The posting
At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products.
We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact.
This position is for an existing vacancy.
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Roofr is growing our Customer Success team, and we're looking for a Customer Success Specialist to own and grow relationships with our customers. We onboard hundreds of new customers every month, and our platform is constantly evolving with new tools, features, and workflows. This team sits at the intersection of onboarding, implementation, support, retention, and account management. While each of those teams plays a critical role, Customer Success focuses on the moments that can otherwise fall through the cracks: helping customers deepen their understanding of Roofr, adopt new tools, expand their workflows, and get more value from the platform over time.
As a Customer Success Specialist, you'll act as a trusted advisor, partnering with roofing contractors and business owners to understand their goals, improve their processes, and help them build stronger, more efficient businesses using Roofr. That means understanding how each customer actually works, spotting where they have access to tools they aren't using, and helping them build workflows that make Roofr a natural part of how they run their operations.
This role is built for someone who earns trust through consistency and genuine curiosity, someone who takes the time to understand a customer's business before suggesting a better way to do things. The question driving everything here is simple: are my customers getting full value from what they've invested in? Are they using what they have access to, and if not, why? Success in this role is measured by depth, not revenue, and by the real difference you make in how a roofing business runs day to day.
What You’ll Do:
- Own the customer relationship after the Onboarding Specialist handoff, serving as the primary point of contact for customers as they deepen their use of Roofr.
- Track and understand what each customer has access to versus what they're actively using, and close that gap through coaching, education, and proactive outreach.
- Build genuine, trust-based relationships with customers who may not be comfortable with technology.
- Serve as the internal voice of your customers, bringing patterns, friction points, and adoption barriers to the right teams so they can be addressed at the root
- Partner cross-functionally with Account Management, Retention, Sales, Product, Account Setup, and the Onboarding team to ensure customers are well-supported and every transition between teams is smooth
- Contribute to how Roofr thinks about and continuously improves the post-onboarding customer experience
What You'll Bring to the Role:
- 2+ years of experience in customer success, account management, or customer enablement in a B2B or SaaS environment
- A genuine interest in how businesses operate, especially in industries where technology isn't always the comfort zone
- Comfort reading adoption data and translating it into a clear, prioritized action plan for each customer in your portfolio
- Strong relationship-building skills; you know how to earn trust over time, not just in a first call
- A proactive mindset: you don't wait for customers to raise their hand; you spot the signals early and act on them
- High ownership mentality with the ability to manage a portfolio of customers independently and follow through consistently
- Strong communication skills across calls, email, and video: clear, warm, and always customer-first
Who You Are:
- A true customer advocate
- Highly organized and results-oriented
- Detail-obsessed (in the best way)
- You know how to adapt your approach depending on who’s in front of you.
- You are always looking for ways to improve and scale what works
- Tech-savvy and comfortable learning new tools quickly
Compensation Band: $70,000.00 - $80,000.00 CAD
Our compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data. While many hires fall within the beginning to midpoint of the band to allow for growth over time, we tailor offers based on each candidate’s experience, seniority, and demonstrated impact.
🏠 What we offer (US + Canada)
When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career:
🏝️ Vacation/Paid Time Off:
- 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
- 1 Friday off per month (we call those our laundry days!)
- Company wide paid shutdown for the week between Christmas and New Years
- Flexible time off
- 80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada
- RRSP/401k match
- Generous Parental Leave policy
🤝 Perks:
- We host an annual company retreat with great team building activities
- Ample learning and development opportunities to continue growing your career
- Home office setup stipend
- Internet and phone allowance
- Remote first culture
- Weekly Friday paydays!
🤖 AI Notice
At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.
Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too.
And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️
⚠️ Important Notice
We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls.
To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers.
If you receive any suspicious messages or have questions, reach out to us at [email protected].
Your safety and security are important to us — thank you for your vigilance!
Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.
