Balancing risk and growth: Strategies for Controllers and CAOs
SaaS companies have entered a new era where financial discipline and operational efficiency are as crucial as growth. The focus has shifted from rapid expansion to building scalable, sustainable businesses. For Finance leaders — particularly Controllers and Chief Accounting Officers (CAOs) — this evolution brings both challenges and opportunities.
No longer confined to compliance and reporting, they now play a pivotal role in balancing risk with strategic expansion, shaping business strategy, and managing monetization models to drive financial stability and growth.
In this article, we offer a gameplan for Controllers and CAOs to navigate this transformation. We’ll explore insights from Finance leaders like Jane Koltsova, Senior Director, Global Revenue Controller at PagerDuty, who are taking ownership of Order-to-Cash (O2C) transformation, aligning cross-functional teams, and building scalable, future-proof financial systems.
The stakes are high, but those who achieve this balance will emerge as essential drivers of sustainable SaaS growth. Let’s dive in.
Watch the webinar: Transforming Order to Cash: Finance’s Moment to Lead
The rising complexity of monetization
New monetization models are not just about changing a price tag; they affect every step of the Order-to-Cash process. For example:
Usage-based pricing: Tracking consumption requires more robust billing and revenue recognition capabilities.
Shifting from PLG to enterprise sales: Traditional product-led growth focuses on user adoption and self-service. Enterprise deals, on the other hand, often include complex terms, larger contracts, and multi-year agreements.
Entering new markets: Global expansion adds local regulations, multi-currency billing, and potentially new tax requirements.
1. These initiatives create tension between teams. Sales wants speed, Finance requires control, and IT must keep everything simple and scalable. Controllers and CAOs must navigate these competing priorities while protecting the integrity of financial statements.
Jane Koltsova, former Senior Director, Global Revenue Controller at PagerDuty, and former Senior Director of Revenue at Salesforce, has seen firsthand how quickly monetization complexity can escalate. “What started as Salesforce being a pure SaaS — the revenue was rather easy — then we bought MuleSoft, which is on-prem, then Slack, which had a consumption component,” she says. “They were coming one after the other. The ability to put everything on one piece of paper didn’t come together. True integration took a long time.”
When dealing with these evolving monetization models, Koltsova emphasizes the importance of prioritizing compliance. “If you’re dealing with changes on the billing side — usage, consumption, whatever it might be — it’s key to keep front and center SOX and financial statements,” she advises. “If you don’t have it right, eventually the CFO’s going to come and ask, ‘Isn’t this going to be a problem?’ and then you have to rework everything.”
If you’re dealing with changes on the billing side — usage, consumption, whatever it might be — it’s key to keep front and center SOX and financial statements. If you don’t have it right, eventually the CFO’s going to come and ask, ‘Isn’t this going to be a problem?’ and then you have to rework everything.”
–Jane Koltsova
Senior Director, Global Revenue Controller, Formerly of PagerDuty
Finance’s role in O2C transformation
When order volume and deal complexity surge, many companies look to transform their O2C processes. However, confusion often arises over who should take the lead. Should it be IT, Sales Operations, or Finance?
In high-growth or public SaaS organizations, Finance is uniquely positioned to drive O2C transformation because:
Risk mitigation: Finance owns compliance, revenue accuracy, and financial reporting.
Business partnership: With visibility into product roadmaps and sales forecasts, Finance leaders can align the back-office systems with the front-end sales motion.
Cross-functional influence: CAOs and Controllers interact regularly with Sales, Product, and the Audit Committee, helping to unify often-siloed teams.
Koltsova is emphatic about Finance’s leadership role and the need for alignment with other departments in order to make an O2C transformation successful. “The only way to know when to do this and when to do this right is to be led by Accounting and Finance,” she says. “But you have to get Sales, Product, Sales Ops, Deal Desk, Legal, and all of the other parts of the organization on board.”
Further emphasizing the stakes involved, Koltsova explains, “If you have a restatement of the financials, none of your stock is going to change. Bad things are going to happen, and people are going to get fired. So if you start with folks who understand that, you end up then widening that aperture and saying, ‘Okay, now bring in Product, bring in Go-to-Market, bring in Sales Ops.’”
