Director of Customer Experience

Proposify; Halifax; Remote; CAD 100,000 - 150,000; Full time

Job summary

Proposify seeks a Director of Customer Experience to lead and enhance customer success strategies for its innovative proposal management platform. The role requires operational excellence and strategic leadership to drive customer satisfaction and business growth in a remote work environment. Candidates should possess strong leadership skills and extensive experience in SaaS, focusing on customer journey optimization.

Benefits

Competitive Salaries

Fully Covered Health Benefits

Virtual Health Care

RRSP Matching

Generous Time Off

Skills Training & Growth

Flexible Work Hours

Home Office Stipend

Qualifications

• 7+ years in Customer Success or related leadership roles.
• 5+ years in a senior leadership position.
• Experience with multi-disciplinary teams.

Responsibilities

• Drive customer success programs to enhance retention and reduce churn.
• Lead and mentor the Customer Success team.
• Shape company strategy with customer-centric decision-making.

Skills

Customer Success

Strategic Thinking

Operational Excellence

Leadership

Communication

Education

Bachelor's Degree

Experience in SaaS Environment

Job description

Description

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 comprising Customer

Success Managers (CSMs), Customer Support Specialists (CSSs), Customer Success

Designers and Managers. 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, CSRs, 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 People & Culture on talent development, succession planning, and career

pathing within the team.

Customer Health & Revenue Impact

●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 to the executive team

and board.

Systems & Process Excellence

●Drive continuous improvement in the tools and systems supporting Customer Success

●Optimize customer support and onboarding processes to enhance experience and

What We’ll Love About You

●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’s 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 mostproductive, 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

●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

●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.

Know someone who would be a perfect fit? Let them know!