The Keys to Getting to $500M ARR In Just 7 Years with Attentive’s CEO

 

Here’s what it really took for Attentive to go from $0 to $500M ARR in just 7 years, sending over 32B text messages and generating $20B+ in revenue for their 8,000+ customers.

CEO Amit Jhawar joined us at SaaStr Annual for a deep dive:

1. Solve The Hard Problem First — And Patent It

The first key insight? Everyone knew mobile commerce was exploding (from 15% in 2014 to 75% in 2024), but reaching customers on mobile was broken. The traditional “Text WHY to 12345” SMS opt-in process was clunky and killed conversion rates.

Attentive spent months with brands, consumers, and regulators to crack this. The result? Their patented TwAP technology that lets customers opt-in with a single click, automatically opening their messages app with a pre-composed text. This wasn’t just an improvement — it fundamentally changed how brands could engage with SMS marketing.

The learning: When you solve a genuinely hard problem, you get three moats for free:

• Technical advantage through innovation
• Legal protection through patents
• Thought leadership in the space

2. Turn Your Customers Into Your Marketing Engine

The second breakthrough was making customer success the core growth engine. Here’s how:

1. Have customers email their exact performance expectations before starting
2. Build custom reporting showing them beating those metrics
3. Run formal reviews comparing results to initial expectations
4. Create Attentive University + certification program
5. Showcase customer wins through “Texts We Love”
6. Host high-value events mixing customers + prospects

The result? A self-reinforcing flywheel where successful customers:

• Get promoted
• Tell their network
• Become champions
• Drive organic growth

3. Going all-in on AI (and other tech waves)

When Attentive saw the AI wave coming, they:

• Moved 30% of their best people to AI
• Shipped two AI products rapidly
• Focused on revenue generation vs cost savings
• Got hundreds of customers using AI personalization

The results speak for themselves: Personalized shopping experiences are driving 124% more incremental revenue compared to generic “20% off” promotions.

The Numbers That Matter

• 0 to $500M ARR in <7 years
• 8,000+ customers
• 32B+ text messages sent
• $20B+ in revenue generated for customers
• 25%+ YoY customer revenue growth
• 124% incremental revenue from AI personalization

The Mobile Commerce Foundation: Learning from Braintree & Venmo

Before Attentive, Amit spent a crucial decade at the intersection of mobile and payments:

• Built mobile APIs at Braintree for Uber, Airbnb, and Wish.com
• Led Venmo through its PayPal acquisition
• Learned the critical lesson: When mobile behavior shifts, massive opportunities emerge

This experience proved invaluable when launching Attentive. Why? Because while the payment problem was solved, the marketing side of mobile commerce remained broken.

 

The Core Problem: Mobile Changed Everything

The Market Forces at Play:

1. Consumer attention was fragmenting
2. Traditional marketing channels were losing effectiveness
3. Mobile shopping sessions exploded:
   • 2014: 15% of shopping on mobile
   • 2018: 40% of shopping on mobile
   • 2024: Nearly 75% of shopping on mobile

The Marketing Crisis:

• Lower ROI on existing channels
• Declining new customer acquisition
• Revenue growth stalling
• No clear solution in sight

The Technical Breakthrough: TwAP Technology

The Old Way (And Why It Failed):

• Traditional SMS opt-in: “Text WHY to 12345”
• Problems:
  • Broke shopping flow
  • Killed conversion rates
  • Created compliance risks
  • Poor user experience

The Attentive Solution:

1. Months of research with:
   • Brands
   • Consumers
   • Regulators
2. Created TwAP technology:
   • One-click opt-in
   • Automatic message app transition
   • Pre-composed message
   • Full compliance
   • Protected by patents

Building the Growth Engine: The Customer Success Framework

1. The KPI Alignment System

• Have customers email explicit performance expectations
• Build custom reporting dashboards
• Weekly cross-team optimization meetings
• Formal performance reviews

2. The Education Ecosystem

• Attentive University
• Platform certification program
• “Texts We Love” showcase
• Industry-standard guides (e.g., Black Friday playbook)

3. The Community Building Strategy

• “Beyond the Message” events
• “Thread” city meetups
• “Luminaries” executive offsites
• Mixing customers and prospects strategically

The AI Revolution: Going All-In

The Strategic Shift:

1. Moved 30% of top talent to AI
2. Customer-driven problem identification:
   • Focused on revenue generation
   • Personalization at scale
   • Individual customer messaging

The Results:

• Two AI products launched
• Hundreds of active customers
• 124% incremental revenue from personalized experiences vs. generic promotions
• Higher click-through and conversion rates

The Numbers Behind the Growth

Revenue Metrics:

• $0 to $500M ARR in under 7 years
• 25%+ year-over-year customer revenue growth
• $20B+ generated for customers

Scale Metrics:

• 8,000+ active customers
• 32B+ text messages sent
• Industry-leading conversion rates

The Three Core Growth Principles

1. Solve Hard Technical Problems

• Create multiple moats
• Patent protection
• Technical innovation
• Market leadership

2. Weaponize Customer Success

• Align on specific metrics
• Build education systems
• Create community
• Drive organic growth

3. Capitalize on Technology Waves

• Early identification
• Bold resource allocation
• Customer-driven development
• Revenue focus

Key Learnings for Founders

1. Technical Innovation Matters
   • Don’t just improve – revolutionize
   • Create defensible IP
   • Make it 10x better than alternatives
2. Customer Success is Marketing
   • Get specific performance commitments
   • Over-deliver on metrics
   • Build education systems
   • Create peer communities
3. Technology Wave Timing
   • Move early and aggressively
   • Allocate significant resources
   • Focus on revenue impact
   • Let customers guide development
4. Community Building Pays
   • Mix customers and prospects
   • Create certification programs
   • Showcase customer wins
   • Build industry standards