The Twenty Minute VCAshley Kelly: The Playbook to Start and Scale Your SDR Team | E1162
CHAPTERS
- 0:00 – 2:33
Ashley Kelly’s path into SDR leadership and why top-of-funnel became her craft
Ashley shares her unconventional start (including NASCAR) and how she accidentally became an SDR at Zenefits—then quickly grew into leadership. She frames sales development as both pipeline creation and a career-launching platform that produces strong AEs and managers.
- •Started as an SDR without fully understanding the role; fell in love with top-of-funnel
- •Progressed rapidly at Zenefits; later built SDR orgs at Lever, Brex, and Rippling
- •SDR as a career accelerator: promotions into AE, AM, implementation, and SDR management
- •Sales development as a distinct discipline she’s committed to long-term
- 2:33 – 3:40
What Ashley wishes she knew earlier: handling unpredictability, rejection, and focusing on controllables
Ashley explains that sales is inherently unpredictable and emotionally taxing. Her core advice is to focus relentlessly on what you can control—especially attitude and effort—while staying adaptable in fast-moving startups.
- •Sales tests patience and sanity; rejection is constant
- •Staying even-keeled is a performance advantage
- •Control the controllables: attitude and effort
- •Adaptability and pivoting are mandatory in startups
- 3:40 – 5:09
Cold calling and outbound aren’t dead—outbound is evolving, not disappearing
Harry challenges whether cold calling still works; Ashley pushes back strongly and argues outbound remains essential. She emphasizes that outbound changes with tools and trends, but fundamentals matter more than any “shiny object.”
- •Outbound is still a major lever; calling remains relevant
- •Outbound tactics evolve (phone book → automation → video → AI)
- •No silver bullet: overcommitting to one channel/tool causes failure
- •Winning teams preserve fundamentals while adapting quickly
- 5:09 – 6:19
AI, infinite spam, and how to use automation without losing the human edge
They discuss the risk that AI-enabled outbound creates overwhelming noise and declining buyer attention. Ashley is cautious about AI, but sees upside in removing busywork so reps can spend more time on high-value personalization and multichannel outreach.
- •AI may create an “infinite spam” problem that devalues outbound
- •Ashley’s cautious adoption stance; prefers practical use cases
- •AI can reduce SDR busywork: data hygiene, contact accuracy, deliverability
- •Freed time should shift to human-driven personalization and channel mix
- 6:19 – 11:06
Where SDRs should report: marketing vs sales vs a standalone ‘third pillar’ in GTM
Ashley outlines when SDRs fit best under marketing (inbound-heavy) versus sales (outbound-heavy). Her strongest view is that sales development should stand alone as the third GTM pillar, acting as the bridge between marketing and sales with its own strategy autonomy.
- •Inbound SDR alignment with marketing improves the MQL→SQL feedback loop
- •Outbound SDR motion is more ‘sales art’ and benefits from sales org alignment
- •Different MQL intents convert differently (demo request vs content download)
- •Her preferred model: SDR as a standalone GTM pillar bridging marketing and sales
- 11:06 – 13:23
How Rippling runs SDR at scale: inbound + outbound + expansion support across functions
Ashley describes Rippling’s unusually large and complex SDR org, including support for new logo, cross-sell, up-sell, regions, and many internal functions. The discussion clarifies why SDRs can be leveraged beyond traditional demo-setting when economics and focus are right.
- •Rippling’s SDR org is ~350 people including leadership
- •SDRs support new logo plus cross-sell/up-sell due to product breadth and CAC logic
- •Complexity comes from multiple segments, regions, and use cases
- •SDRs can extend into customer base prospecting where it frees AE/AM time
- 13:23 – 15:33
When to hire your first SDR and why founders must own the first sales playbook
Ashley advises early-stage founders to start with someone who can both prospect and close (often a junior AE profile), rather than a pure SDR or a senior leader who won’t do the grind. She also insists founders (or top GTM leaders) must craft the initial sales story and playbook.
- •First hire often should be a prospecting-and-closing profile, not a brand-new SDR
- •Avoid assuming SDRs can be ‘plug-and-play’ without process and enablement
- •Founders should be the main seller/storyteller early on
- •The playbook starts with vision: what you’re building and why it matters
- 15:33 – 16:50
SDR hiring profiles that work: recruiting backgrounds, call centers, and phone confidence
Ashley details the candidate profiles she prefers, focusing on transferable skills and early experience rather than perfect SDR resumes. A recurring theme is finding people already comfortable on the phone, since cold calling is the biggest hurdle for many new SDRs.
- •Look for ~6 months experience; doesn’t need to be SDR experience
- •Recruiters transition well: organized, persistent, used to rejection and calling
- •Inbound SDRs: call center experience can be a strong signal
- •Phone confidence beats candidates who hide behind email-only outreach
- 16:50 – 20:51
Interviewing SDRs for traits: coachability, motivation, and organization (and how to test them)
Because SDR outcomes aren’t as directly measurable as closing roles, Ashley interviews for intangibles. She shares specific questions and observable signals that reveal coachability, what truly motivates the candidate, and whether they have the organizational habits to manage high-volume workflows.
