Incumbent vs challenger: why SaaS leaders rarely get disrupted the old way

Distributors: in enterprise SaaS this mostly means systems integrators and consultancies (Deloitte, Accenture, Cognizant) who implement and customize software for large clients, plus increasingly the vendors' own partner marketplaces.

Regulators: bodies like the SEC (Securities and Exchange Commission, the US financial markets regulator) for public company disclosures, and data protection authorities enforcing GDPR (General Data Protection Regulation, the EU's data privacy law) in Europe, which shapes how customer and employee data can move between systems.

Why "better" doesn't win the deal

Three forces protect incumbents that have nothing to do with product quality.

Switching costs. Payroll, benefits, tax compliance, and org data are woven into a company's operations. Migrating Workday to a challenger means re-mapping years of historical data, retraining HR staff, and re-certifying tax and compliance workflows across every jurisdiction the company operates in. For a multinational, that is not a weekend project. It is a 12 to 24 month program with real failure risk (a botched payroll migration can mean employees not getting paid correctly).

Procurement cycles. Enterprise software isn't bought by one person. A switch typically requires sign-off from HR, finance, IT security, legal, and often the CFO's office. Each function runs its own vetting: security questionnaires, SOC 2 audits (System and Organization Controls, a common compliance report SaaS vendors provide to prove data-handling standards), data residency checks for GDPR compliance, and contract renegotiation. This alone can take a year before a single user logs into the new system.

Integration lock-in. Large enterprises don't run Workday in isolation. It connects to Slack, to identity providers like Okta, to expense tools, to custom internal systems built by the client's own engineering teams over a decade. Every connected system is a reason to stay. Ripping out the core HR system means touching dozens of downstream integrations, each with its own owner and its own risk of breaking.

Rippling can be faster, cheaper, and better designed and still lose the deal, because the deal was never purely about the product. It's about the cost and risk of change.

The challenger's real strategy

Smart challengers know this, so they rarely attack incumbents head-on in the largest accounts first. Instead:

• They target the segment incumbents ignore. Rippling built early traction with small and mid-sized businesses that had never bought Workday in the first place, avoiding the switching-cost problem entirely by winning greenfield deals.
• They bundle adjacent products. Rippling expanded from payroll into IT device management, spend management, and benefits, making itself the new system of record before competing directly on HR.
• They wait for trigger events. Companies switch core systems mainly during mergers, private equity buyouts, or leadership changes, moments when the cost of disruption is already being absorbed for other reasons. Challengers position hardest during these windows.

This is the same playbook Salesforce used decades ago against Siebel, and that Snowflake used against on-premise data warehouses: don't fight for the locked-in customer, win the next generation of customers who haven't locked in yet, then grow with them.

Where the money actually sits

Incumbents monetize the lock-in directly. Multi-year contracts, high renewal rates (often cited in the 90%+ range for mature enterprise SaaS, treat this as an industry norm rather than a precise universal figure), and expansion revenue (selling more modules to existing customers) mean an incumbent's real product is the switching cost itself, not just the software.

This shows up in a simple framing:

Customer lifetime value roughly equals average annual contract value × expected years retained × gross margingross marginGross margin is the share of revenue left after subtracting the direct cost of producing goods or services, expressed as a percentage of revenue.View full definition →.

If Workday charges an enterprise $500,000 a year, retains that customer for 10 years because switching is so painful, and runs an 80% gross margingross marginGross margin is the share of revenue left after subtracting the direct cost of producing goods or services, expressed as a percentage of revenue.View full definition →, the lifetime valuelifetime valueLifetime Value: the total revenue (or profit) a customer generates throughout their entire relationship with your business.View full definition → is close to $4 million from that single account. A challenger needs to be extraordinarily better, or extraordinarily cheaper, to justify a buyer taking on migration risk against that kind of embedded relationship. This is why incumbent SaaS valuations often reward net revenue retentionnet revenue retentionNet Revenue Retention measures the percentage of recurring revenue retained and grown from existing customers over a period, including upsell and expansion, net of downgrades and churn.View full definition → (the share of revenue kept and expanded from existing customers, excluding new sales) as heavily as new customer growth: it is a direct measure of how sticky the moatmoatA lasting edge over competitors: a resource, capability or position they cannot easily replicate, letting a firm earn above-average returns over time.View full definition → is.

For more on how these dynamics play out across the enterprise software market, the OECD's work on digital markets offers a useful, non-vendor view of concentration and competition in software markets.

The limits of the moatmoatA lasting edge over competitors: a resource, capability or position they cannot easily replicate, letting a firm earn above-average returns over time.View full definition →

Incumbency is not permanent immunity. Three things erode it over time.

Platform shifts. Incumbents built for on-premise or early cloud architectures can be structurally slower to adopt genuinely new paradigms, for example embeddingembeddingAn embedding is a numerical vector that represents data (text, images, or items) in a way that captures meaning, so similar items sit close together in space.View full definition → AI copilots deeply into workflows rather than bolting them on. If a shift is large enough, it can reset the competitive board, as cloud computing itself did to on-premise enterprise software vendors in the 2000s and 2010s.

Procurement fatigue with bundling. As challengers like Rippling or Deel bundle more functions (HR, IT, spend, payroll) into one platform, they start to look less like a risky point solution and more like an alternative system of record, which lowers the perceived switching risk for the *next* wave of buyers.

Regulatory pressure on data portability. Rules like GDPR's data portability provisions in Europe, and growing scrutiny of software interoperability from competition regulators, can gradually lower the technical cost of switching, even if the operational cost remains high. This is a slow-moving force but a real one to watch.

The realistic picture: incumbents rarely lose the customers they already have. They lose the fight for the customers they haven't signed yet.

🎬 [VIDEO: "Why Enterprise Software is So Sticky" - youtube.com - search for enterprise SaaS switching cost and moatmoatA lasting edge over competitors: a resource, capability or position they cannot easily replicate, letting a firm earn above-average returns over time.View full definition → explainer content from established business/tech channels covering software business models]

Key Takeaways

• SaaS incumbents like Workday defend market position mainly through switching costs, long procurement cycles, and deep integration lock-in, not through product superiority.
• Challengers like Rippling typically win by targeting customers who haven't yet locked into an incumbent, then expanding via bundling and waiting for trigger events like M&A or leadership change.
• Customer lifetime valueCustomer lifetime valueLifetime Value: the total revenue (or profit) a customer generates throughout their entire relationship with your business.View full definition → (annual contract value × retention years × gross margingross marginGross margin is the share of revenue left after subtracting the direct cost of producing goods or services, expressed as a percentage of revenue.View full definition →) explains why incumbents can absorb years of "worse" product perception without losing revenue.
• Net revenue retention is a key signal of strength in enterprise SaaS: it measures how much value is locked in versus how much depends on winning new logos.