Most important take away

SDR is a distinct, third pillar of go-to-market (bridge between marketing and sales), not a glorified order-taker, and the discipline lives or dies on fundamentals: rigorous hiring for coachability/motivation/organization, fast onboarding that puts reps on the phones by week two, ramped quotas tied to stage-2 opportunities (not raw revenue in most SaaS), and relentless attention to inputs. AI helps eliminate busywork but is not a silver bullet, and chasing shiny objects while neglecting fundamentals is how outbound orgs fail.

Summary

Actionable insights and tactics from Ashley Kelly (VP Global Sales Development, Rippling) on building, hiring, comping, and scaling an SDR org.

Career advice (especially for early-career operators):

• SDR is one of the strongest launchpads in tech go-to-market. Top AEs and sales leaders frequently start as SDRs; at Rippling roughly a third of SDR managers came up from the SDR role. Promotion paths include AE, account management, implementation, and lateral moves for good people who decide sales is not for them.
• For someone starting an SDR role tomorrow: find the top performer on the team and copy everything they do before trying to “reinvent the wheel”; add your secret sauce later. There are no asterisks on quota attainment.
• Be proactive with leadership. Ashley says the new hires who immediately book time on her calendar consistently turn into top performers, not because of the meeting but because of what that behavior signals.
• Money motivation is a legitimate (and common) answer in US sales hiring; ambition for growth/title (e.g., “I want to be a VP of sales development”) is equally valid. The worst signal: “my parent was in sales and thinks I’d be good at it.”
• Resilience matters. Ability to face failure, diagnose why a month went badly, and self-correct is what separates SDRs who survive from those who slump permanently.

Org structure and where SDR sits:

• If you are heavy inbound, SDR can report to marketing — the MQL-to-SQL feedback loop benefits from tight marketing alignment. High-intent MQLs (demo requests, contact-us clicks) should convert at much higher rates than low-intent (whitepaper downloads).
• If you are heavy outbound, SDR should report to sales — it is more of a sales motion (educating cold accounts, surfacing pain) and proximity to AEs accelerates SDR-to-AE promotion.
• Ashley’s real view: SDR should be a third pillar alongside marketing and sales. At Rippling she reports to the CRO but partners equally with marketing (ABM, direct mail, events, LinkedIn ads to warm accounts) and sales (targeting accounts that can actually close). AEs should still prospect when they can, but their time is better spent closing if SDRs are delivering volume and quality.
• Rippling’s SDR org is ~350 people supporting 31 different functions including new logo, product-led motions, and cross-sell/upsell into the customer base (only viable because CAC payback works at their scale).

Hiring playbook:

• First SDR hire should not be a fresh-grad SDR. Hire a junior AE who has prospected and closed and is willing to be in the weeds writing sequences and making cold calls. Founders should own the first playbook because they are the main storyteller.
• Ideal SDR profile: ~6 months of any experience, not necessarily sales. Best feeder roles are recruiting (organized, comfortable cold-calling people not in market) and call centers (already have a phone voice and can take rejection).
• Three things to interview for (intangibles, not resume metrics):
  1. Coachability / ability to navigate change — ask for a specific story of failure plus feedback and how they implemented it.
  2. Motivation — money motivation or clear growth/title ambition are both green flags.
  3. Organization — look for evidence they live by their calendar and block time for calls, account scrubbing, and personalization.
• Process: hiring-manager phone screen plus 2-3 panel interviews including a live role play (e.g., elevator pitch to a director of HR at a conference) and an email assessment. The role play is graded on willingness to take feedback and immediately apply it on a second attempt — not on nailing the pitch. The email test checks active reading, mirroring of language, and the “why you, why now” framework.
• Post-COVID shift: Ashley now hires SDRs with prior SDR experience because tech layoffs have surfaced good talent; pre-COVID she avoided this because of habits and tenure concerns. Back-channel candidates impacted by RIFs rather than assuming they were low performers.
• Biggest hiring mistake she has made: 30-minute phone screens with no further vetting just to hit headcount goals at Zenefits. Don’t sacrifice interview rigor for speed.

Compensation:

• 70% base, 30% variable, tied to stage-2 opportunities (S2 = AE-validated demo with next steps, right persona, real fit). Quotas vary by segment based on TAM and persona.
• Generally do NOT comp SDRs on revenue in SaaS. It worked at Brex (3x referred revenue in 6 months) because deal cycles were 2-3 weeks and the model was transactional GMV, but in longer ARR cycles SDR tenure is too short and demo volume tanks when reps hit revenue quota without enough at-bats.
• Lower ACV products require higher S2 quotas to make CAC payback math work; track per-rep production, win rates, ACV, and product attach rates.

