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Director of Mid-Market Sales

350k – 400kSan Francisco, CAAccount ExecutiveHybrid7+ YOE
Summary

Lead and coach a team of Mid-Market Account Executives at a fast-growing Voice AI startup. Drive forecast accuracy, pipeline discipline, and sales methodology adoption to scale revenue.

About the role

What You'll Do

First 30 Days

  • Develop a deep understanding of pipeline health, forecast methodology, ICP segmentation, and deal velocity
  • Build trust with Mid-Market AEs through hands-on deal coaching and field presence
  • Assess the current forecasting process and identify gaps in accuracy, inspection, and accountability
  • Align with Sales Development, Solutions Engineering, Marketing, and RevOps on pipeline coverage and opportunity progression

60 Days

  • Implement a rigorous weekly forecasting cadence with clear inspection criteria and defined commit standards
  • Run structured deal reviews and pipeline inspections to improve win rates and reduce sales cycle time
  • Reinforce outbound discipline within the AE team to ensure consistent self-sourced pipeline generation
  • Begin driving sales methodology adoption (MEDDPICC) to increase consistency across deals

90 Days

  • Deliver reliable forecast rollups to the VP of Sales with clear visibility into risk and upside
  • Demonstrate measurable improvement in pipeline hygiene, stage conversion rates, and forecast predictability
  • Support recruiting, onboarding, and ramping new AEs with clear hiring profiles and success benchmarks
  • Establish a high-performance sales culture grounded in accountability, coaching, and operational rigor

Who You Are

  • 7+ years in B2B SaaS sales with at least 3 years in frontline sales management (Manager, Director, or RVP)
  • Proven forecast accuracy: consistent track record of calling your number and delivering against quota in high-growth environments
  • Mid-Market expertise: experience leading AEs selling into mid-market accounts with deal sizes in the $240K–$1M+ ARR range
  • Complex deal coach: skilled at guiding multi-stakeholder sales cycles involving developers, technical buyers, and C-suite executives
  • Methodology fluency: strong command of MEDDPICC, Challenger, Sandler, Command of the Message, or a comparable framework
  • Builder mentality: hands-on operator who thrives in early-stage environments and can create process from scratch
  • Analytically driven: strong pipeline management skills and CRM discipline — Salesforce experience strongly preferred
  • People leader: excellent communicator who earns trust, leads by example, and brings out the best in their team

Bonus

  • Background in developer tools, API-first products, infrastructure, AI, or voice technology

What We Offer

  • Competitive salary + equity - real ownership in a company with real momentum
  • Comprehensive health coverage - medical, dental, and vision
  • Quarterly off-sites - we invest in the team, not just the work
  • Flexible PTO - take what you need
  • $10K annual L&D budget - we're serious about your growth
  • Perks: catered meals, transportation, and gym access
Skills
B2B SaaS salesSalesforceMEDDPICCChallengerSandlerCommand of the MessagePipeline managementForecastingDeal coachingCRM
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