Director of Sales – Mid Market

Obsidian Security Logo
Obsidian Security
Boston, MASSACHUSETTS, United States
  • Production
  • FullTime
  • Applications have closed

We are seeking a Director of Sales to accelerate growth in our Mid-Market segment. Reporting directly to the Vice President of Sales, Mid-Market, this individual will lead a team of Account Executives responsible for acquiring new logos, expanding customer relationships, and driving consistent ARR growth.

This is a pivotal role as we scale. The Director will build and coach a high-performing team, instill operational rigor, and serve as a key partner in shaping and executing our go-to-market strategy for the Mid-Market business.

Responsibilities:

Team Leadership & Development

  • Recruit, hire, and develop a team of high-impact Mid-Market Account Executives.
  • Foster a competitive, collaborative, and inclusive culture that emphasizes accountability, learning, and results.
  • Provide ongoing coaching in deal strategy, discovery, and value-based selling.
  • Drive performance management through weekly one-on-ones, pipeline inspections, and quarterly business reviews.

Sales Execution & Growth

  • Ensure achievement of team ARR targets by managing pipeline generation, opportunity progression, and forecast accuracy.
  • Lead structured pipeline and forecast reviews with the VP of Sales, Mid-Market.
  • Oversee effective use of territory planning, account mapping, and account reviews to maximize coverage and customer engagement.
  • Act as an executive sponsor on strategic opportunities, supporting AEs in complex or competitive deals.

Customer & Partner Engagement

  • Build strong executive relationships with customers, serving as an escalation point for the sales team.
  • Partner with alliances and channel teams to expand reach and amplify customer value.
  • Collaborate closely with Sales Engineering, Customer Success, Renewals, Marketing, Product, and Legal to deliver a seamless customer experience.

Operational Excellence

  • Establish and track key sales metrics and KPIs to monitor performance and guide decision-making.
  • Drive adoption of sales processes, playbooks, and tools to increase efficiency and consistency.
  • Manage expenses and resource allocation to optimize return on investment.

Required Experience & Skills

  • 5 years of SaaS sales leadership experience, with at least 2 years in cybersecurity or an adjacent market.
  • Proven success leading teams selling into the Mid-Market (ACVs typically $50K–$150K ).
  • Demonstrated ability to hire, retain, and develop top sales talent.
  • Strong grasp of sales fundamentals: territory planning, pipeline management, forecasting, and account strategy.
  • Track record of building pipeline through activity-driven management and disciplined prospecting across the team.
  • Consistent record of exceeding revenue targets through data-driven execution and coaching.
  • Excellent communication and interpersonal skills, with ability to influence cross-functionally and at customer executive levels.
  • Growth mindset with a balance of strategic thinking and hands-on execution.
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