The Path to a Billion Dollars: How to Create Multi-Revenue Streams with Bill.com CRO Tom Clayton (Pod 536 + Video)

Why $1B Is a Different Sport Than $100M

Getting to $100M is often about finding a repeatable motion: one core use case, one primary buyer, one go-to-market engine that actually works. Getting to $1B is about scaling that motion while adding new engineswithout turning your product into a feature buffet nobody can digest.

At scale, your “one revenue stream” has enemies:

• Market saturation: you’ve already sold the obvious customers.
• Procurement gravity: larger buyers want more governance, proof, and predictability.
• Competition: once you look successful, your competitors suddenly become very spiritual about “copying is flattery.”
• Efficiency pressure: boards and markets don’t want growth; they want efficient growth.

Multi-revenue streams help because they give you more ways to grow per customer, more resilience during macro shifts, and more “levers” to pull when one channel gets expensive or one segment gets choppy.

What Tom Clayton Shared in Pod 536

Tom’s talk is essentially a blueprint for moving beyond “single-lane growth.” He frames a set of levers that become especially powerful after the $100M markwhen your brand is stronger, your customer base is meaningful, and your operational muscle is (hopefully) more than vibes.

1) Pursue Diverse Revenue Models (a.k.a. stop selling only one thing, one way)

The simplest version: capture value from different customer segments in ways that match their willingness to pay. That can mean experimenting with pricing tiers, premium offerings, adjacent products, transaction-based pricing, multi-sided monetization, and even white-label optionsso revenue grows with the value customers get, not just with new logos.

The mindset shift is important: you’re not “adding random fees.” You’re charging for real outcomes and aligning your pricing with how customers experience value.

2) Dive Deeper or Go Broader

Once you’re established, you face a strategic fork:

• Go deeper: verticalize your go-to-market, tailor messaging and workflows for specific industries, and become “the obvious choice.”
• Go broader: expand horizontally, simplify positioning, and capture a wider TAM with a more universal platform story.

The “right” answer depends on where you’re winning today. If you’re already dominating a niche, deepen it until competitors feel uncomfortable. If you’re seeing pull across multiple segments, broadenbut don’t dilute.

3) Extend Your Reach Through Efficient Channels

Channels don’t scale overnight. They’re slow-cooked, not microwaved. But at the right stage, they become a force multiplier: integrations, co-selling, bundling, and ecosystem distribution can unlock customers you’d never reach with direct sales alone.

Practical channel shapes include add-ons and bundling with complementary SaaS, upsells to large platform install bases, white-label distribution via big service providers, and partnerships with adjacent players serving the same buyer.

4) Expect Market Resellers to Pay Attention

Resellers, VARs, and SIs tend to follow demand. Once the market is already asking for you, partners become more interested, because you’re not a “bet”you’re a “bring me deals” machine.

5) Explore International Expansion (but with adult supervision)

International expansion can be a massive unlock, but it rewards companies that have a scalable operating model: compliance, localization, support, and product readiness. Global growth isn’t just translationit’s operational choreography.

Bill.com as a Case Study in Multi-Revenue Streams

BILL is a useful case study because its business naturally supports layered monetization. In its reporting, the company describes core revenue made up of subscription and transaction fees, plus float revenue (interest earned on funds held for customers). In other words: recurring revenue, usage-driven revenue, and financial yieldstacked.

Revenue Stream #1: Subscription fees (predictable, compounding)

Subscription revenue is your “rent.” It’s stable, forecastable, and can scale through seat expansion, plan upgrades, and packaging changes. BILL’s pricing structure includes per-user monthly plans, which supports that classic SaaS flywheel: more adoption → more users → more subscription revenue.

Revenue Stream #2: Transaction fees (aligned with activity)

Transaction-based fees scale when customers process more payments, move more money, or run more workflows. This can be a powerful design pattern: if your product helps customers move faster or do more volume, your revenue grows with their success.

Revenue Stream #3: Float revenue (a financial operations tailwind)

Float revenue can emerge when a platform holds customer funds temporarily in the process of moving money. While “float” has a traditional banking definition, in modern fintech platforms it’s often discussed as a yield on funds held during payment flows. This stream can be sensitive to interest rate environmentsmeaning it’s a lever, but also a variable you should respect.

Adjacent products and the “one-stop shop” strategy

BILL also expanded its platform capabilities through acquisitionsmost notably acquiring Divvy (spend management) to broaden the suite and move closer to a one-stop solution for SMB financial operations. That’s not just product expansion; it’s revenue expansion: new modules, new attach paths, and new ways to monetize the same customer relationship.

The key takeaway: multi-revenue streams are often not separate businesses glued together. They’re a carefully designed set of monetization methods that mirror how customers already behavepaying bills, managing spend, approving workflows, and tracking cash movement.

How to Build Your Own Multi-Revenue Stack

Let’s translate the strategy into a buildable model. The goal is to create a “revenue stack” where each layer strengthens the others. Think of it like a burger (stay with me): the bun is your subscription, the patty is the core workflow, and everything else is the delicious monetization that makes customers say, “Yes, I will pay extra for that.”

