Revenue Enablement Director

Ready to embark on the quest to join Hack The Box? At the end of this journey, you will become a proud member of Hack The Box, with the ultimate mission to raise cyber resilience, so that every organization can stay ahead of tomorrow’s threats.

The core mission of the Director of Revenue Enablement is to equip Hack The Box’s entire revenue organisation with the knowledge, skills, and operating discipline required to win increasingly complex enterprise and government deals. This role owns the enablement strategy across BDRs, AEs, Solutions Engineers, Customer Success, and Partnerships to accelerate ramp, improve win rates, enhance deal quality, and improve long‑term retention. In the next 6 months, the focus is on raising cybersecurity industry fluency, standardising enterprise and federal selling motions (MEDDPICC), and reducing ramp time across roles. This role will scale a world‑class revenue enablement function that directly impacts ASP growth, multi‑year expansion, and GRR/NRR performance.

You will report directly to the Chief Revenue Officer and partner closely with Sales, Customer Success, Solutions Engineering, Partnerships, Marketing, Product, and RevOps leaders. You will be enabling a global revenue organisation of approximately 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.

Technology tools & weapons you’ll be using:

• 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.
• 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.
• Strong cybersecurity industry knowledge, with the ability to translate technical value into business outcomes.
• 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.

What your Hack The Box adventure will have in store:

• You will have the exhilarating opportunity to contribute to a product that is highly appreciated by users and the cybersecurity community at large.
• You will experience a highly supportive and caring environment, fostering growth, flexibility, and autonomy.
• You will embark on an exciting journey of continuous learning and problem‑solving, leveling up as our organization grows.
• Most importantly, you will have a blast at HTB because fun is an essential ingredient in our recipe for success!

The gems you will be enjoying:

• Private Health Care & Life Insurance
• Ticket Restaurant Allowance
• Paid paternity leave
• Dedicated budget for training and professional development, participation in conferences
• Full access to the Hack The Box lab offerings; so you can learn how to hack

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 are scaling rapidly across the enterprise market—especially in Financial Services, MSSPs, and Technology—and we are just getting started.

If you are 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.

At 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.