Datadog,
Director, Field Enablement
Overview Datadog is the world’s leading monitoring service for cloud-scale applications, providing a unified view of your entire stack through a SaaS-based data analytics platform that enables Dev and Ops teams to work collaboratively to avoid downtime, resolve performance problems, and ensure development and deployment cycles finish on time. The team Sales Enablement is an integral part of the GTM Enablement organization at Datadog. Our team empowers all Go-To-Market (GTM) teams to drive Datadog’s growth by building, delivering and optimizing enablement programs and partnering with cross-functional teams to meet company goals and help salespeople reach their potential. The opportunity As our Director of Sales Enablement, you’ll lead a team of Field Enablement Managers who design and deliver training that powers our global Sales and Customer Success organizations. You’ll partner with leaders across Curriculum & Strategy, Business Value, Sales, Customer Success, and Product Marketing to create programs with measurable field impact. You’ll be a strategic partner who moves beyond traditional workshops to anticipate field needs, prescribe data-driven solutions, and elevate performance at scale. If you’re excited about shaping the future of enablement at a hypergrowth company, we’d love to talk. Responsibilities Lead and build a high-performing team of sales and customer success trainers delivering world-class enablement programs to the field Execute ongoing field training at Datadog: guide GTM teams through learning journeys via sales kick-offs, quarterly business reviews, classroom sessions, e-learnings and other formats Transition the Field Enablement team from facilitators to data-driven business partners and coaches who proactively identify GTM knowledge and performance gaps and deliver targeted enablement solutions Embed with go-to-market teams and develop a clear understanding of the realities of selling Datadog in each region Partner with subject matter experts and the Curriculum & Strategy team to design engaging live training experiences and measure business impact Create one-to-one and one-to-few coaching programs to develop critical sales and sales leadership skills Represent the field’s perspective by understanding their needs and strengths as you interface with cross-functional teams Qualifications 8 years of work experience including at least 4 years in sales enablement, L&D or equivalent experience 3+ years of experience managing direct reports in highly complex or ambiguous environments Experience leading classroom instruction and developing curricula Strong listening skills, high EQ, and intrinsic drive to help people grow Aptitude for tying enablement programs to business impact Proven track record of building and maintaining scalable programs Agile mindset with the ability to iterate and deliver minimum viable products Outstanding verbal and written communication; ability to simplify complex concepts Experience presenting to and planning summits for hundreds of people Bonus points Experience as a seller or customer-facing representative Experience as a sales coach or enablement business partner Experience at a high-growth SaaS or technology company Knowledge of DevOps or cloud technologies Experience teaching or using MEDDICC Experience building programs at scale or larger Advanced degree in teaching or education Compensation and benefits Datadog offers a competitive salary and equity package, with compensation based on skills, qualifications and experience. Benefits include healthcare, dental, parental planning, mental health benefits, a 401(k) plan with match, paid time off, fitness reimbursements, and an employee stock purchase plan. About Datadog Datadog is a global SaaS business that enables digital transformation, cloud migration, and infrastructure monitoring. We champion professional development, diversity, innovation, and work excellence to empower continuous growth. Learn more about Datadog life on social channels and Datadog Learning Center. Equal Opportunity Datadog is an equal opportunity employer. We consider qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other protected characteristics. We also consider qualified applicants regardless of criminal histories as permitted by law. See our Candidate Legal Notices for reference. Datadog strives to make our Careers Page accessible to all users. For accessibility needs or accommodation requests, please use the form referenced on the site. Privacy and AI Guidelines Any information submitted will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please review our Hiring guidelines.
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Overview Datadog is the world’s leading monitoring service for cloud-scale applications, providing a unified view of your entire stack through a SaaS-based data analytics platform that enables Dev and Ops teams to work collaboratively to avoid downtime, resolve performance problems, and ensure development and deployment cycles finish on time. The team Sales Enablement is an integral part of the GTM Enablement organization at Datadog. Our team empowers all Go-To-Market (GTM) teams to drive Datadog’s growth by building, delivering and optimizing enablement programs and partnering with cross-functional teams to meet company goals and help salespeople reach their potential. The opportunity As our Director of Sales Enablement, you’ll lead a team of Field Enablement Managers who design and deliver training that powers our global Sales and Customer Success organizations. You’ll partner with leaders across Curriculum & Strategy, Business Value, Sales, Customer Success, and Product Marketing to create programs with measurable field impact. You’ll be a strategic partner who moves beyond traditional workshops to anticipate field needs, prescribe data-driven solutions, and elevate performance at scale. If you’re excited about shaping the future of enablement at a hypergrowth company, we’d love to talk. Responsibilities Lead and build a high-performing team of sales and customer success trainers delivering world-class enablement programs to the field Execute ongoing field training at Datadog: guide GTM teams through learning journeys via sales kick-offs, quarterly business reviews, classroom sessions, e-learnings and other formats Transition the Field Enablement team from facilitators to data-driven business partners and coaches who proactively identify GTM knowledge and performance gaps and deliver targeted enablement solutions Embed with go-to-market teams and develop a clear understanding of the realities of selling Datadog in each region Partner with subject matter experts and the Curriculum & Strategy team to design engaging live training experiences and measure business impact Create one-to-one and one-to-few coaching programs to develop critical sales and sales leadership skills Represent the field’s perspective by understanding their needs and strengths as you interface with cross-functional teams Qualifications 8 years of work experience including at least 4 years in sales enablement, L&D or equivalent experience 3+ years of experience managing direct reports in highly complex or ambiguous environments Experience leading classroom instruction and developing curricula Strong listening skills, high EQ, and intrinsic drive to help people grow Aptitude for tying enablement programs to business impact Proven track record of building and maintaining scalable programs Agile mindset with the ability to iterate and deliver minimum viable products Outstanding verbal and written communication; ability to simplify complex concepts Experience presenting to and planning summits for hundreds of people Bonus points Experience as a seller or customer-facing representative Experience as a sales coach or enablement business partner Experience at a high-growth SaaS or technology company Knowledge of DevOps or cloud technologies Experience teaching or using MEDDICC Experience building programs at scale or larger Advanced degree in teaching or education Compensation and benefits Datadog offers a competitive salary and equity package, with compensation based on skills, qualifications and experience. Benefits include healthcare, dental, parental planning, mental health benefits, a 401(k) plan with match, paid time off, fitness reimbursements, and an employee stock purchase plan. About Datadog Datadog is a global SaaS business that enables digital transformation, cloud migration, and infrastructure monitoring. We champion professional development, diversity, innovation, and work excellence to empower continuous growth. Learn more about Datadog life on social channels and Datadog Learning Center. Equal Opportunity Datadog is an equal opportunity employer. We consider qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other protected characteristics. We also consider qualified applicants regardless of criminal histories as permitted by law. See our Candidate Legal Notices for reference. Datadog strives to make our Careers Page accessible to all users. For accessibility needs or accommodation requests, please use the form referenced on the site. Privacy and AI Guidelines Any information submitted will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please review our Hiring guidelines.
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