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

Skedda•Boston, MA

3d•Hybrid

About The Position

Skedda is a leading global workplace management platform serving over 7,000 customers. 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. In 2024, Skedda launched AllBooked to serve community-based facilities, focusing on businesses like golf simulators, art studios, and community centers. We are seeking a dynamic, entrepreneurial, and results-driven Sales Director to 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 where you will help shape how the company sells, coaches, forecasts, and scales. You will have the autonomy to test new ideas, improve systems, and directly influence the company's growth.

Requirements

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.

Nice To Haves

Experience leading within a sales assisted PLG motion a plus.
Experience managing through MEDDIC + BANT-C a plus.

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.