“The only way to know when to do this and when to do this right is to be led by Accounting and Finance. But you have to get Sales, Product, Sales Ops, Deal Desk, Legal, and all of the other parts of the organization on board.”
–Jane Koltsova
Senior Director, Global Revenue Controller, Formerly of PagerDuty
Getting leadership buy-in
Transforming O2C often requires significant budget and resources. Leadership teams, especially in times of slower growth, can be skeptical of non-revenue-generating initiatives. That’s why timing and communication are crucial:
Tipping points: Sometimes a crisis — such as failing to reconcile a key account or being at risk of a SOX deficiency — forces the need for system and process overhauls.
Allies in Sales: The largest champion for O2C transformation is often the Sales organization. If deals are getting stuck or misquoted, Sales loses revenue. By clearly demonstrating how system or process bottlenecks reduce selling time and deal velocity, Finance can earn strong advocacy from Sales leadership.
Executive alignment: In larger SaaS companies, the CFO and CIO are critical stakeholders. A well-defined plan that addresses both current system inefficiencies and future product expansions is more likely to gain executive approval.
Sometimes a crisis is a necessary catalyst, Koltsova says: “In my experience, it is really, really important to say, do you have a situation where you have a tipping point of something going wrong, or is this a scalability question? If something is really going wrong — something is falling through, something is not reconciling, you have a potential SOX issue — it becomes very easy to say, ‘Time out, we’re going to stop. We need to rip it out.’”
But Koltsova also acknowledges the greater challenge of proactive transformation. “The much harder one is to say, ‘We’re going to slow down deals, we’re going to slow down the back end,’” she says. “That costs money. That costs a ton of money to implement in time. So the only way to do this right, especially if the company’s growing very fast, is to get everyone on the same page that the next iteration of the company is based on having a much stronger Order-to-Cash system.”
“So the only way to do this right, especially if the company’s growing very fast, is to get everyone on the same page that the next iteration of the company is based on having a much stronger Order-to-Cash system.”
–Jane Koltsova
Senior Director, Global Revenue Controller, Formerly of PagerDuty
Signals that O2C is no longer working
As companies scale, it can be easy to dismiss early warning signs of O2C stress. Here are a few clues that it may be time for an overhaul:
Sales teams spending more time servicing than selling: If the Sales force is bogged down in explaining billing errors or exceptions, that’s a red flag.
Excessive manual work and spreadsheets: Teams that rely too heavily on Excel for revenue recognition, billing corrections, and reconciliations are at risk of errors.
Revenue leakage: For instance, professional services SKUs not automatically added to deals, or usage-based SKUs that are not billed accurately.
Frequent adjustments: If Finance has to repeatedly fix errors in revenue systems, it indicates the data flow from quoting to billing to revenue recognition is fractured.
“If Sales isn’t selling, I don’t care how good of a revenue accountant you are; you’re not going to have a job. That company is going nowhere.”
–Jane Koltsova
Senior Director, Global Revenue Controller, Formerly of PagerDuty
Deciding whether to rip out your current system
Sometimes the CFO wants to “rip out” existing O2C systems and start fresh. This is no small task, as switching costs are high, and any downtime can impede sales. Ask two key questions before embarking on such a project:
Is it really broken? If SOX compliance or accurate revenue recognition is in danger, that’s a valid reason to replace your system.
Is the solution future-proof? Work closely with Sales Strategy and Product. If the roadmap shows that new monetization models will strain the system in two to three years, a proactive change might be warranted.
When evaluating potential vendors, ensure they offer an implementation plan aligned with your compliance and growth needs. “If you select the wrong vendor, it can be career-limiting,” cautions one CAO.
Koltsova emphasizes that patience is essential. “PagerDuty was in such a mode of changing and shifting, truly shoring up the Order-to-Cash flow,” she recalls. “We made as many improvements as we possibly could. I think if anybody thinks moving to a brand-new O2C is a two-year deal, they are incorrect. It’s at least a five-year process. You do want to take your time, because if you don’t get this right, it can be career-limiting.”
Unifying O2C in a single system
One solution many SaaS companies choose is to consolidate O2C processes onto a single platform. By integrating the quote, order management, billing, and revenue-recognition processes in one place, companies can reduce manual work and maintain a “single source of truth.” According to Finance leaders who have done it successfully, the benefits include:
Eliminating data silos: Reduces risk of duplication or omission.
