Sales Development Representative
Upside, Chicago, IL, United States
Meet Upside
We created Upside to transform brick‑and‑mortem 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‑mortem 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‑mortem 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, DC, 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.
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 accommodations@upside.com. 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.
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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, DC, 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.
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 accommodations@upside.com. 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.
#J-18808-Ljbffr