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

Skedda

$150K — $180K *
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6+ years of experience leading SaaS focused New Business Teams
  • Strong proficiency with HubSpot, ZoomInfo, Outreach, Claap, and sales technologies
  • Proven track record of achieving and exceeding sales targets
  • Data-driven approach with hands-on field engagement
  • Experience managing SMB and mid-market sales globally
  • Knowledge of sales assisted PLG motions is advantageous
  • Familiarity with MEDDIC and BANT-C frameworks is a plus

Responsibilities

  • Lead, train, coach, and mentor a team of Account Executives for quota achievement
  • Create a collaborative high-performance team culture through effective meetings and expectations
  • Collaborate closely with Marketing, Business Development, Product, and Senior Leadership
  • Attend key sales engagements to drive actionable next steps
  • Review Claap recordings weekly to provide actionable coaching to the team
  • Leverage AI and automation to enhance efficiency and coaching quality
  • Provide accurate weekly forecasts and communicate deal progress and risks
  • Gather and share customer feedback to inform product strategy

Benefits

  • Competitive salary, benefits package, and paid time off
  • Flexible schedule
  • Creative and collaborative work environment
  • Direct exposure to leadership across departments
  • Opportunity to significantly influence product and customer experience
Full Job Description
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.

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

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