Office Hours: I'm the Obama Foundation’s head of product and technology. I've led product and tech at Squarespace, Twitter, and Facebook. I'm Gaby Peña Fraga.Featured

Hi everyone! I’m Gaby Peña Fraga, head of product and technology at the Obama Foundation. I oversee the Foundation’s product, technology development, and growth teams, as well as our related strategy and roadmap to scale the Foundation's mission to inspire, connect, and empower individuals to change their communities -- both in the Southside of Chicago (at the future Obama Presidential Center) and beyond, reaching future leaders and changemakers all over the world.Prior to joining the Foundation in August of 2019, I spent 10+ years leading product and technology teams at places like Squarespace, Twitter, and Facebook. I did my undergrad at Harvard and got an MFA in Design and Technology at the San Francisco Art Institute. Growing up in Peru and Brazil, in addition to spending my formative years constantly living and traveling internationally, contributed to a passion for global politics, policy, changemaking, and community building. Combined with my parallel passion for design and technology, these areas have become guiding principles for my active interest in thinking through how technology may be leveraged to magnify positive change in the lives of people around the world.Once a long-time resident of the Bay Area, I now live in Brooklyn. Ask me anything about leading technology teams, product management, civic impact, the intersection of policy and tech, and more!
Thanks so much for joining us @gpena!Elphas – please ask @gpena your questions before Friday, December 18th. @gpena may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
Hi Gaby,In the non- profit world, mission is the guiding force. This often leads to underinvestment in technology. I have seen this first hand during 11 years at a large non-profit that is going through its own digital transformation.What do you see as the digital roadmap for the Obama foundation and what principles would guide your build-buy-partner decisions, in service of the mission?
hi @gpena -I am working on creating an organization to work on economic development in the tech sector for my home state (where there is currently not a big tech presence). My thesis is that people in my home state need awareness and access to schooling/training so that they can participate as a knowledge worker in the economy - instead of having to work in lower wage service jobs. I have a couple of questions for you: 1) Would you have any recommendations on how to create an organization that helps as many people as possible obtain the skills they need to work in tech? 2) What are the skills of the future that people will need to work in tech/start tech companies? Do you think learning how to code is still important with the rise of no code?3) Does the Obama Foundation have any resources/programs I can apply to that would help me with my goals?thank you!
Hi Whitney!What an admirable organization you're starting, it sounds like! I have a lot of potential ideas on this that likely would be best discussed face-to-face, and when possible to get more background from you on your goals, target audiences, "inspiration" set of comparable orgs, etc.Shoot me a message, and we can grab some time to brainstorm!
Gaby - awesome, I would love that! I'll message you from my actual account (Whitney26 is an anon alias). Thank you!
Hello @gpena, thank you for the work you do. My question: any tips for current, basic strategies for those of us building civic impact communities from the ground up? I've noticed the landscape of communities has become quite busy lately, with the word sometimes being used as a Trojan horse for sales and marketing. How do you cut through the noise? Thank you!
Such a great question, and something definitely worth reflecting on. I'd love to hear more from you re: your experiences with civic impact communities, both as a "user" and as a "founder."In any case: the first two pieces that come to mind are: (1) offering differentiation and, relatedly, (b) optimized audience targeting. I'd agree that "online communities" have been multiplying as, to quote Ben Thompson in one of his latest issues of Stratechery, this is the era of "private interest-defined trusted groups." Those that have uptake/succeed, though, whatever the platform they happen to be on, are -- effectively -- those with a clear target audience + a truly differentiated offering (for that target audience, however niche). Starting small with folks that represent your "target audience" is wise, as they will help provide input and feedback on your offering differentiation. Then, once real sustained value is unlocked for that starter wave of community members, they will feel confident about bringing others like them to the community. If no sustained value is unlocked, that can be an indication for you on tweaks you can make to the offering -- or help inform whether you should pivot your audience focus.
Thank you so much @gpena, this is terrific!
What an inspiration! How does one get into product? My background is in digital marketing, but boy do I need a change.
