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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

Jun 7, 2024

Ashley Kelly, VP of Global Sales Development at Rippling, discusses topics such as the importance of outbound sales, the impact of AI on SDR roles, strategies for hiring and training SDRs, and the evolution of SDR hiring strategies. She emphasizes traits and skills over experience in interviews and shares insights on managing sales team morale during challenges.

53:43

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Episode guests

Ashley Kelly

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Quick takeaways

SDRs play a crucial role in bridging sales and marketing, impacting go-to-market strategies.

AI enhances SDR efficiency by automating tasks, allowing focus on personalization and human interactions.

Successful SDR hiring involves varied backgrounds, structured onboarding, and continuous focus on performance metrics.

Deep dives

Finding the Right SDR Hires

Ideal SDR hires include those with recruiting backgrounds and call center experience. Sales development is seen as a crucial pillar within go-to-market strategies.

Trust Your Gut and Interview Process in Hiring

02:29

Navigating the Hiring Process for Sales Development Representatives

02:14

Key Elements of Role Play and Email Test in Evaluating Potential Hires

02:15

Focus on Short-term Goals for Ongoing Improvement

02:23

Intro

4min

Navigating Sales Development Roles and Structures in Tech Companies

13min

Assessing Traits and Skills in Sales Development Interviews

7min

Evolution of SDRs and Hiring Strategies

11min

Identifying and Nurturing Sales Talent in the Early Stages

2min

Strategies for Managing Sales Team Morale During Challenges

3min

Challenges and Strategies in Sales Development

10min

The Future of Sales Development and Career Aspirations

4min

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:

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?

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?

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?

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?

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