Engineering Lead, Strategic Deals

Decagon; New York (NY); On-site; USD 200,000 - 400,000; Full time

Benefits offered by this job

Medical, Dental, Vision benefits

Retirement Plan

Parental Leave

Fertility and family building benefits

Wellness stipend

Daily lunches in office

Generous vacation policy

Job summary

Decagon is seeking a seasoned engineering leader to own the technical build for 1–3 Strategic Deals end-to-end, working directly with customer engineering and product leaders to shape and deliver solutions at scale.

You will drive requirements, de-risk risks, and lead a small team to ship durable improvements to Decagon’s product while ensuring production-grade reliability and performance.

Qualifications

• Proven track record leading software engineering teams or as a technical founder.
• Experience working directly with customers' senior engineering and product leaders.
• Ability to scope, de-risk, and deliver complex technical solutions on large deals.
• Strong capability to balance product strategy with practical execution.

Responsibilities

• Own end-to-end technical build for Strategic Deals, from POC to post-close stabilization.
• Drive technical requirements with customer leaders and build champions inside their orgs.
• Identify early technical risks and de-risk them before they threaten the deal.
• Generalize bespoke deal requirements into durable improvements to the core product.
• Tech-lead a pod of 1–3 Software Engineers per deal, setting direction and mentoring.

Skills

Engineering leadership

Customer-facing work

Risk assessment

Technical strategy

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's Strategic Deals are with the largest companies in the world. Each one puts a Decagon agent in front of millions of users, fielding hundreds of millions of conversations a year. These deals are won on technical execution: hard problems without an off-the-shelf answer, latency and reliability constraints at real scale, and requirements that push the product into new territory. You'll own the technical build for 1–3 Strategic Deals end-to-end, operating like the founding CTO of each. You'll work directly with the customer’s senior engineering and product leaders to figure out what they need for the deal to be successful. From there, you decide what Decagon should build, tech-lead a pod of engineers to ship it, and productionize it so it benefits every customer, not just this one. You're across every technical workstream on the deal, from infrastructure and the agent build to model evaluation, research, and the reliability work that makes it production-grade. You sit at the center of product strategy: your decisions shape not only each deployment, but also the feature set that gets reflected in the product itself.

In this role, you will

• Own the technical build end-to-end for a handful of Strategic Deals, from POC through close and into post-close stabilization
• Drive technical requirements directly with the customer’s engineering and product leaders, and build technical champions inside their organizations
• Identify technical risks early and de-risk them before they threaten the deal
• Dig past feature requests to the underlying problem, then scope solutions that generalize, turning bespoke deal requirements into durable improvements to the core Decagon product
• Tech-lead a pod of 1–3 Software Engineers per deal: set technical direction, own delivery, and mentor the engineers on your team

Your background looks something like this

• A strong engineering leader or ex-technical founder with 5+ years of industry experience in software engineering
• Strong appetite for customer-facing work
• Comfort owning high-stakes accounts with significant ambiguity
• The ability to quickly assess how long different technical paths will take, weigh their risks, and choose between them under pressure

Bonus

experience productionizing agentic systems

Compensation

$200K – $400K + Offers Equity

Benefits

• 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.