Customer Success Manager

Job Summary

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.

Key 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.

Qualifications

• At least 5 years in a customer-facing role, including experience in a B2B SaaS environment.
• 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.

What We Offer

• 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.

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