guiding principles before edge cases arise. They communicate clearly when adjustments are required. And they treat execution as a living process rather than a fixed deliverable.

In a recent webinar, we sat down with two practitioners well-versed in an iterative planning process: 

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

Together, they shared how their teams are handling manual fixes, system limitations, mid-year adjustments, and field questions, and how designing for nimbleness has become a competitive advantage.

Because in modern sales planning, success doesn’t come from eliminating change. It comes from building systems and communication practices that absorb it.

Here are their learnings. 

Were there any parts of this year’s planning process that took longer than you expected? 

Kayla: Yes, really any process where we work closely with the leadership teams takes time. Headcount planning is one example, because we asked for a very collaborative process with them. Ultimately, it ended up being a lot of extra work for sales leaders who already had a ton on their plates at that time. It was more manual and time-consuming than we expected for everyone involved.

The learning there is for RevOps to be more prescriptive. Our sales leaders love it when we can give them clear answers they can trust. If we had been more prescriptive with our recommendation, and how we got to it, it probably could have saved a lot of time on both ends.

The other time-consuming thing is those edge cases. I can definitely resonate with over-documenting edge cases and wanting to make sure you have clear answers if any questions arise, because they’ll continue to come up. But I don’t think you can ever solve for everything. You think your plan is finalized, and then a ton of edge cases come up. You end up going back to ask, “How do we solve this for this manager?” And we need to solve it the same way elsewhere. You really can’t document enough there.

Lastly, the final tie out. We're all working in spreadsheets, and there's a ton of room for human error when you have multiple spreadsheets, multiple versions, and people in and out of them. So just like all of the checks that come into play at the last minute before things get uploaded into the system and then even once they are uploaded, making sure everything's tying out. I think that's just kind of an ongoing struggle. Everyone is using Excel. Excel is an incredible tool, but when you have multiple people trying to use the same Excel file or create multiple copies, things can become challenging pretty quickly.

Johnny: Funny enough, I consider our phased communication plan a best practice in a lot of ways. But, it also added different areas of complexity. Every time you introduce another layer of an employee band into the planning process, more edge cases and more exceptions come up. You end up having to double, sometimes triple, your work in order to make sure that each individual feels like they're being taken care of.

Something that helped us was documenting our core principles prior to when the planning process started. We had to establish what we wanted to achieve in this process. That allowed us to guide ourselves through the decision making process for education and exceptions. That being said, stuff like non-standard territories, hybrid roles, account ownership nuances, and account transitions took more time than expected and those don't show up in the high-level plan.

As much as you want to talk through how you want to execute a plan and how every dollar and cent nets out, you can’t plan for those edge cases and exceptions. Those things are always going to add more time.

But, starting earlier gave us some time to actually work through those nuances.

How did the field react to your plan? 

Johnny: We have a blessing and a curse here at FranklinCovey in that we have a very engaged sales force. It’s awesome because they're people who really care about how their territories and quota numbers are derived. They really care about their jobs, which, of course, is a good thing. However, that also means we get a lot of questions every planning cycle. They want help understanding where the numbers came from.

When you have an exponential amount of those types of questions, it can get overwhelming. The first questions were less about fairness and more about clarity. They wanted to understand how the numbers were built, what assumptions were applied to them, and what they can actually control.

Kayla: A lot of the initial questions we got were around wanting clarity, as well. Sellers wanted to know where the numbers were coming from and better understand why one growth rate looked different from another, or why one rep's quota differed from someone else’s.

It’s important to remind myself that we’d been sitting with these numbers for months. We’d gone back and forth with Finance, leadership, and executive teams. We knew these numbers inside and out.

Even though we did try to bridge that gap and explain the logic, sellers were seeing these numbers for the first time.

[BLOCKQUOTE
| Quote: Sellers are the ones most impacted by these numbers at the end of the day. You can never provide enough clarity on where those numbers are coming from.
| Author: Kayla Giese
| Title: Revenue Operations Lead, StackAdapt
]

Once they understand the logic, they're bought in. It's not a matter of pushback or fairness. It really is just about wanting to understand and trust the numbers.

Johnny, you’re about six months into your annual plan. Are you still getting questions from the field? 

Johnny: I would love to tell you that we are not getting questions anymore, but that would be a lie. We get questions all the time as we move through each quarter. For our current customer base, our account management-type sellers always have questions when they start the QBR process or when a new goal comes up. They ask about the quota assigned to that account and the territory that was designed.

Our account management-style sellers have a bit more of a phased rollout throughout the year, depending on when their renewals are coming up. Typically, that renewal event is when the buying cycle for that specific customer kicks off.

