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, GetApp, and SoftwareAdvice.

In 2024, we launched AllBooked to serve community-based facilities. We built AllBooked 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.

Role overview

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.

Key Responsibilities:

• 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

About you

• 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

Qualifications:

• 6+ years of experience leading a SaaS focused New Business Team
• Strong experience using HubSpot, ZoomInfo, Outreach, Claap, and other sales technologies
• Historical success achieving and outperforming sales targets
• Data-driven leader who will roll up their sleeves and get in the field
• Experience managing SMB and mid-market sales motions across a global customer base
• Experience leading within a sales assisted PLG motion a plus
• Experience managing through MEDDIC + BANT-C a plus

Benefits

• Competitive salary, benefits package, and paid time off
• Flexible schedule
• Creative and collaborative work environment
• Direct exposure to the leadership team across departments
• Be empowered to leave a significant mark on the product and the customers

About us

We're an international team from 20+ countries with a growing presence in Boston. We place a lot of value on collaborating asynchronously across time zones but also understand the benefits of working together in person. Our team has doubled in size in the last year and continues to grow quickly.

At Skedda, our Mission is to empower organizations to bring workspaces to life. We take feedback from customers seriously and constantly iterate to improve our product. We're a self-driven, curious, down-to-earth group of people who know how to balance moving quickly while maintaining a high bar for quality. Every team member at Skedda embodies our six core virtues:

• We are a community
• Quality is at our core
• Take ownership
• Create momentum every day
• Tackle hard problems
• Be curious

We are defining the future of the workplace experience, helping businesses to design meaningful, seamless, fully integrated employee experiences and interactions in the hybrid workplace. We're growing fast with a lot of new opportunities ahead!

To learn more about us, please visit https://www.skedda.com/careers and https://www.allbooked.com/about.