Structural limitations in legacy systems and the rising costs of inefficiency are driving a fundamental shift in how businesses think about operational and financial software. It’s no surprise that 70% of newly implemented ERP initiatives are projected to fall short by 2027, and even basic deployments take 6 to 12 months. Teams still battle mismatched SKUs, oversold inventory, shipment delays, and countless hours spent resolving avoidable errors.
But the landscape is evolving fast. Buyers are demanding AI-native, composable solutions that deploy quickly and scale as their business grows. Advancements in LLMs and foundational models are finally making that possible.
That’s why we are thrilled to lead their $55M Series B, and announce our investment and partnership with DOSS, an AI-powered Operations Cloud that manages the flow of goods, dollars, and data, starting with inventory-based businesses. They have a broader vision to become the system of action for finance and operations without replacing the general ledger, delivered with a customer-centric approach that is efficient yet adaptable to the inherent business complexity. We are joined in this round by Premji Invest, Intuit Ventures, Theory, and a stellar list of angels and seasoned operators.
The Great Re-bundling of the Finance Stack
Over the last two decades, we have seen an unbundling of the finance & accounting stack, which gave way to companies like Zuora in A/R and Zip in procurement. In many ways, while the tools got more specialized, customers lost shared context across their supply chain and operations. It became increasingly hard to get a single view of an item as it traversed the supply chain from idea to prototype to finished good to sale and almost impossible to layer changes if needed. This laid the groundwork for a re-bundling of the stack, this time vertically by segment of the market, through a single pane of glass and with the right integrations to best-in-class solutions within billing or invoicing.
DOSS is building for one of the most complex yet massive segments of the market. Inventory-based businesses have some of the most disjointed workflows that have historically been underserved and require point solutions, integrations, and even homegrown solutions that are typically patched together by an understaffed IT team. The complexity of these types of businesses as they scale combined with advancements in AI have almost forced us to realize that inventory ledger needs to be decoupled from the general ledger.
The core thesis behind this is simple: you can’t build a modern cloud operations platform without unifying the fragmented supply chain workflows beneath it, and the resulting system designed for the modern enterprise needs to be robust, dependable, and adaptable. DOSS is doing exactly that.
The Right Customer-Centric Approach
The typical DOSS customer manages workflows through several point solutions today — QuickBooks for accounting, Shopify for sales, Airtable for inventory tracking, Google Analytics for reporting. This fragmentation leads to limited visibility, mismatched integrations, and multiple points of failure across critical workflows.
Rather than shove “out of the box” software at a complex problem, DOSS is applying the “Service as Software” playbook and doing the work of truly understanding customer pain points. They are implementing one module at a time, plugging into the critical gaps of a supply chain workflow, with the goal of replacing point solutions across the stack over time and evolving into the underlying flow of operations for the business, powered by a unified data layer that underpins the architecture.
Most notably, DOSS prefers to sit alongside and partner with existing solutions rather than rip them out on day one. Their priority has been and will always be optimizing the least disruption to the flow of operations while laying the groundwork for a platform that can evolve into broader use cases. Over time, we believe DOSS is best positioned to disrupt the full stack but in a way that customers will not only accept but welcome.
What Sets DOSS Apart
The operations of inventory-based businesses are incredibly complex and disjointed, so much so that there often isn’t even a single person at a company who knows the end-to-end workflow. For a multi-SKU, multi-product, multi-location business like Verve Coffee, correctly tracking a coffee bean from the source to the roastery ultimately to the final cup of coffee that is sold to an end customer can make or break the flow of operations.
The goal at DOSS is to be that “person” within each organization who understands the full supply chain. This drives their ability to move quickly, guide customers through complexity, and serve as the true transactional system of action. They spent years building their “Unified Master Data” which supports composability, a low-code / no-code interface, and real-time visibility — delivered by their “value-engineering” implementation and deployment team.
What has become increasingly clear is that their master data layer creates a unique opportunity: the potential to codify best practices and drive meaningful operational efficiency across customers. With the infrastructure they’ve built, DOSS is positioned not only to land and expand within existing accounts but also to extend their learnings into adjacent industries with similar operational patterns. Soon, the operations of a coffee business may not look so different from that of a construction business.
As the industry shifts from cloud-native architectures toward agentic ones, DOSS is building for a future where operations are managed by humans and AI agents working together. Their platform is designed so that implementations become living systems that can self-configure, self-correct, and evolve alongside the business. That represents a generational opportunity to transform systems of record into true systems of action, freeing businesses to focus on what they do best: making great products for their customers.
Enter the DOSS Team
Wiley Jones and Arnav Mishra were united as co-founders by their dedication to disrupt a highly complex and underserved market. We were drawn to Wiley’s obsession with prioritizing durability in a market where stickiness is an inherent advantage and Arnav’s ability to get deeply technical while also building a product and team that will stand the test of time. They’ve found the right balance of deep empathy for the customer with first principles thinking, and the learning mindset required to transform the category.
We are thrilled to announce our investment in DOSS and honored to partner and join the board with Wiley, Arnav, and the DOSS team on their journey to power the next generation of adaptive resource solutions. Onwards!
Karan Mehandru is a managing director at Madrona, where he invests broadly in B2B SaaS and AI-native companies across early and growth stages. He is an investor in Zapier, Outreach, Cohesity, Auth0, Fyxer, GrowthX, Algolia, Klaviyo, Deepgram, Clerk, Charta, Trek Health, and others.
Anna Chen is an investor at Madrona, where she focuses on acceleration-stage investments in enterprise software, AI, and consumer technologies out of Madrona’s Palo Alto office. She is an investor in DOSS, OpenHands, Trek Health, WisdomAI, GrowthX, and Fyxer AI. Prior to Madrona, Anna was a growth investor at General Atlantic and investment banker at J.P. Morgan.
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