Madrona is a multi-stage technology investor rooted in the Pacific Northwest and increasingly active across the U.S., especially from Seattle and Palo Alto. The firm is known for partnering from company formation through scale, with a hands-on model built around board partnership, talent access, go-to-market help, and deep ties to the Amazon/Microsoft ecosystem. Today, Madrona is especially focused on AI-native applications, agentic software, and enabling infrastructure where durable workflow and data advantages can be built.
Evaluation weights
How much weight this firm places on each dimension. Totals 100%.
Revenue, growth, and unit economics
Size, timing, and competitive landscape
Founder experience and execution ability
Differentiation and technical quality
- Favors application-layer and agentic AI over direct foundation model bets
- Comfortable investing early before perfect alignment if founder insight is strong
- Prefers measurable customer pull over headline ARR milestones
- Leans into deals where Madrona can take a board role and materially help operationally
Pitch difficulty
How hard it is to get a meeting and close funding from this firm.
- Funded / yr
- 37Deals closed in a typical year.
- Led / yr
- 15Rounds led in the last 12 months.
- Pitches / yr
- ~4628Decks reviewed in a typical year.
- Acceptance rate
- 0.8%Share of pitches that get funded.
Estimated — public data is not fully disclosed.
Why it's hard
- Strong preference for clean metrics and real PMF signals
- Avoids undifferentiated AI/model-layer companies and fragile market positions
- Often seeks active involvement, including board seats and deep operating partnership
- Concentrates heavily in sectors and geographies where it has an edge, especially the PNW and AI-driven software
Madrona is accessible across multiple stages and willing to engage early, but it is highly conviction-driven and filters hard on founder quality, metric clarity, and differentiated AI positioning. Their hands-on style, board orientation, and preference for durable product pull make them selective even when they are risk-on.
Green flags
What drives a yes for this firm.
- Mission-driven founders with strong founder-problem fit
- Evidence of real product pull through retention, usage, and expansion metrics
- AI differentiation at the application or workflow layer rather than undifferentiated model exposure
- Clean, precise metrics and crisp revenue definitions
- A clear path to product-market fit or visible compounding momentum toward it
Red flags
What kills deals and gets a fast no.
- Messy or ambiguous KPIs, especially unclear revenue definitions
- Pilot-driven revenue with weak conversion, retention, or repeatability
- AI products that are thin wrappers likely to be displaced by foundation model vendors or hyperscalers
- Growth that depends on heroic sales effort instead of product demand
- A weak explanation of why this market and team can build a durable company
How to win
Patterns that lead to successful pitches.
- Show precise retention, usage, expansion, and unit economics rather than relying on ARR alone
- Position the company in the application, workflow, or enabling infrastructure layer with clear defensibility
- Demonstrate authentic founder-problem fit and a mission-driven reason for building now
- Make clear how Madrona's network in Seattle, enterprise GTM, recruiting, or partnerships can accelerate the business
- Present evidence of compounding product pull from design partners or early customers
Fund strategy & identity
Who they are and how they operate.
- Invest from Pre-Seed and Seed through Series A, then re-engage at B/C via Acceleration funds
- Lead or co-lead selectively at early stage and frequently at Series B/C
- Concentrate capital in AI-native applications, intelligent software, and selective enabling infrastructure
- Stay heavily involved post-investment on hiring, GTM, partnerships, and future financings
- Prioritize markets where Madrona's Seattle network and operating support can materially accelerate outcomes
Firm identity
Investment focus
Industries, themes, and typical ARR expectations.
Industries
Investment themes
Typical check by stage
Typical ARR by stage
Investment thesis
Core beliefs and strategy behind their investing approach.
Madrona is a multi‑stage, tech‑focused firm anchored in the Pacific Northwest with an expanding West Coast/U.S. footprint. Their core belief is to partner “from day one for the long run,” providing hands‑on company‑building support, board partnership, and deep go‑to‑market and talent networks tied to Seattle’s Microsoft/Amazon ecosystem. Sectorally, Madrona has spent more than a decade championing applied AI and “intelligent applications,” and today concentrates on AI‑native applications and agents, the enabling infrastructure/data layers that remove friction between models and users, low‑code/no‑code, AI‑enabled biotech/life‑sciences intersections, and next‑gen consumer apps. They explicitly emphasize value capture “up the stack” (agentic/application layers) versus competing head‑on with foundation‑model leaders, while selectively backing infrastructure that powers AI apps. Stage and geography: With Fund X (early‑stage) and Acceleration Fund IV (B/C), Madrona invests from formation/pre‑seed and seed/Series A through B/C inflection rounds. The firm remains PNW‑centric while investing nationally; it opened a Palo Alto office (2022) and expects the majority of new capital to continue into the Pacific Northwest, leveraging its “Seattle perspective” and relationships with Amazon and Microsoft. What they avoid: While industry‑agnostic across tech, their public commentary suggests they avoid direct model‑layer battles with OpenAI/Anthropic, preferring domain‑specific apps and enabling layers where durable differentiation can be built.
