Rose Rocket 🚀 is a market leader in Transportation Management Software. We’re a startup going after the $700+ billion dollar trucking industry, leading the shift to SaaS while revolutionizing the way trucking companies sell, service, and innovate. We are a “more human, less corporate” culture that is built around doing work that matters, winning as a team, and celebrating success. We’d love to hear from you if you want to build this with us.

We understand that joining a team is one of the most important decisions you make ❤️, and adding a team member is one of the most important decisions we’ll make. Through our process, we want you to get to know us and understand how you approach problems, learn, and what motivates you. 

Position Overview

Reporting to the CEO, the Director of People and Operations will lead our People, Facilities, and IT functions during our next period of rapid growth and transformation. In this role, you’ll be pivotal in scaling our people strategies and processes for the next phase of expansion, ensuring alignment with the company’s mission and goals. You will collaborate closely with leadership and cross-functional teams to shape the employee experience, champion our culture, and manage key HR initiatives.

Key Responsibilities

• Community Engagement: We’re experts at building our Rose Rocket community—but you won’t find much about us online. We like to say we’re Toronto’s best-kept secret in tech! You will oversee and expand initiatives that strengthen our internal community, enhancing employee engagement and fostering connection.

• Talent Acquisition & Management: At Rose Rocket we prioritize quality and integrity. You will manage the end-to-end talent acquisition process, ensuring we attract, hire, and retain the best talent. You’ll also evolve our programs for employee development and career progression to meet the needs of our growing team.

• Facilities & IT Management: Our office space is chef’s kiss. You will oversee the Facilities and IT functions, ensuring we provide top-tier tools and support to the entire team.

• Employee Relations: Act as a trusted advisor to People Leaders and employees, fostering a positive and productive work environment by resolving conflicts and promoting open communication.

• HR Operations: Ensure compliance with labour laws and optimize HR processes, including payroll, HRIS systems, and reporting, to support the company’s smooth scaling.

• Performance Development: Lead the development and management of performance review cycles, feedback processes, and employee growth plans. Your efforts will drive accountability and continuous improvement across the team.

• Compensation & Benefits: We’re well-prepared for 2024 with strong compensation programs and philosophy, but our next capital raise will prompt a new compensation study. In the meantime, you will manage competitive compensation, benefits, and reward programs to maintain a strong and engaged workforce.

Our Tech Stack

• Hibob, Ashby, Metaview and Deel

Skills & Qualifications

• At least 3 years in a People leadership role within a VC-backed startup in both Canada and the US (via PEO); bonus points if you’ve led expansion into the US or other countries.

• Exceptional interpersonal and communication skills, with the ability to influence and partner effectively with leadership.

• This is a minimum 4-day in-office role, with Wednesday being an optional WFH day currently.

Don’t sweat it if you don’t have everything listed above. We believe in growth and curiosity. If you have some of these qualities and are excited about this opportunity, then we want to hear from you!

Perks & Benefits at Rose Rocket

🏥 A comprehensive benefits program + health care spending account

🐣 Parental leave top-up

💰 Stock option plan

💻 A Macbook and a sweet tech equipment combo to get you started

🏝 Start with three weeks of vacation (with an option to purchase an additional week every year) + winter holidays office closure and 3 personal days!

💼 Downtown Toronto office complete with an in-house coffee shop, music room, library and a few other lifestyle perks that keep our days fun

Equal Employment Opportunity

Rose Rocket does not discriminate in hiring or terms and conditions of employment because of an individual’s race, ancestry, colour, place of origin, religion, gender, gender identity, national origin, citizenship, age, disability, sexual orientation, family status or marital status, or any other protected category recognized by provincial or federal laws.

Should you require any accommodation, please inform us and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application or email [email protected].