Upside

Marketing Operations

• Own the day-to-day administration, configuration, and optimization of Upside's marketing and SDR technology stack including: HubSpot, Outreach, Gong, ZoomInfo, Clay and adjacent tools.
• Serve as the primary systems partner for B2B Marketing and Sales Development, translating business requirements into scalable, well-documented platform configurations and workflows.
• Collaborate closely with the Salesforce Administration team to ensure seamless data flow, data model alignment, and reliable lead / contact routing between marketing systems and our CRM.
• Deliver production support by troubleshooting, prioritizing, and resolving issues raised by end users across marketing and SDR platforms, with a focus on root-cause resolution.
• Support program management for the marketing systems domain, including roadmap definition, backlog grooming, and delivery planning in partnership with business stakeholders.
• Support Upside's GTM AI adoption initiatives by identifying automation and AI augmentation opportunities within the marketing and SDR stack.
• Design and implement automation across the stack to reduce manual work, improve conversion rates, and support campaign execution at scale.
• Stay current on platform releases, new features, and emerging tools and proactively identifying opportunities to extract more value from existing investments and evaluating new tools as needs arise.
• Partner with Data Governance to operationalize data management standards, ensure compliance, and maintain a clean, trustworthy system of record.
• Manage vendor relationships to ensure Upside is maximizing ROI on platform investments and getting appropriate levels of support.

Senior Marketing Systems Manager

Payroll

• Manage and execute end-to-end semi-monthly payroll for 250+ U.S.-based employees across 30 states, ensuring accuracy in earnings, deductions, and taxes
• Handle regular and off-cycle payroll, including bonuses, equity, terminations, and other complex scenarios
• Own payroll tax compliance across federal, state, and local jurisdictions, including filings, reconciliations, audits, and resolution of tax notices
• Lead 401(k) audits and workers’ compensation filings
• Oversee quarterly and annual filings (e.g., 941s, FUTA, SUTA) and ensure timely reporting
• Partner with Finance on payroll accounting, accruals, journal entries, and close processes
• Maintain strong internal controls and documentation to support compliance and audit readiness
• Continuously improve payroll workflows, systems configuration, and data integrity
• Support and resolve complex payroll questions and issues
• Oversee the administration of health, retirement, leave, and ancillary benefit programs
• Lead Open Enrollment planning and execution, including vendor coordination and employee communications
• Ensure compliance with ERISA, ACA, COBRA, HIPAA, and applicable regulations
• Manage relationships with brokers and third-party administrators to maintain high service quality
• Monitor regulatory changes and implement updates as needed
• Continuously improve benefits workflows, system configuration, and data integrity
• Support and resolve complex benefits-related questions

Payroll and Benefits Lead

Engineering Manager

• Co-Create and drive the vision and roadmap for Upside’s data platform, shaping the strategy for data across Upside in alignment with company goals.
• Ensure our data stack, which includes Snowflake, dbt, and Dagster, enables scalable, self-service, and trustworthy workflows for reporting, analytics, and experimentation.
• Drive strategic data platform initiatives that improve reproducibility, reliability, and analytics enablement—such as modernizing legacy infrastructure, implementing tools like Snowflake Semantic Views and Cortex, and transforming 3rd-party data into trusted, production-ready assets.
• Define and track key platform health metrics, including pipeline reliability, SLA adherence, cost-efficiency, and model deployment readiness.
• Partner cross-functionally with Product, Engineering, Data Science, and GTM stakeholders to ensure the data platform supports current and emerging business needs.
• Represent Analytics Engineering in company-wide planning forums, technical councils, and cross-functional working groups.

Engineering Manager – Data Engineering

Systems Engineer

• Act as an administrator and architect for our web-based FP&A tool, designing multi-dimensional models that reflect our complex business drivers.
• Design and maintain automated ETL workflows between our ERP, CRM (Salesforce), and the FP&A platform to ensure "one source of truth" for all financial and operational data.
• Partner with our Data Engineering team to integrate machine learning-based revenue forecasts directly into our rolling financial plans.
• Eliminate manual spreadsheet "shadow systems" by building self-service dashboards and automated variance reporting for department heads.
• Proactively identify data integrity issues and optimize our Chart of Accounts (COA) mapping to improve the granularity of our unit economic reporting.

