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Interview, Fireside Chat

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

  • Hiring Profiles and Experience:

    • Target candidates with approximately six months of experience, though prior SDR-specific background is not mandatory.
    • Prioritize candidates from recruiting backgrounds due to their organizational skills and existing rhythm of high-volume outbound calls to uninterested parties.
    • Consider call center experience for inbound roles to ensure candidates already possess call confidence and resilience.
    • Recent shifts in the labor market have increased the availability of experienced SDRs laid off during tech downturns, shifting hiring preferences from fresh graduates to experienced talent.
  • Organizational Structure and Strategy:

    • Advocate for Sales Development as a distinct "third pillar" of the go-to-market function, reporting to the CRO but operating as a bridge between Marketing and Sales.
    • Recommend placing heavy inbound SDR teams under Marketing to optimize lead-to-demo conversion feedback loops.
    • Recommend placing heavy outbound SDR teams under Sales to leverage proactive selling, education of new accounts, and internal promotion pathways.
    • At Rippling, the SDR organization supports 31 different functions, including new logo acquisition, cross-sell, up-sell, and international expansion.
  • Compensation and Quotas:

    • Adopt a compensation model of 70% base salary and 30% variable commission.
    • Tie variable pay to "Stage 2" opportunities (AEs confirming a qualified demo with next steps) rather than closed revenue, with exceptions made for high-velocity, transactional models like Brex.
    • Set ramped quotas starting at 25% of full capacity in Month 1, scaling to 50%, 75%, and 100% by Month 4.
    • Adjust quota volume based on ACV; lower ACV models require higher volume targets to ensure CAC payback efficiency.
  • Interview and Assessment Methodology:

    • Assess candidates across three core traits: coachability (implementation of feedback), motivation (financial or career growth goals), and organizational discipline (calendar management).
    • Utilize role-play scenarios (e.g., "elevator pitch") followed by immediate feedback and a second attempt to test adaptability.
    • Conduct email assessments to evaluate writing skills, active listening, and the ability to personalize responses without over-reliance on AI.
    • Screen for "grit" by asking candidates to describe specific failures and how they implemented feedback to improve.
  • Onboarding and Performance Metrics:

    • Implement a rapid onboarding schedule where new hires are placed on live accounts by Week 2, with full ramping expected by Month 4.
    • Monitor success primarily through leading indicators (calls made, emails sent, accounts worked) rather than lagging revenue indicators in the early months.
    • Identify mis-hires within the first two months by tracking the inability to consistently hit activity-based KPIs.
    • Boost morale through "micro-ambitions," short-term spiffs (e.g., week-one halfway targets), and regional competitions focused on activity volume.
  • Technology and Market Trends:

    • View AI as a tool to eliminate busy work (account scrubbing, data cleaning) rather than a replacement for the human element of personalization.
    • Acknowledge that outbound is evolving through automation and video prospecting, but fundamentals remain the primary driver of success.
    • Identify "handwritten notes" and pure remote work for outbound teams as declining trends due to efficiency and shadowing benefits.
    • Express strong bullishness on the SDR role's longevity, rejecting the notion that the function is "dead" despite AI advancements.
  • Career Development and Leadership:

    • Emphasize internal promotion paths where SDRs transition into Account Executive, Account Management, or Implementation roles; currently, one-third of SDR managers are former SDRs.
    • Predict that within 10 years, the Head of Sales Development will hold an executive-level title (Chief Sales Development Officer).
    • Suggest that founders hire a junior AE with prospecting experience for the first sales hire rather than a Director, to ensure process building from the ground up.
    • Recommend that founders act as the primary storyteller to create the initial sales playbook and content.
  • Global and Cultural Considerations:

    • Face challenges in scaling globally due to time zone discrepancies, requiring heavy reliance on asynchronous communication (Slack) and monthly in-person travel to maintain team cohesion.
    • Adapt motivation and management strategies to local cultural psychologies, specifically noting differences between US and UK markets.