It's important we start by acknowledging there is no one-size-fits-all for Revenue Operations team structures.

This is not a case for 'one team being better than the other' - both Datadog and Twilio are powerhouse Go-to-Market organizations in their own right but spotting differences in decision making can help inform on your own Revenue Operations resource strategy.

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Background on GTM Teams

Revenue:

• Datadog: $2B ARR (+25% YOY)
• Twilio: $4B ARR (+5% YOY)
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GTM Headcount:

• Datadog: 1,400 Sales Reps + 250 CS Reps
• Twilio: 1,100 Sales Reps + 120 CS Reps
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Rev Ops Team Structures

Datadog
95 people (61% Individual Contributors)

• 36 in GTM Strategy
• 3 in Sales Strategy / Execution
• 1 in GTM Analytics
• 7 in Compensation
• 4 in Success Ops
• 24 in Deal Desk
• 17 in Enablement
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Twilio
84 people (38% Individual Contributors)

• 15 in GTM Strategy
• 8 in Sales Strategy / Execution
• 16 in GTM Analytics
• 19 in Compensation
• 3 in Success Ops
• 1 Channel Ops
• 12 in Deal Desk
• 11 in Enablement
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Biggest Takeaways

1. Team Composition
   Twilio is significantly more top-heavy - only 38% of the team sit at IC level.
   At-a-glance, more ICs per Manager could signal efficiency. But it’s all a question of how that IC headcount is allocated.
   
   Is their delivery efficient?
   Are they working on high impact initiatives?
   
   At Datadog, some of the 58+ Associate-level team members in Rev Ops do appear to be filling in systems or process gaps with manual execution.
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2. Deal Desk Structure
   There is a glaring difference in Deal Desk team size in this comparison.
   Twilio has 12 on Deal Desk vs. 24 at Datadog.
   
   But context matters here!
   Twilio has 306,000 customers generating $4B in annual revenue.
   Datadog has ~25,000 customers generating $2B.
   
   This means an ACV of $13,000 for Twilio’s vs. $80,000 at Datadog. More complex deals requires a greater investment in Deal Strategy.
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3. Team Background
   The background of Twilio’s Rev Ops team is fairly singular. Most come from prior roles in Rev Ops & Sales Strategy.
   A logical hiring strategy.
   
   In contrast, Datadog has far more diverse experience on the team.While some come from Rev Ops, many on the team come from:
   • Broader Biz Ops Strategy roles
   • Management Consulting and M&A
   • Business Intelligence & Analytics
   • Investment Banking
   
   They have a clear focus on analytical rigor, in addition to a background specifically centered on Sales Strategy.
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Regardless, both of these Rev Ops teams know what they're doing.

Twilio generates ~$3m in Revenue per Rep. Datadog generates $1.4m in Revenue per Rep.