Sales Development Representative

About the job

Side Note.ai is a real-time communications governance platform that helps enterprises monitor workplace communication and detect problematic language in real time. The platform provides in-the-moment coaching so employees can align their messages with legal, ethical, cultural, and policy guidelines before sending them. Side Note.ai serves HR, Legal, Compliance, Security, and Privacy teams by reducing communication-driven risk, reinforcing professional conduct, and protecting sensitive data.

The company’s core models cover Employment & Labor, Culture & Safety, Ethics & Corporate Policy, and Data Security & Privacy, with specialized options for highly regulated industries. By combining real-time intervention with business intelligence, Side Note.ai enables organizations to shift from reactive damage control to proactive communication governance.

We're building out our sales development team and hiring five Enterprise SDRs to fuel a high-conviction, multi-stakeholder enterprise motion.

• Own structured, multi-touch cadences (phone + email + Linked In) that nurture warm leads over a 30–90 day enterprise cycle
• Multi-thread into Fortune 500 accounts — engaging the CHRO, VP HR Compliance, and General Counsel in parallel, because enterprise deals rarely close through a single champion
• Qualify and book discovery calls and demos for our Account Executives, and run clean handoffs
• Work a re-engagement queue, escalating prospects who engage with our content (webinars, case studies, regulatory updates) into active conversations
• Become genuinely fluent in our buyers’ world: employment law risk, HR compliance, and the cost of a single bad communication

• 1–2+ years as an SDR/BDR in enterprise B2B SaaS — named-account, considered-purchase environments, not high-velocity SMB or self-serve
• A genuinely strong writer. We sell a communications-quality product; your outbound has to model it
• Comfortable navigating long sales cycles and multiple stakeholders without losing momentum
• Curious about a regulated, legal-adjacent domain and motivated to master it
• Organized, coachable, and persistent

• Experience selling into HR, Legal, Compliance, or Security buyers
• Background in HR tech, legal tech, GRC, or compliance/risk software
• Familiarity with Hub Spot and a modern sales engagement stack

• Base: 50k - 70k
• OTE: 90k - 110k
• Company-paid benefits: health, vision, dental
• A clear path to AE, real coaching, and a product where the demo genuinely makes buyers lean in

Side Note.ai is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, veteran status, or any other protected characteristic under applicable law.