Executive Assistant (Jane Leadership Team)

About this role

ABOUT THE ROLE

Hi, I'm Kas Pawa https://www.linkedin.com/in/kasmirapawa/, VP & Chief of Staff at Jane. I lead several cross-functional initiatives at Jane, including our Business Intelligence / Data & Analytics function. I also oversee operational infrastructure and executive support across our leadership team.

Here's what I've learned: executive assistants are almost invisible when they're doing their job well. But when they're missing or under-resourced, everything falls apart. Leaders spend time on logistics instead of strategy. Teams feel deprioritized. Context gets lost. The work that should amplify leadership impact instead creates friction.

What makes this role special is that it's not just calendar management - it's about creating operational infrastructure that lets leadership focus on what matters. Our Jane Leadership Team leads large teams. They're managing competing priorities across the entire company. They need someone who understands that every meeting they miss, every delayed response, every travel logistics problem sends ripples through the organization. And they need someone who can proactively solve for that.

We've built a proven approach - weekly workflows with each executive, clear communication protocols, partnership with our internal Events team - and now we're ready to scale it. We need someone who gets that this isn't about being organized and responsive (though those things matter). It's about being strategic. About understanding context without being in every meeting. About reading between the lines and saying: "Here's what I think is happening, and here's how I'd solve for it."

I'm looking for executive support as partnership work - which means resourcefulness, curiosity, and the ability to manage competing personalities and workflows without losing sight of what matters. It means seeing complexity as a puzzle to solve, not a burden. It means bringing both genuine care and strategic thinking to the role, and bringing AI into the workflow as a tool to amplify your impact.

WHAT IMPACT WE’RE LOOKING FOR YOU TO MAKE

- Own calendar management across multiple executives with distinct personalities and working styles, creating seamless workflows that protect their time and give them breathing room to focus on what matters most.

- Build trusted partnerships with executives through clear, consistent communication - especially in explaining the "why" behind calendar changes so teams feel supported and cared for.

- Anticipate needs and solve problems proactively by reading between the lines, identifying which recurring meetings are moveable, and proposing solutions instead of waiting for direction.

- Leverage AI tools thoughtfully to amplify your own impact - drafting communications, scanning calendars for patterns, researching travel and onsite logistics - then reviewing and refining before it goes out (always 90% draft, then review).

- Partner across teams and functions - working with People Partners, team leads, our internal Events team, and external vendors - to coordinate department offsites, JLT onsites, travel logistics, and all the operational details that support leadership.

WHAT EXPERIENCE WE NEED

- Approximately 5+ years of experience as an executive assistant in a fast-paced, scaling environment, with demonstrated success supporting multiple executives across different functions and personalities.

- Exceptional organizational skills, attention to detail, and ability to manage competing priorities with grace. Comfort working independently without frequent validation, and genuine curiosity about how to make things simpler and more efficient.

- Strong written and verbal communication skills - you draft correspondence, explain complex calendar decisions in writing, and communicate confidently across all levels. Proficiency with Google Suite (Gmail, Docs, Sheets), Slack, Notion, and comfort learning new tools quickly.

- High emotional intelligence, resilience, and the ability to separate business realities from personal reactions. You understand that an executive's short tone usually reflects workload stress, not friction with you - and you care enough about their success that you show up and support them anyway. You need genuine empathy paired with thick skin.

- Comfort with ambiguity and a growth mindset - this role is still evolving, and we're building the best practices together. You're someone who experiments, asks good questions, and isn't afraid to suggest better ways of doing things.

We're hiring for people based in the Vancouver area who can travel to our North Vancouver office. Being in the same geographic area opens up opportunities for in-person strategy sessions, collaborative working days, and the kind of connection that builds stronger partnerships in a remote-first company.

If you don't meet every single qualification but are excited about this role, we'd still love to hear from you.

MORE ABOUT JANE

Jane is a founder-led, high-growth SaaS company with a remote-first team working across Canada, the US, and the UK, united by our mission to help the helpers.

We build the products and tools that thousands of clinics rely on every day to run their businesses, care for their patients, and grow their communities. That level of impact means every person at Jane plays an important role in how we show up for our customers. We're all responsible for being deeply connected to their needs, obsessed with improving their experience, and proud of the difference our work makes in their day - to - day lives.

Jane is growing fast, and that growth brings exciting challenges that call for adaptability, resilience, learning agility, and humility. We're proud of what we've built and quick to admit what we don't know yet. We listen, learn, and adjust as we go. More than 70,000 businesses run on Jane which has 250,000+ practitioners interacting with our product on a daily basis…