Director of Mid-Market Sales
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 job
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 Sales, Salesforce, MEDDPICC, Challenger, Sandler, Command Of The Message, Pipeline Management, Forecasting, Deal Coaching, CRM
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