Steve Singh
Steve Singh is Co-founder of Concur and Managing Director at Madrona Venture Group, and currently serves as Board Member at Clari and Leaf Logistics, and Executive Chairman at CovenantIQ and Direct Travel. He co-founded Concur, which is still running.
Insurtech Faye raises $50M led by Madrona, bringing total funding to $100M as it scales AI and international growth
Faye, a Richmond-based travel insurance app, raised $50 million led by Madrona, bringing its total funding to $100 million since 2022 to scale AI, expand internationally, and improve claims and UX; the company reported millions of customers and $100 million in annualized revenue last year. Co-founder and CEO Elad Schaffer called the raise a shift from startup to scale-up as Faye pursues growth toward a possible future IPO.
Madrona Leads Faye’s Series C; Chris (Madrona) Joins Board as Faye Reimagines Travel Insurance
Madrona is leading Faye’s Series C investment because Faye has built a better, autonomous traveler care platform and improved whole-trip travel insurance that addresses slow, confusing incumbent products. The firm highlights travel’s growing disruptions and says Faye’s product delivers faster, more usable protection and better claims experiences for modern travelers.
Faye Raises $50M Series C on Aug 5, 2026 to Build Autonomous AI Traveler Care Platform, Total Funding Reaches $100M
Faye announced a $50 million Series C on Aug 5, 2026 to build an autonomous AI platform for traveler care, bringing total funding to $100 million and funding AI investments, partnerships, and global expansion.
Ramp Acquires 2024-Founded Corporate Travel Startup Juno Backed by Madrona
Ramp acquired Juno, a 2024-founded corporate travel expense startup backed by Madrona and Bungalow Ventures, with Juno’s founders continuing as co-CEOs. The acquisition aims to integrate Juno’s platform for managing non-employee expenses into Ramp’s fintech offerings while preserving Juno’s brand and team.
Otto Launches AI Travel Assistant Led by Ex-Expedia Exec to Personalize Business Travel End-to-End
Seattle-based startup Otto, founded by former Expedia executive Michael Gulmann, has launched Otto the Agent, an AI-powered business travel assistant designed to personalize bookings and manage travel end-to-end. The platform learns individual travel preferences and integrates with calendars to proactively suggest itineraries, aiming to replicate the service level of a top executive assistant.
Raj Singh, Concur Co-Founder, Named CEO of Smartsheet to Drive Growth with AI in Enterprise Software
Rajeev 'Raj' Singh, co-founder of Concur and former CEO of Accolade, has been named CEO of Smartsheet as the company looks to leverage its strong foundation and $1 billion revenue base to grow with AI innovations. Singh aims to capitalize on Smartsheet's established enterprise presence and significant opportunity to reshape work management software amid evolving industry dynamics.
Otto Startup, Led by Expedia Veteran and Madrona Chairman, Raises $6M to Develop AI Assistant for Business Travel Booking
Seattle-based startup Otto, led by Expedia veteran Michael Gulmann and chaired by Steve Singh of Madrona Ventures, is developing an AI virtual assistant using GPT-4 to simplify business travel booking. The company raised $6 million in a seed round led by Madrona and aims to offer its product for free while earning revenue through booking facilitation.
Tektonic AI Raises $10M Seed Round from Madrona and Point72 Ventures to Automate Complex Business Workflows
Seattle-based startup Tektonic AI raised $10 million from Madrona and Point72 Ventures to develop AI software automating complex business workflows, initially targeting sales and revenue teams. The company aims to streamline dynamic workflows by using AI agents that understand natural language, enhancing productivity beyond traditional automation tools.
Concur Founder Steve Singh Leads Acquisition of Direct Travel to Enhance Corporate Travel Experience
Steve Singh, former CEO of Concur, led a group of investors in acquiring Direct Travel, a corporate travel management firm with over $300 million in revenue, aiming to create a seamless travel experience. Christal Bemont has been appointed as the new CEO of Direct Travel, with Singh serving as executive chairman.
Center Raises $30M Series C to Expand Corporate Expense Software with API and Bank Partnerships
Center, a Seattle-area startup offering a corporate credit card and real-time expense analytics platform used by over 1,000 companies, raised $30 million in Series C funding to expand via APIs and potential bank partnerships. The company has seen 64% customer growth and doubled revenue, aiming to innovate with AI and industry-specific integrations.
Spotnana Secures $75M Series B Led by Durable Capital to Build 'AWS for Travel Industry'
New York City startup Spotnana raised $75 million in a Series B funding led by Durable Capital Partners LP to develop an open platform for business travel technology, with investments from Madrona Venture Group and others. The company aims to rebuild travel industry infrastructure and anticipates a strong post-pandemic recovery in business travel.
