ATTENTIVE

Brian Long was a serial entrepreneur who had already sold TapCommerce to Twitter for about $100 million. He, Andrew Jones and Ethan Lo founded Attentive in October 2016 after recognizing that SMS was the most underutilized marketing channel in e-commerce.

Email inboxes were overflowing. Social media algorithms were throttling organic reach.

But text messages had 98% open rates, compared to roughly 20% for email, and most brands were not using them. The problem was compliance.

SMS marketing is heavily regulated under the TCPA and GDPR, and brands were afraid of getting sued. Attentive built a platform that made SMS marketing easy and legally compliant, handling opt-in and opt-out, consent management, and regulatory requirements automatically.

Attentive charges brands based on the number of SMS and MMS messages sent. Pricing scales with volume.

They also charge for their subscriber growth tools (sign-up forms, two-tap mobile opt-in) and for AI-powered personalization features. Customers include Sephora, Coach, Urban Outfitters, CB2, and 8,000+ other brands, and the platform sends over 10 billion messages a year.

Attentive announced it had passed $500 million in annual recurring revenue in January 2025.

Attentive's SMS marketing platform handles campaign creation, audience segmentation, A/B testing, and performance analytics. Their two-tap opt-in technology makes subscriber acquisition seamless on mobile.

AI-powered message personalization customizes content based on browsing and purchase behavior. Attentive Concierge provides conversational commerce via text.

Compliance tools automatically manage TCPA, GDPR, and CCPA requirements. They integrate with Shopify, Salesforce, Klaviyo, and 100+ other platforms.

Attentive grew by making SMS marketing stupidly easy for e-commerce brands. Their "two-tap" mobile opt-in technology made it simple for shoppers to subscribe to a brand's text messages — two taps on their phone, done.

They integrated deeply with Shopify, Salesforce Commerce Cloud, and other e-commerce platforms. Aggressive sales and marketing targeted mid-market and enterprise brands.

Once a brand adopted Attentive and saw 25-30% higher revenue from SMS, they increased their messaging volume, driving organic revenue growth for Attentive.

Regulatory risk is real. The TCPA imposes fines of $500 to $1,500 per unsolicited text message.

One compliance slip could cost a brand millions. Consumer fatigue with promotional texts could reduce effectiveness over time.

Competition from Klaviyo, which added SMS, plus Postscript and Yotpo, is intensifying.

The bigger problem is the valuation. Attentive's $7 billion mark was set during the 2021 boom.

It planned to go public in mid-2024 and postponed after watching newly listed tech companies trade badly. Mutual fund investors have since marked the company down to somewhere between $2.7 billion and $5.8 billion.

Growing into that 2021 number is the whole job now.

Tiger Global Management and Coatue Management co-led the $470 million Series E in June 2021 at a $7 billion post-money valuation. Coatue had also led the $230 million Series D.

Sequoia Capital, Bain Capital Ventures, IVP, and Eniac Ventures are also investors. The company has raised about $922 million in total.

Brian Long's track record, having sold TapCommerce to Twitter, attracted top-tier investors early. That $7 billion mark has not held up.

Mutual fund holders including BlackRock have been marking Attentive somewhere between $2.7 billion and $5.8 billion.