Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.Backed by leading technology investors Vista Equity Partners and Insight Partners, Portside is entering an exciting phase of growth. We are expanding our platform, investing in AI driven innovation, and building a global team focused on shaping the future of aviation technology.

Job SummaryAs a Customer Success Manager, you will own a book of mid-market accounts through a scaled, digitally led motion. You will run and continuously improve automated journeys for onboarding, cadence, training, renewal, and expansion, and step in personally when customer signals show an account needs attention.

You will work closely with Sales, Product, Marketing, and Support, using health and usage data to decide where your time matters most and resolving escalations with sound judgment. The ideal candidate has managed a large mid-market book in a tech-enabled Customer Success model and uses data and automation to extend their reach.

Key Responsibilities

Onboarding

Oversee the guided, digitally led onboarding experience, including the automated hand-off from Sales, persona-based journeys, and onboarding checklists. Step in when a customer stalls or misses a milestone.

Cadence

Maintain templated, auto-tracked success plans across your book and oversee automated quarterly business reviews,



refining content and triggers based on performance.

Health and risk

Lead signal-driven health reviews. Use usage, engagement, and support data to spot at-risk accounts early and decide which need a personal touch.

Training

Run quarterly group trainings and webinars, and keep the knowledge base and recorded training library accurate and aligned with product releases.

Renewal

Oversee the automated 120-day renewal outreach. When signals elevate an account, take ownership, resolve the underlying issues, and partner with Sales to protect the renewal.

Expansion

Manage automated lifecycle campaigns, host open office hours, and support self-service onboarding for newly adopted products. Pass qualified opportunities to Sales.

Digital adoption

Deliver prescriptive adoption journeys that guide customers toward the features and outcomes that matter most to them, and flag friction points to Product.

Voice of customer and advocacy:

Contribute to scaled voice-of-customer programs and share feedback trends with Product, Sales, and Support. Identify strong candidates for testimonials, case studies, referrals, and community advocacy.

Escalations and product expertise





Handle escalations across your portfolio with strong judgment and people skills, drawing on deep knowledge of Portside's products and technology to advise customers and troubleshoot issues.

Qualifications

5+ years in a customer-facing role at a SaaS company, including experience in a scaled, tech-enabled Customer Success model managing a book of mid-market accounts

Demonstrated experience using technology and automation to extend reach and efficiency across a large book of business

Strong people skills, with a track record of effectively handling and resolving customer escalations

Strong analytical skills, able to interpret usage data and health signals to prioritize where to step in

Excellent communication, relationship-building, and problem-solving skills, including comfort leading group trainings and webinars

Bachelor's degree or equivalent practical experience

Commercial experience (e.G., upsell, cross-sell, or quota-carrying) would be a strong plus

Experience with AI-powered Customer Success tools would be a strong plus

Experience in aviation, aerospace, or an adjacent industry, or a genuine passion for aviation, would be a solid plus

What We Offer

Fully remote work

Generous time off policy

Health, dental, and vision insurance

Opportunities for professional development and career advancement.

Dynamic, collaborative, and fast-growing work environment.

Portside is an equal-prospect employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Customer Success, Support, Implementation & Safety

📌 Customer Success Manager (Winnipeg)
🏢 Portside
📍 Winnipeg