Technical Support Engineer

As a Technical Support Engineer at Windfall, you’ll own the customer support queue and the systems behind it. You’ll onboard new customers, configure accounts, map high-priority datasets, and resolve technical issues. Then you’ll ask the next question: why did this ticket happen, and how do we stop it from happening again? Sometimes the answer is a better help article. Sometimes it’s a product fix. More and more, it’s an AI workflow that answers the question before the customer has to ask.

This role is a great fit if you’re early in your career, operations-minded, and curious about AI. It isn’t SQL-heavy or a deep engineering role. We want a resourceful problem-solver who likes data, sweats the details, and would rather fix a problem once than answer it a hundred times.

We're on a mission to change how organizations perceive and use people data. And we hold true to our core values of: (1) Be an excellent communicator; (2) Operate with transparency; (3) Provide leverage, not optimization; (4) Win When Our Customers Win; and (5) Act with integrity and trust.

What You'll Do

• Own the support queue: triage, troubleshoot, and resolve inbound tickets in Pylon, and escalate crisply to Product or Engineering when needed
• Support new customer and user onboarding, and get them to first value fast
• Monitor data delivery queues and account and dataset health, and catch issues before customers do
• Support wealth analytics reports and match analysis workflows
• Find the root cause of recurring issues and fix it with an operational improvement (e.g., a playbook, a knowledge base article, product feedback, or AI automation)
• Build and improve AI workflows that deflect and auto-resolve common questions
• When a playbook doesn’t exist yet, build it, and document your work so every handoff is clean
• Keep accurate records in Pylon, Salesforce, and our internal knowledge base
• Turn customer feedback and bug patterns into clear input for the product roadmap

What Success Looks Like In Your First 90 Days

• You run the queue on your own with fast, reliable response times
• Each of the top recurring ticket types has a playbook, a help article, or an AI answer
• Product and Engineering see you as their clearest source of customer signal

About You

• Operational mindset: when you see a repeated task, you want to fix it, template it, or automate it
• AI-curious: you already use tools like Claude or ChatGPT to work faster, and you want to build with them
• Detective instinct: you dig until you find the why, not just the what
• Adaptable communicator: you can switch easily between a frustrated customer, a busy engineer, and an executive
• Natural documenter: you write things down so others don’t have to ask (bonus points if you’re a Checklist Manifesto fan)
• Calm prioritizer: you separate the urgent from the noise, and you know when to solve something yourself and when to ask for help

Requirements

• Must be able to work in office 4-5 days per week. (We are an in-office culture with flexibility for one day per week work from home for employees in good standing, after an initial probationary period)
• 2+ years of professional experience, with 1+ years in technical support, RevOps or sales ops, data or marketing analysis, or another CRM-adjacent role, ideally in B2B SaaS
• Comfortable with CSVs, spreadsheets, and CRM data models (objects, records, fields)
• Experience with Salesforce, HubSpot, or a similar CRM
• Experience with a ticketing or support platform (Pylon, Zendesk, Intercom, or similar)
• Strong written and verbal communication
• Bachelor’s degree or equivalent experience

Nice To Have

Experience building AI workflows, automations (for example, Zapier), or bots
Knowledge base or technical writing experience
Light scripting or advanced spreadsheet formula skills
Exposure to data matching, data enrichment, or nonprofit or financial services data

Additional Information:

Individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. We also offer a comprehensive benefits package, which you can explore on our careers site