Sales Development Representative

About the Role

Paystand is hiring a Sales Development Representative to prospect and generate leads for our Account Executives — showcasing Paystand as the most cost-effective and efficient way for enterprise businesses to facilitate payments and manage their Accounts Receivable (AR) process.

You'll be the first point of contact at Paystand — getting leads excited, handling objections, and moving them through the pipeline. But this isn't just about working harder than the next SDR. We're looking for someone who builds systems that outwork everyone else. At Paystand, a great SDR doesn't just execute the playbook — they help rewrite it.

What You'll Do

• Prospect and generate qualified leads that align with Paystand's Ideal Customer Profile (ICP) for B2B enterprise accounts
• Collaborate closely with Account Executives and your SDR Manager to develop targeted messaging, talk-tracks, and outreach strategies
• Build and run outbound systems — not just campaigns — leveraging AI tools, automation, and data enrichment to generate pipeline at scale
• Identify buying signals automatically and design workflows that prioritize the highest-intent prospects
• Execute high-volume outbound activity via cold calling, email sequences, and social selling — with a system-first mindset
• Qualify new opportunities and navigate complex objections with confidence
• Use data-driven approaches to track, iterate, and continuously improve your outreach performance
• Meet — and exceed — quota while contributing to team-wide pipeline growth objectives

What We're Looking For

• Ambitious and self-motivated with comfort in a quota-carrying environment (prior sales experience is a bonus, not a requirement)
• AI-native mindset: you think about how to automate, scale, and systematize — not just how to work harder
• Demonstrated curiosity or hands-on experience with AI tools — whether building agents, using LLMs for research, or automating outreach workflows
• Ability to thrive in a fast-paced, high-growth, rapidly changing environment
• Willingness to lead high-volume outbound activity daily while maintaining energy and a positive attitude
• Excellent interpersonal, communication, and presentation skills
• Sharp attention to detail with a data-driven approach to self-improvement

AI & Leverage — What Sets You Apart

We're an AI-first company, and this role reflects that. We're not just looking for someone who can outwork the competition — we're looking for someone who can out-think and out-build them. Standout candidates will be able to speak to:

• How they would use AI to research and prospect 500 companies at scale
• A workflow, agent, or automation they've built (or would build) to multiply outreach output
• How they identify and act on buying signals automatically — not manually
• Their philosophy on building systems that perform even when they're not at their desk
• Specific AI tools they've experimented with and what they learned

Note: You don't need to be an engineer. You need to be someone who thinks like a builder.

Bonus Areas of Expertise

• Prior experience using a CRM & Sales Engagement Platform (e.g., Salesforce, Outreach, Salesloft)
• Hands-on experience with AI tools such as Clay, ChatGPT, Perplexity, or custom GPT/agent workflows
• Experience with data enrichment tools and LinkedIn Sales Navigator
• A track record of quota attainment or relevant sales experience
• Knowledge of Finance, Accounts Receivable, ERP Systems, or B2B SaaS sales

Why Paystand

This is a ground-floor opportunity on a growing sales team where your impact is measurable and your growth is real. We invest in people who want to reinvent how the job gets done — not just execute the same playbook as everyone else. If you want to build the future of B2B payments and grow your career in sales with the leverage of AI behind you, we want to hear from you.

Benefits:

• Compensation: $70,000 - $85,000 OTE (Non-exempt role paid hourly + commissions).
• Enjoy generous PTO and sick leave, because we believe in balance.
• 401(k) retirement plan with employer matching.
• We've got your health covered with comprehensive health dental and vision insurance plans.
• Fuel your days with free snacks and paid lunches in the office.
• Unlock stock options and own a piece of our success!
• Work with the best tools and equipment, setting you up to thrive.
• And the best part? Endless growth opportunities await you as we rapidly expand!