Kieran Flanagan
About Kieran Flanagan
Kieran Flanagan is based in Ireland and works in go-to-market and marketing. His LinkedIn profile lists about ten years at HubSpot, where he moved from marketing director to VP of Marketing and Growth and then SVP of Marketing. It also lists a stint as CMO of Zapier from January 2023 to April 2024. His earlier roles included Marketo and Salesforce, according to PitchBook. He holds a computer science degree from Ulster University.
His LinkedIn lists a return to HubSpot as SVP from May 2024, with a current title of SVP Agentic GTM & Systems. He co-hosts the Marketing Against the Grain podcast and publishes a newsletter at kieranflanagan.io. He also advises companies including Miro, Ramp, Postal and Chainlink Labs.
His LinkedIn lists angel investing and advising from May 2021 and a Sequoia Scout role at Sequoia Capital from September 2021. Crunchbase counts 11 personal investments. PitchBook counts 8 and records one exit.
Earlier investments in PitchBook include Workbounce (seed, December 2021), Softr (January 2022), Papaya (October 2022), Oliva Health (2023) and Passionfroot (seed, October 2024). His LinkedIn also names Spektr, Solvimon, Pento, NexHealth, Bytez, Crono and Fl0.
His recent seed rounds are in AI companies. In February 2026 he took part in Agaton's $10M (EUR 8.4M) seed. Agaton is a Stockholm company that analyses customer conversations for sales and service teams. Press coverage says he invested as a Sequoia scout.
In June 2026 he joined Archestra.AI's $10M seed, led by 20VC. Archestra.AI is a London company that helps enterprises connect sensitive data to AI agents. Crunchbase also lists his seed investments in BottleCap AI (January 2026) and CodeWords (May 2026). We found no public detail on his role in those two rounds.
He describes himself on LinkedIn as a pre-seed and seed investor. His recent AI deals are in agentic AI, enterprise AI infrastructure and sales and go-to-market tooling. His earlier portfolio is mostly B2B and productivity software, plus some health tech and fintech. His portfolio spans Europe and the US.
He has not published a check size. His LinkedIn invites founders to contact help@kieranflanagan.io.
- Archestra.AI: enterprise AI platform that connects company data to AI agents; $10M seed led by 20VC, June 2026.
- Agaton: agentic AI for sales and service conversations; $10M seed, February 2026.
- BottleCap AI: AI company; seed round, January 2026 ($7.5M).
- CodeWords: AI company; seed round, May 2026 ($9M).
- Softr: no-code app builder; invested January 2022.
- Workbounce: business software company; seed, December 2021.
- Passionfroot: business software company; seed, October 2024.
- ie.linkedin.com/in/kieranjflanagan
- crunchbase.com/person/kieran-flanagan
- pitchbook.com/profiles/investor/221942-62
- tech.eu/2026/06/02/archestraai-raises-10m-to-unlock-next-gen-agentic-u
- archestra.ai/blog/archestra-announces-10m-seed
- eu-startups.com/2026/02/stockholm-based-agaton-secures-e8-4-million-to
- arcticstartup.com/agaton-raises-10m-in-seed
- blog.hubspot.com/marketing/author/kieran-flanagan
Investing activity
Kieran Flanagan appears in 5 AI deals tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $10M and the largest at $10M. The most recent are Archestra.AI (Seed, $10M, Jun 2026), Archestra.AI (Seed, $10M, Jun 2026) and CodeWords (Seed, $9M, May 2026).
Kieran Flanagan most often invests alongside Olivier Pomel, 20VC, Tenacity Capital and Visible Ventures, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Kieran Flanagan
Does Kieran Flanagan invest in AI startups?
Yes. Recent seed rounds include Agaton (February 2026), BottleCap AI (January 2026), CodeWords (May 2026) and Archestra.AI (June 2026).
What stage does Kieran Flanagan invest at?
His LinkedIn describes him as a pre-seed and seed investor. His recent AI deals are all seed rounds.
What is Kieran Flanagan's check size?
He has not published a check size, and we found no reliable figure.
Is Kieran Flanagan a Sequoia Scout?
Yes. His LinkedIn lists the Sequoia Scout role from September 2021. Press on the Agaton round says he invested as a Sequoia scout.
How can founders contact Kieran Flanagan about investing?
His LinkedIn profile gives help@kieranflanagan.io for founders looking for an investor. He also posts on X as @searchbrat and on LinkedIn.
What is Kieran Flanagan's background?
He spent about ten years at HubSpot in marketing leadership roles and was CMO of Zapier from 2023 to 2024. He co-hosts the Marketing Against the Grain podcast.
Is Kieran Flanagan an angel investor?
Yes. Kieran Flanagan invests personally as an angel.
What AI companies has Kieran Flanagan invested in?
Kieran Flanagan's AI investments include Archestra.AI, CodeWords, Agaton and BottleCap AI. The 5 rounds on Lounge are listed on this page with amounts, dates and co-investors.
Who does Kieran Flanagan co-invest with?
Kieran Flanagan's most frequent co-investors on Lounge are Olivier Pomel (3 deals), 20VC (2 deals), Tenacity Capital (2 deals), Visible Ventures (2 deals) and The Twenty Minute VC (2 deals).
How can founders reach Kieran Flanagan?
Founders on Lounge can see Kieran Flanagan's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add Kieran Flanagan to their Investor Pipeline to track the conversation.