Sales Development Representative , Upside

• This is an ideal role for someone who is adaptable, curious, and excited to experiment with new approaches to outbound and AI-assisted selling
• 3+ years of experience in an SDR, BDR, or customer-facing growth role (B2B preferred)
• Strong written and verbal communication skills
• Comfort testing new tools, processes, and messaging and learning quickly from results
• Interest in working with AI-powered tools and understanding how to train and operate them (no technical background required)
• Highly organized with strong attention to detail and follow-through
• Collaborative mindset and ability to work cross-functionally with Sales, Marketing, and Growth teams

Desirable

• Upside is looking for a Sales Development Representative (SDR) to drive top-of-funnel growth and help shape the future of outbound sales
• This role will be responsible for generating a qualified pipeline through outbound prospecting, inbound lead follow-up, and event-based and ABM outreach
• This role will also be pivotal in testing, training, and operating an AI-powered outreach
• You will partner closely with Sales, Retailer Growth, Product Marketing, and Data & Growth teams to refine messaging, improve targeting, and ensure consistent, high-quality engagement with prospective merchants
• Generate qualified meetings through proactive outbound prospecting across priority verticals
• Own pre-event meeting outreach and post-event follow-up to maximize event-driven pipeline
• Respond quickly to inbound leads and qualify opportunities for the sales team
• Draft, test, and iterate outbound messaging and sequences in collaboration with Sales, DG, and PMM
• Maintain accurate CRM data and strong lead hygiene to ensure performance visibility
• Collaborate with Sales and Retailer Growth on lead nurture strategies and campaign follow-up
• AI Enablement & Experimentation:
• Help test, train, and operate an AI SDR agent alongside human-led outreach
• Experiment with messaging, sequencing, cadence, and channels to understand what drives performance
• Interest in testing new outbound channels beyond email. For example, LinkedIn outreach, direct mail, custom landing page, ad creation, and more
• Review and provide feedback on AI-generated outreach to ensure quality, relevance, and brand alignment
• Act as a human-in-the-loop, helping define best practices for AI-assisted outbound at Upside
• Surface insights around audience targeting, value proposition clarity, and outreach effectiveness