The Systems and Processes That Got You to $20M ARR Won’t Get You to $200M
The path upmarket isn’t just about selling more—it’s about selling smarter. As product-led growth (PLG) companies mature, moving to enterprise sales isn’t a question of if, but when. And when that shift happens, your Order-to-Cash (O2C) process becomes more mission-critical than ever before. Enterprise customers bring bigger contracts, longer sales cycles, custom terms, and complex compliance needs.
Suddenly, simple billing flows and spreadsheet-based revenue tracking aren’t just inefficient—they’re risky. The systems that once worked fine for fast, self-serve growth start to crack under the pressure of enterprise-scale deals. If your finance systems can’t keep up, growth stalls, cash flow slows, and your team gets buried in manual work.
Sound uncannily familiar? If you’re a CFO or Chief Accounting Officer (CAO) gearing up for the next growth phase, this one’s for you.
As companies grow and introduce new revenue models and expand offerings, finance leadership teams often scramble for solutions that can reduce manual tasks and prevent human error without introducing new risks created by poorly structured automated workflows.
As Zuora prepares to roll out a new research survey of CFOs and CAOs , we took a look back at the challenges finance and accounting leaders told us they were facing in our last report and ideas for how to address them.
The upmarket shift is coming—are you ready?
While 69% of today’s fastest-growing PLG companies have introduced an enterprise offering alongside their self-serve model, 68% of finance leaders report not having the right technology to address growing demands from the business. That’s a huge problem. The fallout from multiple Order-to-Cash breakdowns due to enterprise deals doesn’t just impact finance—it can affect the reputation and viability of the entire company.
As we’ve covered previously, Finance leaders alone (not Engineering or Sales) are uniquely positioned to see and solve the end-to-end finance issues that crop up in the move upmarket. So, when should finance leaders start getting prepared? Typically, the inflection point for SaaS companies comes around the $50M annual recurring revenue (ARR) mark. At this stage, the “law of large numbers” kicks in, making it increasingly difficult to sustain rapid growth solely through self-service, transactional sales.
However, this point can vary widely by company. For instance, Zoom accelerated its enterprise sales investment around its Series C funding stage. Even quintessential PLG companies like Slack introduced a formal enterprise sales team as it approached the ~$50M ARR milestone. In the case of cloud communications company Twilio, enterprise salespeople are brought in when an annual contract value reaches $100,000, while Dropbox does so when at least 3% of a customer’s employees already use its product. For companies like these, moving upmarket was not just a strategic choice—it was a necessary evolution to maintain growth momentum.
While this shift is often considered a go-to-market issue, the reality is that finance teams experience significant operational impacts—from order processing complexity to advanced billing requirements. Understanding the differences between these two approaches can help finance leaders prepare for the inevitable challenges ahead.
As companies grow and introduce new revenue models and expand offerings, finance leadership teams often scramble for solutions that can reduce manual tasks and prevent human error without introducing new risks created by poorly structured automated workflows.
As Zuora prepares to roll out a new research survey of CFOs and CAOs , we took a look back at the challenges finance and accounting leaders told us they were facing in our last report and ideas for how to address them.
PLG vs. enterprise: two worlds, one finance stack
In a purely PLG motion, sales are often transactional—users swipe a credit card for a monthly subscription or usage-based spend and agree to the online terms and conditions, a standard contract. Deals close quickly and involve a single end-user or team solving an immediate pain point.
Enterprise deals, on the other hand, are larger, more complex, and higher-touch. Sales cycles tend to extend as reps navigate buying committees and multi-step procurement processes instead of single end-users. Before a deal is won, there are often lengthy contract negotiations and custom implementation requests.
Enterprise contract values also dwarf those of self-service plans, but landing them requires patience and orchestration. Another key difference? Enterprise customers typically expect high-touch support and customization—dedicated account managers, custom onboarding, tailored SLAs—whereas a PLG approach assumes the product largely sells itself with minimal hand-holding.
All told, making the shift from PLG to enterprise sales means moving from a fast, volume-driven, self-service model to a slower, consultative, high-value model. At scale, PLG inevitably evolves into a hybrid—combining bottom-up product-led growth with top-down enterprise sales—to sustain growth beyond the mid-market plateau. The most successful SaaS companies maintain their PLG foundation as a customer acquisition channel while building enterprise capabilities on top—creating an integrated approach rather than siloed motions.
