Sunny Gupta
Sunny Gupta is General Partner at Generative Capital, Executive Chair Board at Smartsheet, Co-founder and Executive Chairman at Thira, and Co-founder, Incoming CEO at Apptio / Smartsheet. He previously served as CEO at Apptio and has founded Apptio, which was acquired, and Thira, where he remains active. His expertise spans enterprise software, AI, and SaaS, with experience as an operator, investor, and board member.
Temporal rises to No. 1 on GeekWire 200 after $550M raise at $12.55B valuation as AI and hardware firms climb
Temporal is now the No. 1 company on the GeekWire 200 after a $550 million raise valuing it at $12.55 billion and surpassing $250 million in annualized revenue; the Fall 2026 ranking highlights growth in AI software and advanced machinery for space, energy and defense across the Pacific Northwest.
Thira Raises $21M Seed Round for AI Workflow Systems
Thira, a Bellevue, Washington developer of AI systems that improve complex workflows, raised $21 million in seed funding. The company’s funding will support its AI system solutions to enhance workflow efficiency.
Apptio Co-founders Sunny Gupta and Kurt Shintaffer Launch Thira, Raise $21M Seed Led by Madrona to Build Autonomous IT Support Agents
Apptio co-founders Sunny Gupta and Kurt Shintaffer launched Bellevue-based enterprise AI startup Thira to build autonomous agents for IT support and back-office work, and raised $21 million in seed funding led by Madrona. Thira will integrate with tools like ServiceNow, Jira Service Management and identity/device-management systems, with plans to expand into finance and HR amid competition from companies such as ServiceNow (Moveworks), Aisera, Rezolve.ai, and Serval.
Thira Secures $21 Million Seed Funding to Automate Enterprise Back-Office Workflows with AI
Thira, founded by Apptio co-founders in 2026, has raised $21 million in a seed round led by Madrona to develop an AI-native platform that automates complex enterprise back-office workflows while ensuring security and compliance.
Madrona Ventures Invests in Thira, Reuniting Founders Sunny Gupta and Kurt Shintaffer to Build AI-Native Systems for CIOs
Madrona announced a new investment in Thira, led by founders Sunny Gupta and Kurt Shintaffer, reuniting experienced enterprise builders to tackle CIO-focused AI-native systems. The firm argues Thira’s team and product strategy will help CIOs deploy AI-driven systems of execution and drive measurable returns on technology and AI investments.
Thira Secures $21M Seed Funding Led by Madrona to Develop AI-Driven Self-Running Enterprise Back-Office
Thira, founded by Apptio co-founders Sunny Gupta and Kurt Shintaffer, raised $21 million in a seed round led by Madrona to develop a secure, self-learning AI system aimed at automating enterprise back-office IT processes. The funding round also includes participation from FUSE and prominent advisors, with key industry veterans joining the founding team.
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.
Smartsheet Appoints Stephanie Berner as Chief Customer Officer; Gradial and Zeno Power Expand Senior Leadership
Smartsheet named Stephanie Berner as chief customer officer amid leadership changes, including a new acting CEO. Seattle startups Gradial and Zeno Power also expanded their senior leadership with new executives to drive growth and innovation.
Tech Startups Shift to Profitability and Sustainable Growth Amid Tight 2023-2024 Venture Capital Market
Tech startups are shifting from growth-at-all-costs to focusing on profitability and efficient growth without relying on new investor funding amid tighter venture capital conditions and challenging market factors. This new approach, termed 'default alive,' emphasizes sustainable business models and cautious investment amid a decline in funding and more down rounds.
Apptio Co-Founder Sunny Gupta Reflects on Building a $4.6 Billion Tech Business Following Key CIO Insight
Sunny Gupta, co-founder of Apptio, shared how a pivotal question from a CIO about managing technology costs inspired him to found the company, which pioneered Technology Business Management. Apptio went public in 2016, was acquired by Vista Equity Partners for nearly $2 billion in 2019, and then bought by IBM in a $4.6 billion deal in 2023.
IBM Acquires Apptio for $4.6B After 16-Year Journey Including 2016 IPO and $1.94B Vista Buyout
Apptio's 16-year journey from a challenging IPO in 2016 to a $4.6 billion acquisition by IBM in 2023 exemplifies perseverance and long-term vision in enterprise tech. Originally valued at over $500 million at IPO, the company rebounded after setbacks, was acquired by Vista Equity Partners for $1.94 billion, and then sold to IBM, highlighting its growing impact in tech spending management.
IBM to Acquire Apptio for $4.6 Billion, Expanding its Cloud and IT Management Capabilities
IBM agreed to acquire Seattle-area cloud and IT management company Apptio for $4.6 billion, marking a significant milestone after Apptio's prior IPO and private equity acquisition. Apptio's SaaS technology helps companies manage tech spending and has grown to over $400 million annual revenue and 1,500 corporate customers, including half the Fortune 100.
Brian Goldfarb named Tenable CMO; Elizabeth Hamren becomes Discord COO; Kurt DelBene confirmed as VA CIO; Madrona adds three strategic directors
Several tech industry hires and appointments: Brian Goldfarb is CMO at Tenable; Elizabeth Hamren is COO at Discord; Kurt DelBene confirmed as VA CIO; Madrona Venture Group added three strategic directors; Christina Mautz joined Panopto.
Madrona Venture Group raises $120M Fund VII Extension to support 10–12 portfolio companies from its 2018 $300M fund
Madrona Venture Group has raised a $120 million Fund VII Extension Fund from prior investors to provide follow-on capital for 10–12 companies from its 2018 $300 million Fund VII, responding to larger, faster rounds in today’s frothy venture market.
Bellevue’s tech boom draws Amazon, Apptio and major firms as city positions itself as Seattle alternative
Bellevue has become a major tech hub attracting companies like Amazon, Apptio, T-Mobile, Smartsheet, OfferUp and Icertis thanks to its downtown, livability, low crime and business-friendly policies, with major expansions including Amazon’s plan to employ 25,000 there.
Wyze names former Nike exec Francis Lee as first CFO; OutSystems raises $150M at $9.5B valuation as CMO relocates to Seattle
Wyze Labs named longtime Nike executive Francis Lee as its first CFO as the Kirkland smart-home startup expands after a Series A; OutSystems closed a $150M funding round valuing it at $9.5B while moving CMO Robson Grieve to Seattle. Additional regional moves include Lisa Nelson joining Flying Fish Partners as a venture partner and Apptio naming Kevin Meeks chief customer officer.
Apptio CEO Sunny Gupta to receive $196 million as Vista Equity closes $1.94B take-private at $38 per share
Apptio CEO and co-founder Sunny Gupta stood to receive about $196 million after Vista Equity Partners completed a $1.94 billion buyout at $38 per share, a 53% premium over Apptio's market price.
Seattle 2.0 Names Finalists From Nearly 7,000 Nominations; Public Voting Open Through May 11 — Winners Revealed May 19
Seattle 2.0 announced finalists for its annual Seattle tech startup awards after nearly 7,000 nominations across 11 categories, opening public voting through May 11 and scheduling the awards event for May 19 with keynote Jonathan Sposato.
Organizations
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Thira Co-founder and Executive Chairman 2026–present · current
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Generative Capital General Partner 2025–present · current
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Smartsheet Executive Chair Board 2025–present · current
Education
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University of South Carolina B.S., Computer Science · 1989–1992
