Account Executive

About the role

Truewind is building the digital accountant for modern finance teams. We build AI agents for finance teams to close faster, reduce manual work, and deliver clean, investor-ready financials. Our product is built for the messy, high-volume accounting work that still creates spreadsheet chaos: Point of Sale tie-outs, payroll accruals, donations and revenue schedules, fixed assets and prepaid rollforwards, and field-services revenue recognition.

What You Will Do

• Own the full sales cycle across inbound, outbound, discovery, evaluation, negotiation, and close.
• Qualify inbound leads with urgency, judgment, and clear standards.
• Build self-generated pipeline through account research, thoughtful outbound, and disciplined follow-up.
• Sell to controllers, CFOs, heads of finance, and accounting firm leaders.
• Run discovery on close workflows, systems, pain points, urgency, controls, and implementation requirements.
• Translate manual accounting pain into a clear business case for adopting Truewind.
• Manage multi-stakeholder deals across finance, accounting, and firm leadership.
• Partner with our accounting and product teams to support evaluations and build implementation confidence.
• Maintain clean pipeline hygiene, forecasting, next steps, and follow-through from first meeting to close.
• Turn market feedback into sharper messaging, qualification criteria, objection handling, and sales process improvements.
• Help build the foundation for a sales organization that can scale beyond the first wave of customers.

What We Are Looking For

• 3+ years of quota-carrying sales experience in B2B SaaS or another consultative sales environment.
• Experience owning deals end to end, not only one stage of the funnel.
• Comfort selling deals in the $40,000-$70,000 ACV range, with the ability to work $100,000+ opportunities.
• Strong discovery skills with buyers who expect substance, accuracy, and clear follow-through.
• Able to manage multiple stakeholders and keep momentum through a consultative buying process.
• Confidence balancing inbound demand with self-generated pipeline.
• Commercial judgment, high ownership, and disciplined follow-through.
• Ability to operate with pace and ownership in a remote environment.
• A desire to grow into broader sales leadership as Truewind scales.

Bonus points

• If you have sold to CFOs, controllers, accounting firms, finance operations teams, or buyers in the office of the CFO.
• Experience with workflow, ERP, accounting, FP&A, Order-to-Cash, or finance operations software.

What We Offer

• $200,000-$275,000 OTE target cash compensation, including base salary and commission.
• Uncapped commission under Truewind's applicable commission plan.
• Equity in a fast-growing startup.
• A remote role with flexibility to work where you do your best work, subject to role, customer, and team needs.
• Direct exposure to founders, product decisions, customer feedback, and the accounting workflows our product automates.
• A real voice in shaping Truewind's sales playbook, sales engine, and future GTM team as we grow.
• A steep growth curve for someone who wants to become a sales leader, not just inherit a finished sales process.

Why This Role

This role is for an AE who wants to sell a product tied to painful, high-stakes operational work, not a nice-to-have tool. You will work with finance and accounting buyers who need substance, build conviction around AI agents for accounting teams, and help define how Truewind sells as the company scales. If you want a comfortable role with a fully built playbook, this probably is not it. If you want to work hard, learn fast, earn upside through performance, and help build the sales engine for a company at the front edge of AI and finance, we should talk.