Director of Sales, Enterprise

Location: Boston, United States. The posting also labels the workplace as remote, while the role description states that Decagon is a fully in-person company based in its Boston office.

Salary: OTE $336,000–$420,000 plus equity and commission.

Company

Decagon provides a conversational AI platform that enables enterprises to deliver personalized customer experiences across voice, chat, email, SMS, and other channels.

What you will do

• Scale enterprise sales operations and drive revenue growth.
• Hire, train, and develop enterprise account executives.
• Manage sales forecasting, reporting, and pipeline performance tracking.
• Identify and capitalize on new market opportunities.
• Collaborate cross-functionally to develop and execute programs aligned with the company vision.

Requirements

• 4+ years of experience managing and leading sales teams, ideally in a B2B or SaaS environment.
• Track record of exceeding sales targets.
• Training in MEDDPICC or a similar value-selling framework.
• Experience hiring, training, and developing enterprise account executives.
• Experience managing forecasting, reporting, and pipeline operations.
• Ability to identify new market opportunities and support business expansion.

Nice to have

• Experience with territory planning and sales playbook development.
• Expertise with sales enablement tools and CRM platforms such as Salesforce or HubSpot.
• Ability to drive large-deal sales processes from planning through close.
• Experience in a rapidly growing startup or technology environment.

Culture & Benefits

• In-office work environment focused on excellence and velocity.
• Medical, dental, vision, life insurance, and disability benefits for employees and families.
• Retirement plan, parental leave, and fertility and family-building benefits.
• Monthly wellness and lifestyle stipend.
• Daily office lunches and snacks.
• Flexible vacation policy subject to local requirements; UK employees receive 25 statutory days.