The sales playbook is crumbling. Email open rates are somewhere between dismal and catastrophic. LinkedIn InMail feels like shouting into a void. So sales teams are eyeing a new frontier, one that lives in your pocket and lights up blue: iMessage.
Enter Chert, a scrappy two-person operation launched in May 2024 as part of Y Combinator's Spring 2024 batch with a bold pitch—turn Apple's locked-down messaging ecosystem into programmable infrastructure for businesses. The idea: deliver the kinds of response rates that make traditional outbound look almost quaint. The company claims early customers are seeing reply rates ten times higher than email. Not incrementally better. Ten times.
Whether that's sustainable, or even advisable, is another question entirely.
Blue Bubbles as Business Strategy
Chert's founders, Ian Fong and Gary Gao, announced their platform in early May, framing it as infrastructure for "trusted, conversational customer messaging." What they've built is a REST API that lets businesses automate iMessage conversations at scale—complete with read receipts, typing indicators, and the visual cachet of those blue bubbles.
When a recipient doesn't use iMessage, the system falls back to SMS or RCS. The API reports which channel carried the message. Integrations with Salesforce, HubSpot, Close, Attio, and GoHighLevel mean sales teams can fire off iMessages from inside their existing workflows. Customer support teams get two-way conversations. AI agent startups—an expanding slice of Chert's customer base—can build booking flows that feel less robotic, more personal.
This isn't Apple's official Messages for Business, the one with the dark-gray bubbles and approval process. Chert markets peer-to-peer iMessage delivery with blue bubbles via its own infrastructure, not endorsed by Apple. That distinction matters more than you'd think. Perhaps more than it should.
"We're building the emotional trust layer for AI agents," Gao wrote in an essay published in April, laying out the company's thesis. Email is saturated. LinkedIn is noisy. iMessage, they argue, is the channel where people actually respond.
The technical hurdle? Staying under Apple's radar.
Deliverability as the Product
Chert has engineered its platform around a central problem: Apple's abuse-detection systems. The company rotates sending identities, warms up phone numbers gradually, caps daily volume per identity. It's infrastructure designed to handle the deliverability minefield so developers don't trip over it themselves.
The platform surfaces live delivery telemetry, verified phone numbers, and message receipts through webhooks. Developers commenting on Product Hunt in mid-May noted what appears to be an "observed state machine" approach to tracking delivery—essentially monitoring message states since Apple doesn't offer a public iMessage webhook.
Beyond the core API, Chert has built connectors to Slack and Vapi, targeting use cases ranging from onboarding flows to cold sales outreach. A pattern has emerged among customers: use SMS or RCS for authentication and transactional alerts, then switch to iMessage for conversations where reply rates matter.
A Gray-Area Gold Rush
Chert has company. Sendblue markets a similar iMessage API with CRM hooks. Linq offers multi-channel messaging including iMessage, emphasizing SOC 2 Type II compliance. LoopMessage and Blooio both provide iMessage APIs with fallback options. Photon offers SDKs for deploying agents across messaging platforms, iMessage included.
The legacy player, Twilio, supports only Apple's official Messages for Business—the approved, dark-gray-bubble channel that requires Apple's blessing. That leaves a gap for companies willing to navigate the murkier territory of programmatic peer-to-peer messaging.
Apple's position on third-party iMessage automation remains deliberately opaque. The company doesn't endorse these tools. Anecdotal reports periodically surface about Apple IDs getting flagged or throttled. Chert's deliverability machinery—the rotation, the gradual warming, the volume caps—is designed to work within those constraints, not bulldoze through them.
How long that arrangement holds is anyone's guess.
The Founders and the Backing
Fong studied mathematics and economics at NYU, working on fast-algorithm research at Courant Institute. His Y Combinator profile mentions eight hackathon wins, a detail that feels very much on-brand for the accelerator. Gao, the CEO, studied computer science and business at Penn, researching machine learning architectures and neuromorphic chips before decamping to San Francisco.
Two people. Backed by Y Combinator, Z Fellows, and Betafund. LinkedIn and Grafana logos appear on their site, though the site does not specify whether these indicate angels from those companies or institutional ties.
A partnership with Series, detailed on a microsite, brings an iMessage-based social network to YC founders using Chert's infrastructure. Customer logos displayed on the site include Tour, Symbal, and Vela.
The company has mentioned a "scalable pricing structure" built to support hundreds of lines and thousands of messages, though specific pricing tiers haven't been publicly detailed. The go-to-market strategy is sharper: B2C startups, customer experience teams, sales organizations, and AI agent companies hunting for channels with better engagement than email and more credibility than SMS.
The Open Question
Whether iMessage can scale as a business channel without Apple eventually stepping in remains uncertain. Businesses crave the engagement lift. Apple values ecosystem control and user experience. Those incentives don't naturally align.
For now, Chert and its competitors are betting that the 10× response advantage—assuming it holds—justifies navigating the ambiguity. Sales teams looking for better open rates may consider this option despite potential risks. How long the blue-bubble gold rush lasts, though, may depend less on the technology and more on how long Apple decides to look the other way.
