About the Role

We are seeking a seasoned SRE / DevOps Manager to lead our reliability and operations engineering team. You will be responsible for ensuring the scalability, security, and performance of our infrastructure while fostering a culture of automation, ownership, and continuous improvement.

At Upshop, we believe that great businesses are built by great people. Our People function is at the heart of our company’s growth, ensuring we attract, develop, and retain A Players who drive our mission forward.

Our Values:

• Extremely Accountable
• Customer Obsessed
• Always Innovating
• Demand Excellence
• Biased for Action

Key Responsibilities

Team Leadership

• Manage and mentor a team of SRE and DevOps engineers.
• Drive hiring, onboarding, and professional development.
• Set clear goals and performance metrics.

Reliability & Incident Management

• Own system uptime, performance, and reliability.
• Lead incident response and root cause analysis.
• Define and monitor SLAs, SLOs, and SLIs.

Infrastructure & Automation

• Oversee cloud infrastructure (Azure).
• Implement Infrastructure as Code (IaC) using tools like Terraform or other similar tools
• Drive automation of CI/CD pipelines and operational tasks.
• Build and manage a DevSecOps process to connect CI/CD pipelines with AzureDevOps, Gitlab etc.

Monitoring & Observability

• Implement and maintain monitoring, alerting, and logging systems.
• Use tools like Datadog or other similar tools like Prometheus, Grafana, ELK stack.

Security & Compliance

• Ensure infrastructure security and compliance with industry standards.
• Collaborate with InfoSec teams on audits and vulnerability management.

Cross-functional Collaboration

• Work closely with software engineering, product, and QA teams.
• Advocate for DevOps and SRE best practices across the organization.

Qualifications

• 10+ years of experience in DevOps, SRE, or infrastructure engineering.
• 2+ years in a leadership or managerial role.
• 3+ years of expertise with Cloud platform deployments
• 3+ years of experience working with MongoDB and cosmosdb
• Strong experience with cloud platforms (AWS, GCP, Azure).
• Proficiency in scripting languages (Power shell scripting, Python, Bash, Go).
• Hands-on experience with Kubernetes, Docker, CI/CD tools.
• Excellent communication and leadership skills.

Preferred Qualifications

• Experience with compliance frameworks (SOC 2, ISO 27001).
• Familiarity with Agile and DevOps methodologies.
• Certifications in cloud technologies or DevOps practices.

Benefits/Perks

• Hybrid Opportunity
• Competitive salary
• Employer-matched 401(k) plan
• Attractive paid time off policy
• Career growth and development opportunities

Compensation Range: $150-$180k CAD

Contract (Fractional) Contracts Manager – SaaS (Upshop) 

Location: Miami
Type: Contract / Fractional (20–40 hours/week, flexible) 
Duration: 3–6 months (with potential to extend) 

About Upshop 

Upshop powers smarter store operations for retailers by combining data, AI, and execution workflows across fresh, center store, and inventory management. Our platform helps retailers reduce waste, optimize inventory, and improve profitability at scale. 

Role Overview 

We are looking for an experienced Contracts Manager (Contract/Fractional) to support our commercial team by managing and negotiating customer agreements. This role will focus on reviewing, redlining, and negotiating SaaS contracts, ensuring alignment with Upshop’s risk posture while enabling deal velocity. 

This is a high-impact, execution-oriented role ideal for someone who has operated in fast-paced SaaS environments and can work directly with Sales, Legal, and Finance stakeholders. 

Key Responsibilities 

Contract Review & Redlining  

• Review, draft, and negotiate customer agreements (MSAs, Order Forms, DPAs, SOWs) 
• Lead redline negotiations with customers and their legal teams 
• Balance risk mitigation with commercial pragmatism to avoid deal friction  

Deal Support  

• Partner closely with Sales to accelerate deal cycles and remove contract bottlenecks 
• Provide clear guidance on acceptable positions, fallback language, and trade-offs 
• Join customer calls when needed to resolve contractual issues in real time  

Standardization & Playbooks  

• Help refine and maintain contract templates and fallback positions 
• Build and document negotiation playbooks and clause libraries  
• Identify recurring negotiation themes and recommend structural improvements  

Risk Management  

• Ensure contracts align with company policies on liability, indemnification, data privacy, and SLAs 
• Escalate non-standard or high-risk terms appropriately  
• Collaborate with outside counsel as needed for complex issues  

Qualifications 

• 5+ years of experience in contracts management, legal ops, or commercial legal roles 
• Strong experience negotiating SaaS agreements (MSAs, DPAs, SLAs, enterprise deals) 
• Deep familiarity with key legal concepts:  
• Limitation of liability  
• Indemnification  
• Data privacy & security (GDPR/CCPA awareness)  
• Service levels & uptime commitments  
• Proven ability to negotiate directly with enterprise customers 
• Comfortable operating in a high-growth, fast-paced SaaS environment 
• Strong judgment with a pragmatic, business-oriented mindset 
• Excellent written and verbal communication skills  

Nice to Have 

• Experience in retail, grocery, supply chain, or store operations software 
• Background working with private equity-backed or growth-stage SaaS companies  
• Familiarity with tools like Ironclad, DocuSign CLM, or similar contract lifecycle platforms  

