Role Models: Hope Pettway, Director of Program Management at Skillz

Today’s Role Model is Hope Pettway. Hope is the Director of Program Management at Skillz, which was named the fastest-growing company in America by Inc. Magazine. She graduated from the University of Southern California with a degree in film and has spent over a decade working in the gaming industry – spanning the gamut from console to web and mobile, before transitioning to eSports.

Prior to Skillz, Hope worked at LucasArts and Zynga as a producer before transitioning into project management at Machine Zone. Today she can be found evaluating, refining, and establishing processes and best practices across a wide range of teams and projects. As a film, TV, and games fanatic, there is no doubting her passion for the industry!

What’s your official title and how long have you been in this role?

I’ve been the Director of Program Management at Skillz since February 2018. When I joined Skillz in August of 2016, I was a Senior Program Manager.

What attracted you to this role?

I was attracted to working on a platform that provided a different set of challenges than just working on specific games, which is what I spent the majority of my career doing. I wanted something where I could leverage my experience working in gaming, but also find new opportunities for growth – an eSports platform checked all those boxes, and I knew Skillz was the top company in this space.

Walk me through a typical day in your role. What activities do you engage in? What types of meetings do you join? When’s lunch?

I get to work around 8:30 in the morning, which normally leaves me with about 30 minutes to update my to-do list, catch up on emails, and respond to Slack messages. As a general rule of thumb, mornings typically consist of team syncs and one-on-one meetings to ensure the goals for the day are clear and to help my team with any challenges. I break for lunch around 11:45, mostly to avoid long lines at the local food trucks or sandwich spot.

My afternoons vary between breakout sessions for brainstorms and blocking out time to work on hiring, project tracking/status review, and making sure we’re continuing to document best practices and processes. I also try to make myself available for people to come ask me questions about the latest releases and help remove any blockers for the team.

What skills/technologies help you succeed?

I think the biggest skill has been being able to multi-task and keep multiple plates spinning – no two days are ever the same, which is why I love this role so much.

What’s the most fun or creative part of your role?

I love building complex project timelines – it’s like putting together a 1000-piece puzzle. Everything has a place and needs to line up perfectly. I also love being around such creative, talented people that bring features we envision to life.

What are the biggest challenges you face in this role?

The biggest challenge is balancing my day-to-day work while also thinking about the long-term strategy for the Program team. We’re growing fast here at Skillz, and my team needs to be focused on making sure we continue to be productive and efficient as we scale.

What teams/individuals do you work with cross-functionally? Can you give an example of a time when you collaborated with another group/individual?

I work with a number of cross-functional teams on a daily basis – it’s really the nature of my role. Typically I work with Product, Design, Engineering, and QA for features during development and then Marketing, Developer Success, and PR to get those features into the hands of our players and developers.

What’s an area where you’re trying to grow in your role?

I’m currently working on my public speaking/presentation skills. It’s never really been my core area of focus, but as I progress in my career it’s becoming increasingly important that it comes naturally (and doesn’t stress me out).

Aside from technical skills, what personality traits/characteristics make for an ideal candidate in your role?

I’d say that communication, organization, and passion are the most important personality traits for someone in my role. Every day you’re working with a lot of people in various disciplines who are all talking about the same things, but from different angles. The objective is to understand how to get everyone on the same page and focus on a single end goal.

What skills (tech/non-tech) have you improved as a result of working in this role?

As a result of working at Skillz, I’ve gotten a lot better at automating my tracking and reporting. I used to think about everything on a very manual level. However, being the only Program Manager for my first year or so really forced me to get creative with spreadsheet customization and script formulas. I’ve also been able to work on my hiring and team building skills. I’ve had the opportunity to find, hire, and manage a great team and I’m looking forward to continuing to flex that muscle.

In your role, what metrics define success?

For me, it’s about not repeating the same mistake twice. This means being able to recognize what is working well and what needs to be adjusted. If the team is missing deadlines, my success is defined by working with them to understand what’s going on and creating a plan to fix it. Likewise, if we’re really hitting our stride and everything is working according to plan, I need to be able to recognize the things we’re doing right and replicate them again and again. At the end of the day, success is hitting the deadlines we set for ourselves.

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Role Models: Jon Gabriel, Digital Producer at REQ

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Today’s Role Model is Jon Gabriel. Jon attended the University of Delaware and studied computer science. While he didn’t want to code for a living, he wanted to stay in the tech space. Immediately out of school, he traveled across the U.S. as a freelance photographer covering action sports. He spent some time in photo studios learning about portrait lighting, and later moved down to Maryland to work as a Traffic Coordinator at Sabre Hospitality Solutions. One year later, he transitioned into a hybrid Product Manager role. Currently, Jon is a digital producer at REQ, a brand management agency.

