How I found founder level ownership again at Decagon
Posted on September 4, 2026
Article
Before joining Decagon, I ran my own startup for years. We did the whole thing: raised millions of dollars, partnered with amazing customers, and sold the business. After a much needed vacation, I thought about what employment might look like, and I was stumped: what would replicate the autonomy and agency I felt as cofounder & CEO?
Enter Decagon, and specifically, the work I get to do today. Now, I’m building a team around that work, starting with a brand new role: Engineering Lead, Strategic Deals.
Let me give you some context….
How we win our largest deals
“Strategic deals” are with the largest companies in the world: think the airline you fly, the hotel you stay at, and the bank you trust with your money. When any one of these companies puts a Decagon agent in front of its customers, the stakes are high. These agents serve millions of people and handle hundreds of millions of conversations each year.
Each prospective customer comes with bespoke requirements. There is no standard playbook for deploying at this scale.
So how do we win? By leveraging people like me (and hopefully, you!) to work directly with the customer’s most senior technology and product leaders, define what technical success requires, and own it end to end.
Operate like the founding CTO
This role is the closest thing I can think of to replicating the technical cofounder experience. Like a cofounder, you’d be the person responsible for ensuring the deployments under your remit are successful. This comes with an astonishing breadth: your work will span infrastructure, model research, agent development, and more.
You also routinely make product calls. By working with the largest companies in the world, you’re the first to get new product feedback, and it’s on you to filter out what’s unique to the customer vs. what should be productized so that every other customer benefits.
In other words, you’ll decide what Decagon should build, lead a pod of engineers to ship it, and drive it all the way to production.
What the job looks like day-to-day
- Own the technical build end to end for one to three strategic deals, from proof of concept to contract close, launch, and into post-launch stabilization.
- Define technical requirements directly with the customer's engineering and product leaders, and build technical champions inside their organizations.
- Identify technical risks early. Resolve them before they threaten the deal or deployment.
- Generalize by default. Turn deal requirements into product that ships to everyone.
- Lead a pod of engineers per deal: set direction, own delivery, and grow the people around you.
Who this is for
We're looking for a strong engineering leader or former technical founder with 5+ years of software engineering experience who wants to be as close to the customer and the code as it gets. Concretely, you probably:
- Want to work directly with customers: You're energized by being in the room with the customer's toughest technical stakeholders.
- Are comfortable owning high-stakes accounts with real ambiguity, where nobody has scoped the answer for you.
- Can make sound technical tradeoffs quickly: You can estimate how long different paths will take, weigh their risks, and choose between them under pressure.
- Bonus: you've productionized agentic systems before.
If "founding CTO of a deal that shapes the product" excites you, you will be a great fit.
Come build with us
Decagon is the leading conversational AI platform, empowering every brand to deliver concierge customer experiences. Industry-defining enterprises, including Avis Budget Group, Block's Cash App and Square, Chime, Oura Health, and Hunter Douglas, already run Decagon agents across voice, chat, email, SMS, and every other channel. We're backed by a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures.
We're an in-office team (five days a week), and this role is open in both New York and San Francisco.
The biggest customer experiences in the world are being rebuilt right now. Come help us build the systems they will rely on.
Start improving your workflow with Decagon
With Decagon, CX teams don’t have to guess whether a change will improve CSAT or deflection. They can move quickly, measure what matters, and act on what works.
Join us
There are very few places where you can prototype with frontier LLMs, ship to production in days, and watch users engage with the systems you built—all while owning the entire stack, from intent parsing and tool usage to API integration and observability. This role at Decagon is one of those places.
From my own experience working across both agent development and broader engineering initiatives at Decagon, I’ve seen firsthand how uniquely impactful this work can be. Whether I’m building intelligent workflows for customers or designing infrastructure that supports our agent platform, it’s rare to find an environment where the work transitions from concept to production within days, actively powering user experiences and transforming how businesses operate.
If you’re looking for a role where you can:
- Build at the frontier of LLMs, automation, and user interaction
- Deploy AI agents that solve high-value business use cases across industries including retail, travel and hospitality, fintech, edtech, and more
- Work directly with customers on high-impact use cases
- Ship fast, iterate constantly, and own your work from idea to production
- Join a fast-moving, collaborative team solving real-world challenges with AI
We’d love to hear from you!
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The AI concierge for every customer.