What Success Looks Like 

• Reduced contract cycle times and faster deal closure 
• Consistent, scalable approach to handling redlines  
• Improved alignment between Sales and Legal on deal strategy  
• Clear documentation of fallback positions and negotiation standards  

Why This Role 

• Immediate impact on revenue velocity and deal execution 
• High visibility with leadership across Sales, Finance, and Legal  
• Flexible structure with potential to evolve into a longer-term role  

About Upshop

Upshop is the foremost provider of a SaaS platform designed to streamline forecasting, ordering, production, and inventory optimization for food retailers and foodservice operators. Our unified platform simplifies and enhances daily workflows, enabling smarter, more connected operations across fresh production, inventory management, food safety, and ordering.

Trusted by over 450+ retailers and operators across 50,000+ locations globally, Upshop helps customers improve sales, reduce waste, increase operational efficiency, and advance food safety and sustainability—especially in complex, production-driven environments.

Role Overview

As an Account Executive focused on New Logo Acquisition for Non-Grocery Food Retailers, you will join Upshop’s Growth team with a singular mission: expanding Upshop into new food retail and foodservice segments. This role is dedicated to winning new customers across markets such as bakeries, central kitchens, butchers, commissaries, prepared-food operators, and specialty food retailers.

You will be responsible for building Upshop’s footprint in these segments from the ground up—identifying high-value prospects, educating operators on modern production and inventory optimization, and positioning Upshop as a strategic partner in their growth and efficiency initiatives. This is a true hunter role requiring a consultative sales approach, strong discovery skills, and an entrepreneurial mindset.

Responsibilities

• Own the full sales cycle from prospecting to close, with a primary focus on new logo acquisition in non-grocery food retail and foodservice segments
• Identify, qualify, and engage bakeries, central kitchens, butchers, commissaries, and specialty food operators with complex production and inventory needs
• Develop a deep understanding of customer workflows, production challenges, labor constraints, and waste drivers—and connect those needs to Upshop’s platform capabilities
• Execute a consultative sales approach, guiding prospects through discovery, solution alignment, and value articulation
• Build and manage a healthy pipeline through outbound prospecting, inbound leads, and strategic targeting
• Partner cross-functionally with Customer Success, Product, and Implementation teams to ensure smooth handoffs and realistic expectations
• Use Salesforce to manage pipeline, forecasting, activity tracking, and reporting
• Conduct competitive and market analysis to refine messaging and positioning in emerging food retail segments
• Contribute to go-to-market strategy, use-case development, and sales enablement as Upshop expands into new verticals

Qualifications

• Proven experience in B2B SaaS sales, ideally within retail technology, foodservice technology, or operations-focused software
• Demonstrated success in new logo acquisition and building pipeline in emerging or under-penetrated markets
• Experience selling into food production, fresh operations, or multi-site operators (bakeries, kitchens, specialty food, etc.) is strongly preferred
• Strong consultative selling skills with the ability to engage operational and executive stakeholders
• Comfortable navigating complex, multi-stakeholder sales cycles
• Proficiency with Salesforce CRM and modern sales methodologies
• Excellent communication, discovery, and presentation skills
• Bachelor’s degree or equivalent experience
• Willingness to travel 30–40% to meet with prospects and customers

Benefits/Perks

• Austin based
• Competitive salary
• Employer-matched 401(k) plan
• Attractive flexible time off policy
• Career growth and development opportunities

We need your passion, sales expertise, and entrepreneurial spirit to help us build the Upshop brand. 

Role Overview

The Director, Demand Generation owns the strategy, execution, and continuous improvement of Upshop’s global demand generation engine. This role is accountable for driving high-quality pipeline through scalable, measurable, and creative demand programs that support Upshop’s growth across grocery and convenience retail markets.

Reporting into the Growth organization, this leader partners closely with Product Marketing, Sales, Revenue Operations, Customer Success, and Partners to translate Upshop’s story into demand, convert interest into pipeline, and optimize performance across the full funnel.

Key Responsibilities

Demand Strategy & Execution

• Own Upshop’s end-to-end demand generation strategy, from awareness through MQL, SQL, and pipeline contribution
• Design, execute, and optimize multi-channel demand programs including digital, ABM, outbound support, events, and partner-led campaigns
• Move beyond templated campaigns—continuously test, iterate, and introduce new ideas when performance stalls
• Translate Upshop’s value proposition into persona-based, industry-specific demand motions

Pipeline & Performance Management

• Establish clear goals and reporting for MQLs, SQLs, pipeline contribution, and conversion rates
• Partner with Revenue Operations to ensure strong attribution, measurement, and visibility into demand performance
• Separate and manage demand goals for new customer acquisition and expansion within existing customers
• Use data and insights to prioritize investments and continuously improve ROI

Systems, Tools & Automation

• Own the demand tech stack and workflows, including marketing automation and CRM integrations
• Leverage tools such as HubSpot, paid media platforms, LinkedIn, and emerging/dark social channels to scale demand efficiently
• Build repeatable, automated programs that learn and improve over time

