Sales Development Representative

Crosscut; Santa Cruz (CA); On-site; USD 70,000 - 85,000; Full time

Benefits offered by this job

Health insurance

401(k) plan

Paid lunches

Stock options

Growth opportunities

PTO & sick leave

Job summary

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. You’ll be the first point of contact, excited to engage leads, overcome objections, and move them through the pipeline.

As an SDR, you’ll build systems that outwork others, leveraging AI and automation to scale outreach, identify

Qualifications

• 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

Responsibilities

• Prospect and generate qualified leads that align with Paystand’s 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

Skills

Quota carrying mindset

AI-native mindset

Communication skills

Data-driven approach

Tools

Salesforce

Outreach / Salesloft

LinkedIn Sales Navigator

AI automation tools

Job description

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

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

Benefits

• Compensation: $70,000 - $85,000 OTE (Non‑exempt role paid hourly + commissions)
• Generous PTO and sick leave
• 401(k) retirement plan with employer matching
• Comprehensive health, dental, and vision insurance
• Free snacks and paid lunches in the office
• Stock options
• Access to top‑tier tools and equipment
• Endless growth opportunities as we expand

Most of our roles are onsite. Positions that are eligible for remote or hybrid work arrangements will be clearly indicated in the job posting.

For roles based in Mexico, only resumes submitted in English will be considered.

We celebrate the belief that diversity in backgrounds and thoughts fuels better problem‑solving and fosters more creative thinking. Our commitment to adding new perspectives to the team reflects our dedication to innovation and inclusivity.