Technical Support Engineer

Posted: 2026-10-15

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.

- 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

- 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

- 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

- 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