Minimizing hand-off errors: Fewer manual entries mean fewer surprises at month-end close.
Agility to adapt to growth: When the product or sales motion changes, you only need to update one system instead of multiple interconnected tools.
Koltsova’s experience at PagerDuty underscores the importance of IT partnerships in this journey. “I want Finance to lead, but IT should be a piece of the puzzle that allows for Finance to be very open with its business goals,” she explains. “At no time should a Finance person say, ‘I need you to do X, Y, and Z with the architecture.’ That’s where you get into trouble.”
She elaborates on this collaborative approach: “It was key for me to say, ‘Here are my requirements as a Finance leader. Here’s where I see risks and compliance issues.’ My IT partner or BizApps partner would say, ‘All right, I hear you, here’s what we need to do.’ So we worked together to come up with a roadmap to unify the solution. We were way more successful than if we went it alone.”
Building the right O2C team
A successful O2C organization is rarely a single group. At one SaaS scale-up, for instance, the “Order-to-Cash team” included five sub-teams, each handling different aspects of the process:
1. Revenue Recognition
2. Order Management / Billing Operations
3. Collections and Accounts Receivable
4. Revenue Accounting
5. Commissions
This O2C function also had dotted-line relationships with Deal Desk and Business Applications — including administrators for systems like Salesforce and Zuora. When these teams work together, they can unify processes across contracts, billing, and revenue recognition, dramatically reducing errors and manual rework.
Measuring success
How do you know your new O2C process or system is actually working? Look for these indicators:
Reduced approvals: If fewer sign-offs are needed for a routine transaction, your system is likely more automated.
Fewer manual touches: An increase in order volume or product complexity doesn’t necessarily mean hiring more Finance staff if the automation is working well.
Greater accuracy in revenue forecasts and SOX compliance: If the restatements and compliance gaps decrease, your risk is better contained.
Speed of change: When new usage-based models or new SKUs are introduced without causing major slowdowns, the new system is paying off.
Koltsova highlights tangible benefits from PagerDuty’s O2C transformation. “We decommissioned a large number of extremely complicated Excel spreadsheets,” she says “We toned down and removed a number of giant risks to the financial statements. And we made our people able to do high-value work instead of double and triple checking Excel functions.”
Shifting the mindset: Finance as a growth partner
Finance leaders often carry the stereotype of being overly cautious or the “Department of NO.” In reality, Controllers and CAOs are strategic partners. By deeply understanding the revenue drivers, competitive landscape, and product roadmap, they can apply their accounting expertise to help the business scale responsibly.
Koltsova passionately advocates for a collaborative rather than combative approach. “Don’t say ‘no,’” she says. “Figure out what it is that will actually move the needle without completely breaking the back. Once you have the front of the business understanding that you’re not just a machine of ‘no,’ they come to you earlier with problems.”
“Don’t say ‘no.’ Figure out what it is that will actually move the needle without completely breaking the back. Once you have the front of the business understanding that you’re not just a machine of ‘no,’ they come to you earlier with problems.”
–Jane Koltsova
Senior Director, Global Revenue Controller, Formerly of PagerDuty
It’s important to also highlight Finance’s role in supporting the business, she adds. “We are not a hurdle to be jumping over,” Koltsova explains. “If Sales isn’t selling, I don’t care how good of a revenue accountant you are; you’re not going to have a job. That company is going nowhere.”
As another Finance leader recently put it: “The entire organization needs to be focused on keeping risk at an acceptable level, not minimizing it at all costs.”
Controllers who step outside their comfort zone — engaging with Sales, listening to Product, and anticipating growth requirements — add tremendous value to both the top and bottom lines.
Balancing risk and growth requires a holistic view of the entire revenue cycle — from GTM strategy to detailed revenue-recognition processes. When Controllers and CAOs have a seat at the table early, they can guide system selection, ensure compliance, and support sales in unlocking new revenue streams.
As SaaS companies evolve from “grow at all costs” to “grow efficiently,” Finance leaders who seize this opportunity and collaborate cross-functionally will differentiate themselves — not merely as stewards of compliance, but as key drivers of sustained and scalable growth.
See the full conversation with Jane in this webinar: Transforming Order to Cash: Finance’s Moment to Lead