Cross-Functional Collaboration

• Partner closely with Product Marketing to activate messaging, positioning, and customer reference stories
• Align with Sales and Customer teams to ensure tight MQL/SQL definitions and smooth handoffs
• Collaborate with Partner and Alliances teams to drive partner-sourced and partner-influenced demand

Team Leadership & Growth

• Lead, mentor, and develop a growing demand generation team
• Establish clear priorities, expectations, and accountability across the team
• Build a high-performance culture that balances creativity, rigor, and ownership

Qualifications & Experience

• 8–12+ years of experience in demand generation, growth marketing, or marketing operations, with at least 3+ years in a leadership role
• Proven track record of building and scaling demand programs in B2B SaaS or technology environments
• Strong understanding of marketing automation, campaign architecture, and funnel analytics
• Experience supporting sales-led and ABM motions
• Comfortable operating in environments without heavy process or templates—able to create structure where needed
• Experience in retail, grocery, or multi-location industries is a plus (but not required)

What Success Looks Like

• A clear, scalable demand engine that consistently drives qualified pipeline
• Improved conversion rates and visibility across the funnel
• Strong alignment and trust with Sales, Product Marketing, and Revenue teams
• A motivated, high-performing demand generation team that continues to grow with the business

Why Upshop

Upshop is redefining how retailers operate by connecting demand, supply, and execution at scale. This role offers the opportunity to shape how Upshop takes its story to market, influence growth strategy, and build a demand organization designed for long-term impact—not just short-term campaigns.

Office Manager/Executive Assistant to CEO

Location: Miami, FL (Full-time, in-office) 
Role Type: Full-Time 

About Upshop 

Upshop powers smarter store operations for retailers by combining data, AI, and execution workflows across fresh, center store, and inventory management. Our platform enables retailers to reduce waste, optimize inventory, and improve profitability at scale. 

Role Overview 

Upshop is seeking a highly effective Executive Assistant to support the CEO and oversee day-to-day operations of our Miami office. 

This role requires sound judgment, strong prioritization skills, and the ability to operate with discretion in a fast-paced environment. The Executive Assistant will serve as a key partner to the CEO—optimizing time, driving follow-through, and ensuring seamless coordination across internal and external stakeholders—while also maintaining a high-functioning office environment for a growing team. 

Key Responsibilities 

Executive Support 

• Manage and prioritize the CEO’s calendar, ensuring alignment with business priorities  

• Coordinate travel, logistics, and meeting preparation  

• Prepare materials for leadership, board, and external meetings  

• Track and drive follow-up on key action items and initiatives  

• Serve as a point of coordination across stakeholders while maintaining strict confidentiality  

Office Operations 

• Oversee daily operations of the Miami office (~40 employees)  

• Manage vendors, facilities, and office services  

• Ensure a professional, efficient, and well-maintained work environment  

• Coordinate onsite meetings, events, and leadership visits  

• Support onboarding and in-office employee experience in partnership with HR  

• Manage office-related budgets and expenses  

Qualifications 

• 5+ years of experience supporting senior executives, preferably at the CEO level  

• Strong organizational, prioritization, and problem-solving skills  

• High level of professionalism, discretion, and attention to detail  

• Ability to operate independently and manage multiple priorities  

• Excellent communication and stakeholder management capabilities  

Preferred Experience 

• Experience in a high-growth SaaS or technology environment  

• Prior responsibility for office operations or workplace management  

What Success Looks Like 

• CEO time is optimized and aligned to highest priorities  

• Strong execution and follow-through across key initiatives  

• Miami office operates efficiently with minimal disruption  

• Employees and visitors experience a well-run, professional environment  

Why Join Upshop 

• Direct exposure to executive leadership  

• High-impact role with broad organizational visibility  

• Opportunity to help shape a growing office and team  

About Upshop: 

Upshop is the foremost provider of a SaaS platform designed to streamline forecasting, ordering, production, and inventory optimization processes for food retailers. Its unified platform simplifies and enhances associate tasks, promoting smarter and more interconnected operations across Fresh, Center, DSD, and eCommerce departments. With over 450+ retailers and 50,000+ stores relying on its mission-critical operations platform globally, customers have witnessed substantial enhancements in sales, shrinkage reduction, food safety, and sustainability throughout their stores.  

At Upshop, we believe that great businesses are built by great people. Our People function is at the heart of our company’s growth, ensuring we attract, develop, and retain A Players who drive our mission forward.  

Our Values:

• Extremely Accountable
• Customer Obsessed
• Always Innovating
• Demand Excellence
• Biased for Action

Data Engineering Manager

Role Overview

We are seeking an experienced Data Engineering Manager to lead the technical evolution of our Databricks Lakehouse. You will be responsible for the architecture, scaling, and reliability of our data products, ensuring that the platform provides high-quality, actionable data for retail and supply chain analytics. This is a leadership role that requires a balance of advanced systems design and hands-on operational rigor.

