Lessons in Agile Sales Planning

In our continued Q&A Series, we sit down with leaders from across the incentive compensation and sales performance management space to explore learnings, trends and opportunities that exist for today’s ICM and SPM professionals.

Today, we’re speaking with three practitioners who lead successful sales planning programs inside some of the world’s most dynamic organizations. Each expert brings a unique perspective on what it takes to design flexible, data-driven plans that adapt to change and drive lasting performance.

• Katia Terentyeva, Head of Global Sales Compensation Operations at Elastic: A seasoned leader with deep experience bridging finance, operations, and compensation strategy to deliver scalable, insight-driven programs.
• Saurabh Mehreja, Senior Director of Sales Incentives at Siemens: An expert in incentive design and sales effectiveness, with a track record of helping organizations drive growth through smarter, performance-aligned plan design.
• Johnathan Warren, Director of RevOps at CaptivateIQ: A veteran RevOps leader who helps companies scale efficiently by building agile, data-connected go-to-market frameworks.

Together, they represent the cross-functional brain trust — finance, operations, and compensation — that makes modern sales planning truly work. 

Let’s dive into their experiences and the practical lessons they’ve learned for building more agile, effective sales plans.

Planning season often means different things depending on your role and responsibilities. From each of your perspectives — finance, RevOps, and compensation — what does the planning season look and feel like in each of your worlds? 

Saurabh: From a compensation perspective, what I'm really interested in is the outcome of the planning cycle. Every rep wants to know: what are the sales territories they’ll be owning, and what is the realistic quota number that they’ll be owning at the end of this planning cycle? That way, sellers can prepare themselves for hitting those numbers and maximizing their earnings.

Also, as we transition more towards territory-based design, sellers want to know: what are all the accounts that will be housed in those territories? Who do I need to sell to, and what do I need to sell, to maximize my earnings?

Katia: For us, sales planning is a really iterative process. It lasts about five months. So, as soon as we are pretty much done releasing the plans, we start planning for next year. 

It starts with setting high-level objectives. When the financial model is ready, we start testing out those models and understanding: What do we want to change, if anything? Then, we present the plans for sales and finance leadership. My team and the finance team are involved in every single step of that process.

[BLOCKQUOTE
| Quote: Sales planning is a fun journey.
| Author: Katia Terentyeva
| Title: Head of Global Sales Compensation Operations, Elastic
]

Johnathan: Fun journey is certainly one way to put it. I have a bit of a love-hate relationship with annual planning. I think it was once more of a four letter word for me than it is today. I think with alignment, repetition, and standardization of our planning processes, I've grown to appreciate the value driver that it can be for organizations. 

That said, if you do it well, it can feel like a never-ending process. Like Katia just mentioned, we just finished up planning, and now we're starting again. So, the last 12 months for me have felt like one long day of planning since we started the process this time last year. Operationally, we went live with it in February. We're patching policies and executing on our holdover rules at the end of Q1. By mid-Q2, we're already replanning the business for the second half.

Now, here we are in mid-Q3 and we're starting that whole annual process over again. That's part and parcel of the job we signed up for here. But, to do it well, that's really what you have to do to see that continuous planning cycle move effectively. 

What’s something that hasn’t gone well in the past that you now make a point to avoid?

Saurabh: It’s really about maintaining ongoing dialogue, which is the key to true collaboration. It is also about understanding the perspective of the other stakeholders. When it comes to annual planning, it is a very community intensive exercise between finance, Go-to Market (GTM), and sales compensation.

But, all of them operate with a different mindset. Finance wants to have controls and governance in place — because it is their job. While those on the sales side want to maximize sales. So, there's always this conflict of opinions and perspectives, and that is where the collaboration has to have a continued dialogue to understand each other's perspective.

As an example, when we talk about continuous planning, we had a situation where the finance community realized that sellers are hitting the numbers, but the numbers are not very profitable. So, they suggested: what if we have gross profit in the compensation plan?

It’s a great perspective — other companies have done it. But, it requires sales collaboration. Being in the software business, we asked: Do you think that sellers actually know how to calculate the gross profit on a deal? Probably not. So, yes, the suggestion of adding gross profit as a 10 - 20% component may look like it'll increase gross profitability. But from a sellers’ perspective, there should be nothing in the compensation plan that they don't understand.

Ultimately, the dialogue continued, and it led to another solution. We explored why we were having this gross profit downfall, and it turned out that we needed more discipline for pricing exceptions. So, we set up a process for pricing exceptions where finance can review them and have real skin in the game. 

Collaboration, to me, is always about understanding each other's perspective.

[BLOCKQUOTE
| Quote: Try to find a common ground to solve the problem. It’s not a one-way street, where something is flowing from a higher authority to someone with a lower authority.
| Author: Saurabh Mehreja
| Title: Senior Director of Sales Incentives, Siemens
]

What is your planning process like and, in particular, what interactions do you have with folks who are designing compensation and sharing the top-down numbers? How do you navigate that delicate balance of arts and science? 