What’s your official title and how long have you been in this role?

I am a digital producer at REQ and I have been in the role for one month!

What attracted you to this role?

I have a background in producer roles. Someone in a producer position is well-connected with the development and design teams and has a high-level view of the landscape of resourcing and project health. My background in computer science and design combined with my overall extroverted nature made me a particularly good traffic coordinator at Sabre. I wanted to return to this position in a different industry to see if I could learn more.

Walk me through a typical day in your role. What activities do you engage in? What types of meetings do you join? When’s lunch?

I get in early to assess the day’s client work deadlines. I run through all the creative and development responsibilities and make sure that the design and tech teams are in a place where they can be successful. As new projects come through the pipeline, I pop in and out of meetings discussing what resources may be best for the client’s requests. I run cost/analysis operations with the different teams. Analyzing their time time tracking shows us how we’re doing compared to how much we’re generating and producing.

What skills/technologies help you succeed?

Being organized and having a caring personality are the most important skills for success in this role. I believe that a company’s success is generated by happy people, so I try and keep that in mind when I request work from individuals. We ask a lot of design and dev teams, so I strive to maintain a caring mindset towards those team members. I rely on my organization skills to keep track of specific tasks and forecasting timelines for the future.

What’s the most fun or creative part of your role?

A digital producer position is a bit of a Swiss Army knife of a role. For the most part, the bulk of the work revolves around efficient resourcing of design and dev. But just like a lot of other positions at a smaller / medium sized company, you will wear a lot of hats. There is a lot of project management in this role which can be fun. Depending on what work is coming in, there can also be a bit of business development. I enjoy the variety of what’s asked of me and I dive into whatever I can get my hands on. I love learning about the business as a whole.

What are the biggest challenges you face in this role?

Since the digital producer role sits between client services and the design / dev teams, I need to interact with a range of personalities. Not everyone’s working style / personalities may be effective at efficient project and resource management, but you have to work through those challenges. For the most part, everyone means well and is trying their best, so having an understanding and caring mindset is important.

Another challenge is keeping design or dev teams to a timeline. When someone has something due and you need it from them, the relationship can quickly turn to a ‘means to an end’ interaction. Balancing an ask with humor and understanding is critical.

What teams/individuals do you work with cross-functionally? Can you give an example of a time when you collaborated with another group/individual?

I frequently work with all teams within my organization – business development, client services (account management), design, development. Recently, we received an ask from a client to develop an email template and then build it out. This project involved first working with the account manager to understand what was being asked. Then, I brought the idea to design to create a standard email template that matched their brand. Once we had a design, the project moves to our copywriting team to write engaging content for the emails. Finally, I brought the completed designs to development to work through creating the actual HTML that would be sent out.

What’s an area where you’re trying to grow in your role?

Forecasting the future is incredibly valuable for project management and efficient resourcing. I would say planning against multiple project deadlines and limited resourcing timelines is something I’m still trying to refine as I grow in this role. Mastering this skill helps organize and turn around good work at the same time giving a better work life for co-workers I care about.

Aside from technical skills, what personality traits/characteristics make for an ideal candidate in your role?

A strong EQ is necessary, since you’ll need to interact with a lot of people in this role. Critical thinking and organization is important as well, because timelines shift daily. Having an opinion about design can help, too. Occasionally, you’ll be asked to chime in on what you think about work. 

What skills (tech/non-tech) have you improved as a result of working in this role?

I am a lot more organized than I have been in the past. I have also tried to be conscious of how I come across to others more. In this role, it’s important to stay level-headed and kind regardless of how you feel, since colleagues across the other teams will feel your sentiments reverberate.

In your role, what metrics define success?

Project progress versus client timelines determines my success. As long as we’re making good progress and hit our deadlines as a design and development team, I’m doing pretty well.

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Role Models: Lindsay Hinman, Senior Project Manager at Sabre

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Today’s Role Model is Lindsay Hinman. Earlier in her career, Lindsay coordinated events and managed internal projects at different firms. Once she got a taste of managing a digital project from end-to-end, she was hooked on building products. Today, Lindsay blends her technical acumen with her strong communication skills as a Senior Project Manager at Sabre, a travel technology company.

What’s your official title and how long have you been in this role?

