20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Ashley Kelly is the VP of Global Sales Development at Rippling, the all-in-one platform for HR, IT, and finance. Before Rippling, Ashley played a crucial role in scaling Brex’s outbound sales from $2M to over $300M in ARR, and has hired over 800 SDRs during her time in some of the best tech companies in Silicon Valley, including Lever and Zenefits.

In Today’s Episode with Ashley Kelly We Discuss:

1. From NASCAR to Silicon Valley SDR

• How did Ashley make her way into the world of sales?

• Why does Ashley think the best AEs and leaders start off as SDRs?

• What is Ashley’s advice to new SDRs starting their jobs today?

2. Age of AI: Is SDR Outbound Dead?

• Does Ashley agree that outbound is dead today? Is SDR dead?

• How will AI change SDR? Why is Ashley hesitant to adopt AI?

• Why does Ashley think founders should always build the first sales playbook?

• What did Ashley mean by SDR is the 3rd pillar between sales and marketing?

• What does Ashley think most companies get wrong about outbound?

3. SDR Hiring: Who, What, When & How

• When does Ashley think founders should hire their first SDR?

• How does Ashley structure the hiring process? What questions does she ask?

• What profile does Ashley look for when hiring for an SDR?

• How does Ashley structure the finance package? How is it different for each team?

• Why did Ashley avoid hiring SDRs with SDR experience? Why has she changed her mind?

• What was Ashley’s biggest hiring mistake? What were her takeaways?

4. Onboarding New SDR Hires

• How does Ashley onboard new SDR hires? What is her onboarding timeline?

• How does Ashley set targets for new hires? When should they be fully productive?

• When does Ashley know if a new hire isn’t working?

• What are common traits among Ashley’s most successful hires?