Director of Information Technology

Meet Upside:

We created Upside to help communities thrive! Our retail 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 cash back than any other product, and tens 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 local retailers, the consumers they serve, and towards important sustainability initiatives. Our mission, values, and commitment to inclusivity guide our team of more than 200 people worldwide, and the quality of our culture is reflected in the impact we’ve had on communities nationwide.

Meet the IT Team:

Our Enterprise IT team is a small but mighty group of doers. We collaborate across every department, from Sales to Engineering, to ensure that everyone has the resources that they need to do their job. We value a supportive work environment where we can learn from our mistakes while solving the challenges that come with a fast-growing business!

About the job:

Reporting to the Chief Information Security Officer, the Director of IT will support the growing IT function across Upside. This Director will be a progressive, transformational problem solver who can build and deliver innovative solutions for various ongoing needs of Upside as we continue to scale domestically and prepare to go international. You’ll work closely with internal and external stakeholders to ensure that business solutions are efficiently delivered in a timely and agile manner.

What you’ll do:

• Lead our current Enterprise IT team and build out the team as the company grows
• Develop internal infrastructure and processes for automating and scaling critical business tasks
• Own the ongoing deployment, monitoring, maintenance, and support of all IT systems
• Manage and administer vendor, 3rd party service provider, and consultant contracts and negotiations
• Partner with InfoSec and Security teams to recommend and implement security measures that best protect data assets
• Establish policies around technology assets and security
• Build, optimize, track, and maintain a technology budget
• Provide updates and effectively communicate across teams and throughout all levels of the company, including executive leadership
• Deliver training and support for hardware/software/technology platforms
• Address IT-related changes and support requests through optimal project management

What you need:

• BS in related field OR equivalent professional experience
• 10+ years of enterprise IT management within a fast-growing company
• 3+ years of people management experience, with a track record of encouraging growth and effectively inspiring and supporting a dispersed team
• Technical Acumen (note that for candidates with strong leadership and strategic skills, covering 80% of desired technical experience is sufficient and will be supplemented with training after on-boarding):
• Demonstrable knowledge of Jira (specifically building in Jira)
• Solid grasp of Okta (or similar modern IAM tooling) and Jamf (or similar MDM), with BetterCloud (or similar SaaS Management Platforms) a plus
• Strong working knowledge of networking, including Switching, Firewalls, WAPs, and experience building out/connecting physical spaces, offices, and conference rooms, etc
• Experience supporting workforce productivity tools and hardware (including supporting remote employees and contractors)
• Advanced player/coach skills, optimally balancing big ideas with a day-to-day desire to be hands on and "in the weeds"
• Inquisitive and adaptable approach to process development and improvement
• A record of success speaking with and persuading high-level leaders through adept presentation and communication skills
• A customer-first attitude, and a true collaborator with people from all disciplines and levels, technical or otherwise

The fine print:

• 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.

At Upside, we believe that diversity drives innovation. Our differences are what makes us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here, come join us!