Sales Development Representative

About Truewind

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, revenue schedules, rollforwards, reconciliations, and review-ready workpapers.

Truewind is a Y Combinator 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, bringing total funding to $17M+.

About The Role

We are hiring a Sales Development Representative to create the conversations that become pipeline. You will be the first person many controllers, CFOs, heads of finance, and accounting firm leaders talk to at Truewind, and your job is to earn their attention and book meetings worth taking.

This is an outbound-first role in an early sales org. You will own your target accounts, your activity, and your number, and you will work alongside sales and marketing to figure out what messaging actually lands in a market that is still forming its opinion about AI in accounting.

We expect you to use AI as leverage. The best SDRs here research accounts, draft and personalize outreach, and prioritize their day with AI tools so their time goes to high-value conversations instead of manual busywork.

This role is open to any experience level, including new graduates. What matters is work ethic, judgment, and how quickly you improve.

What You Will Do

• Prospect and book net-new meetings with target accounts through email, phone calls, and LinkedIn.
• Research accounts and personalize outreach at scale, using AI tools to work efficiently rather than writing every touch from scratch.
• Run and iterate on multi-step outbound cadences, tracking what is working and adjusting messaging and targeting accordingly.
• Work closely with sales and marketing to sharpen targeting, messaging, and positioning based on what is actually landing.
• Hand off qualified meetings with clear context on the account, the pain, and why now.
• Keep clean CRM hygiene so activity, account history, and pipeline contribution stay measurable.

What We Are Looking For

• Strong work ethic. You show up consistently, put in the reps every day, and hit activity goals without needing to be micromanaged.
• Ability to leverage AI. You use AI tools to research accounts, draft and personalize outreach, and prioritize your day.
• Problem solver. When a cadence, channel, or message is not working, you dig into why, test a fix, and adjust rather than waiting to be told what to change.
• Clear, confident written and verbal communication.
• Comfortable with rejection and high call and email volume, and motivated by hitting a number.
• Authorized to work in the United States.

Prior SDR, BDR, or inside sales experience is helpful but not required, and interest in accounting or finance is a plus. If you do not meet every qualification but believe you can succeed in this role, we still encourage you to apply.

What We Offer

• $70,000-$100,000 target cash compensation, including base salary and variable pay.
• Equity in a fast-growing startup.
• The option to work from our San Francisco office or remotely within the US.
• Direct exposure to founders, sales leadership, customer conversations, and the accounting workflows our product automates.
• A clear growth path toward a closing role for someone who performs.
• Unlimited PTO, medical and dental insurance, and complimentary meals and commuter benefits for in-office work.

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

How to Apply

Email your resume or LinkedIn profile to hiring@trytruewind.com with the subject line: Sales Development Representative - [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.