Johnathan: To achieve good alignment, have one source of truth, one operating cadence, and one shared vocabulary. I think shared definitions could stop 80% of arguments or misunderstandings. If I say “dollars” and finance hears “bookings,” are we both talking about ARR? And if we are, are we talking about initial ARR, average, terminal, or first year?

If I say “ramp in four months.” Does everyone know that I'm assuming that there's also a month zero in there, if the person being hired starts after the 15th. I think it's critical to agree on those definitions. It's critical to agree on what the success metrics look like and the guardrails that you need to have in place upfront.

Get alignment on things like: your variable compensation budget, your cost per acquisition (CAC), payback guardrails, productivity floors, ramp curves, over assignment, assumption, buffers, territory, fairness, variance. All of those things, if defined upfront, can make the whole process a lot easier to manage and avoid some surprises down the road.

And, build a real project plan. Don't just leave notes scrambled around on the ether, but have it documented. And you don't need to use a complex project management tool — if you have it, great. But, have something in place that clearly defines the scope, timelines, and outcomes that you're all working towards.

We've talked about the cross-functional nature here between operations, finance, and compensation, but planning is more cross-functional than that. 

• We bring in marketing's perspective, because they're going to help us forecast what the pipeline reality is going to look like. 
• We bring in sales leadership because they're going to know what process changes are being made that could impact some of our velocity metrics. 
• We need to have perspective from the product team, because their roadmap is going to inform how we go to market with new products. 
• Even the talent team needs to be considered, because if we're going to double our headcount plans, how realistic are our timelines? Do we even have the bodies in place to make that happen? 

It's a huge cross-functional effort, and in order to do it well you have to do the boring things like documentation and project management really well. 

[BLOCKQUOTE
| Quote: Good alignment looks boring on paper and beautiful in practice.
| Author: Johnathan Warren
| Title: Director of RevOps, CaptivateIQ
]

What have you learned from incorporating AI into your workflows, and how do you see its role evolving in sales planning?

Katia: While I don't see AI as a tool that can totally displace the planning process as it exists today, AI definitely helps make our jobs more efficient. That includes creating graphs, running data analytics, etc. 

I use it for benchmarking, as well. It helps to summarize scenarios like: If I have this many sellers and this is my revenue, how many plans should I have? It’s interesting to see what the tool gives back to me.

I also use AI tools to think through all of the elements of the planning process. For example, to check whether we’ve overlooked some of the stakeholders. AI has such endless possibilities, and it depends on everyone’s expertise and focus on how they use it. Ultimately, I still believe it's important for people to get together and make the decisions, but these tools are evolving and developing in ways that will make our jobs much easier going forward.

Saurabh: I’ll start with a disclaimer: I am no AI expert. But I can definitely share what AI tools I have been using in the sales compensation world.

We are not using AI for compensation in predictive or generative ways yet, but I'm personally using AI to gain speed on some of the activities that are needed for compensation planning. 

We use some of the GPTs to quickly create bell curves around attainment, quota status. For example, I’ll have these agents check for the overall location of quota top-down beyond a certain threshold. A lot of this would traditionally be an Excel-based exercise — and companies are already doing it that way. The finance community tends to be much faster in Excel than the compensation community, like us.

Johnathan: On the compensation side, I agree with a lot of what was just shared. I think we'll continue to see an acceleration and adoption of AI copilots that help compress cycle times and augment the work that's already being done by humans.

I think we'll see admin agents that are able to explain plan formulas, help troubleshoot, generate plan docs and what-if outputs that make planning cycles take days rather than weeks. 

On the territory planning side of things, we'll see AI and tooling that will help with smarter allocation, with improved fairness and distribution. Predictive models will help score accounts, estimate quota potential, and right-size quotas and territories by rep and segment.

Lastly, something that we've started to “drink our own champagne” with at CaptivateIQ  relates to governance and risk in things like anomaly detection on payouts. We're essentially able to catch outliers earlier, so that we can prevent month-end fire drills and disputes with the team before the payroll cycle closes rather than after. 

Is there one piece of advice that each of you have for your fellow planning professionals as we wrap up today's conversation.

Johnathan: More than anything, start early. If you haven't already, now’s the time. 

More broadly, I'd say treat planning like a product, not a project. Name an owner, keep a backlog, ship releases, and instrument telemetry throughout. When you do that, you'll be able to pivot with intent, protect that field trust, and keep compounding what's working instead of refactoring throughout the year. 

Katia: My advice is to always have your numbers ready — and be a good listener. There’s never a shortage of ideas; however, it's important to stay grounded and be realistic around what will and will not work. When you bring the facts and analysis to the table, it becomes clear which ideas are worth pursuing — and which could turn into costly mistakes you’re better off avoiding.

Saurabh: I’ll steal a statement from both of them — start early. That would be my advice to leadership. And make sure the compensation community has a seat at the table.

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