Senior Customer Success Engineer – AI‑Powered Penetration Testing & Enterprise Cybersecurity Adoption Champion

About brighthush

brighthush is redefining the cybersecurity landscape by fusing cutting‑edge artificial intelligence with proven security practices. Our mission is simple yet ambitious: empower enterprises to transition from reactive, ticket‑driven security to proactive, AI‑driven penetration testing that scales across complex, hybrid environments. With real‑time exposure visibility, automated threat validation, and actionable insights, we help our customers stay ahead of evolving threats while reducing the operational burden on their security teams.

As a fully remote, Canada‑wide role, you’ll join a high‑impact, cross‑functional team that shapes the future of security tooling and delivers measurable value to our clients. At brighthush, we believe that the best security solutions are built by people who understand both the technology and the business context. If you’re passionate about bridging that gap, this is the place for you.

Key Responsibilities

1. Build and Own Trusted Technical Partnerships

• Act as the primary technical advisor for senior security leaders, platform owners, and engineering teams across a portfolio of large enterprise accounts.
• Develop a deep understanding of each customer’s business objectives, security posture, and internal decision‑making processes to anticipate needs before they arise.
• Translate complex platform capabilities into clear, business‑centric value propositions that resonate with both practitioners and executives.
• Lead difficult conversations around product gaps, unmet expectations, and roadmap constraints while preserving trust and credibility.
• Identify and nurture champions within accounts, expanding the breadth of platform adoption and reducing single‑point dependencies.
• Advocate for customers in cross‑functional discussions with Product, Engineering, and Sales, ensuring their feedback drives future enhancements.

2. Drive Technical Adoption and Enablement

• Manage a diverse set of technical requirements across multiple enterprise customers, ensuring seamless integration with existing workflows and security stacks.
• Design and deliver tailored training sessions, workshops, and documentation that accelerate user proficiency and sustained adoption.
• Collaborate closely with Customer Success Managers (CSMs) to onboard new customers, guiding the technical work‑stream from discovery to value confirmation.
• Participate in regular cadence calls with CSMs, resolving technical issues, maintaining momentum, and ensuring alignment with business reviews.

3. Champion AI‑Driven Penetration Testing

• Own the technical journey of our AI‑powered pentesting capability, from initial conversations to full integration into customers’ security cycles.
• Interpret and contextualize findings—attack chains, validated exposures, exploitability—to inform remediation priorities and complement existing third‑party testing.
• Guide customers through the operational shift, mapping AI pentesting into current testing cadences, compliance obligations, and stakeholder responsibilities.
• Collaborate with design partners to refine the user experience, ensuring clarity, safety, and trust in AI‑generated insights.

4. Mentor and Elevate the Customer Success Engineering Team

• Set the technical standard for the CS function, sharing best practices, patterns, and lessons learned.
• Provide mentorship to junior colleagues, fostering a culture of continuous learning and high performance.
• Operate autonomously across a portfolio of complex, strategic accounts, exercising judgment and initiative without constant direction.

5. Drive Commercial Outcomes

• Partner with CSMs throughout the customer lifecycle—onboarding, mid‑year reviews, health checks, and multi‑year maturity plans—to own the technical narrative.
• Identify and articulate upsell and cross‑sell opportunities, collaborating with Sales and Account teams to expand platform usage.
• Leverage deep technical expertise to influence renewal conversations, ensuring customers see measurable value and long‑term ROI.

Essential Qualifications

• 5+ years in customer‑facing technical roles within a SaaS delivery model, with a proven track record of owning relationships rather than merely responding to tickets.
• Demonstrated ability to build trust with both technical practitioners and executive stakeholders in large, complex enterprise environments.
• Experience managing or participating in penetration testing programs—whether in‑house, third‑party, or hybrid—alongside remediation and assurance cycles.
• Strong knowledge of attacker behavior, exploits, vulnerabilities, and operating system structures, and how these translate into real‑world risk.
• Hands‑on familiarity with SIEM, firewalls, IPS/IDS, DNS, WAFs, and cloud infrastructure security tools.
• Comfort leading change in emerging security categories, articulating what a capability does today while remaining credible as it evolves.
• Excellent written and verbal communication skills in English, with experience presenting to senior stakeholders and external audiences.
• Ability to manage multiple complex projects, prioritize effectively, and meet deadlines in a fast‑paced environment.

Preferred Qualifications

• Background in early‑stage SaaS startups or experience taking a new product to market.
• Experience with AI or agent‑driven security tooling, including addressing customer concerns about evidence, safety, scope control, and trust.
• Exposure to external attack surface management or vulnerability management programs.
• Track record of speaking at security trade shows, publishing security blogs, or engaging in external communications.
• Understanding of compliance frameworks such as PCI DSS, DORA, or similar, and how they intersect with penetration testing.

Skills & Competencies

• Consultative Selling: Ask insightful questions, listen actively, and challenge customers constructively to drive adoption and value.
• Technical Credibility: Deep knowledge of security tooling, threat landscapes, and penetration testing methodologies.
• Influence & Leadership: Lead without authority, steering internal stakeholders and external partners toward shared goals.
• Problem‑Solving: Resourceful, independent, and able to navigate ambiguous situations with clear, actionable solutions.
• Collaboration: Work seamlessly across Product, Engineering, Sales, and Customer Success teams to deliver a unified customer experience.
• Adaptability: Thrive in a rapidly evolving security landscape, staying current with emerging threats and technologies.

Career Growth & Learning Opportunities

At brighthush, your career trajectory is as dynamic as the security challenges we solve. As a Senior Customer Success Engineer, you’ll:

• Lead high‑impact initiatives that shape the future of AI‑driven security tooling.
• Mentor junior engineers, building a reputation as a technical thought leader within the organization.
• Collaborate with Product and Engineering on roadmap decisions, influencing the direction of our platform.
• Participate in industry events, conferences, and speaking engagements, elevating your professional profile.
• Access continuous learning resources, including certifications, workshops, and internal knowledge sharing sessions.

Work Environment & Company Culture

Our remote‑first culture empowers you to work from anywhere in Canada while staying connected to a vibrant, collaborative team. brighthush values:

• Innovation: We encourage experimentation and reward bold ideas that push the boundaries of security.
• Transparency: Open communication across all levels ensures everyone is aligned and informed.
• Growth: Continuous professional development is a core part of our ethos, with ample opportunities to learn new skills.
• Impact: Your work directly influences how enterprises protect themselves, giving you a sense of purpose and achievement.
• Diversity & Inclusion: We celebrate diverse perspectives and foster an inclusive environment where everyone can thrive.

Compensation, Perks & Benefits

While specific figures vary based on experience, brighthush offers a competitive base salary, performance‑based bonuses, and equity opportunities. Additional benefits include:

• Unlimited paid time off and flexible work hours.
• Comprehensive health, dental, and vision coverage.
• Professional development stipend and conference reimbursement.
• Wellness programs, including virtual fitness classes and mental health resources.
• Team‑building events and quarterly virtual socials.

Ready to Make a Difference?

If you’re passionate about blending deep technical expertise with customer success, and you’re eager to help enterprises transition to AI‑driven security, we want to hear from you. Join brighthush and become a pivotal part of a team that’s reshaping the future of cybersecurity.

To apply, click the link below and submit your resume and cover letter. We look forward to exploring how your skills and vision align with our mission.