So yes, we get questions all the time. It's helpful because it ensures that as we're kicking off our next planning cycle, we still know what's top of mind for sellers.

Just this morning, for example, one of my team members and I started documenting some of those questions. We're already iterating on a process that will hopefully make FY27 planning for us even easier than FY26 planning.

Did anything in your data, technology, or processes behave differently than you expected? 

Johnny: We have a lot of data, but sometimes it doesn't functionally work for the questions we're trying to answer. If I take territories as an example, we have them aligned to hierarchy as best as we can with the data we have access to. One of the things we kicked off for our new logo team this year was tiering accounts based on a hypothetical ICP score.

One challenge we ran into was this: if you had a tier one account that was a sub-account of a tier three parent account, where should it be assigned? Where should it be weighted? If the parent account was technically less aligned to our ICP than the sub-account, how should that be treated?

The data was there for us to enact a thoughtful plan, but when we went to take action on it, there was a lot more manipulation required than we expected.

So it opened our eyes to some cleanup we needed to do, as well as making sure our CRM was functioning in a way that was truly actionable for our team. There were a few surprises along the way. 

[BLOCKQUOTE
| Quote: The data wasn’t wrong, it was more about operationalizing it correctly.
| Author: Johnny Kerins
| Title: Sr. Director, North American Sales Operations and Strategy, FranklinCovey
]

Kayla: It’s important to remember that the Rules of Engagement (ROE) is a living, breathing document. Every single day, something new is going to come up that doesn’t exist in your ROE.

As we went through planning, edge cases and new scenarios surfaced that we hadn’t documented before. In some cases, they may have come up previously, but they weren’t formally captured.

We made sure we were improving our documentation. Eventually, we’ll have them all covered, but realistically, new ones will continue to emerge.

As it pertains to systems, it goes back to the fact that we're using spreadsheets. There's naturally going to be a disconnect when you don't have a single source of truth. So something as small as naming conventions in our spreadsheets being different from our systems caused an unbelievable amount of headache for internal teams.

Did your team need to step in with manual fixes?

Kayla: My team had to balance being scrappy to get fixes in place quickly while also enabling scalable solutions for future planning cycles.

Right now, we're in a state where most of the fixes we're doing are relatively manual. For example, the field will fill out a form, and then RevOps will investigate. The reason it’s so manual is because we're still operating across multiple data sources. It's not like we can do everything in Salesforce or a single tool.

Johnny: One of the things that will always be a challenge when you're dealing with Excel is that Excel can be static in many ways. The CRM, or whatever tool the field is actually interacting with, is more of a living, breathing organism.

There's always going to be differences between what you're working on in Excel and what's actually living within the system. There's always a margin of error that we try to plan for and ask for grace around, and yet there are still many manual adjustments we need to make.

We just had a conversation yesterday about a nuanced contract situation where a company divested from one assigned region and is reinvesting those dollars into a different region. What do we do with the quota and the crediting? They're downgrading in one place but upgrading in another. How does that work?

We needed to revisit our guiding principles and form a policy around it just yesterday, and we are six months into our fiscal year at this point.

[BLOCKQUOTE
| Quote: It’s important to be nimble and understanding. Documenting our guiding principles and using them to ensure consistency has been key in gaining and maintaining trust.
| Author: Johnny Kerins
| Title: Sr. Director, North American Sales Operations and Strategy, FranklinCovey
]

‍

What will you change for next year’s planning cycle?

Johnny: I’d like to design for more iterations, not perfection. We've talked throughout this conversation about how the planning cycle naturally becomes iterative. Going forward, I want to assume from day one that not only will the plan evolve, but that portions of it — maybe every portion — will require small adjustments throughout the year.

That mindset changes how you document decisions, build systems, and communicate with the field. The goal isn't zero change. It's fast, confident adjustments.

Right now, for example, we have one team that's struggling a bit. We believe it’s due to how we designed the go-to-market (GTM) component of their plan. As we head into the second half, we’re looking for iterative band-aids to help them be more successful.

We're documenting that as thoroughly as possible. We recognize that some of this may be short-term solutioning in the second half, but we’re also making sure we can implement real changes in FY27 to set this cohort up for success in the next planning cycle.

Kayla: I’m aligned with Johnny. The plan is never going to be perfect. So you have to design for the inevitable disruption that will arise. There's always going to be account transitions that affect quotas, split credit, and cross-territory coverage.

That might mean solving for those scenarios with manager buffers, over-assignment, updates to quota logic, or other structural adjustments. It’s about thinking through how your design can absorb those natural imperfections in the field so you're not constantly scrambling to address last-minute issues.

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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.