Senior Customer Support Specialist

Who We Are

Baseline is a 'lending operating system' for Private Lenders based in the US, who make real estate secured loans, primarily to real estate investors (i.e. house flippers and landlords) or developers. Our platform allows lenders to originate and service loans, manage borrowers and investors, streamline business processes and create technology-enabled workflows that allow them to expand their businesses and improve profitability.

Baseline was founded in 2022 and raised a $2.2m CAD seed round in May 2024. We experienced 400%+ revenue growth in 2024 and are have continued on this trajectory in 2025. We have a market-leading product in our category and have ambitions to become the dominant software in the entire private lending industry.

The Role

Baseline is hiring a critical team member to help shape the future of our company: a Senior Customer Support Specialist. This is a full-time, in-person position at our offices in Downtown Toronto.

What is a Senior Customer Support Specialist at Baseline?

As a Senior Customer Support Specialist at Baseline, you'll be responsible for the front line delivery of Baseline's philosophy of customer obsession. Above all else, you will be tasked with developing an exhaustive understanding of the business practices, workflows, needs and pain points of our clients.

The majority of your time as a Senior Customer Support Specialist will be spent in these areas:

• Responding to inbound Intercom tickets and emails to resolve customer issues quickly and accurately.
• Writing support documentation, FAQs, and help centre content to improve customer self-serve resources.
• Recording Loom videos to walk customers through key workflows and troubleshooting steps
• Delivering high-quality 1:1 video support for customers when needed.
• Creating Intercom product tours, walkthroughs, and guides that improve onboarding and feature adoption.
• Training and improving the performance of our AI Intercom bot to scale support quality and responsiveness.
• Relentlessly focusing on platform quality and usability by identifying bugs, and usability issues, and rolling up customer feedback to our product & engineering team.

You will also have the opportunity to work on a vast array of other initiatives that help the Baseline business excel, including but not limited to Customer Success, Product, Marketing, and Events.

Here are the character traits we're looking for:

• Exceptional Intelligence
• Obsessive problem-solving
• Tenacity that gets you past roadblocks
• Exceptional communication skills

For the Senior Customer Support Specialist role, we're also looking for a minimum of 1 year of outlier performance in a similar customer-facing role.

Why this opportunity?

This is not an ordinary 9-5 role - it's a chance to help take an early-stage startup from zero to one and define your future career.

Here's what's in it for you:

• An opportunity to directly enter the Support team of an extremely fast-growing B2B SaaS company without any prior relevant work experience, based on your skills and characteristics.
• An unmatched career accelerant, giving you direct exposure to and ownership of the most important Support disciplines in a customer-obsessed environment.
• The ability to see the tangible impacts on the overall success of the Baseline business, based directly on your efforts, and the associated sense of purpose and meaning in your work that delivers.
• An opportunity to work on, give input to, and learn about the entire operating methodologies of a fast-growing SaaS startup.
• Massively increased earning potential due to the skills and experience you will develop in this role, both inside and outside of Baseline.
• Empathetic and devoted leadership, coaching and mentoring from a tech industry CX veteran.

A comprehensive benefits package including medical, dental, drug, paramedical and vision coverage up to generous maximums.

Interested in applying?

This is your first assessment for the role. To be considered, you must email Henry Hayes, Baseline's Head of Customer Success, at the email address "my last name @ my company website domain", and let me know why you're a fit for this role based on what you read in this job description (LinkedIn DMs not considered), including an example of how you've demonstrated outlier performance in your minimum of a year's experience in a customer facing role before. Despite these direct instructions, a majority of applicants will not follow these instructions and will be immediately eliminated from consideration - so please don't be intimidated if you see '100+ applicants' on LinkedIn