Scaling 6 Products to $100M+ ARR Each: Samsara’s CPO Kiren Sekar on Multi-Product Growth
"Multi-Product Strategy Should Begin at $10M ARR, Not $100M ARR"
Kiren Sekar, Chief Strategy Officer and founding team member at Samsara, came to SaaStr Annual to do one of our best deep dives even on going multi-product. Samsara was intentionally multi-product from the earliest days, and they carefully planned out scaling 5+ products to $100M+ ARR.
And come see so many more great convos like this at 2025 SaaStr Annual + AI Summit on May 13-15 in SF Bay, including the CEOs and CXOs at vertical SaaS leaders ServiceTitan, Clio, MangoMint, Owner and so many more!
The Journey: From WiFi to IoT Fleet Management
Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” Despite his engineering background, Sekar helped Meraki build a scalable go-to-market engine for their wireless networking products.
After Meraki’s acquisition by Cisco, Sekar and several colleagues founded Samsara in 2015 to bring modern technology to physical operations industries that were still using antiquated systems. Their mission: increase safety, efficiency, and sustainability for the industries that power 40% of global GDP.
Samsara achieved remarkable growth – from $1M ARR a year after launch to $100M ARR just 2.5 years later. Now well above $1.3B ARR with 30%+ growth and positive free cash flow, Samsara is one of only six public companies achieving this trifecta.
The Five Lessons
1. CAC Payback Period Predicts Success More Accurately Than Any Other Metric
CAC payback period stands above all other SaaS metrics as the most holistic indicator of business health. Unlike isolated metrics like growth rate or gross margin, CAC payback simultaneously reflects market demand, go-to-market efficiency, and product quality. When customers desperately need your solution, your CAC decreases because they seek you out and move quickly through your funnel.
Sekar emphasizes CAC payback period as the single most important metric for product leaders to track. This metric reveals:
Market demand and product-market fit: Faster sales cycles = lower CAC
Go-to-market execution: Better lead quality, conversion rates = lower CAC
Product quality: Complex implementations, customization, high infrastructure costs = longer CAC payback
When CAC payback is healthy, scale aggressively. When it’s unhealthy, slow down and fix the underlying issues before accelerating.
2. Cross-Vertical Market Expansion Creates Unexpected Innovation Synergies
While many startups laser-focus on dominating a single vertical, Sekar’s experience at both Meraki and Samsara showed that deliberate cross-vertical expansion creates powerful network effects of innovation. By tracking and targeting diverse industries from day one (even pre-revenue), they discovered that solutions developed for one vertical would spark demand in seemingly unrelated industries. This cross-pollination effect accelerated product development in unexpected ways.
At Samsara, they formalized this with practices like “Transportation Tuesdays” where 20% of sales capacity focused on transportation verticals. Years later at $1B+ ARR, transportation still represents precisely 20% of their business—evidence that early market mapping establishes lasting foundations for growth. The biggest benefit wasn’t just revenue diversification but the accelerated innovation that came from customers in different verticals building on each other’s use cases.
Sekar challenges the binary SMB-vs-Enterprise mindset by highlighting the strategic importance of mid-market customers:
Professional buyers who can evaluate your product thoughtfully
Fast sales cycles (months not years)
Willingness to accept tradeoffs if core problems are solved
Substantial ACVs ($20-70K+) supporting full-featured sales motions
Lighter-weight requirements than enterprise
More data points about market needs than enterprise deals provide
3. Mid-Market Is The Perfect Laboratory For Both Product and Go-To-Market Development
Most founders falsely view market segmentation as a binary choice between SMB and Enterprise. Sekar revealed that mid-market customers (like Blue Bottle Coffee with ~100 locations) offer the perfect balance: professional buyers who make decisions like enterprises but with dramatically faster sales cycles and lower expectations for customization. These customers provide the critical advantage of giving you access to knowledgeable IT professionals who can evaluate your product thoughtfully and provide sophisticated feedback, unlike SMB owners juggling multiple roles.
Yet they close in months, not years, with substantial ACVs ($20-70K+) that support full sales motions including SDRs, AEs, and CSMs. This creates an ideal environment to perfect both your product and go-to-market motion before moving upmarket. Samsara leveraged this strategy to build a powerful enterprise business with 1,500+ customers paying $100K+ annually, while maintaining a healthy mid-market foundation.
4. Embed Customer Feedback Into Your Systems, Not Just Your Process
Rather than treating customer feedback as a periodic exercise, Sekar built it directly into the infrastructure of both Meraki and Samsara. During pre-revenue, they hired ADRs to book demos specifically for product managers to gather feedback before writing code. Once generating revenue, they created custom “feature request” objects in Salesforce that allowed salespeople to attach specific opportunities and dollar amounts to requested features, creating an empirical dataset for prioritization that could counter the inevitable end-of-quarter pressure from sales.
Most innovatively, they embedded “Make-a-wish” buttons throughout their product dashboards that captured screenshots of what users were seeing, creating a direct feedback loop from users to engineering via Slack channels. This multilayered approach meant that customer voice wasn’t dependent on formal research cycles but continuously flowed through their systems, allowing them to make data-driven decisions about roadmap priorities based on actual customer needs and attached revenue opportunities.
The most significant advantage came from customer acquisition—customers who might reject an incomplete single-product offering were willing to overlook gaps when presented with a multi-product platform vision. This strategy paid off dramatically: at Samsara, their second product has now surpassed their original offering in ARR. Sekar advises founders to think about multi-product strategy 100x earlier than conventional wisdom suggests, planting seeds that will compound over time.
Sekar described Samsara’s evolution of customer feedback mechanisms:
Pre-revenue: ADRs booking demo calls for product managers with potential customers
Early revenue: Custom “feature request” objects in Salesforce where sales could attach opportunities to requested features
Product-embedded: “Make-a-wish” buttons throughout the dashboard, sending feedback directly to Slack channels
In-person visits: Regular customer site visits to gain deeper context
5. Multi-Product Strategy Should Begin at $10M ARR, Not $100M ARR
The conventional wisdom suggests focusing exclusively on your core product until reaching significant scale ($100M+ ARR), but Sekar discovered that launching multiple products early (by $10M ARR) creates exponential advantages. At both Meraki and Samsara, they launched their second and third products within 1-2 years of their first, deliberately allocating engineering resources away from their successful core offerings. This counterintuitive approach established their identity as platform companies from the beginning, creating organization-wide capabilities for managing multiple products and user personas.
Both Meraki and Samsara launched multiple products within their first few years, a strategy that proved invaluable:
Created differentiation against single-product competitors
Established platform identity early
Attracted customers willing to overlook gaps in exchange for multi-product value
Helped engineering teams think about platform architecture
Created customer expectation of regular innovation
Today, Samsara’s revenue is diversified across multiple products, with their second product now generating more ARR than their original offering. Saer advises launching a second product by $10M ARR rather than waiting until $100M+.
4 Unexpected Learnings:
Their second product (not their first) is now Samsara’s largest revenue generator
Deliberately allocating 20% of early sales efforts to transportation verticals resulted in transportation representing exactly 20% of revenue at $1B ARR
Mid-market customers provide the best unit economics while also offering professional buyers who provide better feedback than SMBs
Embedding a “Make-a-wish” button directly in product dashboards creates a direct feedback loop more valuable than traditional customer feedback channels
As Samsara continues investing in both current products and new frontiers, they’ve structured their resource allocation as 70% to near-term opportunities, 20% to 2-3 year bets, and 10% to higher-risk, potentially transformative opportunities. This balanced approach has enabled them to maintain growth while continuously expanding their platform.