You cannot ignore your PLG motion, just because you want to pivot to a sales-led growth or a sales-led motion. Your PLG is basically what got you to start offering on a more scaled basis.
–Sid Sanghvi
Head of Finance Business Applications at Asana
Order-to-Cash breaking points when finance isn’t enterprise-ready
In the early days of a PLG SaaS company, it’s not uncommon for engineering to take ownership of O2C systems. A few developers spin up lightweight billing logic, maybe integrate Stripe or Recurly, and add a “Buy” button into the product. It works—at first. The architecture is tailored to self-service users: fast sign-ups, automated payments, and minimal finance intervention. But this setup starts to show serious cracks as the business moves upmarket.
Failing to evolve your O2C infrastructure alongside your go-to-market strategy can pose serious operational and strategic risks. As your company transitions from a PLG motion to include enterprise sales, the gap between your existing finance systems and your emerging needs can become a silent drag on growth, efficiency, and compliance. The following are some of the O2C breakages and financial impacts you may begin to see as your company hits progressively higher ARR milestones:
The O2C breaking point timeline
Milestone
Trigger/Breaking Point
What Breaks in O2C
Finance Impact
~$5–10M ARR
Early self-serve traction
Homegrown billing scripts and Stripe setups can’t support multiple pricing models
Manual billing, missed revenue, dev team overinvolved
~$20M ARR
Add teams and tiers to pricing
No visibility into account-level discounts or usage caps
Revenue leakage, inconsistent pricing, no contract control
~$30M ARR
Introduce sales-assisted motion
CPQ lives in spreadsheets, inconsistent quoting
Quote-to-cash errors, slow approvals, friction between Sales and Finance
~$50M ARR
Start landing enterprise deals
Invoices need customization, manual rev rec spreadsheet can’t handle milestones
Missed billing events, audit risk, revenue recognition errors
~$75M ARR
Expansion begins (regional, industry, etc.)
Multi-currency, tax compliance, multiple entities not supported in existing systems
Delayed closes, compliance exposure
~$100M+ ARR
Hybrid GTM in full swing
Disconnected CRM, CPQ, billing, and ERP systems create huge reconciliation workload
Long close cycles, inaccurate forecasts, DSO spike
~$150M–$200M ARR
Complex renewals, custom deals, usage-based pricing proliferate
O2C becomes a Frankenstein system—nothing scales without more headcount or patching
OpEx spikes, team burnout, slow time to market
Contract complexity breaks simple systems
PLG-era systems are built for speed and simplicity: standardized pricing, automated credit card billing, and basic revenue recognition. On the other hand, enterprise contracts introduce bespoke pricing, milestone-based invoicing, and multi-element arrangements. Without a system designed to handle these layers, finance teams are forced into manual workarounds that slow down month-end closes and increase the risk of revenue recognition errors.
Additionally, enterprise customers bring geographic complexity, such as invoices that are billed to one country while provisioning happens in another. Without systems designed for this complexity, finance teams resort to manual workarounds that introduce errors and compliance risks.
AI and usage-based billing add another layer of complexity
The rise of AI features has introduced yet another dimension to the PLG-to-enterprise transition: usage or consumption-based pricing models alongside traditional seat-based subscriptions. This hybrid approach requires billing systems that can simultaneously manage both predictable recurring revenue and variable consumption charges, often within the same contract and invoice. For finance teams unprepared for this complexity, the result can be billing errors, revenue recognition challenges, and frustrated enterprise customers who expect seamless invoicing regardless of the underlying pricing models.
If you’re dealing with changes on the billing side—usage, consumption, whatever it might be—it’s key to keep SOX and financial statements front and center. 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
Former Senior Director of Global Revenue at PagerDuty
Revenue reporting becomes unreliable
Enterprise deals require sophisticated revenue recognition capabilities, including handling allocations, performance obligations, and contract modifications.If your system can’t automatically support these, finance teams must rely on spreadsheets and manual journal entries, exposing the business to audit risk, compliance gaps, and data inconsistencies.
On the PLG side, it’s pretty straightforward. If you are seat-based, it’s ratable throughout the term of your subscription. But the minute you move into your enterprise, or the SLG [sales-led growth] side, that’s where all the complexities come in. Now you have to worry about stand-alone pricing or SSP, your allocations, adhering to your 606 standards for getting all your rev rec, both for your seat-based and for your consumption-based models to adhere to standards.
