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

We’re looking for a Strategic Account Executive that thrives in a highly autonomous environment. You’re product-minded, scrappy, and comfortable building your pipeline with some of the largest brands in the world. We have strong engineers on the team and the ability to aggressively support potential sales with customizations to close the deal.

In this role, you will

• Develop and execute account strategies to break into and close strategic federal accounts, working within the procurement realities of the agencies you own

• Build trusted relationships with stakeholders across the buying committee — program managers, contracting officers, technical evaluators, and end users

• Navigate the relevant contract vehicles (GSA Schedule, SEWP, CIO-SP3, OTA, IDIQ) and work effectively through resellers, SIs, or GovCon primes where deals require it

• Understand each agency's mission priorities, budget cycles, and procurement constraints to shape deal strategy and timing

• Collaborate with internal teams (solutions engineering, deployment, security/compliance) to speak credibly to FedRAMP status, ATO processes, and security posture

• Accurately forecast and report on pipeline given the long federal sales cycle

• Provide feedback to product and leadership on what's needed to win and expand in federal

• Maintain expert-level knowledge of the product, the federal buying landscape, and the compliance requirements relevant to your accounts

• Expect moderate travel.

Your background looks something like this

• 5+ years of experience in federal/public sector enterprise or strategic sales, with a track record of carrying and hitting a strategic-level quota

• Demonstrated experience closing deals through at least one contract vehicle (GSA Schedule, SEWP, CIO-SP3, OTA, IDIQ) or via a reseller/SI/prime relationship

• Strong understanding of federal procurement — RFPs, RFIs, RFQs, sole-source justifications

• Comfort discussing security/compliance requirements (FedRAMP, ATO, CMMC) credibly with technical buyers

• Strong business acumen and ability to speak the language of the C-suite

• Consultative selling approach with a focus on value-based solutions

• Ability to manage multiple stakeholders and cross-functional initiatives

• Bachelor's degree or equivalent work experience

Even better if you have

• An active or recently-active security clearance (Public Trust, Secret, or TS/SCI)

• Existing relationships with relevant SI/reseller partners

Compensation

OTE $350,000 - $400,000k + 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.

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

We are looking for an Enterprise Account Executive with a self-starter mindset and builders mentality to join our GTM Sales Team. This is an opportunity to accelerate your career - you will play an important role in defining and iterating our sales motion, providing customer feedback to help shape our roadmap, and generating revenue to grow our sales business. Decagon is a fully in person company based in our Austin office.

In this role, you will

• Manage the full sales cycle for enterprise accounts, from self lead generation and qualification through negotiation, closing, and renewals.

• Generate a pipeline from ICP accounts via value-driven outbounding

• Collaborate with Solutions Engineering, Product, Engineering, and Marketing team to ensure customer success.

• Foster strong relationships with key stakeholders, including C-suite executives, to drive positive ROI and long term partnerships.

• Leverage internal executive team to accelerate deal cycles and securing buy-in from top-level client decision-makers.

• Play a key role in shaping go-to-market motion and influence how we engage and close key accounts

Your background looks something like this

• 4+ years of experience as a top-performing Account Executive with a strong track record of success.

• Experience in complex solution sales and consistently closing 7 figure deals.

• Consistent performance meeting pipeline generation targets for net new business

Even better if you have

• Previous experience selling AI or Customer Support/Experience software.

• Experience as an early sales hire at a fast growing start-up.

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.

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 Team

Decagon’s GTM Productivity team is focused on building a world-class revenue engine. We believe great enablement unlocks individual performance while helping the business scale through faster ramp, stronger execution, and higher productivity across the field.

About The Role

Decagon is looking for a Technical Enablement Manager — a founding member of our GTM Productivity team — to build and scale the programs that power our Solutions Engineering and technical post-sales organizations. You’ll sit at the center of how we develop technical talent, improve field effectiveness, and scale execution across pre-sales and post-sales teams.

This is a highly visible, high-ownership role with direct impact on how Decagon grows.

In this role, you will

• Build and scale enablement programs — including onboarding, ongoing development, and role-specific training across Solutions Engineering and technical post-sales teams

• Drive field readiness and performance — developing technical playbooks, training, and certification programs that improve how teams position, design, and deliver solutions

• Partner cross-functionally — working with Product, Engineering, GTM, and other stakeholders to ensure alignment and impact

• Lead a consistent enablement cadence — facilitating high-impact sessions with technical leaders and top performers

• Own enablement infrastructure and insights — optimizing content, learning systems, demo environments, and AI-powered tooling while using data to improve ramp and productivity

• Lead key GTM moments — including Kickoffs, technical summits, QBRs, and other field-facing programs

• Partner with Solutions and post-sales leadership — helping define and operationalize excellence across technical roles

• Evolve programs as we scale — building new initiatives and leveraging AI to expand enablement reach and effectiveness

Your background looks something like this

• 7+ years of experience in technical enablement, Solutions Engineering, or related technical customer facing roles

• Experience working closely with technical field teams, including Solutions Engineers, Architects, or product-facing roles

• Proven ability to thrive in fast-moving, ambiguous environments with a high degree of ownership

• Strong program management and execution skills with the ability to drive outcomes

• Strong cross-functional collaboration skills across product, technology, and GTM teams

Even better if you have

• Experience enabling technical products or platforms

• Experience building onboarding, certification, or technical development programs

• Experience in a high-growth SaaS or startup environment

• Familiarity with demo environments, solution architecture, or technical storytelling

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.