Title: Customer Success Engineer
Location: Fully Remote across Canada
Start Date: ASAP
Role Overview:
As a Customer Success Engineer (CSE) reporting the VP of Customer Success, you are the technical heart of the customer relationship. You own technical adoption and integration of our platform, and you do it as a trusted advisor to the people who use it, not as a back-office resource. CSEs pair deep product and security expertise with the relationship skills to build credibility with practitioners and confidence with executives, so that customers adopt the platform, see measurable value, and stay with us.
You will work in close partnership with the Customer Success Managers (CSMs) across a shared portfolio of large enterprise accounts. Technical depth is essential, but it is only half the role. The best CSEs are the person a customer asks for by name: curious about their business, straight with them when something is hard, and consistently the reason a renewal conversation is an easy one.
This role also sits at the front of our move into AI-driven penetration testing, which extends the platform from finding exposure to actively validating and exploiting it at scale. For our customers, this is a different motion to pure external attack surface management: it touches their testing cycles, their compliance and assurance obligations, their existing pentest suppliers and, often, a different set of internal stakeholders. You understand the discipline well enough to guide a customer through adopting it: how engagements are scoped, how findings are validated and reported, and how a security team consumes and acts on them.
You will be one of the first technical voices our customers hear on it, working closely with design partners and shaping how we explain the capability as it matures.
Desired Skills
- Experience of the buying or managing side of penetration testing: running an in-house program, commissioning third-party testers, or owning the remediation and assurance cycle that follows a test.
- Experience working alongside testers or offensive security teams, or supporting customers through compliance-driven testing requirements such as PCI DSS, DORA or similar.
- Familiarity with AI or agent-driven security tooling and the questions customers ask about it: evidence, safety, scope control and trust.
- A track record of taking customers through a change in how they work, not only a change in tooling.
- Experience in an account-facing or account management capacity, or a technical role carrying direct renewal and retention responsibility.
- Experience working with early-stage SaaS startups, or of taking a new product into market
- Experience of external communications, including speaking engagements at security trade shows, written security blogs and similar.
- Exposure to external attack surface management or vulnerability management programs.
Relationship and Commercial Requirements
- 5+ years in customer-facing technical roles, ideally in a SaaS delivered model, with clear evidence of owning relationships rather than only responding to tickets and requests.
- Demonstrable relationship-building skill at both practitioner and executive level within large, complex enterprise organizations.
- The seniority to lead without authority: steering a customer's internal stakeholders, influencing our own Product and Engineering teams, and mentoring colleagues around you.
- Real curiosity about customers and a consultative instinct: you ask good questions, listen properly, and are comfortable challenging a customer when it serves them.
- Commercial awareness, including an understanding of how adoption, value realization and relationship strength drive renewal and growth.
- Credibility and composure under pressure in escalations and difficult conversations, with the judgement to know when to bring others in.
- Excellent communication skills, written and oral, in English.
- Experience and confidence presenting to partners and major customers, including senior stakeholders.
- Strong collaboration across internal teams, with a track record of working as a true pair with account owners rather than in parallel to them.
Technical Requirements
- Experience supporting multiple complex enterprise customer accounts simultaneously.
- A working understanding of penetration testing: how an engagement is scoped, how findings are reported and validated, and how a security team consumes and acts on them. This is not a testing role, so we are not looking for a practitioner, but you do need to be credible in the room with the people who commission and run this work.
- Strong working knowledge of attacker behavior, exploits, vulnerabilities and operating system structures, and how these translate into real-world exposure and risk.
- Solid knowledge and hands-on experience of cybersecurity, intelligence or network security tools and products, including but not limited to SIEM systems, firewalls, IPSes, DNS, WAFs and cloud infrastructure.
- Comfort operating in an emerging category: you can be authoritative about a capability that is still evolving, hold the line on what it does and does not do today, and stay credible while the answers change.
- Ability to solve problems with resourcefulness and independence.
- Ability to manage multiple complex projects, priorities and deadlines.
Key Responsibilities
Relationships and Customer Partnership
- Build and own trusted relationships with key technical stakeholders, security leaders and platform owners across a portfolio of enterprise accounts, becoming the technical partner they turn to first.
- Understand each customer's business, security program and internal dynamics well enough to anticipate what they need before they ask, and to tailor how the platform is positioned to them.
- Translate technical detail into business value, articulating exposure findings, platform outcomes and risk reduction in language that lands with a practitioner and with a CISO.
- Hold the difficult conversations well: product gaps, missed expectations, escalations and roadmap disappointments. You advocate for the customer internally while keeping their trust in us intact.
- Map and broaden relationships within accounts so we are never dependent on a single contact, identifying champions and bringing new users and teams onto the platform.
- Represent the customer internally with Product and Engineering, relaying feedback with the context and credibility that influences the roadmap.
Technical Adoption and Enablement
- Manage a complex and diverse set of technical requirements across multiple customers.
- Identify customers' key technical requirements, including integration with the specific workflows and processes tied to successful adoption of the CyCognito platform.
- Provide technical enablement and training to customer teams to drive real, sustained adoption.
- Support the CSM team in onboarding new customers, and lead the technical work-stream through to the customer confirming value.
- Attend and contribute to regular cadence calls with the CSM team, resolving technical issues and keeping momentum between formal reviews.
AI Penetration Testing
- Own technical adoption of our AI pentesting capability alongside attack surface management, from first conversation through to a customer running it as part of their normal security cycle.
- Interpret and contextualize findings for customers: attack chains, validated exposures and exploitability, and what each means for their remediation priorities and their existing pentest program.
- Guide customers through the change in motion, helping them work out where AI pentesting sits alongside their current testing cycles, assurance requirements and third-party testers, and who internally needs to be involved.
Seniority and Team Contribution
- Set the technical standard for the CS function: mentor less experienced colleagues, share patterns that work, and raise the bar on how we engage customers technically.
- Operate with autonomy across a portfolio of our most complex and strategic accounts, exercising judgement without waiting to be directed.
Commercial Outcomes
- Partner with CSMs across the customer lifecycle: onboarding, mid-year business review, health check and multi-year maturity plan, owning the technical narrative in each.
- Demonstrate and position the platform to surface and progress upsell and cross-sell opportunities within existing accounts, working hand in hand with the CSM and account team.