Key Responsibilities

🔹 Architecture & Platform Ownership

• Lakehouse Strategy: Own the end-to-end design and optimization of the Databricks Lakehouse architecture, leveraging Unity Catalog and Delta Lake for multi-tenant isolation.
• Scalable Ingestion: Drive multi-tenant ingestion strategies from Azure Table Storage, Cosmos DB, and APIs, focusing on watermark logic and idempotent pipelines.
• Framework Development: Lead the evolution of in-house PySpark-based ETL frameworks to support complex transformations and downstream consumption.

🔹 Operational Excellence & Data Observability

• Data Quality Validation: Implement comprehensive data validation frameworks and automated checks to ensure accuracy, completeness, and consistency across the Lakehouse.
• Observability & Monitoring: Drive the strategy for end-to-end data observability, using monitoring and alerting to proactively identify pipeline drifts or failures before they impact stakeholders.
• FinOps & Performance: Improve cost transparency through DBU tracking and compute profiling (Serverless vs. Classic); drive performance tuning via clustering and partitioning strategies.

🔹 DevOps & Technical Governance

• Deployment Integrity: Oversee CI/CD pipelines and Databricks Asset Bundles (DABs) to maintain parity between UAT and Production environments.
• Governance Standards: Implement version control, rollback strategies, and deployment governance to ensure a stable and auditable production environment.

🔹 Cross-Functional Leadership

• Strategic Partner: Partner with BI, Data Science, and Product teams to bridge business requirements into scalable, production-grade data solutions.
• Team Growth: Mentor and lead a distributed team of engineers, focusing on high-velocity delivery and technical excellence.
• Tenant Logic: Support customer onboarding by designing tenant-specific transformation logic that scales without increasing architectural complexity.

Qualifications

• 8+ years in Data Engineering; 3+ years in a leadership/management role.
• Expert in Workflows, Unity Catalog, and Delta Lake.
• Deep proficiency in PySpark, SQL, and Azure Data ecosystem (Storage, Cosmos DB).
• Proven experience managing multi-tenant or enterprise-scale platforms.
• Strong background in CI/CD, Infrastructure-as-Code, and Data Modeling.

Preferred Skills

• Experience with retail or supply chain data forecasting.
• Expertise in optimizing serverless compute environments.
• Experience maintaining production SLAs for customer-facing data dependencies.

About Upshop: 

Upshop is the foremost provider of a SaaS platform designed to streamline forecasting, ordering, production, and inventory optimization processes for food retailers. Its unified platform simplifies and enhances associate tasks, promoting smarter and more interconnected operations across Fresh, Center, DSD, and eCommerce departments. With over 450+ retailers and 50,000+ stores relying on its mission-critical operations platform globally, customers have witnessed substantial enhancements in sales, shrinkage reduction, food safety, and sustainability throughout their stores.  

At Upshop, we believe that great businesses are built by great people. Our People function is at the heart of our company’s growth, ensuring we attract, develop, and retain A Players who drive our mission forward.  

Overview of the role: We are seeking an experienced Engineering Manager to lead and develop engineering teams responsible for delivering high-quality, scalable software aligned with business goals. This is a permanent, full-time position reporting to the Senior Director of Software Engineering. 

The Engineering Manager balances people leadership with technical oversight and selective hands-on contribution. This role is accountable for team performance, delivery predictability, engineering standards, and cross-functional collaboration while ensuring strong alignment with Upshop’s business and customer priorities. 

Responsibilities: 

• Lead and manage engineering teams as they design, build, test, and deliver high-quality software on schedule, balancing efficiency, cost, and customer satisfaction.
• Hire, onboard, train, and develop engineering talent; conduct regular one-on-ones, performance reviews, and team meetings to support career growth and performance objectives.
• Set clear team goals and objectives aligned with departmental and company priorities.
• Provide leadership, coaching, and motivation to drive accountability, ownership, and consistent execution.
• Ensure timely resolution of escalations and partner with the Senior Director of Software Engineering on issues impacting delivery, quality, or timelines.
• Design, code, review, and guide development of customer-facing features and backend services using technologies such as C#, React, PHP, and cloud-native services.
• Participate in architectural discussions and guide teams on N-Tier architectures, microservices, and cloud-based solutions.
• Promote engineering best practices, including clean, maintainable, and defect-free code; enforce standards through source control, pull requests, and code reviews using GitHub and Azure DevOps.
• Support testing cycles and post-production deployments to ensure stable, reliable releases.
• Ensure new work meets the Definition of Ready prior to sprint commitment; provide estimates and ensure timely assignment of work.
• Collaborate closely with Product, QA, Customer Support, and Operations to translate business requirements into functional and technical solutions.
• Monitor and report on team progress, sprint velocity, throughput, and delivery health.
• Leverage observability and monitoring tools such as DataDog to ensure application performance, reliability, and operational health.
• Encourage and guide responsible adoption of AI-assisted development tools (e.g., Cursor) to improve developer productivity, code quality, and delivery efficiency.
• Contribute to technology and product roadmap planning for business-critical applications under the guidance of the Senior Director of Software Engineering. 

