Sales Development Representative

SideNote.ai is a real-time communications governance platform that helps enterprises monitor workplace communication and detect problematic language. The Enterprise Sales Development Representative will generate enterprise sales opportunities by managing multi-touch outreach, engaging multiple stakeholders, qualifying prospects, booking discovery calls and demos, and developing expertise in employment law risk and HR compliance.

Responsibilities:

• Own structured, multi-touch cadences (phone + email + LinkedIn) 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

Requirements:

• • 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 HubSpot and a modern sales engagement stack