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Executive Assistant to the CEO

Rose Rocket

Rose Rocket

Toronto, ON, Canada
Posted on Saturday, April 20, 2024

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.


Rose Rocket is hiring for our first ever Executive Assistant to the CEO. We are a YC-backed, Series B startup with a team of 160 people and growing! The Executive Assistant has the opportunity to support and work directly with our CEO, Justin Sky. This is a great opportunity for someone with previous relevant experience to gain exposure to the inner workings of a growing organization.

The Executive Assistant will be the right-hand person to Justin, providing high-level administrative support and ensuring smooth operations of the CEO's office. This role requires exceptional organizational skills, impeccable attention to detail, and the ability to anticipate the needs of a tech startup CEO.

Why we’re excited

The trucking industry is a vital and important aspect of our economy. The people who make all of this happen deserve a great product that makes their days better, and we’re proud to have been serving this audience for the last 8 years.

We know that what we are building is not an easy feat. Beyond organizational skills, we are looking for an Executive Assistant who is present, curious, responsive, and resourceful. Heading into the next stage of our business, we’re focused on leveling up our C-suite with an Executive Assistant to the CEO playing a major role in helping us get there.

A day in the life of an Executive Assistant to the CEO

  • Trust is everything. You’ll be relied on to handle confidential and sensitive information with the utmost professionalism and integrity

  • Help prioritize our CEO's time by knowing and having ownership of the day to day operations and priorities

  • Know that priorities can change quickly; anticipate and prepare for schedule changes or last-minute requests with a Plan B and C

  • Display a high degree of emotional intelligence and integrity to understand complex situations with a solution oriented approach

  • Support with ad-hoc tasks, everything from managing calendars and ordering lunch to organizing meetings and conducting research

  • Act as an extension of the CEO with external stakeholders and key partners (like our investors and Board members)

  • Provide administrative support by preparing agendas, taking minutes during meetings, and maintaining organized documentation

  • Research and support special/side projects with the CEO by providing innovative ideas and executing on them. No idea is too big or small to surface!

It would be great if you:

  • Have 3 to 5+ years of experience in roles demanding impeccable organizational skills

  • Can distill complex ideas into simple, compelling messages to internal and external stakeholders

  • Are results driven and dedicated to achieving and exceeding your goals

  • Enjoy working cross functionally with everyone from our operations to finance teams

  • Can adapt to the fast-moving environment of a startup where priorities pivot and context switches happen regularly. Know that some processes are still to come, but we think that’s what makes work fun. :)

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