- •Three core buckets: coachability/change navigation, motivation, organization
- •Coachability test: failure + feedback example; look for real implementation behaviors
- •Motivation signals: money drive or clear career ambition; weak signal is ‘my parents said sales’
- •Organization signals: calendar discipline, time-blocking, and structured work habits
- 20:51 – 25:38
Practical hiring process design: panels, live role plays, and email assessments (plus AI implications)
Ashley breaks down a concrete hiring flow: phone screen, panels, role play, and an email assessment. She focuses on improvement between iterations—especially whether candidates incorporate feedback—while acknowledging AI complicates judging written work (and may also reflect resourcefulness).
- •Process: hiring manager screen → 2–3 interviews/panels
- •Role play example: elevator pitch scenario; evaluate iteration after feedback
- •Email assessment: respond to objections, mirror language, write concise follow-ups
- •AI makes email tests harder to attribute—but using tools may be a positive
- 25:38 – 29:24
SDR compensation and what to comp on: stage-based credit vs revenue alignment
Ashley explains Rippling’s comp mix and why SDRs are typically comped on stage-based opportunity creation rather than revenue. She also shares a case where revenue comp worked at Brex due to a transactional motion—and the unintended consequences that emerged.
- •Comp structure: ~70% base / 30% variable (geo-adjusted OTE)
- •Credit tied to ‘Stage 2’ opportunities (demo held + validated + next steps)
- •Revenue-based SDR comp can work in transactional, short-cycle models (Brex)
- •Incentives change behavior: revenue comp increased revenue but reduced demo volume (S2s tanked)
- 29:24 – 32:02
How SDR hiring changed post-COVID: layoffs, talent supply, and avoiding ‘butts in seats’ mistakes
Ashley contrasts pre-COVID preferences for inexperienced hires with today’s reality: more experienced SDR talent is available due to layoffs and RIFs. She also shares her biggest hiring mistake—rushing and hiring off short screens—highlighting how quality degrades when speed becomes the only goal.
- •Pre-COVID preference: hire early-career talent and mold them; avoid bad habits
- •Post-COVID reality: RIFs create a pool of strong experienced SDRs
- •RIF stigma isn’t always fair; rely on process, gut, and backchannel references
- •Biggest mistake: hiring off 30-minute screens to hit aggressive hiring goals
- 32:02 – 37:36
Onboarding that ramps faster: phone by week two, ramp quotas, and using conversion data to set targets
Ashley outlines an onboarding approach designed to reduce time-to-productivity: reps get books early and start calling by week two. She explains ramp quotas through month four and the analytics used (S1/S2 conversion) to set realistic expectations, especially for outbound compounding effects.
- •Week 1: company/product/competitive onboarding; Week 2: tools + job execution
- •Give reps their books early so training is hands-on (scrubbing, sequencing, targeting)
- •Ramp quotas over 4 months (example: 2 → 4 → 6 → 8 S2s)
- •Outbound takes time to compound; targets should reflect sequence response lag and conversion rates
- 37:36 – 42:00
Performance management: spotting mis-hires by month two, morale recovery, and incentive design
Ashley explains she can usually identify mis-hires in month two by looking at inputs and KPI mastery rather than final outcomes. She shares how she rebuilds morale by tightening coaching, celebrating controllable micro-wins, and running spiffs and call blitzes to re-energize teams.
- •Mis-hires show up in month two via weak inputs (calls, emails, sequencing volume)
- •Early signals of greatness: proactive help-seeking and visible floor presence
- •Morale recovery: get close to reps, coach fundamentals, celebrate small wins
- •Spiffs examples: fast-start pacing, call blitzes, region-vs-region competitions, raffles
- 42:00 – 45:10
Scaling the org and staying effective globally: ABM partnership, events, and international leadership challenges
They explore how SDR effectiveness is amplified by marketing partnership (ABM, direct mail, content, ads) and by in-person learning effects. Ashley also describes the operational friction of scaling across time zones and geographies, and how she’s adapting her leadership style internationally.
- •SDR–marketing partnership opportunities: ABM, direct mail, content for nurture, LinkedIn ads
- •Events have become a strong channel again; persona matters (e.g., HR audiences)
- •Scaling breakpoints: need strong senior leaders; biggest challenge is time zones and speed of execution
- •In-office SDRs often outperform remote due to real-time shadowing and floor learning
- 45:10 – 53:43
When good SDRs go bad and the quick-fire: stigma, tactics that died, and the future of the function
Ashley explains that SDRs decline when they can’t diagnose failure, don’t use resources, or realize sales isn’t for them—prompting the need for multiple career paths beyond AE. In quick-fire, she revisits AI skepticism, remote vs in-office realities, common bad advice, and her belief that sales development will become an executive-level function.
- •Good SDRs go bad when they can’t identify why performance dropped or won’t adapt
- •Not everyone truly wants sales; create lateral paths to retain strong talent
- •Quick-fire highlights: handwritten notes declining; shadow top performers; use funnel metrics + coaching
- •She wants to end the ‘SDR is dead’ stigma; predicts a Chief Sales Development Officer role in 10 years
