Customer Success Specialist

About Proposify At Proposify, we're revolutionizing the way businesses create and manage proposals. Our innovative platform streamlines the proposal process, helping teams craft compelling, professional proposals that close deals faster and with greater success. We pride ourselves on fostering a dynamic, inclusive, and collaborative work environment where creativity and innovation thrive. As we continue to grow and enhance our offerings, we are looking for talented individuals who are passionate about technology and driven by the challenge of making complex processes simple and efficient. Join us and be a part of shaping the future of proposal management!

About the Role We, at Proposify, are passionate about helping sales teams win with better proposals. Our Customer Support Specialists are the frontline heroes, delivering first-class service experiences that help our customers thrive. As a core part of the Customer Success team, you’ll provide responsive, insightful support, assist with onboarding and technical troubleshooting, and collaborate cross-functionally to ensure seamless customer journeys. Your goal: help customers get the most out of Proposify by offering fast, friendly, and effective solutions.

***This is a remote position. To support collaboration with our team, candidates must be able to align their work hours with Central to Pacific Time Zones.

What You'll Do And Love Doing Customer Support & Ticket Management

• Manage the daily support queue in Zendesk, responding to customer inquiries with fast, helpful solutions.
• Resolve issues across billing, product, and technical topics with clarity and care.
• Process billing-related items including refunds, credits, and invoicing nuances.
• Engage directly with customers through video chat as needed to resolve issues, provide guidance, and deliver exceptional service.

Technical & Integration Support

• Troubleshoot integration and API-related issues, including basic debugging using tools like Datadog.
• Join customer, sales, or CSM calls to provide deeper technical insight when needed.
• Support backend tasks such as ticket routing, SLA segmentation, and Zendesk reporting on a rotating basis.

Customer & Internal Training

• Deliver onboarding sessions to customers as part of sold training packages 
• Contribute to internal training, including onboarding new team members and educating on new systems or workflows.

Process & Content Enablement

• Maintain and contribute to the knowledge base with articles, videos, and helpful self-serve content.
• Participate in workflow optimization projects to enhance both customer and team efficiency.
• Help manage and enhance the CS Bot to improve self-service and ticket deflection.

What We'll Love About You

• You have 1–3 years in a customer support, technical support, or SaaS customer success environment.
• Proficiency in Zendesk (or similar support platforms), and familiarity with CRM tools.
• Clear, empathetic communicator with a knack for simplifying complex topics.
• Technical curiosity—comfortable learning how integrations work and explaining them to others.
• A team mindset—you thrive in a collaborative, fast-paced environment where everyone pitches in.

What You'll Love About Us While Proposify world headquarters is in Halifax, Nova Scotia, we are a 100% remote company with employees working from all over the world. We’ve invested in all of the systems and tools that make remote work enjoyable, productive, and connected.
People feel empowered to do their best work and test out ideas. They don’t just ask ‘Why?’ but try ‘Why not?’ We are a team that embraces the new, the maybe, the unknown because we know that’s where growth lies; just beyond our comfort zone, just beyond what the experts say, and way beyond the way- we’ve-always-done-things.
Everyone is a leader in their role and has the autonomy and responsibility to contribute, to change, and to challenge. We don’t care how many hours people work, we care about the quality and impact of their work.
We get shit done. We get shit done fast. We are not a static company; we are moving forward and continually evolving to make things better for our business and the businesses of our customers. We have flex hours so employees can design their day to work when they’re most productive, and allow for time each day to spend with family and friends, take advantage of nice weather, focus on wellness, and pursue their hobbies and passions.

Some Of Our Benefits Include

• Competitive market based salaries
• Company provided and paid health benefits from the day you start, paid entirely by Proposify
• Virtual Health Care
• RRSP matching program from the day you start with no vesting period
• Generous Paid Time Off Policy including: 3 weeks of vacation to start; paid sick leave; personal days; birthday leave, company-wide end-of-year holiday break
• Skills Training Enrichment Program to grow your knowledge and skills within your role
• Brightpass (free online fitness and wellness courses)
• Flexible working hours so you can do your best work when you are at your best
• WFH Stipend setting you up for success!

At Proposify, we value and celebrate the diversity of our team and welcome applications from racially visible persons, Indigenous peoples, women in non-traditional positions, persons with disabilities, and persons of the LGBTQ+ community.
Proud to be Great Place to Work® certified, reflecting our commitment to a supportive, inclusive, and growth-oriented workplace.