Webinar On-Demand · October 28, 2026

Scaling Finance Without the Growing Pains: People, Process & Technology for the Mid-Market

About this webinar

Growing companies are asked to scale Finance faster than they can rebuild it. More entities, more systems, and more spreadsheets stitched together, until the team spends its week reconciling numbers instead of guiding the business.

In this 40-minute fireside chat, Chris Ortega (Founder and CEO, Fresh FP&A) and Om Kapoor (OneStream) talk through what actually changes as a business crosses the $100 million mark, and how to get ahead of it across three fronts: people, process, and technology. Drawing on Chris’s experience taking three companies through acquisition, the conversation is candid about what works, what doesn’t, and where to start. The throughline: build the foundation first, because a single version of the truth is what lets Finance move from tactical work to the strategic decisions the business now expects of it.

Speakers

Om KapoorOm Kapoor
Senior Manager Product Marketing, OneStream
Chris OrtegaChris Ortega
Founder and CEO, Fresh FP&A

Key takeaways

Build Finance foundations before growth forces the issue. The processes, people, and tools that carry a startup rarely survive past $100 million. Scale is a day-one design decision, not a later fix.

Finance must shift from tactical work to strategic analysis as it scales. Early teams spend 80 to 90% of their time on tactical tasks; that ratio has to invert, because Finance rarely gets the headcount other functions do.

Don’t automate a broken process. Standardise and fix the process first, then automate. Automating a mess only makes it break faster.

A single version of the truth is the foundation of scalable Finance. When two systems can each defend a different number, credibility and speed collapse. One governed data source raises decision confidence.

Choose technology for the business you have, not the demo. Understand your bottlenecks before buying (“Lamborghini syndrome” is buying features you can’t use). The same rule applies to AI: start with one practical use case, not the hype.

Webinar Transcript

Introductions

Host: Welcome, and thank you for joining us. Over the next thirty minutes, we’ll talk about how growing companies are being asked to scale finance faster than they can rebuild it: what happens when you cross the $100 million threshold, and what to do about it across your people, your processes, and the technology underneath. First, a quick introduction to our guest.

Guest: Nice to be here. I run a global fractional CFO and advisory service company, and we help small and medium-sized businesses grow with financial clarity and confidence.

Before this, I spent over twenty years in accounting, finance, and financial leadership. Most of my background was coming in to build, shape, scale, and exit companies. I had the opportunity to help take three companies through acquisition. The largest was an international marketing platform company, about $130 million in revenue, 2,700 employees across 25 countries. We built that company up and sold it to SAP, and I stayed on for a year to help with the post-merger integration.

After that, I realised two things. First, I know what it takes to transform and scale finance teams, the good, the bad, and everything in between. Second, I felt finance needed a fresh perspective. So just under five years ago I took the leap and started my own advisory firm.

What changes as a business scales

Host: You’ve led finance across multiple stages and taken companies through acquisition. What does that look like for teams as a business accelerates?

Guest: I’d argue even more than seven in ten CEOs and business owners expect finance to be the growth engine, closer to 90%. And most of that pressure comes with the scale of the business.

What starts a business as a startup changes at the scale-up phase. Processes change, people change, there are new people in the conversations, maybe new investment, maybe entities you’ve acquired. A lot of those early processes don’t scale when you go through an acquisition or take on capital.

Processes are the foundational framework of any high-performing organisation, especially in finance. Back in my audit days, I watched publicly traded companies build their internal processes. A CFO told me then: processes are the scale framework of every business. Learn the processes of a public company and you can apply them to a private or scale-up company. Finance has a critical role in that, building the processes around AP, data aggregation, and forecasting. As you grow, that sophistication has to change, or you end up with the wrong people in the wrong seats, or an 80-page Excel model that no longer scales.

Host: That mirrors what we hear from customers. At the helm of all this change is the office of finance and the CFO. The business expects the CFO to navigate it and drive growth.

People: investing as you scale

Host: As teams scale, they have to think about how they invest. We see stats that around 23% of finance teams spend most of their time on analysis, and 28% spend as much time correcting data as analysing it. What have you seen?

Guest: It’s the classic tactical-versus-strategic balance. At a startup or scale-up, 80 to 90% of your time is tactical, you’re building the plane as it flies. That’s not surprising.

But here’s the golden nugget: you can’t be a $120 million business and still spend 80 to 90% of your time on tactical work. At the startup phase you’re at 80/90% tactical. At scale-up you should be closer to 60/40. At enterprise level it should invert, 70% strategic, 30% tactical.

Early on, I made the mistake of throwing people at problems. As you scale, you don’t get that luxury. Finance doesn’t get unlimited headcount like sales or marketing; we’re asked to do more with less. You have to have the right people in the right seats, doing the right level of work, bringing the right level of partnership. People scale when you have platforms, technology, and repeatable processes, not band-aid fixes.

Where AI fits

Host: How do you think about where AI comes into play as people upskill and rethink their org structure?

Guest: I use a framework called the decision cycle. Processes drive data. Data becomes information. Information is shared as knowledge to make a business decision. Process, data, information, knowledge, decision.

Here’s where it gets valuable. A lot of people spend most of their time in the first three phases, process, data, information, churning through reports and downloads. That’s not value-add. Where you want to spend your time is knowledge and decision-making. AI and technology can automate process-to-information, so your people arrive at the knowledge phase ready to collaborate with the business and make a better decision.

And there’s a misnomer that AI will replace your job. I was talking about this fifteen years ago as an FP&A manager. AI isn’t here to replace you, it’s here to get you out of low-value tactical work and into higher-value activities: communication, collaboration, connection, and bringing clarity to the organisation.

