Customer Success Manager at Portside in Austin, TX; Nashville, TN; Toronto, Canada; Raleigh, NC

Job description

• Portside is seeking a proactive and customer-focused Customer Success Manager to own a large book of small and medium-sized business (SMB) accounts through a high-volume, tech-enabled motion. Rather than driving every touchpoint yourself, you will manage and continuously improve automated, self-serve processes for onboarding, cadence, support, renewal, and expansion, stepping in personally where accounts need attention, such as inactivity triggers, escalations, or renewal risk.
• This role will partner closely with Sales, Product, Marketing, and Support to keep these automated journeys running smoothly, identify where the process needs a human touch, and resolve escalations with strong judgment and people skills. The ideal candidate has experience managing 100+ accounts in a high-volume, tech-enabled Customer Success role, is comfortable using technology and automation to extend their reach, and brings strong interpersonal skills to handle escalations effectively.

Responsibilities

• Manage and continuously improve the end-to-end customer journey (onboarding, cadence, support, renewal, and expansion) for your book of business.
• Handle escalations across your portfolio, using strong judgment and people skills to resolve issues and protect the relationship.
• Track customer health, usage, and engagement data to identify where automated processes are working and where a personal touch is needed.
• Maintain a deep understanding of Portside's products and underlying technology to effectively advise customers and troubleshoot issues as they're escalated.
• Oversee the automated, persona-based onboarding journey, including the internal hand-off from Sales, welcome sequences, and in-app tooltips, stepping in personally when a customer trips a no-activity trigger (e.g., day 14 with no activity) to get onboarding back on track.
• Maintain templated, auto-tracked success plans for accounts in your book of business, and oversee automated bi-annual account reviews, email nurture campaigns, and video product tours, refining content and triggers based on performance.
• Monitor AI and self-serve support channels (chatbot, release communications, trigger-based outreach) to ensure customers are getting accurate, timely help, and step in on escalations that self-serve support can't resolve.
• Oversee automated renewal outreach across your book of business, and take ownership of accounts that escalate to the pooled CSM queue (e.g., 2+ support tickets in 7 days), resolving underlying issues to protect the renewal.
• Monitor in-app upgrade prompts and product-led expansion performance across your accounts, flagging trends or friction points to Product and Sales, and identify accounts where a light personal touch could unlock expansion, looping in Sales as appropriate.
• Encourage customer participation in Portside's customer community for peer learning, support deflection, and advocacy identification.
• Identify customers from your book of business who are strong candidates for testimonials, case studies, referrals, or community advocacy.

Requirements

• At least 5 years in a customer-facing role, including experience in a B2B SaaS environment.
• SaaS experience required.
• Demonstrated experience using technology and automation to increase 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, with the ability to interpret usage data and health metrics to prioritize where to step in.
• Excellent communication, relationship-building, and problem-solving skills.
• Bachelor's degree or equivalent practical experience.
• Commercial experience (e.g., upsell, cross-sell, or quota-carrying experience) is a strong plus.
• Experience with AI-powered Customer Success tools is a strong plus.
• Experience in aviation, aerospace, or an adjacent industry, or a genuine passion for aviation is a strong plus.

Skills

Required

• Customer success management
• B2B SaaS experience
• Technology and automation
• People skills
• Analytical skills
• Communication
• Relationship-building
• Problem-solving

Preferred

• AI-powered Customer Success tools

Benefits

• Competitive base salary
• 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.