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. 

Upside was named on Deloitte’s 2021 & 2022 list of Fastest Growing 500 Tech Companies and  #308 in Inc.’s America’s fastest growing private companies of 2022. Upside’s Series D funding round was led by General Catalyst with a $1.5 billion valuation in March 2022. Other notable investors include Bessemer Ventures and Formation8.

Our mission, values, and commitment to inclusivity guide our team of more than 350 people worldwide, and the quality of our culture is reflected in the impact we’ve had on communities nationwide. But don’t just take our word for it! In 2023, Upside was included as a Top Workplace in the USA, received six Best Places to Work awards from Built In, and was named a Top Workplace for Perks & Culture by The Muse.

About the job:

As the Chief of Staff to the Chief Operating Officer, you’ll be the cross-functional glue connecting all teams that the COO oversees (Data, Design, Marketing, Product, and Research) with the rest of the organization. As Upside continues to grow and scale, you’ll be responsible for helping the entire company stay organized to hit our goals, improve our organization’s effectiveness, and take on special projects as needed. This role will require the ability to think strategically and execute effectively in order to create value for the business by seeing around corners and turning ideas into action. This is a role with high cross-functional visibility and the opportunity to work with executives/senior leadership to grow and scale a Series D startup.

What you’ll do:

• Broad support for company and executive team:
• Develop strong, collaborative relationships with key partners across the company
• Own and direct all company-wide strategic planning processes with the goal of enabling all departments and teams to collaboratively organize around the company’s strategic direction
• Own preparation and agenda for company-wide meetings, including monthly Company All-Hands Meeting
• Continuously improve cross-functional collaboration and execution in partnership with Chiefs of Staff in Sales and Engineering
• Drive effectiveness throughout COO organization (Data, Design, Product, Marketing, and Research):
• Act as a trusted advisor to the COO in all areas of strategic and operational initiatives like day-to-day planning, prioritization of departmental activities, and deliverables
• Support COO in identifying strategic priorities and defining success metrics, revisit regularly and evaluate progress as an accountability partner
• Own preparation, agenda, and occasionally facilitation for COO-led meetings and offsites 
• Support the teams on priority projects through project management and coordination
• Help onboard key company hires, ensuring they have the context and support needed to ramp up successfully
• Partner with HR/Finance and COO’s leadership team to assist with recruiting, headcount planning, performance management, budget planning, etc.
• Partner with COO’s Executive Assistant for complex schedule management as needed
• Turn COO ideas into reality with minimal oversight
• As needed, prepare materials for an investor audience in partnership with COO, including for quarterly Board meetings and ad hoc meetings with investors
• Own special/ad hoc projects to get them off the ground and hand off when the time is right
• Champion and role model Upside’s company culture and values

What you need:

• 5+ years of professional experience in management consulting, business operations, or another relevant field.
• Bachelor’s degree or higher.
• Effective communication skills (written, verbal, and listening) and executive presence, with the ability to convey intricate ideas in a clear, concise manner in all forms. Must be experienced in building positive relationships and influencing business solutions.
• Practical experience in running a strategic planning process.
• Excellent time and project management skills, with experience in cross-functional collaboration (PMP certification is a plus).
• A curious mentality with the comfort to ask the right (and hard) questions, using sound business judgment when collaborating with a wide range of partners.
• A self-starter mentality that will thrive in a fast-paced, and often ambiguous environment.

The fine print:

• Location: This role is a hybrid role and required to work from our Washington, D.C. office 2 days/week.
• 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!