Upside

When someone joins Upside, we send them a swag kit filled with goodies so they can get started in style. During their first few months, new hires go through our onboarding program, which includes both team- and company-centric training and information sessions, a meet-and-greet with our CEO and an education on our affinity groups and how to get involved with these groups.

To top it off, we bring our new joiners from across the country to our headquarters in Washington, DC, for our new hire onsite, which is a three-day event that enables them to form friendships and connections through fun events, service projects and interactive sessions with department leaders.

Because of our flexible working policy — which has yielded a blend of hybrid, in-office and remote employees — we find that bringing everyone together both virtually and physically for our onsite helps new hires forge connections and sets them up for success in their role. Our onboarding program provides opportunities to learn more about our company and also offers valuable information about the people on our teams, where to plug into different groups and activities and how to navigate processes within our company, so that they feel comfortable about expectations and connected to both their team and the company culture.

We have a stellar human resources business partner team that partners with each team member from day one. These HRBPs are here for our team to help with any concerns or questions we may have. Each team member also has weekly syncs with their direct manager to stay connected, and teams meet regularly within their department and as a company to stay up-to-date and involved.

Other companywide initiatives, such as our affinity groups and employee spotlights, strengthen our sense of belonging and identity, while events like game nights, talent shows and service projects offer even more ways to plug into our culture and foster connection.

Upside's ERGs are centered around shared identities, cultures and experiences. Each group has an executive sponsor and three-five co-leads, plus the support of our employee experience manager. Co-leads are responsible for the day-to-day management of the ERG, focused on group mission, programming and events and serving as primary points-of-contact for group members.

Executive sponsors provide strategic guidance and advocacy for the group, to help ensure mission and vision can be fulfilled effectively.

First, any employee can join and participate in the ERGs they identify with. If there is need or desire for a new group, any employee can submit a proposal for a new ERG to the employee experience team. Existing ERGs have various means of ensuring input and ideation from group members, such as periodic surveys to collect feedback and ideas, group meetings dedicated to brainstorming and requests, open Slack channels where any member can share their thoughts and direct line of communication with all co-leads, executive sponsors and the employee experience team.

Our ERGs provide programming, activities and events meant to unite people of shared identities, cultures and lived experiences — along with their allies.

Sponsored breakfasts/lunches during group heritage and awareness months to spotlight groups and promote visibility and education across the company Book clubs featuring books that align to group interests/experience Social gatherings to provide the opportunity to connect with members outside of regular, day-to-day work interactions Lunch and learns, panel discussions and webinars to provide education and support (e.g.

"Benefits Deep-dive for Women and Families," "Advocating for Yourself and Your Impact," "Balancing Code and Care: How to Grow Your Career While Caring for Others") Small group roundtables focused on topics of interest (e.g. culture and politics, career growth, mindfulness and self-care, etc.

) to allow participants to share experiences, ask questions and support one another in open and safe spaces.

What drew me to this role, and keeps me energized, is the tangible impact we're making: helping merchants grow and helping consumers earn cash back on everyday purchases. I work alongside smart, collaborative teammates who move fast and push on what's possible.

I also get to shape business and technical strategy, invest in innovation and co-create the systems and culture that bring out the best in our teams.

What helped me land the role was a clear focus on using technology and product innovation to drive profitability. I brought experience scaling engineering organizations and building revenue-generating data products. This is also the fourth two-sided marketplace I've worked on, so I came in with a strong intuition for the dynamics, challenges and levers that make these platforms thrive.

Engineers who rise fast are proactive, reliable and focused on impact. They don't just write good code — they understand the "why" behind their work, help others succeed and make things better without being asked. Strong communication, curiosity and ownership go a long way in standing out and earning trust.

I started at Upside in 2020 as a chief of staff for Wayne Lin, a role that gave me broad visibility into the company's strategy, product and cross-functional teams. I learned about the unique challenge of growing a two-sided marketplace business and collaborated with teammates across product, operations, sales and marketing to drive forward complex initiatives.

After 2.5 years, I transitioned to a product manager role, where I had the opportunity to go deep rather than broad and have a more direct hand in delivering value for consumers and retailers. And over the last 1.

5 years, I've worked on the technical integrations and UX to power our Pay with Upside feature, as well as a major redesign that gives users more choice in how they earn their cash back. This work led to my recent promotion to senior product manager focusing on our entire discovery experience.

My transition to product management has been full of learning — how to ensure the products we build support our company strategy, the technology we use (and its limitations) in order to work effectively with engineering and how to rigorously prioritize based on goals, capacity and projected impact. Stepping into a senior PM role means I'll have a bigger playground on which to play!

I'll rely on the collaboration, communication and execution skills I've already developed to begin influencing the strategic direction of our discovery experience and our consumer app overall. I'm particularly excited by the challenge of building discovery features capable of adapting to each user's unique situation: their preferences, their habits and the specific offers around them.

My career at Upside is a testament to its strong culture of supporting internal mobility. When I first expressed interest in transitioning out of chief of staff, my former manager suggested product management to me! Despite my hesitation (read: imposter syndrome), he assured me that if it wasn't the right fit, we would find something else.

