Director of Sales, Enterprise

Decagon; Boston (MA); On-site; USD 336,000 - 420,000; Full time

Benefits offered by this job

Medical, Dental, and Vision benefits

Life Insurance and Disability Benefits

401K / Retirement Plan

Job summary

Decagon, a Boston-based leader in conversational AI, seeks a Director of Enterprise Sales to accelerate revenue and scale the enterprise sales organization. You will own strategy, coach a high‑performing team, and partner cross‑functionally to launch new programs aligned with Decagon’s vision.

The role is in‑person at our Boston office and targets growth across major enterprise accounts. You will build, manage, and optimize sales processes, forecast rigor, and identify new market opportunities

Qualifications

• 4+ years of experience leading sales teams in a B2B or SaaS environment with a track record of exceeding targets.
• Trained in MEDDPICC or similar value selling framework.
• Hire, train, and develop top enterprise AEs while fostering a high‑performance culture.
• Manage sales forecasting, reporting, and overall pipeline management with accurate performance tracking.
• Identify and capitalize on new market opportunities to drive expansion.

Responsibilities

• Scale sales operations and drive revenue growth across the enterprise segment.
• Develop and execute programs that align with the company vision and cross‑functional initiatives.
• Lead and mentor enterprise AEs to achieve targets and build a high‑performing team.
• Forecast and report on pipeline health and performance to inform strategy and hiring.

Skills

Sales leadership

MEDDPICC

Team development

Forecasting

Market expansion

Tools

Salesforce

HubSpot

Job description

About Decagon

Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences.

Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel.

We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others.

We’re an in‑office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team.

About the Role

Decagon is seeking a dynamic and results-driven Director, Enterprise Sales to join our founding sales leadership team, reporting directly into our VP of Sales. You thrive on identifying opportunities that will increase the business’ and financial impact of your team, work cross-functionally to develop and execute new programs that carry out the companies vision. As the Director, Enterprise Sales you will be instrumental in scaling our sales operations, driving revenue growth, and ensuring the team’s success. Decagon is a fully in person company based in our Boston office.

The enterprise core team is a group of high performing and entrepreneurial minded innovators, focused on transforming customer experience for the better.

Your background looks something like this

• Have 4+ years of experience managing and leading sales teams, ideally in a B2B or SaaS environment with a track record of exceeding target.

• Trained in MEDDPICC sales methodology or similar value selling framework.

• Hire, train, and develop top enterprise AEs while fostering a high-performance culture.

• Manage sales forecasting, reporting, and overall pipeline management, ensuring accurate and timely performance tracking.

• Identify and capitalize on new market opportunities, driving Decagon’s continued expansion in the market.

Even better if you have

• Have experience in territory planning and developing effective sales playbooks.

• Have expertise in sales enablement tools and CRM platforms (e.g., Salesforce, HubSpot, etc.) to drive team efficiency and effectiveness.

• Proven ability to drive the sales process from plan to close on large deals.

• Have experience in a rapidly growing startup or tech environment where adaptability and flexibility are essential for success.

Compensation

OTE $336,000 - $420,000k + Offers Equity

Benefits

We proudly offer the following benefits for our full-time employees:

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• Retirement Plan (e.g., 401K, pension)

• Parental Leave

• Fertility and family building benefits through Carrot

• Monthly stipend to support your wellness, lifestyle, and work-life balance

• Daily lunches and snacks in the office to keep you at your best

• Take what you need vacation policy (subject to local requirements; UK employees receive 25 days of statutory leave)

These benefits are described in more detail in Decagon’s policies, may vary by location, and can change at any time according to applicable compensation and benefits plans.