Upside Services, Inc. logo

Senior Cloud Security Engineer II

Job Overview

Location

Chicago, Indiana, USA

Job Type

Full-time

Category

Security Engineer

Date Posted

February 27, 2026

Full Job Description

📋 Description

  • • Join Upside Services, Inc., a dynamic and rapidly growing company at the forefront of transforming brick-and-mortar commerce through innovative technology. We are seeking a highly skilled and motivated Senior Cloud Security Engineer II to play a pivotal role in enhancing our cloud security posture and enabling secure software development practices.
  • • In this critical individual contributor role, you will report directly to the Director of Information Security and collaborate closely with various technology stakeholders across the organization. Your expertise will be instrumental in identifying, assessing, and remediating cloud vulnerabilities, ensuring the integrity and security of our expansive platform which handles billions of dollars in commerce annually.
  • • You will be a key innovator for our Cloud Security team, driving advancements in security solutions and contributing to the overall security strategy. Your work will directly impact our ability to protect sensitive data, maintain customer trust, and ensure compliance with industry regulations.
  • • A significant aspect of your role will involve leveraging cutting-edge AI technologies to develop and implement advanced security solutions. This includes proactively mitigating infrastructure vulnerabilities and staying ahead of emerging threats in the cloud security landscape.
  • • You will be responsible for codifying Infrastructure as Code (IaC) compliance standards using tools like Terraform, Python, and/or Open Policy Agent (OPA). This ensures that our cloud infrastructure is built and maintained according to best practices and security policies.
  • • You will actively run IaC security scans, analyze the results, and partner collaboratively with our engineering teams to address and remediate any identified unsafe code or configurations, fostering a culture of shared security responsibility.
  • • Engage proactively with technology teams to conduct thorough reviews of security controls, document potential risks, and effectively communicate these risks to relevant stakeholders, ensuring a clear understanding of the security landscape.
  • • Provide expert technical guidance and mentorship to other security engineers within the team, fostering their professional development and elevating the collective expertise of the Cloud Security function.
  • • Ensure our cloud environments and practices remain in strict compliance with relevant security regulations, industry standards, and internal policies, safeguarding our operations and data.
  • • Actively participate in the broader security community, staying abreast of the latest trends, threats, and best practices in cloud security, and bringing this knowledge back to Upside to continuously improve our defenses.
  • • You will work with a modern technology stack including Github Suite (Advanced Security, Actions, Copilot), Python, Terraform, AWS services (Lambda, DynamoDB, S3, SNS, SQS, IAM, VPCs), ChatGPT, Snowflake, and SQL.
  • • This role offers a unique opportunity to make a substantial impact on a company that is revolutionizing how consumers shop and how businesses operate, all while contributing to important sustainability initiatives.
  • • Your contributions will directly support our mission to provide users with more value on their everyday purchases and help brick-and-mortar businesses acquire new, profitable customers, all powered by secure and robust technology.
  • • We are looking for someone who is not only technically proficient but also possesses a strong professional growth mindset, demonstrating a willingness to learn, adapt, fail, and grow in a fast-paced environment.
  • • This hybrid role is based in our Austin, Chicago, DC, or NYC office, requiring in-office attendance on Monday, Tuesday, and Thursday, with potential for increased in-office presence based on project needs and evolving company policies.
  • • The compensation package is competitive, including a US base salary range of $165,000 - $185,000, plus equity and comprehensive benefits, with final pay determined by skills, experience, qualifications, location, and market conditions.
  • • You will be an integral part of a company that values transparency, diversity, and inclusion, fostering a supportive and collaborative work environment where everyone is welcome and encouraged to contribute their unique perspectives.
  • • This is an exciting opportunity to leverage your deep cloud security expertise to protect and advance a platform that delivers significant value to millions of users and hundreds of thousands of businesses.

Skills & Technologies

Python
Java
DynamoDB
AWS
Terraform
Senior
Hybrid
$165k-185k
Degree Required

Ready to Apply?

You will be redirected to an external site to apply.

Upside Services, Inc. logo
Upside Services, Inc.
Visit Website

About Upside Services, Inc.

Upside Services provides a cash-back platform that connects consumers with nearby fuel stations, grocery stores, and restaurants. The company earns revenue through performance-based marketing agreements with merchants, who pay only when Upside drives incremental profit above baseline sales. The mobile app delivers personalized offers and processes rebates to users’ bank accounts or digital wallets. Founded in Washington, D.C., Upside uses anonymized transaction data and machine-learning models to forecast demand and set dynamic incentives, aiming to increase foot traffic and basket size for partner businesses while rewarding consumer loyalty.

Similar Opportunities

Essen, Canada
Full-time
Expires May 3, 2026
Python
Go
AWS
+4 more

6 days ago

Apply
Shift Technology SAS logo

Shift Technology SAS

Paris, France
Full-time
Expires Apr 25, 2026
Azure
Kubernetes
REST
+3 more

14 days ago

Apply
Essen, UK
Full-time
Expires May 6, 2026
Onsite
£80k-95k

3 days ago

Apply
KissMyApps SAS logo

KissMyApps SAS

UK
Full-time
Expires Apr 27, 2026
JavaScript
Node.js
AWS
+3 more

12 days ago

Apply