Seattle startups include: Inflection.io acquires Keyplay, brings together long-term entrepreneurs

Two Seattle startups with intertwined histories are joining forces.

Inflection.io, a B2B marketing automation company, announced Wednesday that it has acquired Keyplay, a startup that helps sales teams identify and acquire target accounts.

The deal includes Inflection CEO Aaron Bird and Keyplay CEO Adam Schoenfeld, who have known each other for 15 years, and have collaborated and invested in each other’s companies.

Schoenfeld joins Inflection as CMO, and his Keyplay co-founder Andrew Rothbart joins the company as a senior member of the engineering team.

As Schoenfeld puts it, Inflection creates the platform he wants to have as a marketer, putting him in the role of both a marketing leader and a target customer for a brand.

Terms of the deal were not disclosed. Keyplay has raised $3 million in a seed round in 2022. Inflection has raised nearly $14 million to date, most recently a $7.6 million round in June 2024.

The combined company will have 47 employees worldwide, with team members throughout North America and an office in Bangalore, India. Inflection recently opened a new office in Seattle’s Pioneer Square neighborhood, where its CEO, CMO, SVP of Customer Experience, and senior engineers are based.

The backstory: Schoenfeld said the acquisition shows how the market has changed since Keyplay was founded in 2022, focusing on helping B2B companies identify their best accounts. He realized, in the middle of last year, that this was a factor beyond the company.

He explained that “it became clear that consumers were driving towards a small number of key platforms built for AI agents. I didn’t see a way for Keyplay to become a developer.”

It was a difficult thing to admit after building his career as an entrepreneur by spending money and working in certain areas, but he finally concluded that Keyplay needed to connect with a wider platform.

“When agents start creating campaigns, writing emails, choosing audiences, the question stops being ‘what is the best tool for finding accounts?’ then ‘does my rendering layer have the context it should work on?’ ” said Schoenfeld.

Main forum: Inflection is positioning itself to provide that context, as a native AI approach to Marketo, the B2B marketing automation software that has dominated the category for two decades.

Bird knows the market (and Marketo) well. He founded Bizible, a Seattle marketing analytics company, in 2011. Marketo acquired Bizible in 2018 and was itself acquired by Adobe later that year for $4.75 billion.

Bird served as SVP of Product at Adobe Marketo before leaving to launch Inflection in 2021 with former Bizible colleagues Dave Rigotti and Vic Davis.

In response to questions about the acquisition, Bird said he was “very motivated” to bring on Schoenfeld, Rothbart, and their team, realizing how they can accelerate Inflection in both marketing and engineering, while adding top talent to the Seattle office.

He said Rothbart has been “at the leading edge of how modern engineering teams should work with AI, and has deep domain expertise right in our sweet spot – building and growing intelligence-driven GTM systems.

Shared history: Schoenfeld, formerly the founder of Simply Measured, the Seattle-based social analytics firm acquired by Sprout Social, was on Bizible’s board during its growth and acquisition, and invested in Inflection’s $5 million seed round.

Bird, in turn, invested in Keyplay’s $3 million seed round.

Schoenfeld called cross-investment “a funny situation for small countries,” noting that their long friendship naturally led to supporting each other’s startups as angel investors.

“This had no direct impact on the deal,” Schoenfeld said. “But because we were following each other closely from the beginning, on both sides, it helped us to get even faster than two strangers.”

Bird had floated the idea of ​​a deal early in Keyplay’s life, putting in objections such as “one day we have to buy it.” Keyplay was engaging with a few potential buyers, but Inflection rose to the top of the list. Negotiations became critical in January, and the deal was closed in mid-March.

What’s next: Inflection plans to integrate Keyplay’s account scoring and intelligence into its platform starting this quarter, giving its AI agents built-in knowledge of which accounts to target and why. Existing Keyplay customers will continue to use the standalone product for now, with access to their capabilities within Inflection over time.