AllBooked Director of Sales

Full-time – Boston, MA (Hybrid) or Central/Eastern Timezone – US/Canada (Remote)

AllBooked by Skedda is a leading global booking management platform for SMBs who want to monetize their spaces. Our customers include athletic facilities, studios, creative spaces, event venues, community centers, and coworking spaces. AllBooked serves over 4,000 customers and is experiencing significant growth, making it an exciting time to join the AllBooked team.

We are seeking our first Director of Sales to lead and scale our high-velocity SMB sales team as we grow from over $4M ARR toward doubling over the next two years. You will manage a small team of Account Executives focused on new logo acquisition, as well as an Account Manager focused on expansion into our 4,000+-strong customer base. This is a builder role — you will create our first formal sales playbook, refine our inbound sales motion, and coach a largely junior team to consistent success.

The ideal candidate is a hands-on sales leader who thrives in high-volume, fast-cycle SaaS environments and has successfully built and scaled teams from our stage toward $10M+ ARR.

• Lead & Coach: Manage, mentor, and develop a team of sellers, focusing on skill development, process discipline, and quota attainment.
  
• Build the Playbook: Design, document, and implement scalable sales processes — from lead qualification to close — to drive high win rates and fast deal cycles.
  
• Drive Results: Achieve revenue goals, and ensure each AE consistently achieves quota.
  
• Be Hands-On: Jump into high-priority deals and customer calls to model best practices and win critical accounts.
  
• Hire & Scale: Partner with leadership to recruit, onboard, and ramp high-potential sales talent.
  
• Collaborate Cross-Functionally: Work closely with Marketing on inbound funnel optimization, with RevOps on reporting and forecasting, and with Customer Success on expansion strategies.
  
• Measure & Optimize: Use data to identify gaps, run experiments, and iterate quickly to improve conversion rates, pipeline velocity, and ACV.
  
• Culture Champion: Foster a high-energy, accountable, and collaborative sales culture that aligns with Skedda’s values.
  

• Experienced Builder: 6–10+ years in B2B SaaS sales, including 3+ years managing AEs in a high-volume inbound environment with ACVs in the $1–5K range. Experience with PLG motions is a big plus.
  
• Stage-Fit Leader: Have scaled from ~$3->$10M ARR, building process and structure where none existed.
  
• Coach at Heart: Proven ability to train and elevate junior salespeople into consistent performers.
  
• Metrics-Driven: Comfortable using CRM data (HubSpot) and sales enablement tools (e.g. Claap) to manage performance and forecast accurately.
  
• Hands-On Closer: Confident jumping into deals to secure wins and lead by example.
  
• Hiring Pro: Track record of recruiting and ramping high-potential reps quickly.
  
• Collaborative: Skilled at working with Marketing, RevOps, and Customer Success to achieve shared revenue goals.

If the above sounds like you, we'd love to meet!