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.
NEW - Business Development Manager
Sales Role | February 2025
At HighVail, we believe work-life balance isn’t just nice—it’s essential. For over 20 years, we’ve helped organizations modernize their IT so they can work smarter, run smoother, and focus on their business.
For the HighVail team, whether that’s family, travel, adventure, or just unwinding, we get it. We’re a tight-knit, agile tech company that specializes in data resiliency, digital transformation, cloud, DevOps, and automation. Our team is fun, collaborative, and driven—not by endless hours at a desk, but by delivering top-tier solutions while enjoying life along the way.
Location & Work Setup
- Hybrid Work: 2-3 days in our Midtown Toronto office (Yonge & St. Clair), with remote flexibility
- 1-Year Full-Time Contract (maternity leave coverage) with an opportunity of a permanent Account Manager role
- Start Date: ASAP – Only 1 position available!
- Eligibility: Must be a Canadian Permanent Resident (2+ years) for full-time; open to flexible contract arrangements.
Responsibilities
As our Business Development Manager, you will be driving HighVail’s growth, helping clients modernize their IT, and closing deals that make an impact. You’ll work closely with our sales, marketing, and tech teams to craft tailored solutions and grow our business.
Your Role Includes:
Business Development & Sales
- Find and qualify new business opportunities in IT transformation & professional services
- Build and nurture client relationships—understanding their tech needs and providing solutions
- Work on marketing-generated leads and turn them into solid business wins
- Develop account plans & strategies to grow HighVail’s footprint
Collaboration & Strategy
- Work closely with Inside Sales, Marketing, and Tech teams to align on sales strategies
- Interact and collaborate with our vendor partner's business development and marketing resources
- Join weekly sales meetings to optimize efforts and drive results
Closing & Execution
- Present customized proposals and business cases that connect with client needs
- Attend industry events & partner functions to expand your reach
- Own your sales pipeline—forecast, track, and crush targets
Continuous Learning & Growth
- Stay ahead of emerging tech trends, tools, and our partner ecosystem
- Take part in certification programs with top-tier tech partners
Qualifications
- 3+ years in business development/sales (IT background is a bonus, but not a must)
- Knowledge of Cloud, DevOps, IT Ops, Automation, and XaaS solutions
- Excellent communicator – you can connect, engage, and present with confidence
- Organized multitasker who thrives in a fast-moving environment
- Proactive, self-motivated, and a true team player
- Friendly, approachable, and eager to grow
- Resilient and loves a good challenge
- Super organized with a client-first mindset
Why Join HighVail?
- Competitive Compensation: Base salary + commissions + bonuses + expense reimbursement
- 2 weeks’ vacation + Christmas to New Year’s off
- Company laptop, paid cellphone & home internet
- Professional certification opportunities
- Health benefits
- Fun & Supportive Culture: Weekly happy hours, a team that has your back, and an entrepreneurial spirit
- Work-Life Balance: Hybrid setup, no micromanagement—just results
- Career Growth: Access to top tech industry events and work with leading technology partners
Make an Impact. Grow Your Career. Work Smarter.
Join a team that truly cares about its people and its clients. Apply now and take your career to the next level—while enjoying the journey! Please send a cover letter and CV to: hr@highvail.com
DIRECT APPLICANTS ONLY – NO RECRUITERS.
NEW - System Specialist, DevOps & Platform
Technical Role | February 2025
HighVail Systems Inc. is a leading, Toronto-based boutique IT services company celebrating 20+ years of excellence in the industry. We are seeking a dynamic individual to add as a DevOps Engineer, who’ll play a pivotal role in optimizing our clients’ software development processes through automation, collaboration, and continuous improvement.
As a DevOps Engineer, you’ll bridge the gap between development and operations, ensuring seamless integration and deployment of software solutions. This is an exciting opportunity to leverage cutting-edge technologies and practices to enhance our software delivery pipeline and drive innovation within our organization.
Responsibilities:
- Design, implement, and maintain automated CI/CD pipelines for efficient software delivery.
- Collaborate with development and operations teams to streamline processes and enhance productivity.
- Manage and configure infrastructure as code using tools such as Terraform and Ansible.
- Monitor system performance and troubleshoot issues to ensure optimal operation of production environments.
- Implement and maintain robust monitoring, logging, and alerting solutions.
- Continuously evaluate and recommend improvements to enhance reliability, scalability, and security.
- Stay current with industry trends and best practices in DevOps and cloud technologies.
Qualifications:
- Bachelor's degree in Computer Science, Engineering, or related field.
- Proven experience in DevOps or related roles.
- Strong proficiency in scripting languages.
- Experience with containerization technologies such as Docker and orchestration tools such as Kubernetes (K8s).
- Expertise in the Azure cloud platform, along with experience in Google Cloud Platform (GCP) and Amazon Web Services (AWS).
- Familiarity with version control systems such as Git.
- Excellent problem-solving skills and the ability to work effectively in a collaborative team environment.
- Strong communication skills and the ability to convey technical concepts to diverse audiences.
- Canadian resident (preferably in the Greater Toronto Area)
This is a full-time, hybrid position, so if you’re passionate about leveraging technology to drive organizational success and thrive in a fast-paced, collaborative environment, we’d love to hear from you! Apply now to become a key contributor to our DevOps team and help shape the future of our software delivery processes. Please send a cover letter and CV to: hr@highvail.com
DIRECT APPLICANTS ONLY – NO RECRUITERS.
Join us in shaping the future of IT services!
Why Work for 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 3 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.
News Flash
Check out the upcoming industry events we will be part of, and read about HighVail news and awards.