Step 1: Map value by segment (before you touch pricing)

Start with three lists:

• Segments: Who buys, who uses, and who approves?
• Outcomes: What measurable value do they get (time saved, errors reduced, faster cash collection, compliance)?
• Constraints: What they fear (risk, audits, downtime), and what they can’t easily change (legacy systems, regulated workflows).

Multi-revenue streams work best when each stream maps to a different slice of valuenot when it feels like you invented “Premium Premium” because the VP of Finance looked too happy on a customer call.

Layer A: Packaging and tiers (charge for maturity)

Tiering should reflect customer maturity:

• Starter: the core job-to-be-done, minimal governance.
• Growth: approvals, controls, reporting, integrations.
• Enterprise: multi-entity, SSO, APIs, advanced security, compliance workflows.

The cleanest upsells are the ones customers already asked forbecause they’re not upsells; they’re “please save me from this pain.”

Layer B: Usage- or transaction-based monetization (charge when value happens)

Usage-based revenue works when value scales with activity: number of payments, invoices processed, workflows run, API calls, seats active, or volume under management.

A simple test: if customers say “we love you more when we do more,” usage-based pricing may fit. If customers say “we love you most when we don’t notice you,” keep it subscription-led.

Layer C: Add-ons that are genuinely optional (and genuinely valuable)

Add-ons should be:

• Outcome-specific: advanced analytics, audit trails, premium support.
• Role-specific: procurement tools, admin controls, finance ops automation.
• Industry-specific: vertical compliance modules, templates, integrations.

If an add-on is required for basic success, it’s not an add-on. It’s the product. Price it accordingly.

Layer D: Partnerships and channel revenue (let other people sell your product)

Channel strategy is where “multi-revenue streams” becomes “multi-growth engines.” Examples:

• Accounting ecosystem: partner with firms who onboard clients and earn margin.
• Platform integrations: become the default add-on inside larger systems.
• Resellers and SIs: let service providers implement, configure, and expand you.

The trick is alignment: partners need a reason to care (margin, pull-through demand, services revenue), and customers need a reason to trust (quality, outcomes, support).

Layer E: Product expansion into adjacent workflows (earn the right to charge more)

Adjacent expansion works when it reduces tool sprawl: fewer logins, fewer exports, fewer “who approved this?” email threads. If you can take a messy financial workflow and make it feel boringin the best wayyou can justify new modules and higher total contract value.

Layer F: Inorganic growth (M&A as an accelerant, not a crutch)

Tom’s framework also emphasizes using both organic and inorganic tactics. Acquisitions can add product lines, technology, or distribution, but they only work if you can integrate into a coherent suite. Customers should feel “wow, this got easier,” not “wow, now I have three dashboards.”

Metrics That Prove It’s Working

Multi-revenue streams aren’t a flex; they’re a math problem. You want to know if your streams are compoundingor quietly canceling each other out.

Net Revenue Retention (NRR): the “are customers buying more?” test

NRR captures expansion, churn, and contraction in one number. If your NRR stays above 100%, your existing base is growing even before new customers show up. That’s how $100M becomes $1B without requiring your sales team to survive exclusively on caffeine and motivational quotes.

A commonly used formula is: NRR = (Starting revenue + Expansion − Churn − Contraction) / Starting revenue.

Attach rate: the truth about add-ons and suites

If you add a second product/module, track how often it gets adopted:

• New-logo attach: % of new customers who buy the add-on at purchase.
• Expansion attach: % of existing customers who adopt within 6–12 months.

Low attach rates usually mean one of three things: unclear value, poor packaging, or friction in implementation. (Sometimes all three. Overachievers.)

Revenue mix health: don’t let one stream become a single point of failure

Subscription revenue stabilizes planning. Usage/transaction revenue rewards customer success. Financial yield (where applicable) can be a tailwind. The healthiest mix is one where no single stream is the only reason you hit the quarter.

Five Signs You’re Actually on the Path

In the Pod 536 breakdown, Tom highlights signals that your new growth levers are workingnot just “we had a good month,” but structural progress.

1) You’re crossing the chasm (from early adopters to pragmatists)

When mainstream buyers show up, they expect references, predictable outcomes, and a sense that you’re the category’s safe bet. If your deals increasingly involve structured evaluation and peer validation, congratulations: you’re no longer “a cool tool.” You’re a decision.

2) A seismic shift expands your opportunity

Major shifts (market changes, tech shifts, regulatory changes, macro events) can increase demand for automation and financial control. The best companies don’t just ride the wavethey reshape their packaging and messaging to match the new reality.

3) Your growth rate accelerates after becoming established

Growing is hard. Growing faster while you’re bigger is harder. If your growth rate accelerates as you scale, it usually means your monetization and distribution are compounding.

