OUR CAREERS
Explore an Exciting Career With HighVail
I truly believe you should enjoy what you do, as you will be more successful and happier in all aspects of your life.
All of our job positions are hybrid roles, combining remote and on-site work at our North York office, unless otherwise stated. Candidates must be a Canadian citizen or Canadian Permanent Resident with a minimum of 2+ years of permanent residency status. Additionally, applicants for technical roles must be eligible for Reliability Security Clearance or above.
NEW - Platform & DevOps Specialist / Managed Service Engineer
Technical Role | September 2026
In joining our team, your primary responsibilities will involve client-facing activities, both in pre- and post-sales capacities. Your secondary responsibilities will be to support internal functions related to both the operational infrastructure at HighVail as well as research, training, and personal development efforts.
Key Responsibilities
- Be a SME in DevOps, automation and open source technologies
- Deliver project-based professional services
- Architect, implement and support a wide-range of proprietary and open-source technologies
- Support multiple Managed Service customer's on-going modernization initiatives
- Manage complex sales cycles from discovery through to close, with a strong focus on long-term customer value
- Take part in certification programs with top-tier tech partners
- Stay ahead of emerging tech trends, tools, and our partner ecosystem with continuous learning paths
Required Experience & Skills
- Someone who is technologist at heart, loves solving problems, enjoys working in a dynamic environment and is comfortable in a client-facing capacity, delivering services and interacting with individuals at all levels of the organization
- Strong Unix/Linux system administration skills (minimum 5+ years)
- Experience with automation and configuration management (Ansible, Terraform, and others)
- Docker, Kubernetes, Open Shift, Rancher working experience
- Working knowledge of containers and related technologies
- Strong understanding of application development and GitOps; version control systems, configuration management, continuous integration, delivery and deployment
- Working knowledge with application modernization; lift and shift, re-factoring, re-platforming, re-hosting, and migration
- Experience leading infrastructure and application modernization initiatives
- A versatilist with experience designing and deploying solutions in the cloud
- Someone who is willing to learn, grow and challenge themselves for personal development
- Has flexibility to occasionally travel and work with customers on-site; primarily in the GTA
What Sets You Apart
What sets you apart for this role is hands-on experience across multiple cloud platforms (i.e. AWS, Azure, and GCP, rather than familiarity with just one). A Red Hat RHCSA or RHCE certification (or equivalent) reflects a validated depth of Linux expertise, while a Certified Cloud Practitioner or Architect/Associate credential shows us you can operate confidently across infrastructure and cloud architecture. Proficiency in at least one programming or scripting language such as: BASH, Python, Ruby, Perl, Go, JavaScript, Swift, C++, C#, or Scala, further signals your ability to automate and build solutions, not just manage them manually.
Why Join Us?
This role offers the opportunity to shape and grow a high-impact territory, working alongside leading technologies and strategic partners. You’ll be part of a collaborative, high-performance culture focused on long-term customer success, all backed by competitive compensation.
NEW - Account Manager
Sales Role | September 2026
We are looking for a high-performing Account Manager to drive growth across medium and enterprise customers. This role is ideal for a commercially savvy seller who thrives on building new territories, creating long-term value, and partnering closely with both business and technology leaders. You’ll be responsible for developing trusted advisor relationships, shaping solutions that deliver real business outcomes, and creating win-win success for customers, partners, and the business.
Key Responsibilities
- Build out and develop new business through strategic prospecting, strategic account planning, and relationship development with vendors, partners and customers.
