Sales Development Representative

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

The Impact You’ll Make:

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. This is an ideal role for someone who is adaptable, curious, and excited to experiment with new approaches to outbound and AI-assisted selling.

• 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

What You Should Have:

• 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

Nice to Have:

• Experience working with CRM tools such as Salesforce or HubSpot

• Exposure to AI-powered sales or marketing tools

Location:

This hybrid role is required to work onsite at our NYC, Chicago or Austin office three days/week.

Compensation:

The U.S. base salary range for this full-time position is $67,000 - $80,000 + commission + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.

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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!

Diversity and Inclusion:

Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

If there's anything we can do to support a disability or special need during your application or interview process, please email [email protected].

This email is for accessibility accommodations only, it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.