Jobs in Milton, Canada

The Senior Director/Director of Product Marketing will shape and own HTB's market narrative, driving how our products (B2B & B2C) are positioned, launched, and adopted across industries and buyer segments. This role blends strategy with execution, ensuring our story resonates with CISOs, practitioners, and security leaders while enabling our go-to-market teams to win consistently. Success means building a category-defining presence in continuous cyber upskilling, translating complex technical capabilities into compelling business outcomes.

• USA (Strong preference on the East Coast, or Central US) / UK
• Fully Remote

You’ll report directly to the SVP of Marketing and collaborate daily with leaders across Product, Sales, Customer Success, Community, and Brand. The role sits at the center of HTB's growth engine, orchestrating cross-functional alignment while mentoring a product marketing team of 6. Together, you’ll operate in a fast-paced, agile environment where ideas are tested, iterated, and scaled—always with customer adoption and field success in mind.

• Mastering momentum: A look back at HTB 2025 Revenue Kickoff event
• Case studies
• Introducing the Avengers Marketeers of Hack The Box

• Own the narrative & category
  • Define and continually sharpen HTB's positioning and messaging across personas (CISO, security leaders, SOC managers, red/blue/purple team leads, L&D) and segments (mid-market, enterprise, public sector)
  • Establish and evangelize the category around continuous cyber upskilling, cyber ranges, Table Top Exercises (TTX), live-fire exercises and adversarial training—grounded in real attacker and defensive tradecraft
  • Drive the narrative and build analyst relationships with the likes of Forrester and Gartner
• Lead GTM & Launches
  • Comfortable working in an Agile environment, staying closely aligned with rapid product iterations and continuous delivery, while ensuring that market positioning, messaging, and go-to-market strategies evolve in step
  • Translate continuous delivery cycles into clear, customer-focused narratives that drive adoption and engagement
  • Drive GTM strategy and integrated launch plans for new capabilities and product launches; set the bar for “what good looks like” from beta to general availability
  • Own cross-functional alignment and sales enablement for product launches, analyst relations, and community building across Product, Sales and Marketing
  • Partner with Sellers, Demand Gen and Field Marketing to map plays to buying stages and accounts; localize for regions and verticals where needed
  • Partner with the SVP of Marketing to align launch priorities with quarterly business goals and brand strategy
• Price, package, and scale adoption
  • Collaborate with Product and Revenue Ops on pricing and packaging, trial/POC experiences, and adoption motions that reduce time-to-value
  • Instrument, test, and iterate messaging and offers across the funnel
• Bring the outside in
  • Run market, customer, and competitive research; turn insight into action for Product and GTM
  • Lead analyst briefings and customer references; represent HTB at events and with key accounts
• Enable the field
  • Build sales playbooks, pitch narratives, competitive talk tracks, objection handling, demo/POV guidance, and ROI storytelling
  • Coach AEs/SEs/SDRs and scale enablement with reusable assets and training
• Build and lead the team
  • Mentor, and develop a high-performing product marketing team (PMM, competitive intel, analyst relations) comprising B2B and B2C
  • Create operating rhythms: messaging reviews, launch post-mortems, win/loss loops
  • Report progress and insights to the SVP of Marketing; drive cross-functional accountability on launch outcomes and messaging consistency
• Skills, knowledge, and experience
  • 8-10+ years in B2B SaaS product marketing (Director) or 11-15+ years (Senior Director), including 5+ years in cybersecurity (identity, SecOps, training/upskilling, or adjacent/AI)
  • Demonstrated success owning positioning and GTM for multi-product portfolios and launching products at a high-growth company; introducing new categories
  • Proven experience managing Analyst Relations (AR), including building relationships with firms like Gartner and Forrester
  • People leadership: Coaching, mentoring and creating leverage through a small, mighty team
  • Fluency with security buyer and practitioner journeys; translate deep technical value into clear business outcomes
  • Proven ability to partner with Product and Sales, influence executives, and drive cross-functional execution
  • Excellence in storytelling—written, visual, and on stage
  • Strong analytical chops: data-driven, with customer insight and rigorous testing
• How We'll Measure Success
  • Adoption and engagement of newly launched products/capabilities (activation, time-to-first-value)
  • Pipeline and revenue influenced by product launches and plays; win rate against key competitors
  • Sales productivity: relationship building, message adoption, talk-track adherence, and POV/demo conversion
  • Pricing/packaging impact on deal velocity and expansion
• What your Hack The Box adventure will have in store
  • You’ll contribute to a product highly appreciated by users and the cybersecurity community
  • You’ll experience a supportive environment with growth, flexibility, and autonomy
  • You’ll embark on an ongoing journey of learning and problem-solving as the organization grows
  • You’ll have fun at HTB and enjoy our global meet-ups
• The gems you’ll be enjoying as the Sr Director, Product Marketing
  • Compensation: USD 170,000-200,000
  • Medical, Dental & Vision (employee coverage 100% paid)
  • 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
  • State-of-the-art equipment
  • Full access to the Hack The Box lab offerings
• About Hack The Box

Hack The Box is the cybersecurity upskilling and talent development platform trusted by individuals, enterprises, and government agencies to sharpen offensive and defensive capabilities. We help security teams practice like attackers, validate skills, and move faster against threats. We’re scaling rapidly across the enterprise market, especially in Financial Services, MSSPs, and Technology.

News & Resources
• Get the most important updates on HTB’s latest year
• HTB’s entities in the US, the UK & Greece certified as a Great Place to Work (2024-2026)
• Insights on HTB culture and employee experience via our site, career site, and Glassdoor

At Hack The Box, we are committed to fostering a diverse, inclusive, and equitable workplace. 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 provide a fair and respectful work environment that reflects our values.

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