Comparing Revenue Operations Teams: Datadog vs. Twilio

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.

Background on GTM Teams

Revenue:

• Datadog: $2B ARR (+25% YOY)

• Twilio: $4B ARR (+5% YOY)

GTM Headcount:

• Datadog: 1,400 Sales Reps + 250 CS Reps

• Twilio: 1,100 Sales Reps + 120 CS Reps

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

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

Biggest Takeaways

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.

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, while 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.

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.

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.