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

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

The Twenty Minute VCJun 7, 202453m

Ashley Kelly (guest), Harry Stebbings (host)

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

In this episode of The Twenty Minute VC, featuring Ashley Kelly and Harry Stebbings, Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162 explores building Elite SDR Teams: Hiring, Onboarding, Metrics, and Motivation Playbook 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.

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

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.

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.

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.

Ashley also explores how AI, layoffs, international expansion, and evolving buyer behavior are changing SDR hiring profiles, processes, and expectations.

Key Takeaways

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’.

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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.

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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.

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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.

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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.

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Use leading activity metrics and behavior to spot mis-hires early.

By month two she can usually tell if a hire is wrong based on calls, emails, sequencing volume, and responsiveness to coaching—long before lagging opportunity metrics surface—and is clear that effort and inputs are non-negotiable.

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Protect morale with micro-goals, tight coaching, and fun competition.

Because SDR work is rejection-heavy, she leans on daily/weekly spiffs, ‘fast start’ goals, call blitzes, and celebrating small input wins, while leaders stay very close to reps’ calls and data to help them climb out of slumps.

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Notable 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

Questions Answered in This Episode

How should a founder decide the exact moment to hire their first SDR versus another AE or sales leader?

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.

Get the full analysis with uListen AI

What concrete signals indicate that it’s time to move SDRs from being under marketing or sales into a standalone pillar?

She argues SDR is a third, standalone go-to-market pillar that bridges marketing and sales, with distinct strategies for inbound vs. ...

Get the full analysis with uListen AI

How can teams balance AI-enabled scale in outbound with the need for genuine personalization and diminishing buyer attention?

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.

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What adjustments are needed in SDR profiles, comp, and playbooks when moving from SMB/transactional sales to large enterprise ACVs?

Ashley also explores how AI, layoffs, international expansion, and evolving buyer behavior are changing SDR hiring profiles, processes, and expectations.

Get the full analysis with uListen AI

How should SDR orgs evolve in a world where strong content and self-serve funnels can drive many buying journeys without human outreach?

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Transcript Preview

Ashley Kelly

I would say you wanna look for anyone that has about six months of experience. Does not have to be in sales development. My favorite hires that I've ever made are people that actually come from recruiting. They're super organized. On an inbound side, if you found someone that's ever worked in a call center, again, that's, that's another really good profile. 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. The SDR is kind of the bridge between marketing and sales.

Harry Stebbings

Ready to go? Ashley, I am so excited for this. So first, thank you so much for joining me today.

Ashley Kelly

Yeah. Thank you for having me. Um, I've been following along for, for a little while now, and just feel very honored to be on, uh, the 20 Sales Podcast.

Harry Stebbings

That is very, very kind of you. I, I always love to start with kind of Ashley, the love of sales. I think it's often a moment. When did you realize that you loved sales and that this was what you wanted to do as a career and for life?

Ashley Kelly

I actually started my career working for NASCAR, which is probably, um, a topic for, for a whole nother day. But, uh, world of sales, I started as an SDR at Zenefits. Um, I, very truth be told, I did not know what an SDR was. I thought I was going to be doing demos, uh, in person with, with customers. I was clearly very wrong about that. Um, but I, I ended up falling in love with the top of funnel. Um, SDR to me is just such a special, um, role that is, you know, both pipeline building but also career development at the same time. And so I stayed on the side of, of the sales funnel, and, uh, within three years of Zenefits, I left as a director. And then, uh, since then, I've built out sales development orgs at different tech companies out of the Bay Area, so, um, Lever, Brex, and now Ripley. So, I guess you could say I'm a lifer for, for sales development.

Harry Stebbings

SDRs, traditionally is thought of as like, uh, respectfully, a grind and fricking hard. Career development? Like, talk to me about that element.

Ashley Kelly

I would say the top AEs and best leaders that I've ever worked with have started their, their careers as sales development reps. So, we do a lot of, uh, I've always done this at all the, uh, all the companies I've been at, um, but we do a lot of promotion from within. So we promote, uh, SDRs into the account executive role, um, account management, um, into implementation. In fact, if you look at my org today, about a third of my SDR managers have actually come from the SDR role internally. So it's definitely a, uh, you know, career trajectory for, um, for salespeople.

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