Director of Sales, Enterprise
Remote · USFull-time$336–420K/yrPosted todayStill listed today
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At a glance
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Job overview
Decagon seeks a Director of Enterprise Sales to join its founding sales leadership team and report to the VP of Sales. The role focuses on scaling sales operations, driving revenue growth, and supporting team success. The director will work cross-functionally on programs that advance the company’s vision. Decagon describes itself as an in-office company, and this role is fully in person at its Boston office.
Skills & qualifications
Skills
Qualifications
Benefits
Full 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
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Have 4+ years of experience managing and leading sales teams, ideally in a B2B or SaaS environment with a track record of exceeding target.
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Trained in MEDDPICC sales methodology or similar value selling framework.
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Hire, train, and develop top enterprise AEs while fostering a high-performance culture.
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Manage sales forecasting, reporting, and overall pipeline management, ensuring accurate and timely performance tracking.
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Identify and capitalize on new market opportunities, driving Decagon’s continued expansion in the market.
Even better if you have
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Have experience in territory planning and developing effective sales playbooks.
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Have expertise in sales enablement tools and CRM platforms (e.g., Salesforce, HubSpot, etc.) to drive team efficiency and effectiveness.
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Proven ability to drive the sales process from plan to close on large deals.
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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:
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Medical, Dental, and Vision benefits for you and your family
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Life Insurance and Disability Benefits
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Retirement Plan (e.g., 401K, pension)
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Parental Leave
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Fertility and family building benefits through Carrot
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Monthly stipend to support your wellness, lifestyle, and work-life balance
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Daily lunches and snacks in the office to keep you at your best
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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.
How this job compares
Set against the 4,833 open Enterprise Sales jobs on Olive Jobs, counted November 4, 2026.
- Pay
- This posting$336–420K/yr
- Massachusetts median$139–200K/yr105 salary ranges
- US median$138–210K/yr3,914 salary ranges
This range's midpoint, $378K, is 122% above the Massachusetts median midpoint ($170K) — in the top quarter of Enterprise Sales salary ranges in Massachusetts.
- Openings
- Olive Jobs lists 121 open Enterprise Sales jobs in Massachusetts and 4,833 across the US. 21% of them nationwide are listed as remote or flexible.
- Experience
- This posting asks for at least 4 years of experience — less than three in four Enterprise Sales postings that state a minimum ask for (median 7 years, across 4,169 postings).
- Education
- 367 of the 4,833 open Enterprise Sales jobs (8%) ask for a bachelor's degree or higher.
Counted across the open, public US postings on Olive Jobs on November 4, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.
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