At Madrona, we’ve long believed that the next great enterprise applications wouldn’t just store and organize information—they would actively work for users, automating tasks, making decisions, and continuously improving.
Back in 2016, we predicted that applications failing to leverage data and continuous learning systems would become obsolete. We called this shift Intelligent Applications, and today, that transformation is accelerating. AI-powered software is no longer just a tool; it’s becoming a dynamic workforce — handling tasks, anticipating needs, and driving real business outcomes.
Every area of enterprise software is being reinvented with modern intelligent applications: CRM, ERP, HR, marketing automation, and more. One of the biggest areas and most successful companies is ServiceNow ($160B market cap, $11B revenue, 22% growth, 31% FCF margin), which is masterfully serving the enterprise market and has repositioned itself around AI. But a product like ServiceNow is completely inappropriate for growth, mid-market, and startup companies. Yet these companies need a solution. Who will be the ServiceNow for the born-in-AI generation?
That’s why we’re excited to announce Ravenna’s $15M fundraise, which we’ve led with fellow co-investors Khosla Ventures and Founder’s Co-op.
The Problem: Outdated Internal Operations Are Holding Companies Back
Despite advances in AI and automation, internal operations remain frustratingly manual. Employees still navigate clunky portals, submit tickets into a black hole, and waste time switching between systems just to get simple requests handled. IT support, HR workflows, finance approvals — these processes are often slow, disjointed, and deeply inefficient.
Meanwhile, the teams running these workflows are buried in repetitive tasks that prevent them from focusing on higher-value work.
Ravenna is fixing this by applying AI-native automation to internal operations—seamlessly integrating into the collaboration tools employees already use, starting with native integration into Slack.
The AI-Native Service Management Solution: Built from First Principles
Many AI-powered enterprise tools take the same old processes — the same helpdesk systems, the same rigid ticketing flows — and try to speed them up with AI. That’s not what Ravenna is doing.
Ravenna was built from first principles, starting with a deep understanding of how work actually gets done inside companies — and, more importantly, where it gets blocked, delayed, or frustrated. Instead of trying to patch outdated workflows with automation, Ravenna reimagines internal operations from the ground up to remove friction entirely.
How Ravenna Works Differently
We evaluated the other companies using AI to address the IT service management (ITSM) space (including Moveworks, which ServiceNow subsequently acquired last month for $2.85B), but we concluded Ravenna is different in several critical ways:
- Embedded where work happens: Instead of forcing employees to switch contexts and log into separate systems, Ravenna lives inside Slack and Teams, making requests and workflows a seamless part of daily work.
- AI that understands work at a system level: Ravenna isn’t just responding to requests; it integrates deeply across enterprise systems to surface real-time information, automate tasks across multiple tools, and streamline handoffs.
- Proactive problem-solving, not reactive helpdesk: Most internal systems rely on employees pulling information when they need help. Ravenna flips this by pushing intelligent recommendations, automating repetitive tasks, and preemptively resolving common issues.
- Frees people to do deeper work: Instead of burdening internal teams with repetitive, manual tasks, Ravenna automates the busywork, so IT, HR, finance, and other teams can focus on higher-value initiatives.
This isn’t just about efficiency — it’s about transforming how work actually gets done. Ravenna ensures that employees spend less time navigating systems and more time on the creative, strategic, and high-impact work that drives businesses forward.
Ravenna: An AI-Powered User-Centric Approach to Internal Support
Most enterprise software companies build incrementally, tacking AI onto legacy systems in an attempt to modernize them. Ravenna takes the opposite approach.
Instead of retrofitting AI into outdated help desks, Taylor and Kevin worked back from the customer, asking:
- Where does work actually happen inside modern enterprises? (Hint: Not in portals or ticketing systems.)
- What’s blocking teams from getting the support they need? (Spoiler: Context-switching, outdated knowledge, and manual processes.)
- How can AI solve these problems in a way that fundamentally improves work?
The answer? An AI-native system designed to work inside the collaboration platforms where work already happens.
Ravenna lives in Slack (for now—Teams and other integrations are coming!), embedding AI directly into workflows so team members — both humans and soon AI Agents — get instant answers and operations teams are freed from repetitive, manual requests. Instead of employees wasting time filing tickets or searching outdated knowledge bases, Ravenna creates an instant, intelligent knowledge base that proactively resolves issues, automates workflows across systems, and ensures internal teams can focus on higher-value work.
Ravenna customers typically start with IT; however, the vision is much broader. Their system for automating internal work queues and support is broadly applicable to HR, RevOps, Customer Success, Finance, and beyond. During our due diligence, we were impressed to hear customers’ excitement about the breadth of Ravenna’s applicability.
The Founders: Deep Expertise in AI and Enterprise Operations
Ravenna’s founders, Taylor Halliday and Kevin Coleman, have spent their careers at the intersection of AI, automation, and enterprise operations.
Taylor, formerly director of AI engineering at Zapier, saw firsthand the demand for automation in business operations, especially around question-queue-response workflows, where employees constantly seek support for repetitive tasks and used Zapier extensively to cobble together workflows.
Kevin, who led GTM for AWS containers and serverless, experienced the challenges of large-scale knowledge sharing and coordination, working with some of the world’s most complex enterprise systems. He also saw the power of AI-driven automation in transforming internal operations, as well as the way Amazon’s internal ticket queue system was indispensable for getting work done across teams.
Their experiences — shaped across multiple startups, enterprise software companies, and even their own entrepreneurial journey — gave them a unique insider’s perspective on what was broken in enterprise service management and what it would take to fix it.
They realized that traditional help desks were stuck in the past, weighed down by bloated ticketing systems, rigid processes, and fragmented workflows. More importantly, they understood that AI wasn’t just a tool to speed up these processes — it was a chance to fundamentally reimagine how internal support should work.
That’s why they founded Ravenna: to create a first-of-its-kind AI-powered internal support platform that removes inefficiencies and enables teams to focus on meaningful work.
We also loved the way Taylor and Kevin have attracted an incredible team of A+ talent and created a distinct culture, where everything and everyone is focused on customers, relentless execution, while also caring about each other and having fun.
The Bigger Picture: Why AI-Native Service Management Matters Now
It’s not news or an exaggeration to say that we’re in the midst of a seismic shift in enterprise software.
- SaaS is evolving because of AI. Instead of static tools, AI-powered applications actively work for users, use natural language UIs, handle tasks, automate workflows, and adapt to real-world needs.
- Enterprise employees expect consumer-grade experiences. Nobody wants to log into a clunky portal or wait days for a response — they expect instant, seamless support inside the tools they already use.
- AI-native applications are creating massive productivity gains. Companies that embrace AI-driven automation aren’t just moving faster; they’re fundamentally changing how work gets done.
Ravenna is at the forefront of this transformation. By embedding AI-native automation inside Slack and Teams, they’re not just making help desks more efficient — they’re redefining enterprise service management for the AI era.
Looking Ahead
At Madrona, we invest in the frontier of intelligent applications — and Ravenna is exactly that.
AI isn’t just improving enterprise software; it’s redefining how work gets done. The best applications won’t just help employees do their jobs — they’ll become part of the team.
That’s why we’re proud to lead Ravenna’s $15M Seed round, alongside Khosla Ventures and Founder’s Co-op, and partner with Taylor and Kevin as they build the future of AI-powered internal operations.
Congratulations to Team Ravenna on this milestone! If you want to see what AI-Native Service Management looks like in action — and how intelligent applications can come to life in your organization’s workflow, check out their product here. And if you’re looking to build at the forefront of the space, they’re hiring!
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