Onboarding and ramp:

• Week 1: company onboarding, product, competitors.
• Week 2: tooling (Sales Navigator, ZoomInfo, Outreach), and reps get their book and start calling by end of week.
• Full ramp at month 4. Ramping quota example: 2 S2s month one, 4, 6, then 8 at full ramp. Sequences typically take ~2 weeks to start producing real responses, so compounding takes time.
• Spot a mis-hire by month 2 — usually visible from input KPIs (dials, emails, accounts in sequence), not S2 output yet. Inputs are easy to do; failing on inputs signals effort or fit problems.
• Tells of future top performers: in-office presence (making calls at the desk, not hiding in phone booths) and proactively booking time with senior leaders.

Managing the team:

• Tech patterns / tools mentioned: Clay (data enrichment + AI personalization, recently adopted at Rippling), Outreach (sequencing), Sales Navigator, ZoomInfo, Salesforce, Snowflake. Lean on reps to surface tooling — they are in the weeds and know what helps.
• AI’s real role for SDR: eliminate busywork (account scrubbing, contact/phone/email hygiene, deliverability) so reps can focus on personalization and multi-channel (LinkedIn) work. Resist chasing the shiny object at the expense of fundamentals.
• Concern raised by Harry: infinite-scale AI outbound will collapse appreciation for the channel and trigger blocks; treat outbound as a craft.
• AI also affects hiring tests — candidates likely use ChatGPT on email assessments; if output is the same, give them credit for being resourceful.
• Morale recovery: get close to the team, celebrate small wins (dials, connects, individual conversations), and use short-cycle SPIFFs/competitions (fast-start to hit half-quota by week 1, call blitzes, regional comps, March Madness brackets, raffles) because SDR is a daily function where you can still hit quota with 6 days left in the month.
• In-office SDRs outperform remote ones, especially on outbound, because of shadowing, screen-watching, and overhearing calls.
• International scaling is the hardest break point: time zones, cultural differences (UK vs US motivation styles), and the need to physically visit offices rather than impose US playbooks remotely.
• AE pushback that SDRs need to “qualify more” is largely BS — a good AE should want to take any conversation with a top-account contact rather than leave it to a less-trained SDR.

Brand and marketing partnership:

• SDR/marketing tension is really untapped ABM opportunity. Direct mail, content (white papers as easy follow-ups), LinkedIn ads, and events (especially for HR personas) all warm accounts before SDR outreach.
• Harry’s content-as-funnel idea: pick an ICP, start a podcast interviewing that ICP — instant lead funnel. Ashley agrees and notes Rippling has had strong success at HR events.

10-year prediction: Sales development will sit at the executive level (Chief Sales Development Officer).

Chapter Summaries

• Intro and Ashley’s background: From NASCAR to SDR at Zenefits to building SDR orgs at Lever, Brex, and now Rippling (350 SDRs, 200 hired in the last year, 800 total over her career).
• Career path of an SDR: Top AEs and leaders often start in SDR; ~1/3 of Rippling SDR managers came up internally; promotion paths into AE, AM, and implementation.
• Is outbound dead?: No. Outbound is evolving (AI helps with busywork) but fundamentals win; chasing shiny objects is how orgs fail.
• Where SDR should report: Marketing for heavy inbound, sales for heavy outbound, but Ashley’s real view is SDR as a third GTM pillar bridging both.
• Should AEs prospect?: Yes when they can, but their time is better spent closing if SDRs deliver quality pipeline.
• First SDR hire: Hire a junior AE first, not a fresh-grad SDR; founder should own the first playbook.
• Ideal SDR profile and sources: 6 months of any relevant experience; recruiting and call-center backgrounds are top feeders.
• Interview process: Phone screen + 2-3 panels including role play (elevator pitch with feedback loop) and an email test scoring active reading and the why-you/why-now framework.
• Three traits to interview for: Coachability, motivation (money or growth/title ambition), and organization.
• Compensation: 70/30 base/variable on S2 quotas; don’t comp on revenue in long-cycle SaaS; example from Brex where it worked due to short cycles.
• How hiring has changed post-COVID: Now open to experienced SDRs from layoffs; rely on back-channeling, not blanket “RIF means bad” assumptions.
• Biggest hiring mistake: 30-minute phone screens at Zenefits to hit headcount.
• Onboarding: Phones by week 2; full ramp at month 4; ramped quotas (2, 4, 6, 8 S2s).
• Spotting good vs great early: Input KPIs by month 2; proactive booking of leadership time; in-office presence.
• Managing morale: Celebrate inputs and small wins; run short-cycle SPIFFs (fast-starts, call blitzes, regional competitions, raffles).
• SDR x marketing: ABM, direct mail, content, events, LinkedIn ads — partner, don’t compete.
• Scaling to 350 and internationally: Senior leaders, async/Slack culture, in-person travel, learning local cultural differences.
• How good SDRs go bad: Inability to diagnose failure or realizing they don’t actually want sales — provide lateral exit ramps.
• Self-assessment: Time management across many regions and functions.
• Quick-fire: Handwritten notes are dead (offices empty); remote SDR is the hardest pattern; AE complaints about SDR qualification are BS; copy the top performer if you’re new.
• Wrap: Ashley predicts a Chief Sales Development Officer role at the exec level within 10 years.