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Head of Enablement

About Decagon:

Decagon is building the most advanced conversational AI agents for the enterprise. Since starting the company, we've been on a tear, winning over customers like Duolingo, Notion, Rippling, Eventbrite, Webflow, BILT and many more. Our AI agents provide a human-like customer support experience that enables enterprises to better serve their customers and efficiently manage their customer experience organizations.

We've raised $100M in total funding from Bain Capital Ventures, Accel, a16z, BOND Capital, A*, Elad Gil, and notable angels, including the founders of Box, Airtable, Rippling, Okta, Lattice, and Klaviyo.

About the Role:

Decagon is looking for a Head of 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. We will rely on you to:

  • 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

You may be a good fit if you have:

  • 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

Even better if you possess:

  • 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

Benefits:

  • Health, dental, and vision insurance

  • Take what you need vacation policy

  • Career growth opportunities within a fast-growing AI company

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Average salary estimate

$125000 / YEARLY (est.)
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$100000K
$150000K

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What You Should Know About Head of Enablement, Decagon

Are you ready to take your career to the next level at Decagon as the Head of Enablement? Based in the vibrant city of San Francisco, this pivotal role is your opportunity to shape and accelerate our Revenue Enablement team from the ground up. At Decagon, we are revolutionizing customer support through advanced conversational AI solutions used by industry giants like Duolingo and Notion. As Head of Enablement, you will develop innovative tools, create engaging content, and lead training initiatives for our go-to-market teams. Your mission will be to enhance the onboarding experience for newly hired representatives, boost our sales and partnership teams’ capabilities, and elevate the skills of our senior sellers and managers. Collaborating with various departments, you will play a crucial role in executing strategic revenue events and monitoring key performance indicators critical to our growth. The ideal candidate will have over 5 years of experience in revenue enablement, showcasing a deep understanding of sales methodologies and SaaS technology. If you have a passion for fostering high-performance sales organizations and nurturing teamwork, this could be the perfect fit for you. Plus, with our generous benefits including health insurance and a flexible vacation policy, Decagon is committed to supporting your career while you help drive our mission forward.

Frequently Asked Questions (FAQs) for Head of Enablement Role at Decagon
What are the main responsibilities of the Head of Enablement at Decagon?

The Head of Enablement at Decagon is responsible for creating and running best-in-class enablement programs for the Revenue team, which includes SDRs, Account Executives, and Account Managers. In this role, you will collaborate cross-functionally with various stakeholders, plan strategic Revenue events, and monitor KPIs such as certification pass rates and new hire ramp times, ensuring that all teams exceed their targets.

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What qualifications are required for the Head of Enablement position at Decagon?

To be considered for the Head of Enablement position at Decagon, you need at least 5 years of experience in revenue enablement along with a strong grasp of sales methodologies and SaaS technology. Candidates who have successfully executed change management initiatives or have experience in a high-growth SaaS startup environment will stand out as excellent fits for this role.

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How does the Head of Enablement support the Sales team's success at Decagon?

The Head of Enablement supports the Sales team's success at Decagon by developing impactful training programs that enhance the skills and knowledge of all team members. By focusing on new hire onboarding and ongoing education, the Head of Enablement helps ensure that the Sales team can manage customer needs effectively and achieve their quotas.

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What unique benefits does Decagon offer to the Head of Enablement?

As a Head of Enablement at Decagon, you can look forward to an array of unique benefits. Aside from competitive health, dental, and vision insurance, the company offers a take-what-you-need vacation policy, which allows for work-life balance. Additionally, there are career growth opportunities within a rapidly growing AI company.

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How does Decagon's revenue enablement strategy evolve over time?

Decagon's revenue enablement strategy evolves by closely monitoring performance metrics and adapting training programs based on feedback from the Revenue teams and market changes. The Head of Enablement plays a critical role in defining and prioritizing projects that align with our growth objectives to maximize effectiveness and ensure scalability.

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Common Interview Questions for Head of Enablement
What strategies would you implement as the Head of Enablement to onboard new sales representatives?

To effectively onboard new sales representatives, I would develop a comprehensive training program that includes a mix of e-learning modules, hands-on role-playing exercises, and mentorship opportunities with experienced team members. This diverse approach allows new hires to gain confidence in their roles quickly and adapt to our company's sales processes.

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How do you measure the success of enablement programs in a SaaS company?

Success of enablement programs in a SaaS company can be measured through key performance indicators such as ramp-up time for new hires, certification pass rates, and feedback from team members on the training provided. Regularly analyzing these metrics also helps refine programs for continuous improvement.

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Can you describe your experience with cross-functional collaboration?

In my previous roles, I have frequently collaborated with various departments, including marketing, product, and sales teams, to align enablement programs with company goals. This involves regularly communicating updates, gathering insights, and ensuring that all teams are working towards common objectives, ultimately driving revenue growth.

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What do you believe are the best practices for developing sales training content?

The best practices for developing sales training content include ensuring it is relevant, engaging, and easily accessible. Incorporating real-life scenarios, interactive elements, and continuous updates based on feedback and market trends helps maintain the training's effectiveness and keeps sales teams motivated to engage with the material.

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How would you approach the task of improving sales team performance?

To improve sales team performance, I would conduct a thorough analysis of existing challenges and strengths. From there, I’d implement targeted training, provide ongoing support and coaching, and create a system for regular feedback to foster a culture of continuous improvement and learning within the team.

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What experience do you have with modern sales technologies?

I have extensive experience with modern sales technologies, including CRM systems, sales enablement platforms, and analytics tools. My background entails utilizing these technologies to track performance metrics, optimize sales processes, and support training initiatives, ensuring the sales team has the best resources at their disposal.

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Describe a time when you successfully executed a change management initiative.

In my previous position, I led a change management initiative that involved transitioning to a new CRM system. This required close collaboration with all stakeholders, comprehensive training, and ongoing support to ensure a smooth transition. The initiative resulted in improved sales tracking and better resource utilization across teams.

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What role do you believe sales enablement plays in a company's overall success?

Sales enablement plays a critical role in a company’s overall success by equipping sales teams with the tools, skills, and confidence to effectively engage customers and close deals. By aligning enablement efforts with business objectives, we drive higher revenue, improve customer satisfaction, and increase employee retention.

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How do you prioritize initiatives within a fast-paced environment?

To prioritize initiatives within a fast-paced environment, I focus on aligning projects with strategic company goals and assessing their impact on revenue growth. Utilizing a matrix for prioritization based on urgency and importance ensures that my team is focused on high-impact initiatives that drive results.

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What motivates you to succeed in a revenue enablement role?

My motivation in a revenue enablement role stems from seeing sales teams thrive and succeed. I am passionate about driving growth through training and support, and knowing that my efforts contribute to the success of both individuals and the company as a whole fuels my drive to continuously improve and innovate in this space.

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DATE POSTED
April 4, 2025

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