Qualifications: 

About You 

• Strong people management and leadership skills with the ability to coach, motivate, and develop high-performing teams.
• Solid understanding of Object-Oriented Programming (OOP/OOD), functional programming, and N-Tier architectures.
• Experience working with cloud-based, microservice-oriented systems.
• Strong written and verbal communication skills with the ability to work effectively with both technical and non-technical stakeholders.
• Strong organizational, analytical, troubleshooting, and problem-solving skills.
• Customer-, service-, and results-oriented, with a strong sense of ownership and accountability.
• Process-oriented and able to operate effectively in a fast-paced environment with minimal supervision. 

Experience & Education 

• Bachelor’s or Master’s degree in Computer Science, Engineering, or equivalent experience.
• 6+ years of professional experience across the full software development lifecycle.
• Hands-on experience with:
• React, JavaScript, TypeScript, HTML, CSS/Bootstrap
• C#, PHP, Laravel Framework
• Azure Cosmos DB, Azure SQL, MS SQL, and ODBC
• Experience with source control, pull requests, and code reviews using GitHub and Azure DevOps.
• Experience working in agile development environments using tools such as JIRA and GitLab.
• Familiarity with CI/CD pipelines, release management, and deployment automation.
• Experience using DataDog or similar observability and monitoring tools.
• Understanding of test-driven development (TDD) and testing frameworks such as PHPUnit, Jest, and Google Test.
• Knowledge of Linux and Windows operating systems, command-line tools, and basic scripting (PowerShell, Bash).
• Comfortable guiding teams in the use of AI-assisted development tools such as Cursor.
• Ability to adapt to change and thrive in a dynamic, fast-paced environment. 

Preferred Qualifications (if applicable):  

• Experience working with large enterprise software deployments and solution-based products.
• Exposure to retail grocery, food retail, or large enterprise technology environments.
• Experience working in cross-functional, fast-growing organizations. 

Compensation Range: $130,000-$170,000 CAD/year

About Upshop

Upshop is the market leader in Total Retail Operations solutions for the Grocery and C-Store markets. We offer an AI-powered SaaS platform connecting Fresh, Center Store, eCommerce, and DSD operations to deliver a simplified, smarter, more connected retail supply chain. Customers running Upshop realize significant improvements in sales, shrink reduction, food safety, inventory utilization, and sustainability across the entire retail ecosystem. Over 450 companies trust Upshop software across more than 50,000 stores globally.

Upshop is expanding its platform capabilities upstream in the supply chain, partnering directly with Consumer Packaged Goods (CPG) manufacturers to improve demand planning, forecasting accuracy, and on-shelf availability across retail networks.

Overview of the Role

We are seeking a highly motivated and results-oriented Senior Account Executive to drive significant revenue growth with large Consumer Packaged Goods (CPG) manufacturers. This role is responsible for introducing and expanding Upshop’s demand planning and supply chain forecasting solutions with strategic manufacturing partners.

The ideal candidate will have experience selling complex SaaS or analytics solutions to supply chain, operations, or demand planning leaders within CPG organizations. This individual will engage executive-level stakeholders and guide customers through pilot programs and proof-of-concept engagements that demonstrate measurable improvements in inventory utilization, on-shelf availability, and forecasting accuracy.

As a trusted strategic partner, you will work with manufacturers to connect retail execution signals with upstream demand planning processes, helping align production, distribution, and retail demand. You will collaborate closely with internal stakeholders across product, analytics, and customer success to deliver successful pilots and long-term solution adoption.

Responsibilities

• Strategic Account Development: Develop and execute account strategies focused on acquiring and growing relationships with large CPG manufacturers and strategic supply chain partners.
• Driving Supply Chain Outcomes: Help manufacturers improve demand planning, inventory utilization, and forecast accuracy by leveraging Upshop’s AI-driven forecasting capabilities and retail execution insights.
• Executive Engagement: Build and maintain strong relationships with senior leaders across supply chain, operations, demand planning, and commercial teams within CPG organizations.
• Solution Selling: Demonstrate a deep understanding of Upshop’s forecasting, demand planning, and retail execution capabilities and how they integrate with existing enterprise planning systems.
• Pilot and POC Development: Identify and guide customers through proof-of-concept engagements designed to demonstrate measurable improvements in sales, inventory allocation, and on-shelf availability.
• Business Impact & ROI: Develop value-driven proposals that quantify the impact of improved demand planning, reduced shrink risk, and increased in-stock performance across retail partners.
• Consensus-Driven Engagement: Navigate complex, cross-functional buying environments that may include demand planning, sales operations, supply chain, and executive leadership.
• Pipeline & Forecast Management: Maintain accurate opportunity records, account activity, and pipeline forecasting in Salesforce CRM.
• Industry Insight: Stay informed on CPG supply chain trends, demand planning technologies, and evolving retail-manufacturer collaboration models.
• Cross-Functional Collaboration: Partner closely with product, analytics, marketing, and customer success teams to deliver successful pilot programs and long-term customer value.
• Contract Negotiation: Lead pilot agreements and long-term subscription discussions that support scalable adoption of Upshop solutions within CPG organizations.

