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Mid LevelFull-timeAI
Salary Range
$68,000 - $92,000 /year
This salary is estimated based on similar roles. The actual salary may vary.
About the Role
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.
Key Responsibilities
- →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
- →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
Requirements
- ✓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
Benefits
- ★Medical, dental, and vision coverage starting on Day 1
- ★Equity (ISOs)
- ★401(k) program
- ★Family planning programs + paid parental leave
- ★Physical fitness and wellness memberships
- ★Emotional and mental health support programs
- ★Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break
- ★Flexible work environment
- ★Lunch reimbursement for in-office employees
- ★Employee Resource Groups
- ★Learning and Development stipend
- ★Transparent culture
- ★Amazing mission!
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