Director of Sales - Mid Market

Obsidian Security•Boston, MA

64d

About The Position

Founded in 2017, Obsidian Security was created to close a critical gap: securing the SaaS applications where modern business happens-platforms like Microsoft 365, Salesforce, and hundreds more. Backed by top investors including Greylock, Norwest Venture Partners, and IVP, we've built a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Our team includes leaders who helped define the categories of endpoint and identity security at CrowdStrike, Okta, Cylance, and Carbon Black. Now, we're transforming how SaaS is secured-in the era of agentic AI. Today, Obsidian is trusted by global enterprises like Snowflake, T-Mobile, and Pure Storage. We protect more than 200 organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand-including many of the world's largest Fortune 1000 and Global 2000 companies. With strong global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and a major fundraise on the horizon, we're scaling quickly toward long-term growth and IPO readiness. Join us as we define the future of SaaS security! 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.

Requirements

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.

Responsibilities

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.
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.
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.
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.