Qualifications

• 10+ years of experience in B2B SaaS or enterprise software sales/account management
• Proven success selling into CPG manufacturers or supply chain organizations
• Experience engaging demand planning, operations, or supply chain leadership within large enterprises
• Strong consultative selling approach focused on measurable operational outcomes
• Experience navigating complex buying processes and long sales cycles
• Proficiency with Salesforce CRM and enterprise pipeline management
• Excellent communicator, self-starter, and collaborative team player
• Bachelor's degree in Business, Marketing, Supply Chain, or related field

Preferred Qualifications

• Experience selling demand planning, forecasting, or supply chain software solutions
• Experience working with CPG manufacturers, distributors, or retail supply chains
• Familiarity with demand planning platforms
• Experience operating in high-growth SaaS environments

Benefits / Perks

• Remote (or Hybrid)
• Competitive compensation package with commissions and performance incentives
• Employer-matched 401(k) plan
• Attractive paid time off policy
• Career growth and development opportunities
• A culture built on trust, collaboration, and customer success
• Work with a passionate team at the forefront of innovation in retail and supply chain technology

Product Manager 

Role Overview 

Upshop is seeking a Product Manager responsible for helping define, build, and deliver product capabilities within Upshop’s retail operations platform. This role will partner closely with engineering, design, data, and customer-facing teams to develop solutions that help grocery retailers improve operational efficiency, reduce waste, and drive profitability. 

The Product Manager will work directly with customers and internal stakeholders to understand operational challenges and translate them into clear product requirements and priorities. This role requires someone comfortable working in a SaaS product environment with an understanding of APIs, integrations, and platform-based software systems. 

The ideal candidate can effectively collaborate with both technical teams and retail operators, ensuring that product solutions are technically sound while addressing real-world operational needs. 

Key Responsibilities 

Product Strategy & Planning 

• Contribute to the development and execution of product strategy and roadmap initiatives 

• Identify product opportunities based on customer feedback, operational challenges, and market trends 

• Define product priorities aligned with company objectives 

• Develop product requirements, use cases, and user stories 

Product Development & Delivery 

• Partner with engineering and UX teams to design and deliver new product capabilities 

• Participate in agile development processes including sprint planning, backlog grooming, and release planning 

• Ensure product features meet functional, usability, and scalability requirements 

• Support testing, validation, and product launch activities 

Customer & Market Engagement 

• Engage directly with customers to understand operational workflows and product needs 

• Conduct customer interviews, feedback sessions, and discovery activities 

• Gather insights from sales and customer success teams to inform product decisions 

• Represent customer needs within the product development process 

Technical Collaboration 

• Work closely with engineering teams on features involving APIs, integrations, and SaaS platform capabilities 

• Translate business and operational requirements into technical product specifications 

• Support integration requirements with retailer systems and third-party solutions 

Cross-Functional Collaboration 

• Partner with engineering, UX, data science, revenue, and customer success teams 

• Support go-to-market readiness for new product releases 

• Communicate product updates and priorities across internal stakeholders 

Qualifications 

Required 

• Bachelor’s degree in business, technology, engineering, or related field (or equivalent experience) 

• 3–6+ years of experience in product management or product-related roles 

• Experience working in SaaS or enterprise software environments 

• Experience collaborating with engineering teams in an agile product development environment 

• Strong communication and stakeholder management skills 

• Ability to translate customer and business needs into clear product requirements 

Technical Knowledge 

• Working knowledge of APIs, integrations, and modern SaaS platform architecture 

• Ability to collaborate effectively with engineering teams on technical product features 

• Familiarity with product management tools and agile workflows 

• Familiarity with AI-enabled tooling and emerging AI capabilities, including the ability to evaluate opportunities for AI-driven features within SaaS products. 

Preferred Experience 

• Experience in grocery retail, food service, supply chain, or store operations technology 

• Exposure to data-driven product development 

• Familiarity with AI-enabled tools, automation technologies, or predictive analytics 

Key Competencies 

• Customer focus and empathy for operational users 

• Analytical and problem-solving skills 

• Cross-functional collaboration 

• Strategic thinking and prioritization 

• Communication and stakeholder management 

Working Relationships 

This role collaborates closely with: 

• Engineering 

• UX / Product Design 

• Data Science 

• Revenue / Sales 

• Customer Success 

The estimated pay ranges for this role are as follows:

• $100,000 - 150,000 CAD

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.

About Upshop 

Upshop is the market leader in Total Store Operations solutions for the Grocery and C-Store markets. We offer an AI-powered SaaS platform connecting Fresh, Center, eCommerce, and DSD department operations to deliver a simplified, smarter, more connected store experience. Customers running Upshop realize significant improvements in sales, shrink, food safety, and sustainability across the entire store. 450+ retail chain accounts trust our software in over 55k+ stores across 35 countries and 3 continents. 

At Upshop, we believe great businesses are built by great people. We hire high-agency builders who take ownership, move with urgency, and raise the bar for those around them. 

Overview of the Role  

We are seeking a Senior Software Engineer to operate with a high degree of autonomy within one of Upshop’s core product teams. This is a hands-on individual contributor position focused on owning and driving complex initiatives, shaping technical decisions at the project level, and delivering high-quality systems in an evolving platform environment. 