4) Retention and expansion improve over time

Improving NRR typically means your product is becoming more embedded, your customers are expanding usage, and your monetization fits the value delivered. It’s also the cleanest proof that multi-revenue streams aren’t “extra fees”they’re extra value.

5) You’re using both organic and inorganic fuel

Organic growth is the engine. Inorganic growth can be the turbo. But the turbo only works if the engine is tuned. When M&A adds capabilities that increase suite adoption and reduce churn, it becomes a legitimate lever toward $1B.

Common Traps (and How to Dodge Them)

Trap #1: Monetizing complexity instead of outcomes

Customers don’t want to pay for “more settings.” They want to pay for less chaos. Tie pricing to outcomes: speed, control, compliance, visibility, risk reduction.

Trap #2: Launching five new revenue streams at once

Multi-revenue does not mean “multi-distraction.” Add one stream, instrument it, learn, then scale. Otherwise you’ll be running experiments that all look like they worked because nobody knows what changed.

Trap #3: Channel conflict

If your direct sales team and partners are fighting over the same deal, nobody wins (except your competitors). Define rules of engagement, margins, implementation responsibilities, and how customer success works in a partner-led motion.

Trap #4: International expansion before operational readiness

Going global is exciting until you meet local compliance, local payments norms, local support expectations, and local definitions of “ASAP.” Make sure your product, legal posture, and support model can scale.

A 90-Day Action Plan

Here’s a practical plan to start building multi-revenue streams without turning your roadmap into a junk drawer.

Days 1–30: Diagnose and choose one lever

• Segment your customer base by value drivers and willingness to pay.
• Identify the highest-potential second stream (add-ons, usage fees, payments, partner distribution, or adjacent product).
• Define success metrics: attach rate, NRR impact, payback, expansion velocity.

Days 31–60: Design packaging and run controlled tests

• Create a clear packaging story (who it’s for, what outcome it delivers, how it’s measured).
• Test pricing with a small cohort (new deals or expansions) and collect qualitative feedback.
• Enable Sales/CS with a tight narrative: “why this exists” and “how customers win.”

Days 61–90: Operationalize and prepare scale

• Build dashboards for the new stream (revenue, attach, churn, expansion lift).
• Fix friction: onboarding, billing clarity, documentation, implementation time.
• Decide: iterate, expand, or kill the experiment (yes, killing is a strategy).

The end goal isn’t “more revenue streams.” It’s more durable growthwith multiple paths to win.

Conclusion

Tom Clayton’s Pod 536 playbook is refreshingly practical: diversify monetization, choose a depth-vs-breadth strategy, build efficient channels, let resellers follow market pull, and expand internationally when you’re ready. Underneath it all is a simple truth: the path to $1B is paved with compounding systems, not one heroic quarter.

If you’re aiming for that billion-dollar milestone, build a revenue stack that matches customer valuesubscription for stability, usage/transactions for alignment, add-ons for outcomes, partners for scale, and (when it makes sense) platform expansion for suite growth. Then measure relentlessly, simplify constantly, and keep your customers winningbecause churn is the only competitor you can’t out-market.

Field Notes: of Experience-Based Lessons on Building Multi-Revenue Streams

Multi-revenue strategy sounds glamorous until you try to ship it. Then you discover the real final boss is not your competitorit’s internal alignment. The most successful teams treat new revenue streams like product launches, not pricing toggles. They write a crisp “why” document, define the customer outcome, and make it painfully obvious who should buy it and when.

One pattern shows up again and again: the second revenue stream often fails the first time because it’s framed as “more monetization” instead of “more value.” Customers can smell a cash grab the way dogs can smell fear. If the story is “we added a fee,” push pause. If the story is “we removed three hours of manual work per week and reduced month-end close stress,” now you’re talking.

Another lesson: bundling is powerful, but only when it reduces decisions. Customers do not want to assemble IKEA furniture made of pricing SKUs. If your packaging requires a calculator, a translator, and a support ticket, you’ve created frictionnot choice. The best bundles feel like: “This is the set of capabilities you need at your stage,” and the upgrade path feels like: “You’ve grown; here’s the next set.”

Usage-based pricing is also frequently misunderstood. It works beautifully when usage correlates with value, and it backfires when usage correlates with anxiety. If customers are afraid to use the product because the bill might surprise them, you’ve turned your value into a horror movie. The fix is predictable guardrails: clear meters, spend controls, alerts, and tiers that cap the fear factor.

Channels are the long game. Early on, partners may smile politely and then disappear like a ghosted first date. That’s normal. Partners move when customers pull. The teams that win in channels invest in partner enablement like it’s a product: training, deal registration, simple packaging, implementation playbooks, and a clear “what’s in it for you” that doesn’t require interpretive dance.

Finally, remember that multi-revenue streams increase complexity, and complexity demands operational excellence. Billing, forecasting, customer success motions, and product analytics all need upgrades. The companies that reach $1B don’t just add streams; they add systemsso the business can scale without becoming a maze where revenue goes in and nobody knows where it came from.