Director, Sales (Hybrid ​/ Boston, MA or Remote - East Coast

Director, Sales

Location requirement:
We can only consider candidates who are based in, or able to relocate to, Massachusetts, Rhode Island, New Hampshire, Michigan, Florida, North Carolina, New York, Ohio, Tennessee, or Toronto, Canada.

Skedda is a leading global workplace management platform, serving over 7,000 customers including Toyota, Siemens, Mercedes-Benz, MIT, and Harvard University. The company is a key player in shaping the future of the modern workplace experience with interactive floor plans, desk and meeting room booking, visitor management, rich utilization analytics, and integrations with Slack, Microsoft 365, and Google Workspace. Each year, Skedda wins awards from G2, Capterra, Get App, and Software Advice.

In 2024, we launched All Booked to serve community-based facilities. We built All Booked on top of the core Skedda booking platform and gave the product a new brand and new features focused on the types of businesses our founders ran. Our customers are golf simulators, art studios, and community centers. They’re the places you create something you can’t wait to tell your family about - the places that give you a community of people that are obsessed with the same thing you’re obsessed with.

They’re the third places that add meaning to your life.

We are seeking a dynamic, entrepreneurial, and results-driven Sales Director to join our growing team. You’ll lead a global team of eight Account Executives who engage prospective customers through both inbound interest and outbound-booked demonstrations. Reporting directly into the Chief Revenue Officer, this is a high-impact leadership opportunity for someone who wants to do more than manage a number. You’ll help shape how we sell, coach, forecast, and scale while working closely with an experienced and highly engaged leadership team.

You’ll have the autonomy to test new ideas, improve our systems, and directly influence the next stage of our growth.

• Lead, train, coach, and mentor a team of Account Executives to ensure consistent quota achievement and to support career development
• Create a high-performance, collaborative team culture through effective team meetings, thoughtful 1:1s, and clear expectations
• Partner closely with Marketing, Business Development, Product, and Senior Leadership to turn market insight into action
• Attend and support key sales engagements to drive actionable next steps and build mutual action plans
• Review Claap recordings weekly and deliver specific, actionable coaching that improves discovery, positioning, objection handling, and closing skills
• Use AI and automation thoughtfully to increase team efficiency, improve coaching quality, accelerate research and follow-up, and allow the team to spend more time on high-value customer conversations
• Provide accurate weekly forecast updates to the Chief Revenue Officer, clearly communicating deal progress, risks, opportunities, and projected monthly performance
• Identify and share customer and market feedback that informs product strategy and platform development
• Lead from the front by staying close to customers, deals, and the day-to-day realities of the sales team

You’re energized by the opportunity to build, iterate, and lead in a fast-moving environment where strong ideas can quickly become meaningful business outcomes You’re a strong verbal and written communicator who can create clarity, alignment, and momentum You’re a systems thinker who can help bring clarity to complex ideas You’re entrepreneurial and energized by the opportunity to build, experiment, and improve You keep customer needs at the center of your decisions and approach You balance a pragmatic problem-solving approach with a strong attention to detail You welcome feedback to improve your skills and work You take initiative and work with a healthy sense of urgency You’re excited by the potential of AI and emerging technology to make sales teams more effective, focused, and impactful and have rolled out AI native workflows for your current sales team with success

• 6+ years of experience leading a SaaS focused New Business Team
• Strong experience using…