Decision patterns
How they evaluate and make investment decisions.
What makes them invest: (a) mission‑driven founders who deeply understand why a problem exists; (b) clear signals of product‑market fit (PMF) or the path to it; (c) momentum and clean metrics that prove real demand; and (d) markets where AI‑native differentiation (data/workflow moats, agentic UX) can compound. Madrona emphasizes judgment over rigid ARR thresholds—particularly in applied AI. They explicitly state that investors “have stopped caring” about hitting a specific ARR milestone; instead, they underwrite unit economics, retention/usage cohorts, expansion and trajectory. A $500K‑ARR company with crisp pull‑driven data may be more fundable than a $5‑10M‑ARR company with one‑off pilots. Deal‑breakers: ambiguity and imprecise metrics; unclear revenue definitions; stalled or non‑compounding usage; “heroic” sales masking weak product pull; and category positions likely to be disrupted by hyperscalers or foundation‑model vendors. Timing matters—Madrona will often engage early but delay a check until product, team, and market are sufficiently aligned. When they invest, they typically take active board roles and help on hiring, GTM, partnerships, future financing, and customer access—weighting team and market/traction roughly equally, with a premium on evidence of durable pull and differentiated workflows/data. Typical check sizes and ARR/traction at investment (by stage): - Formation/Pre‑seed/Seed: first checks from hundreds of thousands up to several million (≈$0.5‑$8M). Companies can be pre‑revenue; emphasis is on founder/problem fit, early design partners, crisp hypotheses, and speed of iteration. - Series A: No fixed ARR threshold; examples include ~$500K ARR with crystal‑clear unit economics and strong retention/usage, or ~$1M ARR growing 30% MoM beating larger but slower growth. - Acceleration (B/C): Initial checks around $7‑12M, leading or co‑leading with board seats, at strong PMF and an inflection to scale. Lead/follow and board: Frequently lead/co‑lead at B/C and selectively lead early rounds; typically take a board seat and provide full‑stack operational support.
Risk appetite
Madrona blends disciplined early‑stage partnering with a clear “risk‑on” posture in the current AI/innovation cycle. At formation/seed/A, they engage before perfect alignment, often ideating and testing alongside founders—then wait or proceed based on timing and milestone clarity. They are patient and supportive through volatility (e.g., reinvesting through product rebuilds) and maintain significant reserves. At B/C, the Acceleration Funds lean in at growth inflection, often leading or co‑leading and taking/holding board seats. Practically, they lead or co‑lead many B/C rounds and will lead selective early rounds; they are comfortable being highly active but can also collaborate with existing syndicates. Public guidance in 2025 explicitly frames the macro backdrop as “risk‑on,” with internal conversations encouraging “foot on the gas” execution plans for strong companies. Overall, the firm is conviction‑driven but avoids “tourist” risk—eschewing head‑to‑head model wars—preferring agentic/app‑layer differentiation and enabling infrastructure where they can help unlock customers, talent, and partnerships.
Notable investments
Key portfolio companies and why they fit the thesis.
- SmartsheetLeadSeattle‑originated no‑code SaaS platform aligns with Madrona’s PNW and intelligent‑applications thesis; Madrona led the Series A in 2007.
- RedfinLeadPNW consumer marketplace/proptech; Madrona was the first institutional backer and led early rounds, fitting the “Day One” strategy.
- ApptioLeadEnterprise B2B SaaS from the Seattle region; Madrona co‑led the 2007 Series A, reflecting its focus on cloud‑infrastructure software.
- RoverLeadSeattle‑based pet‑care marketplace incubated by Madrona; Madrona led the 2012 Series A, matching its consumer‑marketplace focus.
- OctoMLLeadUniversity of Washington spin‑out for ML model optimization; Madrona led the seed round, fitting its AI/ML and intelligent‑applications emphasis.
- Turi (formerly GraphLab)LeadFoundational horizontal ML platform with UW roots; Madrona co‑led the Series A, aligning with its AI infrastructure thesis.
