Ashley Kelly on Hiring, Onboarding and Scaling Sales Development

Rippling sales-development leader Ashley Kelly sees sales development as a bridge between marketing and sales and a career path in its own right. She favors candidates with relevant calling and organizational experience, including recruiters and call-center workers. These are her hiring preferences, not universal requirements.

Kelly tells Harry Stebbings she began her sales career as an SDR at Zenefits after working at NASCAR. She says she had not understood the role at first but grew to enjoy building the top of the funnel and developing people, later leading teams at Lever, Brex and Rippling.

She says many strong account executives and leaders started as SDRs and describes internal promotion into sales, account management and implementation. Roughly a third of her current SDR managers came from the role internally, she says; this is a company-specific figure from her account.

Sales is unpredictable, Kelly says, so she focuses on effort, attitude and adaptability. She believes outbound calling still works but evolves alongside email automation, video and AI. She warns against abandoning sales fundamentals for a new tool that is treated as a silver bullet.

Stebbings worries that AI could produce unlimited low-quality outreach. Kelly shares the concern but thinks AI could reduce administrative work such as cleaning accounts and contact details, leaving more time for personalized communication. This is her expectation, not measured evidence of productivity gains.

Kelly has worked with SDR teams reporting to marketing and to sales. She sees close marketing alignment as useful for inbound leads, where a demo request signals more intent than a content download, and sales alignment as useful for outbound prospecting and career development.

Her preferred model treats sales development as a third go-to-market pillar, even though she reports to Rippling’s chief revenue officer. She wants SDRs to work with marketing on account campaigns and with sales on targets that can become revenue, while having autonomy over their own strategy.

She says account executives should be able to prospect, but believes their time may be better spent closing when a team supplies enough qualified pipeline. She praises Rippling’s inbound and outbound operation and describes work on cross-sell as well as new customers. This favorable account comes from a leader of that organization.

Kelly estimates she has hired about 800 SDRs across companies and says Rippling’s organization included about 350 people, including managers and leaders, at the time. She recommends an early hire who can both prospect and close, often a junior account executive, rather than assuming an inexperienced SDR can build a process alone.

The founder should normally be the primary storyteller and help develop the first sales playbook, she says, translating the vision and customer problem into prospect conversations. The exact role of a senior marketing or sales leader depends on company size.

For subsequent SDRs, Kelly looks for about six months of relevant experience, not necessarily in sales development. Recruiters are used to organized outreach and phone conversations; call-center experience can help on inbound. She treats comfort on the phone as a useful starting point, not a guarantee of performance.

Her three interview themes are coachability, motivation and organization. She asks for a concrete example of failure, feedback and how the candidate responded, rather than accepting a general claim of being coachable. She values both financial motivation and a desire for career growth, while recognizing that answers can vary by context.

To understand organization she asks how candidates structure their calendars and protect time for calls, research and email. That is one signal in her process, not proof that a particular calendar habit causes success. She says candidates in her US experience readily discuss money motivation.

Kelly describes phone screens, panel interviews, role plays and an email exercise. The role play is not expected to be perfect: an interviewer gives feedback, then asks the candidate to try again so the team can observe whether it is applied. She says about half perform an initial pitch well in her experience, a rough interview estimate.

The email test looks for concise writing that responds to a prospect’s actual objection and explains why the outreach is relevant. Kelly worries AI can obscure authorship; Stebbings suggests effective use of a tool might itself be resourceful, and she says she will reconsider. They do not establish a measured effect of AI on hiring quality.

She relies on representatives to suggest tools because they see day-to-day problems firsthand and says the team recently began testing Clay for personalization. She is interested in both performance and whether the team likes the tool; the interview reports no results from the test.

Kelly says compensation varies by geography and describes a 70% base, 30% variable structure at Rippling. Variable pay is tied to stage-two opportunities: an account executive has held a demo, confirmed a suitable prospect and agreed next steps. Different teams have different quotas. This is a specific company plan, not a recommended standard for every business.

Stebbings asks why compensation is not tied directly to revenue. Kelly says the entire financial model must ultimately lead to revenue, but long sales cycles and shorter SDR tenure can make a revenue-only goal difficult. She previously used revenue compensation at Brex, where she recalls referred revenue tripling in six months but stage-two volume falling; these company-specific results lack disclosed methodology.

Before the pandemic, Kelly preferred inexperienced SDRs she could train and worried prior habits would be hard to change. She says layoffs have made experienced talent available and she has since hired strong people affected by reductions. A layoff alone, in her revised view, does not establish poor performance.

Her own hiring mistake was making decisions after only a 30-minute phone screen while trying to fill many roles quickly at Zenefits. She says the process did not adequately assess quality or candidate commitment. The lesson she draws is to invest in a consistent interview process.

For onboarding, she aims to get new SDRs working real accounts and making calls by the second week, while recognizing people learn differently. The first week covers the company and product; the next covers tools, prospecting and account workflows. New hires have graduated quotas rather than full expectations immediately.

She illustrates a four-month ramp with a full target of eight stage-two opportunities per month and progressive targets of two, four and six beforehand. Outbound sequences can take weeks to yield responses, she says. These are Rippling-specific examples, not universal benchmarks.

The team examines account-to-stage-one and account-to-stage-two conversion and time to conversion when setting targets. Lower contract values require more opportunities for acquisition economics to work, she says; revenue operations also considers win rates, contract values and product attachment. The interview does not disclose the full financial model.

Kelly says she often sees signs of a mismatch by month two in activity inputs such as calls, emails and accounts worked, even before opportunity results mature. She also looks for proactive requests for coaching. These are her signals and personal experience, not proof that early activity alone determines long-term success.

When morale falls, she recommends leaders get close to the team, review calls and celebrate smaller controllable improvements. Short-term incentives and call competitions can create energy while people work toward a monthly quota. She acknowledges that recovering morale is difficult and that team conditions vary.

Stebbings argues brand and content can warm a sales conversation. Kelly sees opportunities for SDR and marketing teams to coordinate account-based campaigns, direct mail, content and events. She says the right channel depends on the audience and gives HR events as an example from her company.

Scaling internationally has made time-zone coordination difficult, she says, so the organization uses asynchronous communication and needs strong senior leaders. She adds that strong SDRs may enter a slump or discover sales is not their desired career; lateral moves can retain valuable contributors.

Kelly wants to improve her own time management across teams and says motivating people in different geographies requires listening locally rather than imposing a US playbook. She describes visiting the Dublin team to learn. These are ongoing leadership lessons, not a complete cross-cultural framework.

In quick fire, she says she is more open to AI helping efficiency and that handwritten notes may be less useful when recipients are not in offices. She says Rippling’s in-office SDRs performed better in her experience, especially outbound, but the interview gives no controlled comparison; remote and office groups may differ in other ways.

She advises a new SDR to shadow a top performer before adapting the method, and to use funnel metrics and call recordings for coaching. She rejects a blanket claim that the SDR function is dead and says industries and markets differ.

Kelly pushes back on asking SDRs to overqualify every opportunity: for an important account, she thinks a capable account executive may want the conversation directly. She values executives who give sales-development leaders trust and autonomy, and praises leaders she has worked for. These are her professional judgments.

Looking ten years ahead, Kelly hopes sales development will have a chief-level role. This is her career ambition and prediction about organizational structure, not a current industry standard. The conversation closes with thanks.