Revenue Enablement Director

The fellowship you’ll be joining

You’ll report directly to the Chief Revenue Officer and partner closely with Sales, Customer Success, Solutions Engineering, Partnerships, Marketing, Product, and RevOps leaders. You’ll be enabling a global revenue organisation of ~80 people, spanning BDRs, Enterprise AEs, SEs, CSMs, and Partner-facing roles that operate across commercial, enterprise, and federal segments. This role sits at the intersection of strategy and execution, acting as a force multiplier for both revenue leadership and frontline teams.

Location & Work Mode

US (East Coast preferred)
Fully Remote or Hybrid (role-dependent, aligned to HTB hiring standards)

Technology tools & weapons you’ll be using

• Hubspot
• Gong
• Highspot
• LinkedIn Learning
• Okta Post

Additional Resources for you to check

• Mastering momentum: A look back at HTB 2025 Revenue Kickoff event
• Customer Stories
• Meet our sales team
• Read about Vasilikis’ journey into commercial sales

The adventures that await you after becoming Director of Revenue Enablement at Hack The Box

• Collaborate, design, and own the global revenue enablement strategy across Sales, CS, SE, and Partnerships.
• Embed cybersecurity industry knowledge into onboarding, continuous training, and deal execution.
• Standardise enterprise and federal selling motions, including MEDDPICC qualification and deal reviews.
• Build and own the AI enablement roadmap, equipping every revenue role with the skills, workflows, and judgement to use AI tools in prospecting, discovery, deal execution, and account planning.
• Design and run AI-augmented enablement programs, using AI for content generation, call analysis, role-play simulation, and personalized coaching at scale.
• Reduce ramp time for new hires across revenue roles through structured onboarding and certification.
• Improve win rates and deal quality by enabling teams to navigate complex buying committees and procurement cycles.
• Partner with RevOps to connect enablement initiatives to pipeline, conversion, ASP, and retention metrics.
• Enable multi-year and expansion motions by strengthening value articulation and customer outcomes selling.
• Coach frontline managers to become strong enablement multipliers through frameworks, tools, and data.
• Continuously evolve enablement programs as HTB expands further into enterprise, government, and regulated markets.

Skills, knowledge, and experience points required to unlock the role of Director of Revenue Enablement at Hack The Box

• Proven experience as a SaaS seller (AE or equivalent), with firsthand ownership of complex deals.
• Experience in implementing AI solutions (tools, agents) in enablement workflows.
• Experience supporting or selling into enterprise and/or government customers, including complex buying cycles.
• Deep understanding of enterprise sales methodologies (MEDDPICC) and how to operationalise them at scale.
• Demonstrated ability to build and scale enablement programs that improve ramp time, win rates, and retention.
• High analytical and systems mindset, with comfort in tying enablement initiatives to revenue metrics.
• Strong executive presence and cross-functional influence across senior revenue leadership.

About Hack The Box

Hack The Box (HTB) is the cybersecurity upskilling and talent development platform trusted by individuals, enterprises, and government agencies to sharpen offensive and defensive capabilities. Powered by a vibrant global community and hands‑on, real‑world training, HTB helps security teams practice like attackers, validate skills continuously, and move faster against emerging threats. We’re scaling rapidly across the enterprise market—especially in Financial Services, MSSPs, and Technology—and we’re just getting started. If you’re excited to turn technical depth into crisp stories, to shape a category, and to fuel measurable growth in a fast, collaborative environment—come build with us.

Exciting News

• We are super proud to share that Hack The Box’s entities in the US, the UK & Greece have been certified as a Great Place to Work (2024-2026).
• Hack The Box’s Greek entity has been listed by the Great Place to Work Institute in the Top 5 of Best Workplaces for three consecutive years (4th, 2nd, 3rd).
• On the European level, the Greek entity has been listed as Best Workplace in Europe for three consecutive years.
• Get the most important updates on HTB’s latest year!

What you’ll be enjoying at Hack The Box

• USD 200,000 - 240,000 OTE (US-specific compensation)
• Medical, Dental & Vision (employee coverage 100% paid for by Hack The Box)
• 401K w/ employer match
• Employer-paid Life and AD&D Insurance
• Supplemental Life Insurance
• Short-term and Long-term Disability
• Healthcare and Dependent Care FSAs
• Paid paternity & maternity leave
• 25 annual leave days
• Home Office Allowance
• Dedicated budget for training and professional development, participation in conferences
• State-of-the-art equipment
• Full access to the Hack The Box lab offerings; so you can learn how to hack 😉

About Hack The Box

We are committed to fostering a diverse, inclusive, and equitable workplace. We believe that diversity enriches our performance, services, and the communities we serve. As such, we ensure that all job applications are considered solely based on merit, skills, and qualifications. We do not discriminate on grounds of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. We are dedicated to providing a fair and respectful work environment that reflects our values.