That gave me all the confidence I needed to take the leap knowing I'd be supported every step of the way — and I was! I am endlessly grateful to my former manager, my fellow PMs and my engineering and design partners, all of whom had a hand in showing me what it looks like to be a great PM.

If you earn the trust of those around you through high performance, the sky's the limit! I've seen coworkers transition from sales to accounts, from analytics to product, from strategy to marketing and more. In some cases, we have even created brand new roles to facilitate an internal transition.

Upside genuinely invests in helping people grow, whether that's through internal training, mentorship programs or simply fostering an environment where people feel empowered to explore new career paths.

Working at Upside has been rewarding. Everyone at this company brings value and is making an impact in the real world. Through all the challenges, it's a privilege to be part of a team where everyone is willing to help one another work towards success.

I feel appreciated here at Upside and I know that I have the support I need to grow in my career.

What I like the most about working for Upside is the amazing people I get to team up with. Everyone here is willing to jump in, help and put in the work to make sure we deliver a great product to our Merchants and our Consumers. I have been given tons of possibilities to develop professionally, and my managers truly believe in me and support me.

Upside is integrating AI, specifically GitHub Copilot, into its product development process, focusing on enhancing developer productivity and velocity. Data has shown that our developers using Copilot are 56 percent more productive and complete tasks 36 percent faster than those not using the AI tool.

For example, a project that would typically take 100 days can now be completed in 64 days with Copilot. These improvements have directly contributed to faster product delivery, which in turn positively impacts our revenue and profit.

To keep up with rapid AI and ML advancements, we allocate resources to internal research and development teams to explore and prototype new applications, ensuring we stay ahead of the competition and integrate the latest AI innovations for better user experiences and operational efficiencies. Additionally, we prioritize upskilling our teams through training sessions and demos and provide access to cutting-edge resources, keeping our teams up to date with the latest technologies and fostering a culture of continuous learning and innovation.

One example of how AI is poised to enhance Upside's product line is our ongoing work on AI-powered semantic search for our app. We're focused on significantly improving the user experience by shifting from simple keyword matching to understanding the intent behind a user's search.

This AI-powered search will allow users to enter natural language queries, such as, "I want a salad, but my kids want pizza," and receive results that match the meaning and context of their requests. It will support multiple languages, handle spelling errors and interpret user needs with high accuracy.

We anticipate this improvement will directly impact user engagement by helping people find what they need more effectively, increasing offer claim rates and reducing frustration and churn. Once launched, this will be Upside's first AI-powered feature that directly benefits the end user and will help accelerate time to market by leveraging vector databases and AI embedding models for faster, more relevant search results.

We use everyday commerce to empower people and businesses — and to protect the world around us. We've committed one percent of all revenue to sustainability initiatives tied to our areas of operation, a pledge we began in 2016 and strengthened further in 2022 by joining the global Pledge 1% movement.

While millions of people use Upside to stretch their dollars and tens of thousands of businesses use it to earn more profit, we do our part behind the scenes to transform everyday errands into greater change.

We use the commerce of today to help our world for tomorrow. Our platform is built to deliver value — financially for consumers and businesses, and environmentally for the planet. That alignment is intentional and central to how we operate.

As our footprint grows, so does our ability to reinvest in carbon offsetting, food rescue and other meaningful impact areas. With our massive financial impact, this model has put us in league with some of the world's largest companies doing good.

Start with your business model. The most effective sustainability strategies are the ones that scale with your success. Our advice: Identify how your company's operations naturally intersect with opportunities to do good, then build in a mechanism — like a revenue pledge — to turn everyday business growth into long-term impact.

Even small, consistent actions can drive meaningful change when they're embedded into the core of what you do.

At Upside, our mission is simple and bold: We exist to advance the economic power of people living and working in the real world. We've already put over $1 billion back into people's pockets by connecting them with retailers on our two-sided marketplace.

The best part is, we're just getting started. That mission shapes how we work: We act like owners, make everything measurable and build for real people. It absolutely influenced my decision to join.

I've spent my career in mission-driven roles, and I love that we also commit 1 percent of revenue to offset emissions and fight food waste. The more we grow, the more good we do. It's rewarding being in a data-driven role at a truly data-driven company.

One fun cultural touchstone is celebrating "twinning," when multiple people on the team wear the same outfit. Whenever this happens, we snap a photo and post it to Slack!

As a product analytics manager, I helped build App 360, a suite of dashboards that keeps our team dialed into product performance. Living our "Make it Measurable" value, we've used these insights to spot friction in the user journey, prioritize fixes and even catch bugs early so we can ship better experiences faster.

Measuring app performance leads to better user experience, which leads to more successful trips and more cash back in people's pockets.

Start by using the Upside app at a gas station, grocery store or restaurant near you. Seeing the marketplace in action is the best intro. Then come ready to "Be an Owner:" Propose what you'd improve and why; "Make it Measurable:" Bring a hypothesis and the metrics you'd track; and "Represent the Real World:" Consider both consumers and retailers.