Upside · 3 hours ago
Senior Customer Service Systems Manager
Washington, DC
Full-time
Hybrid
Senior Level, Lead/Staff
$130K/yr - $150K/yr
8+ years expUpside is a company transforming brick-and-mortar commerce through technology that enhances customer value and business profitability. The Senior Customer Service Systems Manager will design and optimize the Consumer Operations technology stack, focusing on AI-enabled solutions to improve customer experience and reduce operational costs.
AppsBusiness DevelopmentData ManagementMarketplaceMobile AppsRetailRetail Technology
Responsibilities
Be a thought leader/owner in the development and maintenance of reporting that surfaces Voice of the Customer (VOC) insights across Consumer Operations channels
Build scalable, automated reports and dashboards that highlight customer sentiment, recurring issues, friction points, and experience trends
Partner with Consumer Operations, Product, and Marketing to ensure VOC insights are actionable and regularly incorporated into decision-making
Use data to connect customer feedback to operational drivers and improvement opportunities
Own the operational effectiveness of core Consumer Operations systems, including Zendesk, Retool, Slack integrations, and related tooling
Ensure systems are stable, scalable, well-integrated, and optimized for frontline and back-office teams
Act as the technical point of accountability for system enhancements, integrations, and issue resolution
Proactively identify gaps or inefficiencies in the current tech stack and propose durable solutions
Research, evaluate, and build AI and automation opportunities to enhance the Consumer Operations technology stack
Partner directly with Product and Engineering to design and build AI-powered tools that: Reduce Consumer Operations OpEx, Improve agent efficiency and response quality, Enable smarter routing, triage, and decision support
Lead proof-of-concept development, pilots, and scaled rollouts of AI-enabled solutions
Ensure AI implementations meet standards for accuracy, security, customer trust, and regulatory compliance
Qualification
Required
8+ years of experience in a fast-paced, high-growth environment (fintech or similarly regulated industry preferred)
Strong technical background with hands-on experience in: SQL / MySQL
Strong technical background with hands-on experience in: Python/Java or similar backend programming languages
Demonstrated experience building operational reporting and dashboards to support Voice of the Customer (VOC) or customer experience initiatives
Experience working with modern analytics and data platforms such as Snowflake, Hex, Looker, or similar tools
Demonstrated experience working with AI and LLM-based systems, including: Model integration and orchestration
Demonstrated experience working with AI and LLM-based systems, including: AI-assisted workflows or automation
Demonstrated experience working with AI and LLM-based systems, including: Evaluation of model performance and quality
Experience designing and supporting complex system integrations
Proven ability to work cross-functionally with Product, Engineering, and Operations
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!
Company
Upside
Upside is a two-sided marketplace focused on driving value to all points of brick and mortar commerce.
201-500 employees
Funding
Current Stage
Late StageTotal Funding
$165MKey Investors
General Catalyst
2022-04-26Series D· $65M
2022-04-26Debt Financing· $100M
2020-08-31Series C
Leadership Team
Alex Kinnier
Co-founder & CEO
Jan Rubio
Co-founder
Recent News
2025-07-02
Progressive Grocer
2025-02-18
Company data provided by crunchbase