Spotnana raises $34M Series A led by Madrona and ICONIQ to modernize business-travel software
Spotnana, a business-travel software startup founded by Sarosh Waghmar and Shikhar Agarwal, raised $34 million in a Series A led by Madrona Venture Group and ICONIQ to offer an API-friendly, integrated travel platform with consumption-based pricing. The company, chaired by Concur co-founder Steve Singh and with former Expedia CFO Greg Stanger on its board, serves about 50 corporate customers and aims to modernize booking, spending visibility, and integrations with HR and expense systems.
Madrona Venture Group’s Steve Singh Details Six Post-COVID Tech Trends and Reasons for Hope on GeekWire Podcast
Steve Singh, managing director of Madrona Venture Group and former CEO of Docker and Concur, joined GeekWire to discuss reasons for hope and six technology trends to watch as the Pacific Northwest emerges from the pandemic, in a special episode tied to the 2021 virtual GeekWire Awards.
Madrona Venture Labs raises $8M and turns investors like Spencer Rascoff into co‑founders of spinouts
Madrona Venture Labs has raised $8 million for its fourth fund and introduced a model that makes investors — including Spencer Rascoff, Julie Larson-Green and Elena Donio — co-founders, board members, and advisors of its spinouts to attract talent and accelerate startup formation. Founded in 2014, the Seattle-based studio has spun out more than a dozen companies, including recent spinouts Zeitworks, Simplata, and Stratify.
Madrona Venture Labs Raises $8M Led by Madrona, Adds Former CEOs and Operators as Investors
Madrona Venture Labs (MVL), the incubation arm of Madrona Venture Group, has raised $8M with Madrona leading the round and brought on a roster of experienced operators and former CEOs as investors to help build spun-out companies. MVL will continue partnering closely with Madrona’s investment professionals on startups like Stratify and Strike Graph as it expands its incubation efforts.
Madrona hires John Torrey as first partner outside Pacific Northwest, expands Acceleration Fund investing to Texas and Utah
Seattle-based Madrona Venture Group hired John Torrey, its first investment partner based outside the Pacific Northwest, to help source and support Acceleration Fund investments from Texas and Utah as the firm expands geographically. Madrona also raised $161 million for its Acceleration Fund II and hired Katie Chiupka as manager of business development and partnerships.
Madrona Venture Group Raises $345M for 8th Fund and $161M for 2nd Later-Stage Fund in Largest Ever $500M Capital Raise
Madrona Venture Group raised over $500 million for its largest fundraise ever, including $345 million for an eighth early-stage fund targeting 35-40 Pacific Northwest startups and $161 million for a second later-stage Acceleration Fund. The firm continues to focus on supporting the Pacific Northwest tech ecosystem while also backing later-stage companies across North America.
Tom Alberg invested in Amazon’s 1995 seed round, joined its board and co-founded Madrona to build Seattle’s tech scene
Tom Alberg invested in Amazon’s 1995 seed round, joined its board, and later co-founded Madrona Investment Group to back Pacific Northwest internet startups, helping shape Seattle’s tech ecosystem. His early bets and leadership influenced regional tech growth and left a legacy noted by Jeff Bezos and others.
Ex-Docker CFO Brian Camposano launches stealth Seattle fintech Stratify; Concur founder Steve Singh named chairman
Former Docker CFO Brian Camposano launched a stealth Seattle fintech called Stratify after spinning out from Madrona Venture Labs, with Concur co-founder Steve Singh serving as chairman. The early-stage company — currently one employee and no public website — aims to use machine learning and AI to modernize corporate finance and deliver real-time insights for CFOs and finance teams.
Madrona Venture Group Leads $8.5M Investment in Vendor Management Startup VNDLY; Steve Singh Joins Board
Seattle-based Madrona Venture Group led an $8.5 million investment round in VNDLY, a Cincinnati-based vendor management startup, with Steve Singh joining VNDLY's board. VNDLY, founded in 2017, has raised a total of $57.5 million to help companies manage and pay their non-employee workforce.
Madrona Venture Labs launches Founders Unite to connect startup founders with veteran execs through AMAs during pandemic
Seattle-based Madrona Venture Labs launched Founders Unite, a community and AMA series connecting startup founders with veteran tech leaders for advice and peer support during the pandemic. MVL — which raised $11 million for its third fund last year and has launched around ten companies — organized the initiative after polling 100+ founders about what they value most.
Organizations
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Direct Travel Executive Chairman 2024–present · current
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Spotnana Chief Executive Officer [Interim] 2024–present, Executive Chairman 2020–present · current
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Leaf Logistics Board Member 2021–present · current