Our platform powers real-time retail operations at global scale, spanning mobile applications, barcode scanning workflows, multi-tenant SaaS APIs, enterprise integrations, and data-driven decision systems. You will work across cloud-native infrastructure in Azure and GCP, building and operating services in languages such as C# and PHP, alongside modern frontend technologies like React and TypeScript. The platform leverages a variety of frameworks, containerized deployments with Kubernetes, and data systems including SQL and NoSQL databases, Redis, and analytics pipelines. 

AI is core to how we build at Upshop. From drafting specifications to generating code, expanding test coverage, refactoring legacy modules, and improving observability, we expect engineers to actively explore and leverage AI tools throughout their workflow. Curiosity and disciplined AI usage are part of the role. 

Key Responsibilities 

Project Leadership & Technical Execution 

• Lead significant technical initiatives within your product area, driving projects from design through production rollout. 

• Break down ambiguous problems into structured, deliverable increments. 

• Collaborate with other engineers and engineering leadership to align project decisions with broader architectural direction. 

• Contribute to design discussions, propose trade-offs, and help reduce decision latency within the team. 

Hands-On Development 

• Leverage AI tools to design solutions, generate production-grade code, expand test coverage, and improve implementation quality. 

• Contribute across backend and frontend systems, ensuring clarity, maintainability, and strong engineering discipline. 

• Write comprehensive unit and integration tests covering core paths and edge cases. 

• Own features end-to-end: design, implementation, deployment, monitoring, and iteration. 

• Design with observability in mind — logging, metrics, tracing, and performance considerations built in by default. 

Platform Evolution & Collaboration 

• Support ongoing system evolution and integration across product lines. 

• Work collaboratively across team boundaries, stepping into gray areas when necessary to move work forward. 

• Mentor less experienced engineers through thoughtful code reviews and structured feedback. 

• Participate in improving engineering practices, including spec-driven development and AI-assisted workflows. 

Qualifications 

Required 

• 5+ years of professional software engineering experience. 

• Demonstrated interest in and active exploration of AI tools, with experience integrating AI into daily development workflows. 

• Strong backend engineering experience in PHP, C#, or similar languages and frameworks. 

• Frontend experience with React, modern TypeScript/JavaScript ecosystems, or comparable frontend technologies. 

• Experience operating systems in cloud environments (Azure, GCP, AWS, or similar) and containerized deployments (e.g., Kubernetes or equivalent platforms). 

• Demonstrated ability to lead projects and influence technical direction without formal authority. 

• Strong written and verbal communication skills; able to document intent, specifications, and decisions clearly. 

• Experience working effectively in ambiguous environments where requirements and integration paths evolve. 

Preferred 

• Experience using or experimenting with agentic development and spec-driven development patterns. 

• Experience working in multi-tenant SaaS environments. 

• Deep familiarity with AI-assisted development tools and practical application of agentic or spec-driven engineering practices. 

• Experience integrating systems across product boundaries. 

What We Value 

• Initiative over passivity. 

• Structured thinking over reactive execution. 

• Methodical system evolution over reckless rewrites. 

• Data-informed decisions over opinion-driven debates. 

• Ownership from concept to production health. 

Benefits/Perks: 

• Competitive compensation. 

• Generous PTO and benefits package. 

• Career development opportunities. 

• Collaborative, growth-oriented culture at the forefront of grocery tech innovation. 

Principal UX Designer 

About Upshop 

Upshop is the market leader in Total Store Operations solutions for the Grocery and C-Store markets. We offer an AI-powered, SaaS platform connecting Fresh, Center, eCommerce, and DSD department operations to deliver a simplified, smarter, more connected store experience. Customers running Upshop realize significant improvements in sales, shrink, food safety and sustainability across the entire store. 450+ retail chain accounts trust our software in over 55k+ stores, 35 countries, and 3 continents. 

Role Summary 

As a Principal UX Designer at Upshop, you will own the evolution of our Design Platform and Design System while acting as both a senior craft practitioner and mentor to the design organization. In this role, you will have the opportunity to be a platform-minded design leader, partnering with other PMs to shape and operationalize Upshop 360 platform across all product suites. You will shape direction through hands-on contribution and thoughtful influence, helping the team make decisions confidently in ambiguity and complexity.  

You are a player-coach: a strategic thinker who leads by doing, builds with your hands, and elevates others’ work through mentorship and example. You will help define the future of Upshop’s design ecosystem — from foundational components to interaction patterns and scalable UX paradigms — ensuring consistency, coherence, and quality across products.  

This role requires a strong blend of senior UX craft, systems thinking, advanced prototyping, cross-functional influence, and coaching experience. 

What You’ll Do 

Design Platform & System Leadership 

• Own and evolve the Upshop Design Platform and System: components, guidelines, interaction language, motion principles, and shared patterns.  

• Partner with engineering to ensure consistency, scalability, performance, and technical feasibility at platform scale.  

• Define and document standards for how design is expressed across products — from tokens to complex state behaviors.  

• Advocate for accessibility, performance, and inclusive design across the system. 

Hands-On UX & Interaction Craft 

• Create and iterate high-fidelity prototypes, interaction models, and design artifacts that clarify intent and drive alignment. 