I’m a Senior Project Manager on the Digital Experience team. I started at Sabre in early 2017 as a Project Manager and transitioned into the Senior role about four months ago.


What attracted you to this role?

Ever since I led my first website redesign project in 2014, I was hungry for a role that allowed me to lead digital initiatives year-round. This opportunity promised (and delivered) a fast-paced environment with plenty of potential to learn and grow.


Walk me through a typical day in your role. What activities do you engage in? What types of meetings do you join? When’s lunch?

Meetings are pretty frequent. You can typically find me in stand-up meetings, weekly client check-ins, or internal planning sessions.

I also spend a good amount of time helping scope out new projects, evaluating client requests for enhancements, and performing iterative quality assurance testing. Outside of project-specific responsibilities, I focus on internal process improvement. Our team is very receptive to new ideas and ways we can work more efficiently.

Lunch is flexible; while it can sometimes be hard to step away, I usually take a break from screen time and go for a stroll.


What skills/technologies help you succeed?

I rely most on my communication skills in this role. It’s important to adjust communication styles based on the variety of audiences I speak with on the regular. For example, if the development team brings me a technical recommendation, I need to distill it into a more digestible summary for clients, while making sure nothing gets lost in translation.

Tech-wise, the tools can vary based on the type of project, but being well-versed in Jira can be a huge time-saver. Creating custom queries and dashboards can give a quick snapshot of project progress without having to scroll through an endless Kanban board.


What’s the most fun or creative part of your role?

I get really energized by requirements-gathering sessions and design review meetings. I’m enthusiastic about mapping out detailed pieces of functionality and achieving consensus among technical experts and clients alike. It’s exciting to build a razor-sharp vision of the finished product.

Also — QA! Finding and reporting bugs is a dream for a self-proclaimed pedant like myself.


What are the biggest challenges you face in this role?

Managing expectations among a variety of stakeholders is a common area for pitfalls; it can be challenging to ensure alignment on every detail of every project, but it’s critical in ensuring the client receives the products they expect. Documentation is clutch.

I think PMs can also struggle with time management, especially when overseeing a lot of initiatives simultaneously. It can be difficult to find blocks of time for focused tasks like QA among the sea of meetings and other tasks. I have a pretty robust priorities document for this reason.


What teams/individuals do you work with cross-functionally? Can you give an example of a time when you collaborated with another group/individual?

Collaborating with designers, front-end developers, back-end developers, and QA engineers is a huge part of my job. I work closely with our design team to bring the project vision to life while staying true to the client’s brand. I rely on our technical experts to assess the level of effort of client requests, confirm the best approach for those requests, and evaluate designs to ensure a seamless UX.

I also collaborate with account managers to gain a broader understanding of client priorities. This helps inform my client communications.


What’s an area where you’re trying to grow in your role?

I find it rewarding to collaborate with my fellow PMs and help them brainstorm solutions to creative problems, so I’m aiming to level-up my supervisory skills.

Also, there’s always more to learn in terms of code; I use our biweekly demos to soak up some technical knowledge from our scrum teams.


Aside from technical skills, what personality traits/characteristics make for an ideal candidate in your role?

The ability to keep calm under pressure. A common mantra among my team is “don’t pass the panic.” If something goes wrong on a client’s site and they are (understandably) anxious to have it resolved, there’s a way to communicate that sense of urgency without compounding everyone’s stress.

Additionally, curiosity is an important trait. Don’t hold back on asking questions. It’s good to get into the minutiae of business requirements and technical requirements to ensure the project runs smoothly.


What skills (tech/non-tech) have you improved as a result of working in this role?

My technical knowledge has grown exponentially since starting at Sabre; I’ve expanded my expertise particularly in content management systems (including a custom CMS) and in QA metrics like WCAG. I’ve also further honed my skills in project management tools; I consult a variety of platforms to craft and maintain my iterative plans across the roadmap.  

In terms of soft skills, I’ve gained substantial experience in client services overall, including handling difficult conversations with tact. I’m also much more comfortable with managing conflicting viewpoints and finding common ground among stakeholders with seemingly disparate priorities.

In your role, what metrics define success?

Put simply: Meeting deadlines. This requires a thorough understanding of the project’s scope and dependencies in order to map out an efficient and realistic project plan. Consulting with technical leads early and often is key. While I don’t need to know how to write code, I do need to “speak the language” enough to ask the right questions.

A more subjective measure is client satisfaction. It’s critical to know the client’s brand inside and out, especially when it comes to making pivotal decisions during the course of the project.

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