- Base
- Not disclosed
- OTE
- $336K–$420K
- Posted
- 8h ago
Still open · checked 5h agoon Decagon's careers page
The job
- What you'd do
- Lead a team of salespeople selling AI that handles customer calls and chats to very big companies. You'd hire and coach them and track their sales forecast, all in person in Boston.
- What you'd sell
Has AI answer customer questions by chat, phone, and text
When a company gets a question from a customer, it usually sends them into a queue of support tickets or puts them on hold. The problem is, customers wait around for answers, and each wait is one more reason to give up on the company. Decagon builds AI that answers customers over chat, voice, email, and text, so questions get resolved faster.
In plain English, from their own job posts. Something wrong? Tell me · More Customer support companies →
- Who you'd sell to
- Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”
- Where deals come from
- Not stated in the posting.
The Braun Read
Ask hard questionsToo much is left unsaid. Make them answer before you invest.
- Pay
- OTE is listed. Ask what the base is.
- Transparency
- Says nothing about quota, attainment, deal size, territory or sales cycle. Ask about all five.
- Time on market
- Brand new.
- Company hiring
- 16 sales roles open, hiring at a steady pace.
Red lights
None spotted.
Green lights
- Publishes OTE. It tells you the on-target earnings up front. Most postings don't.
Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.
Questions to ask on the first call
Built from what this posting leaves out. How they answer tells you as much as what they say.
- 1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
- 2.
What's the base, and how is the rest paid out?
OTE without a base doesn't tell you what you can count on.
- 3.
Who's the economic buyer, and who else is in the deal?
Selling to a CFO and selling to a developer are different jobs.
- 4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
- 5.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.
Got an offer from Decagon? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
Full posting
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.