- Sell a portfolio of cloud, data centre, IT automation, and data protection solutions, including consulting and managed services
- Engage confidently with senior business leaders, and technical decision makers to understand challenges and align solutions to create value and customer success
- Work closely with key technology players and solutions partners to create differentiated, outcome-based solutions
- Manage complex sales cycles from discovery through to close, with a strong focus on long-term customer value
- Consistently meet or exceed revenue and growth targets
Required Experience & Skills
- Minimum 5+ years experience selling cloud, data center, IT automation, and/or data protection solutions
- Proven success selling consulting and managed services to medium and enterprise customers
- Strong business acumen with the ability to articulate ROI, business value, and strategic outcomes
- Demonstrated experience building new territories and growing accounts from the ground up
- Established relationships with key vendors and ecosystem partners
- Track record of success working with senior business and technology decision makers
- Highly driven, self-motivated, and accountable, with a consultative sales approach
What Sets You Apart
You’re a self-starter with a strong entrepreneurial spirit and a natural problem solver who thrives in a boutique environment. Motivated by creating win-win outcomes and long-term, value-based customer relationships, you balance strategic thinking with hands-on execution and are comfortable navigating complexity while influencing across multiple stakeholders. Ultimately, you see yourself not just as a seller, but as a trusted advisor.
Why Join Us?
This role offers the opportunity to shape and grow a high-impact territory, working alongside leading technologies and strategic partners. You’ll be part of a collaborative, high-performance culture focused on long-term customer success, all backed by competitive compensation and uncapped earning potential.
The Benefits of Working at HighVail
HighVail proudly offers competitive and fair salaries, plus yearly salary reviews and potential bonus structures.
All of our employees work from home and only come to our centrally located office on occasion. You will also get to choose between a Mac or PC for your home office.
At HighVail, we think of ourselves as one big family. We work hard together, and laugh hard together. You will also get to attend fun customer and corporate events, along with our annual company holiday party.
We offer all employees a minimum of 2 weeks of vacation per year, accommodation for personal days, opportunities to earn additional vacation time in exchange for time in lieu, holiday downtime at the end of the year, and of course, the day off for your birthday!
We all have personal lives and we understand the importance of finding the right balance in both your personal and professional life. We support remote work, provide opportunities to earn additional time in lieu when working during vacation or personal time off, and provide the opportunity to work in a live face-to-face setting.
We are happy to offer a monthly allowance to aid with your cell phone, home internet, technology required to perform your daily duties (laptop, home office supplies, etc), physical and virtual lab infrastructure, as well as travel and living expenses.
We offer full health coverage for you and your dependents including health, dental, vision, life insurance, and more.
At HighVail, we ensure you’re ready for success. Throughout your employment with us, we provide mentorship opportunities for personal and career development. We ensure your skills continue to expand and remain relevant in today’s market, and in line with your goals and objectives. This is achieved through shadowing, formal vendor training and certification, as well as mentorship opportunities from senior members of our team.
With our company working remotely, we make a point to have a virtual happy hour every Friday to catch up with each other, and share some laughs.
Our Key Values
We care for people.
Although we are a boutique business, we have a lot of heart. We care for people regardless of whether you are a client, partner or employee. You are not just a number to us but a pivotal part of our HighVail foundation.
We are committed to excellence.
There is an old quote that if you love what you do, you never work a day in your life. At HighVail, we love what we do, and take great pride in always giving our best at every single opportunity.
We share an entrepreneurial spirit.
All of us at HighVail handle our day to day duties as if it were our own company. We rely on the collective to drive our strategy and direction and always see the value in collaborative idea sharing.
We are dependable.
We work as a team and constantly support one another. We all benefit from our combined successes, and our team will not walk away until the job is completed.
Ready to Apply?
E-mail your resumé and cover letter to (hr@highvail.com), and please indicate the position applied for in the email subject line. Only qualified applicants will be contacted.
DIRECT APPLICANTS ONLY – NO RECRUITERS.
Learn More About HighVail
Who We Are
We support our clients as they navigate through the complexities of IT modernization, capitalizing on the value captured by transformation.
Our Team
We’re invested in your success, turning technology needs into tangible value added business driven outcomes. Meet some of the faces behind HighVail, including Founder & CEO, Bradley Brodkin.
The HighVail Edge
Check out our blog posts, articles, and announcements from our thought leadership.