– Sid Sanghvi
Head of Finance Business Applications at Asana
Collections grind to a halt
PLG companies often thrive on automated, credit card-based collections with minimal AR oversight. But enterprise deals rely on POs, net payment terms, and procurement approvals. Without a robust collections process—backed by systems that integrate with O2C workflows—you’ll encounter delayed payments, higher DSO, and ballooning cash flow unpredictability.
Manual effort consumes expensive talent
When your systems can’t handle custom quoting, approvals, or billing integrations, Engineering or IT often steps in to bridge the gaps. This pulls high-value resources away from product innovation and burdens them with patchwork code and ad-hoc scripts—creating long-term technical debt and unreliable processes. The more time your sales team spends on administrative work (manually creating documents with quotes or requesting approvals), instead of selling, will also cost you.
Fragmented systems lead to bad data and slow decisions
As you bolt on CPQ, invoicing tools, or revenue spreadsheets to plug gaps, data becomes fragmented. Finance ends up reconciling deals across disconnected systems—CRM, billing, revenue recognition—creating delays, inconsistencies, and mistrust in financial data. In fact, only 44% of finance leaders fully trust their revenue data due to these siloed processes.
Inability to scale with confidence
Ultimately, when your O2C systems aren’t integrated and flexible enough to support both PLG and enterprise motions, you can’t scale. Finance becomes reactive rather than strategic—focused on fixing yesterday’s issues instead of enabling tomorrow’s growth. These gaps might be invisible during PLG growth, but when the company introduces enterprise sales, they become unavoidable blockers.
“When I first became CFO, it took us almost a month to close the books. Once the month ended, we’d spend the next 20-something days trying to close the books again, only for the month to be over. This is typical for a lot of startups early on but is a level of maturity that would not work in the public markets.”
– Howard Wilson,
CFO of PagerDuty
The solution: Build a finance engine that can handle enterprise velocity
You can’t afford to wait until finance becomes the bottleneck. CFOs across industries are gearing up for rapid change, with 63% placing IT and digital transformation spending at the top of their priority list for the next year—that’s even more than cyber risk/security, at 48%.
Invest in your finance back office early
One often overlooked aspect of the PLG-to-enterprise transition is the impact on finance back-office teams, who bear the brunt of system inadequacies. When finance systems can’t handle enterprise complexity, it’s the finance team that creates manual workarounds, builds complex reconciliation spreadsheets, and works nights and weekends to close the books. This not only creates burnout risk but diverts talented finance professionals from higher-value strategic work. Early investment in robust systems isn’t just about efficiency—it’s about building a sustainable finance function that can support your growth journey from $20M to $200M ARR and beyond.
Build for change, not just current state
The transition from PLG to enterprise isn’t a one-time event but an ongoing evolution requiring systems that can adapt to changing business models. This rapid evolution means your finance infrastructure must be flexible enough to handle not just today’s challenges but tomorrow’s innovations. Building adaptability into your order-to-cash systems isn’t just good practice—it’s essential for maintaining competitive advantage in fast-changing markets.
If you just look at AI, in the last twelve months, you have seen the prices drop significantly and every SaaS company [with] an AI offering has to tweak their pricing and packaging because of the dynamics of the market.
– Sid Sanghvi
Head of Finance Business Applications at Asana
Start your O2C readiness assessment today and make sure your company is ready for transformation—identify the gaps, align your teams, and invest in the systems and skills that will power your enterprise future. Investing early in a scalable, integrated O2C platform—and in team members who understand both finance and systems—can prevent costly inefficiencies and delays. By aligning Finance, Sales, and IT, you can lead the charge to build an agile, enterprise-ready infrastructure where closing a $1M deal is as seamless as a $1K one.
Let’s talk about how to build a finance engine that scales with your ambitions. Or, explore Zuora on your own and watch a demo.
Want to learn more? Watch our webinar featuring Sid Sanghvi, Head of Finance Business Applications at Asana, who shares firsthand insights on successfully navigating the PLG to enterprise transition. Discover how Asana balanced its self-service foundation while building robust enterprise capabilities, managed the complexities of multi-product offerings and consumption-based pricing, and equipped their finance team with the right tools for success. Sid provides practical advice from his four years leading Asana’s finance transformation that you can apply to your own scaling journey.