Join Our Mission: Help the Helpers with Jane

Let's kick things off with a quick intro. Jane is a team that's all about fostering growth, spreading delight, and serving our healthcare community. We're on the hunt for people ready to jump in and join us while we simplify the lives of healthcare practitioners and patients daily. And guess what? Jane is a remote-first company, meaning every role at Jane, including this one, is remote, giving you the freedom to work from any corner of Canada.

Your Role in Our Journey

We're looking for a collaborative, strategic, and empathetic leader to take our product support and enablement to the next level. As Jane continues to ship more impactful features, it's critical that our internal teams are equipped to support them - and that the voice of our customers is heard, understood, and actioned.

As our Product Enablement & Insights Lead, you will lead our Co-Pilot program and customer insights function. Your role is to ensure our support teams are not only informed, but enabled with the knowledge, confidence and tools to support every new product update. You will be responsible for turning customer voices and team feedback from a variety of channels into actionable, data-driven insights to help ensure our Product team has a clear, data-rich understanding of what customers need and where they’re getting stuck.

This role will report to the Director of Customer Success Operations and work cross-functionally within the broader Customer Team at Jane.

Learn More About Us

We're founder-led, which means we live our values while maintaining a clear vision for the future. Our product enables the likes of physiotherapists, mental health counsellors, chiropractors, and other allied health practitioners to run their practices in a digital-first way through features such as online booking, charting, scheduling, telehealth, secure payments and billing along with an evolving library of features. You can see more of them here.

There is often a high bar set, not just for the quality of work, but for the care we show for each other and our customers. And it’s our customers raising that bar, never standing still and continually improving which keeps us on our toes. It's not just about what you've done before or how quickly you work; it's about your curiosity and drive to solve the right problems and your agility in learning new ways of thinking.

No doubt, Jane's a special place to work. There is autonomy and flexibility to help integrate work into your life in a way that makes sense for you. Need to block out time to pick up the kids? Go for it. That's normal here. And yes, we have a Slack channel for parents, but we've also got channels dedicated to plants, furry friends, food, pride, wellness - you get the idea! While we love to connect virtually, the Jane team also connects in person throughout the year. That comes in the form of departmental get-togethers, company retreats, or possibly a conference or two across North America if you’re keen to learn more about our community of healthcare providers. We're on the search for folks who are ready to dive in and become part of our journey toward making healthcare professionals' lives easier every single day.

You can also learn more about Jane as a company and a product by checking out our Glassdoor reviews and our Capterra Reviews

But we’ll also keep it real — as much as we love our work, the mountain we're climbing is always getting taller. We're a growing company, and with that comes the challenge of navigating an environment with many moving parts, often without a clear-cut path laid out in front of us. This is where you come in. If you're the kind of person who gets a kick out of being resourceful and loves solving problems, you'll fit right in.

We believe in collaboration, humility, and keeping a growth mindset. We're looking for people who can embrace our way of working, which often means being flexible and open to change. So, if after reading this, you feel excited about the opportunity — all in the name of helping those who help others — reach out to us to learn more.

In short, if you're excited by our growth, ready to contribute to a challenging yet rewarding environment, and eager to be a disruptor alongside a team of talented individuals, we’d love to hear from you!

The Impact You Could Have

Team Leadership: Cultivate a high-performing, inclusive, and collaborative team environment aligned with Jane’s values.
Manage, coach and grow a team of Co-Pilots and Feature Request Experts, ensuring alignment on goals and accountability for deliverables.
Champion a culture of ownership, knowledge-sharing, and collaboration between Support, Product, and PMM.
Drive clarity through 1:1’s, team meetings, and goal-setting that foster personal and team growth.
Customer Feedback & Insights (Canny): Own the full lifecycle of community sourced feedback on Jane’s Feature Request board, ensuring customer requests are accurately captured, prioritized, and translated into actionable insights.
Establish consistent processes for prioritizing customer feedback, tagging and surfacing feature requests to ensure alignment with product strategy.
Work with Product to ensure Jane’s public-facing roadmap is up to date, accurate, and reflective of current priorities.
Ensure customers receive clear communication and updates through the feature request tool.
Product Enablement & Co-pilot Program: Lead the Co-pilot program to support smooth, customer-focused product launches.
Ensure Support is proactively trained and enabled to handle new feature rollouts with confidence - through async learning sessions, messaging and clear documentation.
Celebrate wins and track adoption impact, sharing measurable stories with Product and beyond.
Customer Intelligence & Reporting: Design and maintain a scalable framework for gathering feedback and sentiment from support interactions and other key channels.
Deliver regular insights and dashboards that surface emerging trends, pain points, and opportunities for improvement.
Use insights to create compelling, data-backed reports and presentations to inform Product decisions.

The Experience We Feel We Need

3-5 years of experience in a customer success, product operations, or enablement role, with at least 1 year of people management experience.
Strong analytical and storytelling skills- you can turn data into actionable recommendations and craft compelling presentations that influence decision-making.
Experience working cross-functionally, especially with product, support, and product marketing teams.
A deep understanding of customer-centric thinking, paired with a structured approach to problem-solving.
Comfort with tools such as Canny, Help Scout, Talkdesk, or other customer feedback and enablement platforms.
Experience designing and rolling out enablement programs at scale.
Strong communicator who can bridge technical and non-technical stakeholders.
Empathy-led leader who believes that a well-informed support team leads to a better customer experience.

Compensation & Benefits

Jane’s committed to paying our team members fairly, clearly, and above all, paying for growth. This role has a minimum annual salary of $95,000 and maximum annual salary of $138,000. As you may have noticed, this salary range is quite large, and this is intentional to account for the growth someone will experience in the role throughout their time at Jane (i.e., from building the skills, to accomplished, to highly proficient, all the way to achieving excellence in the role).

Paying clearly is one of our compensation fundamentals. Watch this short video to learn how our salary bands are set. You’re also encouraged to ask questions about compensation at any point during the interview process.

We also offer a comprehensive benefits package; you can learn more about it here!

At Jane, we’re committed to fostering an environment that allows you to come to work as your truest self. We believe it’s important to actively recognize, embrace, and celebrate our differences in order to make Jane an inclusive, equitable, and diverse workplace.

We want to build a team of people who make conversations rich with perspective and experience. We are committed to listening to every voice in order to learn and grow because doing this will allow us to meet the needs of the diverse community of helpers that Jane serves.

We do not tolerate discrimination, prejudice, or oppressive isms of any kind. Employment is decided on the basis of qualifications, merit, experience, and the needs of the Jane community. We encourage anyone who requires accommodation or adjustments throughout the interview process to let us know, and we will do our best to support you.

Product Enablement & Insights Lead

Jane Software

Compensation Overview

The Impact You Could Have

The Experience We Feel We Need

Simplify's Take

What believers are saying

What critics are saying

What makes Jane Software unique

Benefits

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