Hi Briana! Thanks so much for your lovely note!I'll briefly quote a part of an answer I had for @leighchristopher -- "The advice I would have given to someone trying to break into product management 8 years ago is very different to the advice I give now. It used to be that PMs had to jump truly through so many hoops to be even considered for a PM role. I believe the discipline has evolved (in the right way!) this last decade, however, and these the best way to break into product management these days is just by doing the work -- and by demonstrating an undeniable ability to reliably and consistently ship good products, which solve real problems and that users love. Companies/hiring managers care less about your background these days, but about a combination of demonstrated experience and your having the raw attributes that make a good product manager."I'm wondering -- is there a way for you to finagle a way to work with a product development team as part of your current company?
Hi Gaby (@gpena), your background is an inspiration. Well done you! Very grateful for you taking the time to take questions and provide insights. According to in depth survey by Accenture, 81% percent of donors surveyed said it was important for them to know the real impact for their charitable donation and in return they would likely be willing to donate up to 10% more. Yet, many nonprofits and foundations have not yet fully embraced technologies to help provide more personal donor impact insights. My questions are: 1. What do you think of the concept of personalized donor reports that reflect the progress and impact of for an individual donors grants to supported charitable initiatives (vs. overarching organization impact reports)?2. In your opinion, what are the biggest hurdles preventing more agencies in the philanthropic sector from adapting technologies used in the private sector to generate efficiencies?3. What advice do you have for getting a foundations attention in order to demonstrate a new technology that can be used to generate efficiencies? Thank you in advance.
Hi Kerstin!Thanks so much for the lovely note and the great questions!I'll take them in order:1) I'm a big believer in feedback loops. Personalized donor reports seem like a great idea. For instance, I've always loved Watsi's approaches to donation/impact personalization and transparency: I can't really speak about philanthropic sector agencies, as we do most of our channel/campaign work in-house. I have some guesses, but not properly substantiated, so I'll defer to anyone better equipped to answer this question!3) Foundations are often resource-constrained, bandwidth-constrained, or both. Cold outreach is not the most effective, so I'd deprioritize that sales pipeline tactic. But when it does work, it tends to clearly point the recipient to proven examples of how comparable non-profit organizations benefitted from a new technology. Then, if there's a bite, there's something to be said about the importance of offering "trial" periods for more cash-constrained organizations, which may otherwise be hesitant to make an investment (even of the time required for implementation), unless the ROI is expected to be high and worth the money/effort.
@gpena - thank you so much for taking the time to respond to my questions. Super helpful. I’m a huge fan of Watsi. Their execution is superb and meaningful. Thanks for the link to the article very insightful. Happy holidays!
Hi @gpena ! Your work sounds amazing - thank you for sharing your experience with us! I would love to hear your thoughts on the role of tech and technologists in the not-for-profit world. Where is technology most needed for nonprofits? What kinds of problems can technology help solve for foundations and grant recipients? How can a technologist engage responsibly and productively with a non-profit organization or network? Basically: how can we help?
Emma! First off -- I'm in love with the bunny on your profile picture.Thanks so much for these questions! They are all very thoughtful.I should start by saying that I'm against the folly of a priori technological solutionism. Not every non-profit is or should be reliant on technology to achieve its goals.With that major caveat out of the way, - I do believe that a fuller-fledged digital transformation is happening, and most non-profits at the very least need to be able to stay up-to-date with that transition, as it has implications not only on operations but on how to best engage the groups and communities they serve.- I also believe that "product/design" thinking, and its emphasis on human-centricity, can do a great deal of good at non-profits and help streamline objectives, audiences of focus, and ways to measure impact -- even if the proposed solutions may not be technical in nature at all. - Lastly, I believe that a lot of non-profits do a lot of good in the world but are limited to how much good they can do, because their offerings/services haven't yet been scaled. This is where technology can help, and ensure that access to a particular offering a non-profit may have is further expanded.As for how to engage with a non-profit organization or network responsibly, I guess my main piece of advice is -- be ready to listen and learn. Whether it is in the cultural sector, government sector, etc., there are so many kinds of incredible expertise out there. True magic happens when different disciplines meet, interact, and build together.I'll end by saying that my take -- to date, at least -- is that our technologist DNA really does sets us up to do good things wherever need exists for making sense out of gnarly problems, leading despite fuzzy objectives, growing and nurturing multi-disciplinary teams of people, proving out and scaling ambitious ideas, and thinking expansively and innovatively -- especially in spaces where there’s been no natural discipline of mixing technology and other things... so there's a lot of opportunity, especially at this time, to get involved and add genuine value.
