Intermediate Security Engineer - Red Team

Join Our Mission: Help the Helpers with Jane
Let's kick things off with a quick intro. Jane is a team that's all about fostering growth, spreading delight, and serving our healthcare community. We're on the hunt for people ready to jump in and join us while we simplify the lives of healthcare practitioners and patients daily. And guess what? Jane is a remote-first company, meaning every role at Jane, including this one, is remote — giving you the freedom to work from any corner of Canada.
Your Role in Our Journey
Join Jane’s Cybersecurity team as a Security Engineer, Red Team, where your curiosity and collaboration will help us strengthen our security posture. In this role, you’ll contribute to red team activities, support our bug bounty program, and foster meaningful relationships across teams to enhance Jane’s culture of security awareness. This position offers the opportunity to grow your skills in offensive security, all while working in a supportive environment that values emotional intelligence, collaboration, and inclusivity. If you’re passionate about offensive security and motivated by the opportunity to make a tangible impact, we’d love to hear from you.
Learn More About Us
We're founder-led, which means we live our values while maintaining a clear vision for the future. Our product enables the likes of physiotherapists, mental health counselors, chiropractors, and other allied health practitioners to run their practices in a digital-first way through features such as online booking, charting, scheduling, telehealth, secure payments and billing along with an evolving library of features. You can see more of them here.
There is often a high bar set, not just for the quality of work, but for the care we show for each other and our customers. And it’s our customers raising that bar, never standing still and continually improving which keeps us on our toes. It's not just about what you've done before or how quickly you work; it's about your curiosity and drive to solve the right problems and your agility in learning new ways of thinking.
No doubt, Jane's a special place to work. There is autonomy and flexibility to help integrate work into your life in a way that makes sense for you. Need to block out time to pick up the kids? Go for it. That's normal here. And yes, we have a Slack channel for parents, but we've also got channels dedicated to plants, furry friends, food, pride, wellness - you get the idea! While we love to connect virtually, the Jane team also connects in person throughout the year. That comes in the form of departmental get-togethers, company retreats, or possibly a conference or two across North America if you’re keen to learn more about our community of healthcare providers. We're on the search for folks who are ready to dive in and become part of our journey toward making healthcare professionals' lives easier every single day.
You can also learn more about Jane as a company and a product by checking out our Glassdoor reviews and our Capterra Reviews
But we’ll also keep it real — as much as we love our work, the mountain we're climbing is always getting taller. We're a growing company, and with that comes the challenge of navigating an environment with many moving parts, often without a clear-cut path laid out in front of us. This is where you come in. If you're the kind of person who gets a kick out of being resourceful and loves solving problems, you'll fit right in.
Our vision as we move towards 2025 is all about creating More Happier Helpers. That means not just growing in numbers, but growing a community of thriving healthcare professionals who provide top-notch care with Jane at the heart of their operations. If you're someone who's feeling stifled by bureaucracy, itching to shake things up, or just someone who wants to make a genuine impact in the world, consider if the Jane team is the place for you.
We believe in collaboration, humility, and keeping a growth mindset. We're looking for people who can embrace our way of working, which often means being flexible and open to change. So, if after reading this, you feel excited about the opportunity — all in the name of helping those who help others — reach out to us to learn more.
In short, if you're excited by our growth, ready to contribute to a challenging yet rewarding environment, and eager to be a disruptor alongside a team of talented individuals, we’d love to hear from you!

The impact you could have

• Perform penetration testing and vulnerability assessments on Jane’s systems, applications, and infrastructure under the guidance of senior team members, helping to identify and mitigate security risks while working collaboratively with stakeholders.
• Assist in the operation and improvement of Jane’s bug bounty program by validating reported vulnerabilities, reproducing exploit scenarios, and engaging empathetically with external researchers to foster trust and partnership.
• Execute red team activities such as phishing simulations, lateral movement scenarios, and application security testing, maintaining a balance between technical rigor and organizational empathy.
• Help develop and refine security testing tools and processes, including automating repetitive tasks and integrating tools into workflows, while collaborating effectively with cross-functional teams.
• Build strong relationships with software development, IT, and other teams to champion security initiatives and foster a shared sense of responsibility for maintaining a secure platform.
• Contribute to incident response efforts by providing insights on potential attack vectors and assisting in post-incident reviews with a focus on growth and improvement.
• Stay current on offensive security trends, tools, and tactics, sharing knowledge openly with colleagues to enhance team capabilities and cultivate a learning-oriented culture.

The Experience We Feel We Need

• Educational background in computer science, information security, or a related field, or equivalent experience.
• Two (2) to three (3) years of experience in penetration testing, vulnerability assessments, or security research.
• Experience in web application and API penetration testing, with the ability to discover and exploit vulnerabilities such as business logic flaws, broken access control, injection (e.g., SQL Injection, XSS, SSRF), and broken authentication.
• Familiarity with penetration testing tools like Burp Suite, Metasploit, and Kali Linux. Experience with scripting languages (e.g., Python, Bash) is preferred.
• Foundational knowledge of Web Security Testing Guide (WSTG), ASVS, OWASP Top Ten, MITRE ATT&CK framework, and secure coding practices.
• Strong interpersonal skills, including active listening and the ability to empathize with diverse stakeholders. You communicate findings with clarity and care, tailoring your approach to meet the needs of technical and non-technical audiences alike.
• Certifications like OSCP, CEH, Burp Suite Certified Practitioner (BSCP) or equivalent are beneficial but not required.

Compensation Expectations for the Role
Jane’s committed to paying our team members fairly, clearly, and above all, paying for growth. This role has a minimum annual salary of $95,100 and maximum annual salary of $142,600. As you may have noticed, this salary range is quite large, and this is intentional to account for the growth someone will experience in the role throughout their time at Jane (i.e., from building the skills, to accomplished, to highly proficient, all the way to achieving excellence in the role). When hiring talented folks to join the Jane team, we’ve found that new team members are best set up for success when hired with the expectation of being fully accomplished in the role, which for this role would reflect a starting salary of $118,800. It's also possible to join Jane at a salary above or below this, which would mean a salary below $118,800 typically reflects someone who has all the potential to be fully accomplished in the role but doesn't yet possess all the skills required, while a salary above $118,800 is typically for individuals who are currently in this role at Jane and had the opportunity to make a significant positive impact on our customers, product and company with deep Jane knowledge. At Jane, we pay for growth, which means that you’ll continue to have conversations about your career development with your manager and see your compensation grow over time as you build an amazing career with us.
Paying clearly is one of our compensation fundamentals to help folks build trust in the compensation process at Jane. To better understand Jane’s compensation fundamentals and how this range is determined, click on this link here for a short video walkthrough of how it all works! We also welcome you to ask as many questions as you’d like about compensation throughout the interview process to ensure you feel confident and build trust through the process.
More information on our benefits can be found here!
At Jane, we’re committed to fostering an environment that allows you to come to work as your truest self. We believe it’s important to actively recognize, embrace, and celebrate our differences in order to make Jane an inclusive, equitable, and diverse workplace.
We want to build a team of people who make conversations rich with perspective and experience. We are committed to listening to every voice in order to learn and grow because doing this will allow us to meet the needs of the diverse community of helpers that Jane serves.
We do not tolerate discrimination, prejudice, or oppressive isms of any kind. Employment is decided on the basis of qualifications, merit, experience, and the needs of the Jane community. We encourage anyone who requires accommodation or adjustments throughout the interview process to let us know, and we will do our best to support you. Apply