- SeekOutLeadSeattle‑area AI‑powered talent platform; Madrona led the Series A, reflecting its applied‑AI and local‑founder focus.
- Crowd CowLeadPNW‑based marketplace for premium meat; Madrona led the 2018 Series A, consistent with its consumer‑commerce thesis.
- The RiveterLeadSeattle‑based women‑focused co‑working platform; Madrona led the seed round, matching its support for local, mission‑driven founders.
Co-invested with
Other firms in this catalog who've backed the same companies.
Partners
Full firm roster — key partners, partners, and the wider team.
Key partners
Matt McIlwain
Managing Director
Madrona
Matt McIlwain is a Managing Director at Madrona focused on applied machine learning, cloud computing, intelligent applications, and the intersection of life science and data science. He joined Madrona in 2000 and has backed companies including Apptio, Smartsheet, Isilon Systems, Read AI, MotherDuck, and A-Alpha Bio.
S. Somasegar
Managing Director
Madrona
S. Somasegar, known as Soma, is a Managing Director at Madrona focused on B2B and enterprise startups across AI, cloud infrastructure, developer tools, DevOps, intelligent applications, and life-science/data-science intersections. Before Madrona, he spent nearly 27 years at Microsoft, most recently as senior vice president of the Developer Division.
Karan Mehandru
Managing Director
Madrona
Karan Mehandru is a Managing Director at Madrona based in Palo Alto, investing across SaaS, data infrastructure, security, cloud computing, and intelligent applications.
Tim Porter
Managing Director
Madrona
Tim Porter is a Managing Director at Madrona focused on B2B software in the Pacific Northwest, including intelligent applications, SaaS, cloud-native infrastructure, the modern data stack, machine learning, DevOps, and cybersecurity. Before Madrona, he worked in Microsoft's corporate development group.
Steve Singh
Managing Director
Madrona
Steve Singh is a Managing Director at Madrona focused on next-generation B2B and enterprise startups across AI, intelligent applications, and cloud infrastructure. He previously founded and led Concur and served on SAP's executive board running its cloud business group.
Scott Jacobson
Managing Director
Madrona
Scott Jacobson is a Managing Director at Madrona focused on marketplaces, consumer-facing technologies, proptech, and digital commerce. Before joining Madrona in 2007, he held senior product and business roles at Amazon Kindle and Amazon Marketplace.
Partners
Len Jordan
Managing Director and Venture Partner
Madrona
Madrona managing director and venture partner focused on software, hardware, analytics, and consumer tech.
Sabrina Albert (Wu)
Partner
Madrona
Madrona partner investing from Seed to Series C in intelligent apps, enterprise software, and agentic systems.
Paul Goodrich
Co-Founder
Madrona
Madrona co-founder and early-stage investor with prior law firm and environmental venture fund experience.
Vivek Ramaswami
Partner
Madrona
Madrona partner investing in enterprise software, cloud infrastructure, data tools, intelligent apps, and fintech.
Karan M.
Managing Director
Madrona
Madrona managing director investing in SaaS, data infrastructure, security, cloud, and AI apps.
Chris Picardo
Partner
Madrona
Madrona partner investing in life sciences, machine learning, consumer tech, marketplaces, and Web3.
Troy Cichos
COO & Partner
Madrona
Madrona COO & Partner overseeing firm operations, finance, administration, legal, HR, IR, tax, and audit.
Team
Anna Chen
Investor
Madrona
Madrona investor focused on acceleration-stage intelligent apps, enterprise software, and consumer tech.
Rasik Parikh
Investor
Madrona
Madrona investor focused on B2B software, intelligent applications, enterprise AI, and infrastructure software.
Rolanda Fu
Investor
Madrona
Madrona investor focused on intelligent apps, consumer technology, marketplaces, and enterprise software.
Ishani Ummat
Investor
Madrona
Madrona investor focused on new investments, portfolio growth, and digital-physical experiences in fintech and healthcare.
Public voice
Notable statements and public positions.
- “We think a lot of the value is going to be captured in the agentic and application layers.” — Matt McIlwain to GeekWire (on AI investment focus)
- “Investors have stopped caring whether you hit a specific ARR milestone. They care whether your metrics prove that customers need what you’re building.” — Madrona, “Fundraising in the AI Era”
- “We are looking to lead rounds, partner with your existing investors and roll up our sleeves as a team to have a positive impact on your company’s trajectory.” — Madrona, Acceleration Fund page
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