Hi Gaby, thanks for your thoughtful response! If you feel inclined to share more, could you describe an interaction between tech and a nonprofit was a great success? It could be introducing a new technology, or digitizing a process, or anything really! It sounds like you have seen this go really well in your career, and I would love to hear about some of your positive experiences.
@gpena I am helping Newness find a Dir of Product. Do you know someone that might be interested? We are giving out a $5,000 referral fee if someone you refer gets matched to the role (or $100 if they get interviewed) - as a way to compensate women for the networks they worked hard to build! PM / Dir of Product for Newness ( Looking for a founding PM or Head of Product depending on their experience. Candidate needs at least 3 years of work experience as a PM (no upper limit)- Needs to be willing to roll up their sleeves- Two female founders, from Twitch and FB Live- Team consists of early Twitch and early Glossier employees- Raised seed already (Sequoia led their round) and they are gearing up for a Series A in early 2021- Currently 12 employees- Comp in $150K range plus good equity package can email me at: [email protected]
Hi @gpena! As someone that transitioned from climate change policy into the technology and product management space, I'm particularly interested in your stories about how to use technology for making the world a better place. Specifically, I would love learn what's been challenging and what's been good about managing technology product development with a social mission at the Obama Foundation as opposed to managing product for a tech company like your previous employers? What advice would you give to women like me that are looking to have product management careers in the social and environmental space? Thanks for joining this community!
Hi Maria --I'm so excited to hear that you're considering this career transition! So much opportunity for impact!I'm clearly hugely biased, but my advice would be to take the leap. Particularly as someone with a dual background -- a product manager that is also a deep subject matter expert -- I bet there will be no shortage of opportunities for you. If you have been toying with the idea of making the switch for a while -- my strong "yes" would apply even more so. Some personal context: having fallen out of love with "tech proper" really since the mid-2010s, I had wanted to make the switch years before I actually could. As an H1B visa holder, and then a green card applicant, I didn't have job mobility for a long, long time (11 years, to be exact). This Foundation role was the first job I took shortly after receiving my permanent residency. It was all serendipitous timing. I got my green card, and then immediately took this job. I had always wanted to be a part of President Obama's campaigns and administration, but was unable to given my immigration status. It felt incredibly special to finally be able to join and be of service.Doing big things isn't easy, though, and that's the same whether you're in the private or the public sector. Resilience, scrappiness, stamina, passion -- these are needed everywhere. As President Obama says, "hard things are hard."At the Foundation, my task is figuring out how we scale our mission of inspiring, empowering, and connecting people to create change in their communities and in the world. Our vision for the portfolio of experiences we will make available virtually and at the future Obama Presidential Center in the Southside of Chicago in the coming years is to move individuals from a place of anguish, hope, and/or nostalgia to a sense of agency and belief in their ability to make positive change in the world. We are in the early days of building a digital and physical one-stop shop for anyone ready to embark on the path of community transformation, and for future leaders to find inspiration, community, and concrete resources that aid them in continuing charting their changemaking journeys.Lots of people and combined talents will be needed over the next few years to bring this vision to life -- engineers, designers, product managers, researchers, marketers, analysts, data scientists, technical program managers, community managers, localizers, content and media producers, infrastructure and hardware specialists, technicians, conservators, collections specialists, digital stewards, etc. As is the case with any startup in any industry, or with whatever market that has not yet been “disrupted” or gone through a digital transformation, the path hasn’t been and won’t be straightforward. It’s a challenge I still, on the daily, feel both urgency and excitement to take on.I can't really say I ever felt the same level of urgency or excitement in any of my past roles.
Hi, @gpena! So wonderful to see you thriving. Hello from a fellow, former tweep. 👋🏽
Hi, Kayla! Sending love your way!
So wonderful to e-meet you here @gpena! I would love to learn: how do you assess how many projects is "reasonable" to give a given PM or dev team? We are a super intimate team right now (5 FT, 1 PM and 1 dev), and I want to strike the balance of meeting our ambitious product goals (and keeping my ambition high, leveling up my team) without burning my team out or setting unrealistic expectations. Thoughts on this, or helpful reads and listens on the topic?
