Location: Remote, But prefer if SF-based!

Experience Level: 6–12 months in sales (entry-level)

Who we are:

Truewind is building the future of accounting with AI. We partner with startups and growing companies to simplify financial operations, reduce manual work, and deliver clean, investor-ready financials. Our founding team includes two-time Y Combinator founders, experienced operators, and a world-class engineering team.

We’re growing quickly, and 2026 is shaping up to be a big year. That’s where you come in.

About the Role:

As a GTM Associate at Truewind, you’ll be the first point of contact for many of our future customers. Your mission: turn cold leads and warm inbound interest into qualified pipeline for our GTM team. This is a chance to learn how modern B2B sales is done - directly alongside our CEO and GTM team.

This role is perfect for someone early in their sales career who’s excited about startups, technology, and accounting.

What you’ll do:

• Build and run outbound campaigns (emails, LinkedIn, cold calls) to engage accountants, finance leaders, and founders
• Research target accounts and craft personalized outreach that actually gets replies (no spray and pray here)
• Qualify inbound leads and book meetings for AEs with mid-market firms and startup CFOs
• Experiment with new sales tactics - personalized video, creative gifting, event invites, and more
• Collaborate closely with sales leadership to refine our outbound playbook
• Become fluent in how accounting workflows operate and where AI can save hours of manual work

Who we’re looking for:

• 3–12 months of prior sales experience (SDR/BDR, inside sales, or similar)
• Comfortable with cold calls and outbound prospecting - you don’t shy away from the chase
• Interest in accounting/finance - ideally, you’ve taken 1–3 accounting classes in undergrad
• Curious, resilient, and scrappy - you like to figure things out rather than wait for instructions
• Strong communicator with a balance of professionalism and creativity in outreach
• Excited about startups and the chance to grow into an AE role within 12–18 months

Why Truewind?

• Be part of a fast-growing YC-backed startup redefining how accounting is done
• Work directly with experienced founders and a high growth trajectory team - real mentorship, not “sink or swim”
• Clear growth path into AE roles and beyond
• Competitive compensation + commission + equity

OTE & Pay:

• $60-$80K OTE (On-Target Earnings)
  • Uncapped commission
• Equity in a fast-growing YC-backed startup
• In-person OR 100% remote option

Interview Process

1. Initial call - Quick behavioral/fit interview with our GTM team
2. Prospecting exercise – Research a target account and create a short outbound sequence, including cold call, LinkedIn outreach, and email.
3. Role Play - Simulate a sales call with one of GTM team to test your cold call and discovery skills
4. Final conversations – Meet with our CEO to talk about growth, culture, and your career goals