Hack The Box · 9 hours ago
Revenue Enablement Director
New York, NY
Full-time
Hybrid
Director/Executive
$200K/yr - $240K/yrHack The Box is a cybersecurity upskilling and talent development platform, and they are seeking a Director of Revenue Enablement to equip their revenue organization with the necessary skills and knowledge to win complex enterprise and government deals. This role will focus on developing enablement strategies, improving win rates, and enhancing deal quality across various sales teams.
Artificial Intelligence (AI)Cyber SecurityInformation TechnologyPenetration TestingSkill AssessmentTraining
Responsibilities
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
Qualification
Required
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
Benefits
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 FSA
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 😉
Company
Hack The Box
The leading AI-powered cybersecurity readiness and upskilling platform, trusted by Fortune 500 enterprises, government agencies, and MSSPs.
Founded in 2017
201-500 employees
Funding
Current Stage
Growth StageTotal Funding
$66.9MKey Investors
The Carlyle GroupPaladin Capital GroupMarathon Venture Capital
2023-01-11Series B· $55M
2021-04-12Series A· $10.6M
2019-04-02Seed· $1.3M
Leadership Team
Haris Pylarinos
Chief Executive Officer
James Hooker
Co-Founder and CTO
Recent News
ChannelPro
2025-12-24
Calgary Herald
2025-12-12
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