Head of Sales Enablement
Decagon
Sales & Business Development
San Francisco, CA, USA
Posted on Mar 6, 2026
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 looking for a Head of Sales Enablement, a founding member of our Revenue Enablement team that will develop tools, content, and training for our GTM teams. In this role, you will accelerate the onboarding of our newly hired reps, support our sales and partnership teams to meet - and exceed - quota attainment targets, elevate the skillset of our most senior sellers and managers, and accelerate the overall growth of Decagon. This highly visible and impactful role will be critical to ensuring sustainable growth and scalability of our world-class Revenue organization.
In this role, you will
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 looking for a Head of Sales Enablement, a founding member of our Revenue Enablement team that will develop tools, content, and training for our GTM teams. In this role, you will accelerate the onboarding of our newly hired reps, support our sales and partnership teams to meet - and exceed - quota attainment targets, elevate the skillset of our most senior sellers and managers, and accelerate the overall growth of Decagon. This highly visible and impactful role will be critical to ensuring sustainable growth and scalability of our world-class Revenue organization.
In this role, you will
- Create and run best-in-class Enablement programs for our Revenue team, including SDR's, Account Executives, Sales Leaders, Solution Engineers, Account Managers and Partners among others
- Collaborate cross-functionally with stakeholders across Decagon's Marketing, Product, Engineering, and other teams
- Plan and coordinate the execution of strategic Revenue events such as QBR's, Sales Kick Offs, President’s Clubs, and more
- Monitor progress towards improving Revenue KPIs such as new hire ramp, certification pass rate, time to first deal, sales team attainment etc.
- Support the evolution of our GTM strategy, helping to define and prioritize projects and initiatives to maximize Decagon's rate of growth
- 5+ years of experience in revenue enablement and demonstrated knowledge of enablement best practices, sales methodologies, and modern SaaS sales technology
- Experience in executing change management initiatives and supporting fast growth, high performing, highly scalable Sales organizations
- Superior project and program management capabilities
- Strong interpersonal, cross-functional collaboration and teamwork skills
- Experience navigating rapidly developing AI technology landscape
- Involvement and participation in sales enablement groups or communities
- Experience working at a high-growth SaaS startup environment
- Medical, dental, and vision benefits
- Take what you need vacation policy
- Daily lunches, dinners and snacks in the office to keep you at your best