Process: don’t automate a mess

Host: We can build the best team, but without the right processes it all breaks apart. There’s this idea of an “iron band-aid”, a spreadsheet that lived on someone’s computer for four years, became the linchpin for the whole organisation, and then they left. The point is: don’t automate a mess. 71% of the finance teams we talk to still stitch together data across siloed systems, and 66% want a unified data layer to speed up insight. How should teams think about this?

Guest: As you grow, one of the biggest challenges is the version of the truth. We’ve all sat in front of the sales and marketing team with a revenue number on screen, and the revenue leader says, “I thought that number was higher.” In that moment, credibility is gone and you’re spending all your time working out which number is right.

A central version of the truth is vital at every phase. When a platform centralises your marketing, sales, operations, and financial data, and the business runs on one version of the truth, everything changes. I think of finance as building a house: the foundation is the concrete slab, and the whole business is built on it. A centralised version of the truth is part of that foundation.

In a startup you operate with velocity, sometimes making decisions at 30% confidence because you have to. With one clean, aggregated source of truth, you move from 30% confidence to 80%. That speed is power. If there’s one process you centralise to help you scale, make it a single version of the truth.

Host: I’ve had countless conversations with customers who were on a legacy tool, asking whether “v63 final” or “v63 final final” was the right version. One customer, a growing business managing multiple divisional ERPs, used to start every meeting working out which version of the model was correct. Now it’s all on one platform with no architectural changes, so everyone works from the same page.

Technology: choosing the right tools

Host: When teams move from spreadsheets to point solutions to a unified platform, building the case for technology is hard. Finance often holds the purse strings but doesn’t get to cash the cheque. How do you build that case?

Guest: Let me highlight where I failed, and the right way to do it. The failure I call Lamborghini syndrome. You walk into the showroom, see the tool with all the bells and whistles, the AI, the predictions, and you decide you need it, without understanding your business’s pains, frustrations, and opportunities. So you buy the Lamborghini and run it in a school zone. It doesn’t translate, and I’ve made that mistake.

The right way: learn the business first. Know the bottleneck pains, the opportunities to bring clarity, the challenges your partners and your finance team face, and the scale you need. Then find the technology to match. The cost of a bad implementation, ERP, FP&A tool, whatever, is monumental, and it hits your credibility. Nobody wants to replace technology every six months. Software implementations are painful.

When you know the business and pair it with the right technology, you can show not just how finance gets more efficient, but how the whole business, sales, marketing, operations, HR, collaborates and makes decisions with clarity and confidence. Everyone’s looking out the same windshield. They may watch different metrics from different seats, but everyone knows where they’re going.

And if you build these people, process, and technology disciplines into the foundation early, you don’t have to rebuild them as you scale from $50 million to $100 million to $200 million.

Host: There’s so much hype in the market, especially around AI. A demo looks beautiful, then implementation is night and day. We work with customers to build the baseline and the use case first. We’ve done close to 2,000 implementations, and we’ve packaged those best practices into CPM Express to shorten time to value. One customer replaced a legacy consolidation tool with CPM Express, went live in about three to four months across 12 production sites, and took their close from ten days to three. That lets teams spend less time on the past and more on driving the business forward.

Making AI practical

Host: What are you seeing in how finance teams evaluate AI?

Guest: Every solution has its own AI now. Here’s my practical tip: when a vendor says “we’ll show you our AI,” ask to see behind the scenes, the proprietary algorithms they built. A lot of them are just a back end to Claude or ChatGPT. That’s not innovative. You want technology that has built proprietary algorithms on your data, while still letting you use the generative AI tools you want.

Get beyond the hype and make AI applicable. If you’re at the beginning, find one use case, ideally in your tactical operations, accounting, tax, and one you can partner with the business on, like contract management or billing. If you want to move fast, move alone. If you want to move further, move together. Build a use case with sales, marketing, HR, or operations, and you’ve created a playbook: here’s how I used AI, here’s the value we built together.

Don’t start with pie-in-the-sky use cases. AI in finance can feel like an elephant, and you tackle it one leg at a time. Get it practical, applicable, collaborative, and build the value together.

Host: We recently launched our agentic capabilities on the platform. They’re grounded in your business, your chart of accounts, your data, so natural language maps to the right financial intersection deterministically. One enterprise customer helped build this during private preview. Rather than throwing the kitchen sink at it, they identified their top pain points, built a matrix, prioritised the high-velocity items, and planned the change management so teams actually used it, saving thousands of hours. And that intelligence extends to the tools you already use, Claude, ChatGPT, Copilot, Gemini.

Audience questions

Host: How do you work with IT on these conversations, so you’re collaborating rather than butting heads?

Guest: Bring your IT professionals along, it’s a collaborative function. A practical takeaway you can act on now: go build data governance and an AI sandbox together. Most organisations have shadow AI running everywhere, lots of licences with no governance or framework. Partner with IT to build the data governance, choose the tools, build the training, and centralise licensing and token usage. When finance and IT partner on that, you build a framework for the whole organisation. As you adopt more tools, keep bringing your CTO, chief data officer, and CIO along, so you add governance and scale in a way that’s cost-conscious and collaborative.

Host: How do you think about finance readiness as you go through an acquisition, post-acquisition, or raising capital?

Guest: It tests everything we talked about, your people, your processes, and how you built the organisation to scale. So here’s what I’ll leave everyone with: build your foundations now. You may be early, at $100 or $120 million. Start with your processes. Look at your baselines and where the opportunities are. Make sure you have the right people in the right seats doing the right level of work. We’re in Q4, there’s no better time to set your baselines and plan how to improve over the next quarter.

Closing

Host: If you have questions or need resources, visit our Mid-Market Finance Hub. It’s a foundation for everything we discussed across people, process, and technology. Thank you all for joining.

Guest: Thank you, everybody. I really enjoyed this.

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