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!
The Director of Customer Experience is a strategic, people-first leader responsible for the vision, direction, and performance of Proposify’s Customer Success organization. This executive-level role combines operational excellence with strategic leadership and plays a critical part in shaping company growth through exceptional customer outcomes.
The Director of Customer Experience oversees a multidisciplinary team encompassing Customer Success, Support, Professional Services, & Account Management. This leader is accountable for the overall health of the customer base, driving product adoption, retention, revenue expansion, and customer advocacy.
What You’ll Do
Strategic Leadership
- Serve as a key member of the executive leadership team, contributing to company-wide strategy, customer-centric decision making, and long-term growth planning.
- Own and evolve the customer journey, identifying opportunities to scale experience across onboarding, support, success, and design enablement.
- Partner cross-functionally with Product, Sales, and Marketing to ensure alignment around the voice of the customer, roadmap influence, and lifecycle health.
Team & Functional Management
- Lead, mentor, and scale a diverse Customer Success org (CSMs, CSSs, Designers, Onboarding, etc.) with clear goals, roles, and performance expectations.
- Foster a high-performance, collaborative culture focused on delivering measurable outcomes for customers and the business.
- Partner with Human Resources on talent development, succession planning, and career pathing within the team.
Customer Health & Revenue Impact
- Accountable for key customer success metrics such as retention, expansion, and product adoption.
- Develop and implement customer success programs that drive renewals, reduce churn, and identify upsell opportunities in collaboration with revenue teams.
- Leverage data to report on performance, trends, and insights into customer health, loyalty and value derived, and as well as points of friction.
Systems & Process Excellence
- Drive continuous improvement in the tools and systems supporting Customer Success (e.g., CRM, CS platform, onboarding workflows).
- Optimize customer support and onboarding processes to enhance experience and improve scalability.
- Leverage technology to deliver exceptional service
What You Bring
- 7+ years of experience in Customer Success, Customer Experience, or related leadership roles in a SaaS environment.
- 5+ years in a senior leadership position, ideally with executive team exposure.
- Experience overseeing multi-disciplinary teams (e.g., Success, Support, Design, Onboarding).
- Strong strategic thinking paired with operational execution—able to toggle between high-level planning and hands-on leadership.
- Demonstrated success in reducing churn, improving retention, and driving customer outcomes.
- Deep understanding of SaaS metrics, lifecycle management, and customer journey mapping.
- Exceptional communication, stakeholder influence, and people leadership skills.
- Experience in contract lifecycle management, proposal software, or B2B SaaS preferred.
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.
Why You'll Love Working at Proposify
We believe that happy, healthy people do their best work. That’s why we offer a competitive and comprehensive benefits package designed to support you from day one:
- Competitive Salaries – We pay fair, market-based salaries so you can focus on doing your best work.
- Fully Covered Health Benefits – Your health matters. We provide and fully pay for group benefits starting on day one.
- Virtual Health Care – Access healthcare professionals from the comfort of your home.
- RRSP Matching – We match your RRSP contributions from the day you start, with no vesting period.
- Generous Time Off – Recharge with 3 weeks of vacation to start, plus paid sick leave, personal days, your birthday off, volunteering time off, and a company-wide holiday break at year-end.
- Skills Training & Growth – Level up your career with our Skills Training Enrichment Program.
- Brightpass Access – Enjoy free virtual fitness and wellness courses to support your well-being.
- Flexible Work Hours – Whether you're an early bird or a night owl, we trust you to work when you're at your best.
- Home Office Stipend – We’ll help you create a comfortable and productive workspace at home.
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.