Account Executive

Account Executive

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.

Truewind is a YC company backed by a $13M Series A co-led by Rho Capital and Thomson Reuters Ventures, with Pathlight Ventures, Fin Capital, and Y Combinator participating. We have raised $17M+ to build AI agents for accounting teams.

About The Role

We are hiring an Account Executive to help build the sales engine for one of the most important shifts in finance: AI agents taking on the manual accounting work that slows teams down every month.

This is not a seat inside a mature sales machine. You will be close to the founders, close to product decisions, close to customers, and close to the number. You will work inbound demand, generate your own pipeline, run discovery, manage evaluations, build business cases, and close deals with controllers, CFOs, heads of finance, and accounting firm leaders.

The work will not always be neatly packaged. We are still early, and the way we sell will keep changing as we learn. Your calls, objections, follow-up, win/loss feedback, and customer conversations will help shape our messaging, qualification standards, sales process, account strategy, and eventually the sales team itself.

This role is for someone who wants more than a quota-carrying AE seat. You want to grow into sales leadership over time. You want to help build the playbook, not just run it. You want upside tied to your own performance. You want to sell into a market that is being reshaped by AI, and you want your work to matter in how that future gets built.

You should expect to work extremely hard here. The bar is high, the company moves fast, and the role will demand ownership, pace, and judgment. For the right person, the tradeoff is equally clear: meaningful responsibility early, direct influence on the GTM motion, performance-based cash upside, equity, and the chance to grow with a company building in a category that is still being defined.

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.
• Ability 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.
• Comfort using AI and modern sales tools to research accounts, personalize outreach, move quickly, and stay organized.
• 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 is helpful, but not required.

If you do not meet every qualification but believe you can succeed in this role, we still encourage you to apply.

What We Offer

• $200,000-$275,000 OTE target cash compensation, including base salary and commission. Commission is uncapped 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.

Actual compensation will depend on experience, qualifications, location, and scope of the role. Where required by applicable law, Truewind will provide additional pay-range and commission-plan details for the relevant jurisdiction.

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.

To apply, email your resume or LinkedIn profile to with the subject line: Account Executive - [Your Name].

Truewind is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other legally protected characteristic.