Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowPosted 149 days ago

Pentesting Team Lead

Software Secured3 open roles

Where
Canada
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowPentesting Team LeadSoftware Secured · Canada

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Software Secured's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

8.2% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 1.8%1 day
  2. 3.8%3 days
  3. 8.2%7 days
  4. 15.2%14 days
  5. 34.2%30 days
This job: posted 149 days ago

The posting

Pentesting Lead

We’re looking for a Penetration Testing Team Lead to oversee day-to-day pentesting and delivery across our offensive security services while remaining actively hands-on. This is not a purely managerial role. You’ll continue to lead and execute your own penetration testing engagements, contribute directly to complex assessments, and stay close to the technical details that define high-quality penetration testing and other related work.

You’ll manage and mentor a team of elite pentesters and security engineers, ensure every engagement meets our standards for depth and accuracy, and act as the technical owner for complex client engagements.

This role sits at the intersection of hands-on offensive security, people leadership, and delivery excellence. You’ll work closely with Sales, Product, and Leadership to support scoping, improve delivery processes, and help evolve our service offerings as the business scales.

Responsibilities

Manage and execute offensive security engagements

  • Personally lead and execute penetration testing engagements across web applications, APIs, cloud environments, networks, and other offensive security service lines.
  • Oversee and contribute to penetration tests, red team activities, and advanced security assessments.
  • Act as the technical escalation point for complex findings, edge cases, and client questions.
  • Stay close enough to the work to challenge assumptions, validate findings, and model strong testing methodology for the team.

Lead and mentor the offensive security team

  • Manage a team of pentesters and security engineers, providing technical guidance, feedback, and career development.
  • Mentor team members through hands-on review of methodology, findings, reports, and client communication.
  • Foster a culture of learning, curiosity, accountability, and high professional standards.

Ensure delivery quality and consistency

  • Own engagement scoping, execution quality, and reporting standards.
  • Ensure findings are accurate, reproducible, risk-focused, and actionable for engineering and compliance teams.
  • Review and improve reports so they meet a high bar for technical depth, clarity, and client readiness.
  • Help ensure delivery remains consistent across engagements, regardless of tester, client size, or service line.

Support sales and pre-sales efforts

  • Partner with Sales on technical discovery calls, scoping discussions, and proposal input.
  • Help prospects understand real-world risk, testing depth, and value beyond checkbox compliance.
  • Bring practical, hands-on testing experience into scoping conversations so engagements are realistic, valuable, and properly structured.

Improve delivery operations

  • Track and improve key delivery metrics, including SLA adherence, retesting turnaround, utilization, client satisfaction, and reporting quality.
  • Identify bottlenecks and continuously refine delivery processes and tooling.
  • Balance operational oversight with direct participation in billable technical delivery.

Contribute to service evolution

  • Provide hands-on input into the design and refinement of service lines such as Red Teaming, AI/LLM testing, Secure Code Review, IoT, and other emerging areas.
  • Help operationalize new offerings by defining scope, methodology, delivery standards, and quality expectations.
  • Use direct engagement experience to improve how services are packaged, delivered, and explained to clients.

Requirements

  • 6-8+ years in offensive security with strong hands-on experience in penetration testing, red teaming, or related domains.
  • 2-3+ years in a technical leadership or management role within a consultancy or internal security team.
  • Proven ability to personally execute high-quality penetration testing engagements, not just manage them.
  • Proven experience managing client engagements end-to-end in a professional services environment.
  • Strong understanding of manual testing methodologies and frameworks, including OWASP, ASVS, WSTG, and NIST 800.
  • Working knowledge of compliance and audit contexts, including SOC 2, ISO 27001, and PCI DSS, and how offensive testing maps to them.
  • Ability to balance hands-on technical delivery with people leadership, quality ownership, and delivery management.
  • Clear, confident communicator with engineers, executives, and non-technical stakeholders.
  • Bias toward action, accountability, and high-quality outcomes.

Nice to Have

  • Experience working with SaaS, FinTech, or HealthTech companies.
  • Familiarity with PTaaS or portal-driven delivery models.
  • Offensive security certifications such as OSCP, OSEP, OSCE, or equivalent.
From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against Software Secured's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on Software Secured's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    Software Secured's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.