FP&A Systems Analyst

Full-stack Engineer

• Build high-impact applications and tools that accelerate Upside's go-to-market motion. Develop AI-native tools that help revenue teams manage pipeline, analyze performance, and automate operational workflows
• Partner deeply with cross-functional teams to understand business workflows and translate them into scalable technical solutions. Prototype, iterate, ship and maintain
• Own systems end-to-end. Design across the stack from front-end interfaces to backend services, automation pipelines, and AI orchestration layers
• Continuously improve the systems you build. Identify opportunities to increase reliability, performance, and scalability while reducing manual work for the teams that rely on these tools
• Strong understanding of prompt design and prompt engineering as a core part of building AI-powered systems, including structuring prompts, evaluating outputs, and iterating on prompt strategies to improve reliability and quality
• Drive quality through clear communication and documentation. Record design decisions, communicate tradeoffs, and ensure others can build upon your work
• Deliver reliably and transparently. Set clear expectations, communicate progress, and keep stakeholders aligned as priorities evolve

Staff Full Stack Engineer, GTM Systems

Product Marketing

• Drive Early Engagement & Activation: Develop and refine strategies to ensure customers quickly realize the value of our platform, increasing adoption and reducing time to activation.
• Support Expansion & Upsell Efforts: Create compelling materials and messaging that help Account Managers identify and execute expansion opportunities within existing accounts.
• Develop QBR & Account Review Positioning: Develop frameworks, templates, and content that improve the effectiveness of Quarterly Business Reviews (QBRs) and Annual Reviews (ARs), helping our teams articulate impact and long-term value.
• Develop Playbooks & Scalable Strategies: Build repeatable, scalable playbooks that empower the Account team to improve customer engagement, retention, and advocacy.
• Boost Referral & Advocacy Programs: Collaborate with Customer Success and Marketing to increase referrals, testimonials, and case study participation from happy customers.
• Identify & Address Churn Risks: Analyze customer data and feedback to proactively identify churn risks and implement targeted initiatives that improve retention.
• Represent the Product in Customer Meetings: Join key account discussions to support messaging, address product questions, and gather insights to refine positioning and customer education.
• Close the Loop with Product & GTM Teams: Actively contribute to the product feedback loop, ensuring customer insights shape product development and go-to-market strategies.

Principal Product Marketing Manager, Product Commercialization

Account Executive

• Identify and close new growth opportunities with large restaurant franchisees across the U.S.
• Develop a knowledge of prospective clients in order to tailor the Upside sales approach for maximum efficiency
• Implement a strategy to gain access to prospective clients to better compress the sales cycle
• Collaborate with internal Upside teams, including Product Marketing and Operations, to ensure a consistent and positive experience for new merchants
• Maintain deep understanding of Upside’s unique features and demonstrate their value to new customers
• Work in a fast-paced, evolving environment, while delivering elite results and continuously challenging yourself

Senior Account Executive

Account Manager

• Build and operationalize a scalable, one-to-many enablement strategy to accelerate merchant adoption of Upside’s Pay and marketplace products.
• Drive meaningful merchant growth through channel and referral partnerships across POS platforms, processors, hardware providers, SaaS companies, and fintech partners.
• Explore and execute marketplace and embedded distribution opportunities within SaaS ecosystems while maintaining strong unit economics.
• Act as the voice of the merchant in all partner relationships.
• Develop and execute a long-term partnership strategy aligned with Upside’s growth goals and vertical expansion.
• Lead cross-functional deal teams to build operational plans for each partnership and manage execution end-to-end.
• Establish performance metrics, monitor results, and ensure on-time, in-full delivery of contractual commitments.
• Champion prioritization of initiatives that maximize holistic impact while balancing product and engineering investment.
• Structure and negotiate multi-year commercial agreements across fintech, merchant processing, and retail technology ecosystems.
• Partner with Legal, Finance, Product, and Operations to deliver scalable, durable agreements that unlock long-term value.
• Serve as a senior external ambassador for Upside at industry forums, partner events, and merchant coalitions.
• Position Upside as the leading incremental-profit platform for brick-and-mortar businesses.

