Nick Caldwell
About Nick Caldwell
Nick Caldwell is a technology executive. He has been Chief Product Officer at Peloton since November 2023. He holds a computer science and electrical engineering degree from MIT and an MBA from U.C. Berkeley Haas.
His earlier roles include 13 years at Microsoft, ending as General Manager of the Power BI product family. He was VP of Engineering at Reddit, then Chief Product and Engineering Officer at Looker, which Google acquired for $2.6B. Most recently before Peloton he was General Manager for Core Technologies at Twitter, where he oversaw a 2,000-person team.
His board work has included HubSpot, Bitly, the executive recruiting firm True, and the nonprofit /dev/color.
His own bio says his venture portfolio includes more than 50 seed and Series A startups. He has also spoken publicly about getting started in angel investing, including on a Village Global podcast episode alongside Sheel Mohnot and Anne Dwane.
Crunchbase lists 16 investments for him, and Tracxn lists 8. The two trackers cover different subsets, so neither is a full record.
In April 2026, Gravity (Orion by Gravity) announced $10M in total funding, including a $7M round led by Next Frontier Capital. Gravity builds business analytics software. Its announcement names Nick Caldwell of Peloton among the strategic angels in the round.
His own bio lists AI as a main focus of his portfolio, and NFX Signal ranks him in its AI seed category.
His bio says his portfolio is primarily AI, data analytics, future of work and social media. NFX Signal places him at pre-seed and seed in categories including analytics, cloud infrastructure, data services and AI.
NFX Signal lists an investment range of $10K to $50K with a $25K sweet spot. That is a third-party listing, not a statement from Caldwell. He has not published a check size on his own site that we found.
- Gravity: business analytics software, named as an angel in its $7M round led by Next Frontier Capital (April 2026).
- Select Star: listed by Tracxn as a notable investment. The year is not confirmed.
- zeroheight: design systems software. Tracxn lists him as an investor in its $10M Series A (August 2021).
- Honeycomb: Tracxn lists him as an investor in its $4M seed round (December 2021).
- ByteChek: Tracxn lists him as an investor in its $3M seed round (December 2021).
- CodeZero Technologies: Tracxn lists him as an investor in its $3.5M seed round (March 2024).
Investing activity
Nick Caldwell appears in 1 AI deal tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $7M. The most recent is Gravity (Seed, $7M, Apr 2026).
Nick Caldwell most often invests alongside NEXT Frontier Capital, K5 Global, Ed Hallen and Godard Abel, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Nick Caldwell
Does Nick Caldwell invest in AI startups?
Yes. His bio lists AI as a primary focus of his portfolio. He was named as an angel in Gravity's $7M round in April 2026.
What check size does Nick Caldwell write?
He has not stated one publicly that we found. NFX Signal lists a range of $10K to $50K with a $25K sweet spot, but this is a third-party listing.
What stage does Nick Caldwell invest at?
His bio describes seed and Series A startups. NFX Signal lists him at pre-seed and seed.
Who is Nick Caldwell?
He is Chief Product Officer at Peloton. He previously held senior roles at Twitter, Reddit, Looker and Microsoft.
Which sectors does Nick Caldwell back?
His bio names AI, data analytics, future of work and social media. Several of his listed investments are in data and developer infrastructure.
How can founders contact Nick Caldwell?
His public channels are his personal site, his LinkedIn profile and his X account @nickcald. We found no published pitch process.
Is Nick Caldwell an angel investor?
Yes. Nick Caldwell invests personally as an angel.
What AI companies has Nick Caldwell invested in?
Nick Caldwell's AI investments include Gravity. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
Who does Nick Caldwell co-invest with?
Nick Caldwell's most frequent co-investors on Lounge are NEXT Frontier Capital (1 deal), K5 Global (1 deal), Ed Hallen (1 deal), Godard Abel (1 deal) and Denver Ventures (1 deal).
How can founders reach Nick Caldwell?
Founders on Lounge can see Nick Caldwell'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 Nick Caldwell to their Investor Pipeline to track the conversation.