Customer Success Engineer / Manager

Transparent Search Group • New York, NY

2d • Onsite

About The Position

CollectWise is a Y Combinator-backed startup automating debt collection, a $35B US market, with generative AI agents that outperform human collectors about 2x at a fraction of the cost. Its agents handle the full arc of debt recovery, from outreach to resolution, while keeping interactions respectful and data-driven. With a small team, CollectWise has scaled to a $3M annualized revenue run rate and is pushing toward $10M. CollectWise is hiring a founding Customer Success Engineer to own customer relationships after the implementation handoff, keeping accounts healthy and expanding and preventing churn. The forward-deployed engineers handle the launch; you take over from there, owning ongoing AI agent support, proactive account monitoring and upsell execution across a growing book of accounts. Success means smooth handoffs, strong satisfaction, 100% retention and expansion revenue.

Requirements

• 3+ years in technical customer success, solutions engineering or a closely adjacent role
• Experience managing multiple accounts with strong written and verbal communication
• A commercial mindset with a record of upsell or expansion
• Comfort troubleshooting technical issues and adjusting configurations
• Based in New York City and able to work in person

Nice To Haves

• AI, SaaS or automation startup experience with hands-on customer enablement
• Familiarity with AI agents, prompt engineering or workflow automation
• Owning a book of accounts at an early-stage company without a playbook

Responsibilities

• Serve as primary contact for a growing book of post-implementation accounts.
• Monitor usage, performance and health signals to catch churn risk early.
• Resolve technical and configuration questions independently, escalating the rest with clear context.
• Drive upsell and expansion by finding new use cases.
• Tune AI agents through configuration and prompt-level changes to improve outcomes.
• Manage smooth handoffs from the forward-deployed engineering team.

Benefits

• upsell commission
• retention bonuses
• equity

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed