Painful lessons learned from leading fiscal planning last year

Welcome to Evidently—the bi-weekly newsletter where I share my biggest hits (and get honest about my misses) as a first-time VP of Marketing. If this was forwarded to you and you like what you saw, you can subscribe here.

Fiscal planning.

Just reading those two words might stir up feelings of anxiety, confusion, or frustration. Maybe even all of the above.

Unless you’ve done fiscal planning before, especially as a first-time VP of Marketing, it’s easy to feel lost or stuck. Pretty much every emotion you can imagine.

From talking with mentors and other B2B marketing leaders, the overwhelming consensus about fiscal planning is clear:

Does it get a little easier the more you do it? Yes. Is it always messy? Also yes.

The key is understanding that it’s part of the process and will be okay.

The trick is staying grounded and level-headed throughout. It’s easy to get caught up in the emotions—to feel frustrated, overwhelmed, or hyper-focused on the details.

But the sooner you can take a step back and realize it will be alright, the better off you’ll be. And the better headspace you’ll be in to approach the process thoughtfully.

Let’s dive into what went wrong during last year’s fiscal planning process, how we’re doing things differently this year, and my lessons learned along the way.

What went wrong last year

If you’re an OG Evidently reader (thank you), you might remember when I wrote about building our pipeline model last June.

Thanks to the help we got from Matt Avero-Sturm and Kyle Lacy, we built a solid V1 of our pipeline model last year, but it was just that: a V1. It was also only one piece of the larger fiscal planning process.

Here’s where we hit quite a few roadblocks last year:

• Timing: Last year, our planning process as a group kicked off in January, which was extremely late considering our fiscal year starts on February 1st (we’re on the weird Salesforce fiscal year). This left us with little time to iterate.

• Data trust issues: We were cleaning up our attribution at the same time. Historical data was being updated in bulk, and we didn’t have enough clean, directional data to work with initially. That made our co-founders less confident in trusting the numbers.

• Over-simplified assumptions: We only had three static assumptions modeled across three scenarios: conservative, stretch, and aggressive. The assumptions were the % increase in win rate, the % increase in ACV, and the % increase in opportunities generated. None were broken out at the channel level, so the model wasn’t granular enough.

How we’re doing things differently this year

This year, we’re taking a more collaborative and iterative approach to our entire fiscal planning process. Here’s how we leveled up the second time around:

1. Starting earlier and setting clear, upfront expectations

We began the process in November, holding our first meetings in December. This gave us more time to refine and iterate.

We clearly defined the timeline and expectations upfront, breaking the process into four key meetings over ~6 weeks:

• Meeting #1: Review the bottoms-up approach, data, and initial assumptions

• Meeting #2: Validate and refine assumptions to model more realistic scenarios

• Meeting #3: Make trade-offs between program spend, headcount, and other investments

• Meeting #4: Address open questions and get agreement on the plan

We stuck closely to this plan. And while there may be one additional meeting to finalize a hiring decision, the new structure has been a game-changer.

2. Getting more granular and improving our confidence level in the assumptions

We moved away from oversimplified assumptions and focused on a more detailed approach:

• Breaking performance down by channel (e.g., Inbound vs. SDR Outbound vs. AE Outbound vs. Events vs. Referral).

• Tracking key metrics like stage 1-to-stage 2 conversion rates and win rates

• Using median ACV instead of averages to avoid big deals skewing the numbers.

It’s more work, but the trade-off is confidence in the data. When the team can see what’s driving results, it’s a whole different ballgame.

3. Taking the time to manage up and run better meetings

We tightened up our meeting cadence and expectations:

• Clear agendas and pre-reads sent to the group ~24 hours in advance

• Follow-ups after every meeting to recap decisions

• No surprises so people don’t see data for the first time in meetings anymore

We sent this out before Meeting #1 to set expectations:

Then, I recapped some modeling changes and scenarios going into Meeting #2:

And the reminded the group about where we were at in the process and reset expectations before Meeting #3.

I also introduced Kyle Lacy’s brilliant (and kind of ridiculous) idea of a safe word to keep meetings on track. Whenever a meeting starts to lose focus, anyone can use the safe word to bring the conversation back during tense moments.

Ours became “cheesesteak” since I had just gotten back from CyberMarketingCon 2024 in Philly before our first planning meeting.

Not only did that meeting trick work as intended and lighten the mood during tough moments, but someone even “cheesesteaked” themselves. I’m never NOT using this trick again.

My biggest takeaway

The biggest shift for me as a leader had nothing to do with data. It was about collaboration.

Last year, I treated planning like a grand reveal. I’d build a model in isolation with my Marketing Ops guy and spring it on the group, only to face endless questions, skepticism, and confusion that stalled progress.

This year, I leaned into sharing before ready. I partnered with our VP of Sales Heather Bell to get agreement on the assumptions we were proposing, tested them in small conversations with our co-founders Evan and Ray, and iterated from there.

Fiscal planning, especially at Series A startup, isn’t about perfection. It’s about building trust, getting everyone on the same page, and moving forward as a group. Kinda like most things in life.

One more funny story

During a recent session in Exit Five’s CMO Club, they brought in Kipp Bodnar, the CMO of HubSpot. We made it through the entire session without anyone asking a question about fiscal planning, before I asked Kipp for his best fiscal planning advice in the last 90 seconds of the calendar invite.

He said, “Don’t waste all your energy arguing over the last 10%. Your focus should be on the first 90%."

That made me laugh and put things into perspective. It’s advice I’ll always carry with me moving forward.

Stay tuned for part two. I’ll share more in a couple of weeks…

Stuff I’m digging this week

• Do Better Work from Max Yoder—I had heard of this book before but never read it until Kyle Lacy ordered me a copy. This book is packed with practical ideas like “share before you’re ready.” A reminder that progress beats perfection every time. This book is a must-read (and it’s not super long either).

• Another hilariously relatable LinkedIn short from Heike Young and Devin Reed—they break down an all-too-common issue for B2B marketers (that’s very near and dear to our hearts at UserEvidence). More of this kind of content on my feed, please.

• How Clay put their own spin on “boring” website logo bars—Show me a B2B website, and I’ll show you the same cookie-cutter customer logo bar everyone uses—except for Clay. They put their spin on it by showing which customers also have case studies and testimonials to back everything up. (And Alex, our Director of Product Marketing, had some great commentary on the launch from a PMM perspective, too.) Check it out here:

Opinions are cheap. Proof is gold.

Last December in Philly, I sat down with our customer Sam Langrock of Recorded Future at CyberMarketingCon.

We had a super tactical conversation about why understanding customer fears is the greatest way to win their trust.

If you’re in Sales or Marketing, this episode is loaded with tips (like this one) you can start using today.

My biggest call-outs:

• Skepticism is the default mindset for cybersecurity buyers—making trust-building even more critical for the buyer’s journey.

• Traditional case studies tend to feel fluffy. Sam leans on bite-sized testimonials for a more personalized and versatile punch.

• Teams should be using their customer surveys to build their customer evidence libraries and grow their advocacy pipelines. He talks about how they’ve used our platform to make booking guests for their webinars 10x easier.

Listen on Spotify or Apple, or head over to YouTube.

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