• Use prototypes as a primary language for exploration, communication, and decision-making. 

• Translate research insights, user data, and business goals into elegant, scalable solutions.  

Player-Coach Leadership 

• Serve as a mentor and coach: provide regular design critique, career guidance, and hands-on support for more junior designers. 

• Lead and facilitate cross-disciplinary workshops to solve complex UX challenges collaboratively 

• Elevate team craft through shared best practices, tooling improvements, and patterns for reuse. 

Cross-Functional Collaboration 

• Partner deeply with Product, Engineering, and Brand teams to shape outcomes that balance user needs with business strategy. 

• Influence product direction through strategic reasoning and exceptional design judgment 

• Represent design decisions to senior leadership and stakeholders with clarity and confidence. 

Working in Ambiguity & Evolving Practice 

• Thrive in exploratory environments where problems are undefined and outcomes are emerging. 

• Define and refine processes that help teams navigate ambiguity while maintaining velocity and quality. 

Qualifications 

Experience 

•  7+ years of UX / product design experience with a strong portfolio of work that demonstrates both strategic depth and craft excellence. 

• Experience creating and scaling design systems or shared UX platforms in complex multi-product portfolios across different medium (web, tablet, mobile)  

• Proven track record of mentoring designers and elevating team quality. 

Skills & Expertise 

• Hands-on design fluency: end-to-end interaction design, advanced prototyping (Figma), motion where applicable.  

• Deep systems thinking: ability to decompose and organize design patterns that scale across products and teams. 

• Excellent communication: ability to articulate decisions to both technical and non-technical audiences. 

• Comfort working with engineering on implementation patterns, constraints, and performance realities. 

• Strong understanding of user-centered design, accessibility, and usability best practices.  

• Experience contributing code to UI component libraries: React, Tailwind, Design Tokens, shadcn, CSS-in-JS; able to meaningfully engage on component structure and implementation quality. 

• Familiarity with analytics data used to inform design decisions 

• Experience in high-growth SaaS or platform organizations 

What Makes You Successful Here 

• You set direction through clarity of thought and strength of craft, not hierarchy. 

• You enjoy making complexity feel simple for others - both in product and in how design works. 

• You are motivated by empowering others, sharing craft expertise, and defining scalable design strategies. 

• You embrace ambiguity and drive forward with both curiosity and discipline. 

Portfolio Requirement 

An online portfolio is required and should highlight: 

• Design system thinking and platform-level impact 

• High-fidelity prototypes and interaction work 

• Examples of coaching, mentoring, or elevating team outcomes 

The estimated pay ranges for this role are as follows:

• $120,000 - 170,000 CAD

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.

About Upshop: 

Upshop is the market leader in Total Store Operations solutions for the Grocery and C-Store markets. We offer an AI-powered, SaaS platform connecting Fresh, Center, eCommerce, and DSD department operations to deliver a simplified, smarter, more connected store experience. Customers running Upshop realize significant improvements in sales, shrink, food safety and sustainability across the entire store. 450+ retail chain accounts trust our software in over 55k+ stores, 35 countries, and 3 continents.

Overview of the Role: 

The Account Executive at Upshop will drive revenue growth and strategic expansion within key enterprise grocery and retail accounts. This role blends strategic account management, executive-level engagement, and solution-oriented selling to ensure clients derive measurable value from the Upshop platform. Success hinges on the ability to link Upshop’s technology to business outcomes, foster deep partnerships, and navigate complex client organizations. 

• Strategic Growth: Build and execute account plans to expand solution adoption and increase share of wallet within existing clients.
• Value Delivery: Partner with clients to translate Upshop’s data, technology, and insights into tangible business outcomes.
• Executive Relationship Management: Engage and influence C-suite and senior stakeholders with a consultative approach.
• Solution & ROI Selling: Align Upshop’s SaaS solutions with client objectives; articulate business impact and ROI.
• Cross-Selling/Upselling: Identify and close opportunities to introduce complementary solutions across product lines.
• Forecasting & Reporting: Maintain visibility into account activity, pipeline health, and forecasts using Salesforce.
• Collaboration: Partner cross-functionally with product, marketing, implementation, and customer success teams.
• Contract Management: Lead renewals and expansion negotiations to ensure long-term partnership success.

• 10+ years in enterprise SaaS sales or account management, with a focus on strategic/enterprise clients.
• Demonstrated success in growing complex, multi-stakeholder accounts.
• Experience in grocery, retail, or fresh food technology preferred.
• Skilled in consultative selling, business case development, and executive engagement.
• Proficiency in Salesforce CRM, pipeline management, and forecasting best practices.
• Strong communicator, strategic thinker, and collaborative operator.
• Bachelor’s degree in Business, Marketing, or related field.

• Experience in retail or grocery tech environments, including warehousing or supply chain.
• Exposure to high-growth SaaS environments.
• Familiarity with CRM tools (Salesforce, ZenDesk).

Benefits/Perks:

• Remote Opportunity 
• Competitive salary 
• Private benefit supplement 
• Attractive paid time off policy 
• Career growth and development opportunities