Customer Support Ops Tooling Expert
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 process-oriented, technically strong systems specialist to help elevate the tools that power Jane’s Support team. As our Customer Success Operations Systems Expert, you’ll join our Customer Support Operations team on a 6-month contract to ensure that the platforms our team relies on, such as Talkdesk and HelpScout, are running smoothly, efficiently, and in alignment with our evolving support goals. This is a 6-month contract role with the possibility of extension, depending on performance, team needs and project scope.
This role is a great opportunity to drive meaningful change in how we serve our customers. You’ll lead tooling improvements, enhance workflows, and identify automation opportunities, all in close partnership with CS Ops, Support leadership, and cross-functional stakeholders. If you thrive on making systems more intuitive and effective for humans, we’d love to meet you.
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
Tool Ownership & Optimization: Serve as the day-to-day administrator of Talkdesk and HelpScout (and other support tools as needed).
Identify inefficiencies and opportunities for enhancement, and scope, implement, and test improvements.
Ensure tools are configured for reliability, scalability, and ease of use.
Change Management & Stakeholder Collaboration: Work closely with CS Ops and Support leadership to identify team pain points and translate them into systems solutions.
Lead the rollout of system changes, communicating clearly, minimizing disruption, and ensuring smooth adoption across the team.
Document tool changes and support ongoing education around best practices.
Process Automation & Workflow Design: Optimize team workflows using automation, smart integrations, and configuration updates.
Partner with relevant stakeholders to streamline operations and reduce manual overhead.
Maintain a mindset of continuous improvement, always looking for ways to make things simpler and smarter.
Approach every system and workflow with deep curiosity - asking why, exploring how, and uncovering opportunities that others might overlook.
Data-Driven System Insights: Leverage analytics from Talkdesk, HelpScout, and other tools to surface trends and evaluate the impact of changes.
Monitor key performance indicators (e.g., response times, ticket routing effectiveness) to guide future iterations.
Translate findings into clear recommendations to inform CS Ops and leadership strategies.
The Experience We Feel We Need
Proven experience administering support platforms such as Talkdesk, HelpScout, Zendesk, Intercom, or similar.
Strong problem-solving skills and a bias toward action - you can identify a gap, propose a fix, and make it happen.
Familiarity with workflow design, process mapping, and automation tools.
Confidence working with data to validate decisions and measure impact.
Clear and empathetic communicator, especially when explaining technical changes to non-technical teammates.
A systems thinker who balances usability with long-term maintainability.
Compensation & Benefits
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.
About the job
Apply for this position
Customer Support Ops Tooling Expert
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 process-oriented, technically strong systems specialist to help elevate the tools that power Jane’s Support team. As our Customer Success Operations Systems Expert, you’ll join our Customer Support Operations team on a 6-month contract to ensure that the platforms our team relies on, such as Talkdesk and HelpScout, are running smoothly, efficiently, and in alignment with our evolving support goals. This is a 6-month contract role with the possibility of extension, depending on performance, team needs and project scope.
This role is a great opportunity to drive meaningful change in how we serve our customers. You’ll lead tooling improvements, enhance workflows, and identify automation opportunities, all in close partnership with CS Ops, Support leadership, and cross-functional stakeholders. If you thrive on making systems more intuitive and effective for humans, we’d love to meet you.
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
Tool Ownership & Optimization: Serve as the day-to-day administrator of Talkdesk and HelpScout (and other support tools as needed).
Identify inefficiencies and opportunities for enhancement, and scope, implement, and test improvements.
Ensure tools are configured for reliability, scalability, and ease of use.
Change Management & Stakeholder Collaboration: Work closely with CS Ops and Support leadership to identify team pain points and translate them into systems solutions.
Lead the rollout of system changes, communicating clearly, minimizing disruption, and ensuring smooth adoption across the team.
Document tool changes and support ongoing education around best practices.
Process Automation & Workflow Design: Optimize team workflows using automation, smart integrations, and configuration updates.
Partner with relevant stakeholders to streamline operations and reduce manual overhead.
Maintain a mindset of continuous improvement, always looking for ways to make things simpler and smarter.
Approach every system and workflow with deep curiosity - asking why, exploring how, and uncovering opportunities that others might overlook.
Data-Driven System Insights: Leverage analytics from Talkdesk, HelpScout, and other tools to surface trends and evaluate the impact of changes.
Monitor key performance indicators (e.g., response times, ticket routing effectiveness) to guide future iterations.
Translate findings into clear recommendations to inform CS Ops and leadership strategies.
The Experience We Feel We Need
Proven experience administering support platforms such as Talkdesk, HelpScout, Zendesk, Intercom, or similar.
Strong problem-solving skills and a bias toward action - you can identify a gap, propose a fix, and make it happen.
Familiarity with workflow design, process mapping, and automation tools.
Confidence working with data to validate decisions and measure impact.
Clear and empathetic communicator, especially when explaining technical changes to non-technical teammates.
A systems thinker who balances usability with long-term maintainability.
Compensation & Benefits
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.