Senior Enterprise AE - Cybersecurity Sales Career HTB

Hack The Box; United States; Remote; USD 300,000 - 350,000; Full time

Benefits offered by this job

Medical, Dental & Vision (100% paid by

401(k) with 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

Training & conference budget

Lab access to Hack The Box offerings

Job summary

Hack The Box is seeking a Senior Enterprise Account Executive to expand Fortune 100 footprints across the United States and Canada. You will own the full sales cycle, collaborating with BDRs, SEs, and marketing to land strategic, multi‑million-dollar cybersecurity solutions.

The role emphasizes MEDDPICC, high-value relationships, and a proven ability to close six-figure deals with notable enterprise brands. Remote work is supported nationwide in the US.

Qualifications

• Experience selling to CISOs and CTOs at large enterprises.
• Proven track record in six-figure deals and MEDDPICC.
• Remote, US-based with enterprise SaaS background.
• Ability to manage multi-threaded deals and build business cases.

Responsibilities

• Own end-to-end sales cycle from prospecting to closure.
• Collaborate with BDRs, SEs, marketing, and CS teams.
• Expand Fortune 100 accounts across the US and Canada.
• Develop growth strategy focusing on revenue and customer success.
• Attend conferences and industry events.

Skills

MEDDPICC framework

CISOs/CTOs targeting

six-figure deals

enterprise SaaS sales

relationship building

Tools

HubSpot

Gong

JIRA

HighSpot

Job description

Senior Enterprise AE - Cybersecurity Sales Career HTB — Remote

This Senior Enterprise AE role at Hack The Box sits at the top of the enterprise sales career ladder in the cybersecurity space — and the compensation reflects it. $300K–$350K OTE (50/50 base/variable split, implying ~$150K–$175K base) is above market average for enterprise AEs in SaaS, where typical OTE ranges from $200K–$280K. The cybersecurity premium and Fortune 100 focus justify the higher range.

• Selling to CISOs and CTOs at Fortune 100 companies builds elite-level executive relationship skills that transfer across industries.
• Mastery of MEDDPICC and six-figure deal management is highly transferable and valued by any enterprise SaaS employer.
• Experience with a category-defining cybersecurity brand (4M+ community members) adds strong brand equity to your resume.
• Collaboration with Solutions Engineers and BDRs develops cross-functional leadership muscles without requiring a management title.

Culture signals: HTB has won Great Place to Work awards for 4 consecutive years — a consistent signal of real culture investment, not just marketing. The gamified, community-driven brand attracts technically curious people, which can make internal collaboration more energizing than a typical sales environment.

Potential flags: The 50/50 OTE split is aggressive — half your compensation is variable, so pipeline health matters enormously. This suits high-performers but adds income volatility. Conference attendance is a job requirement, so full remote isolation isn't realistic.

Ready to embark on the quest of joining Hack The Box?

At the end of this thrilling journey, you'll become a proud member of Hack The Box, with the ultimate mission to help redefine cybersecurity expertise. Get ready for an exciting adventure into the world of cybersecurity!

The Core Mission of the Senior Enterprise Account Executive

Expand the client roster of Fortune 100 accounts across the United States and Canada. Your task? Expand existing relationships with high-value existing customers and secure new enterprise clients, armed with self-generated leads and backed by collaborative efforts with our Business Development Representatives (BDRs) and Marketing team. Our product has a natural fit with this customer segment — we're looking for someone who can own the strategy to realize the full value of this market opportunity.

You’ll be championing a one‑of‑a‑kind, highly specialized product that stands tall amidst minimal competition. Renowned among cybersecurity aficionados, our product boasts a stellar reputation thanks to its loyal fan base within the cybersecurity community.

• Location: United States
• Fully remote
• Full‑time role

The Fellowship You’ll Be Joining

You’ll team up with our Business Development Representatives (BDRs) to supercharge lead generation, while Solutions Engineers will join forces for in-depth technical discussions. The Customer Success team will be your partners in ensuring top‑notch customer experiences. You’ll also collaborate with our marketing, product, and content teams, leveraging valuable customer insights to fuel continuous improvements.

