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Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162

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. ----------------------------------------------- Timestamps: (00:00) Intro (00:52) Journey into Sales (01:52) The Role of SDRs in Sales (03:39) Cold Calling in Sales (05:09) Outbound: AI and the Infinite Spam Dilemma (06:19) Should SDRs Roll into Marketing or Sales? (12:45) SDR Hiring: Who, What, When & How (29:24) Onboarding New SDR Hires (33:07) Effective Onboarding Strategies for SDRs (45:10) When Good SDRs Go Bad (47:27) Cultural Differences in Motivation Methods (48:44) Quick-Fire Round ----------------------------------------------- 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? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Rippling on Twitter: https://twitter.com/Rippling Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #ashleykelly #rippling #sales #venturecapital #startup #sdr #hiring #chatgpt #outbound #inbound

Ashley KellyguestHarry Stebbingshost
Jun 6, 202453mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Building Elite SDR Teams: Hiring, Onboarding, Metrics, and Motivation Playbook

  1. Ashley Kelly, a veteran sales development leader, breaks down how to build, structure, and scale high-performing SDR organizations from first hire to a 350-person global team.
  2. She argues SDR is a third, standalone go-to-market pillar that bridges marketing and sales, with distinct strategies for inbound vs. outbound, compensation, and reporting lines.
  3. The conversation covers who to hire, how to interview and onboard them, how to set quotas and comp, and how to maintain morale and performance over time.
  4. Ashley also explores how AI, layoffs, international expansion, and evolving buyer behavior are changing SDR hiring profiles, processes, and expectations.

IDEAS WORTH REMEMBERING

5 ideas

Treat SDR as its own strategic function, not just support.

Ashley believes sales development should be a standalone GTM pillar that bridges marketing and sales, with its own leadership, strategy, and autonomy instead of being viewed as mere ‘order takers’.

Hire for traits and adjacent experience, not just pure sales backgrounds.

Her best SDRs often come from recruiting and call centers because they’re organized, used to high-volume outreach, and comfortable on the phone; she screens heavily for coachability, motivation, and organization rather than quota history.

Design a rigorous, skills-focused interview process with live testing.

Use structured phone screens, panel interviews, a cold-call/elevator-pitch role play (run twice to test coachability), and an email-writing test to assess real communication skills and responsiveness to feedback.

Onboard fast and get SDRs on the phone by week two.

Ashley front-loads company and product training in week one, then tools and workflow training in week two, gives them real books of business early, and ramps quotas over four months to encourage learning through doing.

Set comp and quotas using conversion data, not guesswork or dogma.

Her SDRs are typically on a 70/30 base-variable OTE tied to stage 2 opportunities (qualified demos), with quota and S2 targets calibrated by geography, ACV, win rates, and CAC payback; she’s cautious about tying SDR comp directly to revenue except in very transactional models.

WORDS WORTH SAVING

5 quotes

I actually am very bullish on sales development. I think it's the third pillar within the go-to-market function and I think that it can stand alone.

— Ashley Kelly

If you're still doing the same thing that you were six months ago, you're not going to be successful.

— Ashley Kelly

Sales is very unpredictable. It can really test your patience and your sanity… what you can control are your attitude and effort.

— Ashley Kelly

The hardest part about being an SDR is the little details you have to pay attention to all day every day.

— Ashley Kelly

There’s no asterisk in sales when you hit your quota because you mimicked a top performer.

— Ashley Kelly

Why SDR is a distinct third pillar in go-to-marketHiring strategy: ideal SDR profiles, interview design, and selection criteriaOutbound vs. inbound SDR org design and where the team should reportOnboarding, ramp, quotas, and the metrics that actually matterCompensation structure, revenue alignment, and incentive designScaling from small teams to a 350-person global SDR organizationMotivation, morale management, career paths, and preventing SDR burnout

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