Senior Director, Retailer and Channel Partnerships

Data Analyst

• Act as a go-to-market analytics generalist, gaining exposure to overall go-to-market strategy and insights generation by working directly on projects for Planning & Analytics team members and GTM leadership.
• Support the forecasting process and its effectiveness across Sales and Accounts - leverage existing forecasting models to deliver weekly revenue and bookings forecasts in a clear, repeatable format.
• Own analytical support and act as the “first line of defense” for reporting needs for various functional areas, such as Partnerships, SMB and Enablement.
• Maintain, update, and develop dashboards in Looker and Salesforce to facilitate the day-to-day activities of customer-facing teams. For example, tracking our meeting-to-opportunity conversion ratio and establishing benchmarks for weekly meeting volume per salesperson.
• Use data analysis and storytelling to generate actionable insights for our customer-facing teams. Develop relationships with customer-facing team members to better anticipate their needs.
• Provide pre-sales account performance estimates for the Restaurant and Grocery verticals, managing requests in a timely and accurate manner.
• Analyze funnel performance, sales productivity, and pipeline health to identify opportunities to improve revenue organization efficiency and inform strategic decisions.
• Contribute to the evolution of our forecasting models, to increase their ease of use, sophistication, and accuracy.
• Support annual and quarterly planning efforts for the RGTM org as needed, especially providing reports that help sales and accounts managers design their books of business equitably.
• Partner with the Rev Ops team to design processes and data capture that deliver the analytics needed with Salesforce and in other BI tools, deriving from Salesforce data.
• Contribute to the direction of the Revenue Analytics function by helping define core metrics, analytical priorities, and scalable reporting frameworks.

Senior Revenue Analytics Manager

Technical Recruiter

• 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.

Lead Technical Recruiter

Sales Development Rep

• 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
• 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

Sales Development Representative

• Scope and lead data analysis to help our merchant partners understand the impact of Upside to their business, how we drive incremental profit, and answer their broader business questions
• Interface directly with our merchant partners to deeply understand their business and build strong analytics relationships
• Manage and lead analysis projects to identify opportunities to improve our product, merchant acquisition strategy, and optimization of our two-sided marketplace
• Scale meaningful analyses and information across merchants via scripting, sales enablement, and business intelligence tools
• Partner closely with Product Marketing to define the ideal solution for articulating the sophistication of our technology to our partners
• Pioneer new data and analysis strategies as Upside expands our presence in growing verticals

Senior Merchant Analytics Manager

Merchant Analytics Manager

Marketing

• Own end-to-end reporting and insights for the consumer marketing funnel across acquisition and retention: media efficiency, on-site/app conversion, activation, engagement, and long-term retention/LTV.
• Independently scope, prioritize, and drive end-to-end analytics projects in partnership with Marketing, from problem framing through recommendation and follow-through.
• Build and maintain clear, reliable metrics frameworks for channel, campaign, ad-set and audience performance (e.g., CAC, ROAS, LTV:CAC, conversion rates, retention), ensuring a single source of truth that provides fast, reliable reads on channel mix, creative, audience, and offer performance across all channels.
• Serve as the primary analytics partner for Consumer Marketing—collaborating with acquisition, brand, and lifecycle teams to translate business questions into analysis, insights and experimentation plans.
• Proactively surface insights on creative, audience, and funnel performance, and bring forward recommendations on where to double down, fix, or test next—going well beyond pull-and-paste reporting.
• Partner with the senior team members to interpret MMM, attribution, and incrementality outputs, and translate them into channel and funnel-level recommendations and recommend future experiments.
• Partner with lifecycle and product marketing to test and iterate on messaging, sequencing, and surface areas (email, push, in-app, onsite) to improve activation, engagement, and reactivation over time.
• Diagnose pockets of under-performance across all areas of consumer growth and identify experiments and optimization levers such as new audience strategies, creative, offer structures, or on-site/app conversion opportunities to improve consumer performance.
• Develop automated reporting and alerting to flag significant shifts in performance and funnel health, helping the team respond quickly to risks and opportunities.
• Partner with Finance and Consumer team members to align on forecasting, pacing, and performance targets, tying media and lifecycle performance back to profitable, scaled growth and IRR.
• Support deeper analytics projects (e.g., cohort and retention analyses, audience segmentation, attribution/measurement deep-dives) in partnership with senior analytics leaders, helping connect detailed findings into clear, executive-ready narratives.
• Collaborate with Analytics Engineering, Product, and MarTech partners to improve upstream data assets that power marketing reporting and experimentation (e.g., event tracking, attribution signals, identity stitching, channel taxonomies).

Senior Marketing Systems Manager

Payroll and Benefits Lead

Engineering Manager – Data Engineering

FP&A Systems Analyst

FP&A Systems Analyst

Staff Full Stack Engineer, GTM Systems

Principal Product Marketing Manager, Product Commercialization

Senior Account Executive

Senior Director, Retailer and Channel Partnerships

Senior Revenue Analytics Manager

Lead Technical Recruiter

Sales Development Representative

Senior Merchant Analytics Manager

Merchant Analytics Manager

Senior Analyst, Marketing Analytics