Role OverviewOBRYN GUARD® is seeking a highly entrepreneurial, hands-on Head of Marketing to build the company’s marketing function from the ground up.

This is not a traditional “manage a team” marketing role. You will initially be the strategist, creator, operator, and growth driver responsible for shaping how OBRYN GUARD is positioned, understood, trusted, and adopted in the market.

You will work closely with the Founder, Sales, Product, Cybersecurity, Compliance, and Customer Success teams to translate a complex cybersecurity and compliance platform into clear messaging, robust brand positioning, educational content, qualified demand, and measurable revenue impact.

As an early leadership hire, you will help shape not only the marketing function but also the broader commercial identity of the company.

This role is highly autonomous, execution-focused, and ideal for someone who wants meaningful ownership, creative control, and long-term upside tied to company growth.

Marketing and Brand Strategy

- Develop and execute OBRYN GUARD’s overall marketing strategy.
- Build clear positioning for the company, product, and target markets.
- Develop messaging that makes cybersecurity and compliance understandable to business decision-makers.
- Strengthen OBRYN GUARD’s enterprise brand and market credibility.
- Define buyer personas, ICPs, market segments, and campaign priorities.
- Conduct competitor and market research.
- Ensure messaging remains consistent across website, sales, social media, email, and customer-facing materials.

Content and Social Media
- Own the company’s content strategy across LinkedIn, Instagram, website, email, and other relevant channels.
- Create high-quality B2B content designed to reach hotel owners, operators, executives, IT leaders, and compliance stakeholders.
- Develop educational content around cybersecurity risk, compliance readiness, PCI DSS, SOC 2, ISO 27001, vendor risk, access risk, cyber insurance, and Continuous Control Monitoring.
- Create executive and founder-led content.
- Develop thought leadership, articles, case studies, guides, white papers, sales content, and campaign assets.
- Maintain an enterprise-level standard across all public-facing content.

Video Production and Editing
- Develop concepts, scripts, and creative direction for company video content.
- Produce or coordinate professional short-form and long-form video content.
- Create product, educational, social, promotional, and executive-facing videos.
- Edit content into polished,



brand-consistent assets suitable for enterprise audiences.
- Coordinate external creative support when required.

Email Marketing
- Build and manage email marketing campaigns.
- Develop outbound and nurture sequences.
- Improve email messaging, targeting, segmentation, and conversion.
- Support deliverability and sending reputation.
- Develop automated email journeys for prospects and leads.
- Measure campaign performance and continuously improve results.

Demand Generation and Product Marketing
- Build campaigns designed to create qualified pipeline.
- Develop inbound and outbound marketing programs.
- Support hotel and multi-property customer acquisition.
- Work closely with Sales on lead quality, qualification, campaign follow-up, and conversion.
- Develop product messaging, use cases, sales decks, one-pagers, battlecards, objection handling, and competitive positioning.
- Support new product launches and feature announcements.
- Translate technical product capabilities into clear business outcomes.

Website, Analytics, and Performance
- Own marketing strategy for the company website and landing pages.
- Improve messaging, structure, calls to action, and conversion paths.
- Support SEO and organic search growth.
- Track high-value actions including booked demos, form submissions, campaign responses, and qualified opportunities.
- Build reporting around campaign performance, lead quality, conversion, pipeline contribution, and customer acquisition.
- Use data to identify what should be scaled, improved, or stopped.
- Focus on measurable commercial outcomes rather than vanity metrics.

Leadership and Team Building
- Build the marketing function as the company grows.
- Identify when contractors, specialists, agencies, or future employees are required.
- Create repeatable systems, processes, documentation, and quality standards.
- Work closely with leadership across Sales, Engineering, Product, Security, Compliance, Operations, and Customer Success.
- Take ownership of execution rather than relying solely on external teams.




- Help develop OBRYN GUARD into a recognized and trusted brand within its target markets.

Qualifications
- Strong experience in B2B marketing, SaaS, technology, cybersecurity, compliance, or another complex professional-services environment.
- Proven experience developing positioning, messaging, campaigns, and content.
- Strong copywriting and communication skills.
- Experience with demand generation and lead acquisition.
- Experience with email marketing and automation.
- Strong understanding of LinkedIn and B2B social-media marketing.
- Ability to work directly with Sales and executive leadership.
- Strong analytical and performance-measurement skills.
- Ability to operate independently in an early-stage company.
- Comfortable moving between strategy and hands-on execution.

Preferred ExperienceExperience in one or more of the following is highly valuable:
- Cybersecurity
- GRC or compliance technology
- PCI DSS
- SOC 2
- ISO 27001
- Hospitality technology
- B2B SaaS
- Enterprise software
- Product marketing
- SEO
- Paid acquisition
- CRM and marketing automation
- Video production and editing
- Website conversion optimization

Direct cybersecurity experience is valuable but not required if you have demonstrated the ability to quickly understand and market technical B2B products. Ideal CandidateWe are looking for someone who:
- Thinks commercially, not just creatively.
- Can build a marketing function rather than simply execute assigned tasks.
- Understands how marketing supports pipeline and revenue.
- Can turn complex technical information into clear business messaging.
- Is comfortable working directly with a Founder and leadership team.
- Takes ownership and identifies problems without waiting to be told.
- Can operate effectively with limited early-stage resources.
- Values measurable outcomes, accountability, and high standards.
- Wants to help build something long term rather than simply manage campaigns.

This Role Is Not a Fit IfThis role is unlikely to be a fit if you:
- Only want to manage a large existing team.
- Need a large marketing budget before producing results.
- Prefer strategy without hands-on execution.
- Focus primarily on followers, likes, impressions, or vanity metrics.
- Are uncomfortable being accountable for qualified demand and commercial outcomes.
- Require highly structured day-to-day direction.
- Are not comfortable working within an early-stage environment.

OBRYN GUARD®

Automated Cyber Assurance. Built for hospitality.

📌 Head of Marketing | Sept 21, 2026 (Toronto)
🏢 OBRYN GUARD
📍 Toronto