• HubSpot
• Gong
• JIRA
• HighSpot
• Manage the entire sales cycle from finding a client to securing a deal
• New Business Development: find or create new logo opportunities and grow a robust pipeline of sales opportunities
• Develop a growth strategy focused on both financial gain and customer satisfaction
• Conduct research to identify new markets, customer needs, and map out the existing market landscape and industry trends
• Prepare sales contracts ensuring adherence to law‑established rules and guidelines
• Keep records of sales, revenue, invoices, etc. and update the company’s sales tools
• Build long‑term relationships with new and existing customers
• Increase the value of current customers while attracting new ones
• Attend conferences, meetings, and industry events
• High technical aptitude is a requirement; experience selling cybersecurity solutions is a bonus
• Experience selling to CISOs, CTOs, and other senior stakeholders; alternatively, experience with EduTech SaaS products
• Demonstrated understanding of how large enterprises operate and the business problems they aim to solve
• Deep experience working on six‑figure deals, multi‑threading, co‑building business cases, and utilizing MEDDPICC as a selling framework
• Demonstrated results in growing a business and expanding a market
• Intrinsic drive to achieve and exceed sales targets, while adaptable and resilient to changes
• Strong process orientation — ability to leverage CRM, prospecting tools, and AI augmentation to work hard and work smart
• Ability to build strong business relationships by personalizing, creating value, and collaborating effectively
• Curiosity, openness, resourcefulness, and a team‑oriented mindset

What Your Hack The Box Adventure Will Have in Store

• Contribute to a product highly appreciated by users and the cybersecurity community at large
• A highly supportive and caring environment fostering growth, flexibility, and autonomy
• Continuous learning and problem‑solving, leveling up as the organization grows
• A blast at HTB — fun is an essential ingredient in our recipe for success, including global meet‑ups!
• Compensation: USD $300,000 – $350,000 OTE (50/50 split)
• Medical, Dental & Vision (employee coverage 100% paid for by Hack The Box)
• 401(k) with 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
• Dedicated budget for training and professional development, and participation in conferences
• Full access to the Hack The Box lab offerings — so you can learn how to hack

Hack Your Career, Today. Join us in this epic adventure of cybersecurity at Hack The Box!

About Hack The Box

Hack The Box is the leading cyber readiness platform for the agentic era, battle‑testing and upskilling both humans and AI agents to enhance organizational cyber resilience. Trusted by the Fortune 500, government agencies, and MSSPs, the platform delivers threat‑informed learning paths consisting of real‑world scenarios in gamified labs and live‑fire simulations that build and validate offensive and defensive cyber capabilities. With a loyal community of more than 4 million members and 800+ enterprise customers, Hack The Box empowers teams and intelligent systems alike to strengthen cyber defenses and reduce breach risk effectively.

Rapidly growing its international footprint and reach, Hack The Box is headquartered in the UK, with additional offices in the US, Australia, and Greece.

• Certified as a Great Place to Work for 4 consecutive years (2023–2026) across the UK, Greece, and US entities.
• The Greek entity has been recognized among the Best Workplaces in Greece and Europe during this period.

At Hack The Box, we are committed to fostering a diverse, inclusive, and equitable workplace. 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.

Hack The Box participates in E‑Verify. For more information, please click here and here .

Is this Senior Enterprise AE role fully remote? Yes, the role is fully remote and based in the United States. You’ll work from home and are expected to attend conferences and industry events as part of the job. What is the compensation for this role? The total on‑target earnings (OTE) are $300,000–$350,000 USD with a 50/50 split, meaning approximately $150,000–$175,000 base salary and an equal amount in variable/commission. Do I need cybersecurity experience to apply? Cybersecurity sales experience is a bonus, not a strict requirement. High technical aptitude is required, and experience selling EduTech SaaS or to senior enterprise stakeholders like CISOs and CTOs is an acceptable alternative background. What selling methodology does Hack The Box use? The role requires deep experience with MEDDPICC as a selling framework, as well as multi‑threading and co‑building business cases for six‑figure enterprise deals. What does the hiring process look like? The process has six levels: application, talent screen, manager conversation, practical task and panel presentation, senior leadership conversation, and finally an offer. The panel presentation involves a real‑world scenario — no trick questions.

Remote work & career advice that actually works.