Lead Technical Recruiter

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:

You’ll help shape the teams building Upside’s product by leading full-lifecycle recruiting for B2C technology roles. By combining deep knowledge of the tech talent market with strong relationship-building and thoughtful sourcing strategies, you’ll identify and attract exceptional candidates. Your work will help Upside scale quickly while maintaining a high bar for talent in an evolving and competitive hiring landscape.

What You’ll Do:

• Lead full-lifecycle recruiting end-to-end. Guide role launch, sourcing, interview coordination, debrief discussions, offer approvals, and closing across multiple job families and levels.

• Create clarity from the start. Facilitate thoughtful intake conversations, align on success profiles and leveling, and ensure interview plans and evaluation criteria are clear, consistent, and grounded in what the team truly needs.

• Build and sustain strong pipelines. Execute multi-channel sourcing strategies and actively manage funnel health, pacing, and offer acceptance rates. Adjust quickly when signals are mixed or priorities evolve.

• Maintain a disciplined, candidate-centered process. Keep stages progressing, ensure timely feedback, schedule pre-briefs and debriefs, and uphold strong documentation and ATS hygiene while preserving a positive candidate experience.

• Design scalable recruiting systems. Develop templates, playbooks, scorecard standards, and interviewer enablement resources that make hiring more consistent and easier to execute across teams.

• Represent Upside with warmth and professionalism. Communicate clearly, follow through reliably, and create a candidate experience that reflects our values and standards.

Competencies You'll Need:

• 10+ years of full-lifecycle recruiting experience across multiple technical functions, including Engineering, Product, and Data/Analytics, in fast-paced, high-growth environments.

• Consistent delivery with measurable impact. Track record of improving speed, funnel conversion, slate quality, and offer acceptance through strong execution and thoughtful systems improvements.

• Strong sourcing expertise. Experience building pipelines across channels, engaging passive talent, and tailoring outreach and value propositions to different audiences.

• Effective stakeholder partnership. Trusted collaborator to Hiring Managers and cross-functional leaders, able to create clarity, uphold standards, and support timely decisions.

• Operational discipline. Skilled at running structured workflows from launch through close, maintaining timelines, and ensuring strong documentation and ATS practices.

• Sound judgment. Balances structure and flexibility, escalates thoughtfully, and uses both data and experience to guide decisions.

• Clear communication and influence. Communicates effectively in writing and conversation, manages candidates with care, and supports leaders through tradeoffs and closing strategy.

• Collaborative and team-oriented. Builds trust quickly, shares context openly, offers support proactively, and contributes to a positive, accountable team environment where everyone can do their best work.

Location:
This hybrid role is based in our DC office. In-office attendance is required on Monday, Tuesday, and Thursday, and may increase based on project-based needs and changes to Upside’s in-office policy over time.

Compensation:
The U.S. base salary range for this full-time position is $140,000 - $160,000 + 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.

#LI-Hybrid
#LI-LR1

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.