Thanks for the question, Alyssa, and it's great to e-meet you, as well!As we know, not all projects are made the same -- optimizing a landing page is not tantamount to creating a prototype for a new feature, much less a new product. The challenge of keeping a well-balanced portfolio of active initiatives, all stack-ranked in a way that maximizes ROI is ongoing, relatable, and tough...A question for you, which may help me provide a better answer to your question would be, to what degree is your team following the agile framework? And if they are following the agile framework, are the PM/Dev keeping track of level of effort for different tasks, and/or story points?
Really great q, thank you @gpena. We actually are using the agile framework! We are now making a concerted effort to get back into sprints in the New Year, as well. Q4 last year we found ourselves slipping back into ticket by ticket dev and deployment, especially as we had unexpected things arise that fed our roadmap but not necessarily in the order we were expecting. 2021, we're gearing up to have 80% of our resources focused on our sprints, leaving 20% for anything unexpected, bugs, things that pop up as a side effect of our deployments that we weren't expecting ,etc.
Hi Gaby, what an impressive background! I love that you have been able to build a career and find a role at the intersection of your passions-- policy and civic impact in addition to tech and product. I am not too familiar with tech/product roles at non-profits, even though the idea excites me. Could you tell us more about what it was like transitioning from very traditional "tech" companies (Squarespace, Twitter, FB, etc) to non-profit/more socially minded companies? How do the engineering/product cultures differ? Also, what are the key metrics you measure impact/success by (is there less emphasis on revenue, for example)?
Hi Michelle! Thanks so much for the lovely note.To answer your first couple of questions: the answer is, "it depends!" The specifics of one's transition and the perceived difference in product/eng cultures will likely range based on the level of product/technology maturity a given non-profit or socially minded company has. There are non-profits, like TED Conferences for instance, which have very mature product/technology cultures and have been tech-native from the beginning. As a result, moving there from a more "regular" technology organization may not feel too different, for instance.A great number of mission-oriented organizations, though, are in the germinal stages of digital transformation. Oftentimes, you may even be their first technology/product hire. As such, your experience there may be very different than, say, a TED, and you may be tasked with not only product/technology planning, strategy, execution, but with a great deal of education and evangelism, hiring, process setup, etc., as well. My recommendation, were you to be interested in a potential switch, would be to gauge your level of comfort stepping off the known and into a place where *you* may need to be the driver of product/technology maturity. The answer to this question can help narrow down which kinds of mission-oriented organizations may be the best fit.In either case, my quick plug for anyone interested in transitioning to the non-profit, civic, or government space is this: these are among the areas most in need of well-rounded, innovative leadership. Your backgrounds in "tech proper" are sure to be invaluable in helping mission-oriented organizations develop a deep, contextual understanding of the problems they seek to solve and then figuring out what resources, what talent, and what kind of community they need to have their best shot at addressing those problems.
As for KPIs, these also vary by organization. Most non-profits have a documented "theory of change" with a clearly stipulated measurement and evaluation framework. This framework may not always be easily equatable with the universe of dashboards we are familiar with, but they effectively act as organizational KPIs, at any rate.Beyond these core indicators, growth/marketing funnel-like metrics are as top-of-mind at non-profits as they are at for-profits, even if notions, definitions, and methods for reach, acquisition, activation, and retention may vary.Depending on the organization, fundraising metrics (whether fundraising is online/grassroots or more traditional) are also considered to be KPIs and are constantly monitored.
Thanks for the thorough response @gpena!
Wow - Hey Gaby! It's been a long, long time since the Twitter days. Just saw your name and wanted to say hi! Amazing what you've accomplished. Congratulations.
Hi Sofi! I hope you're doing great! Sending love right back!
Hi @gpena! What an impressive resume! I have been considering product management as a future career option but I have little experience in this area. My background is in academia (science) and now I work in behavioral consulting but I have a passion for technology. It seems like as a product manager you would learn great management skills, get to be connected to several different teams/ domains, and think strategically about solving big challenges. It also seems like a great job for someone with an entrepreneurial spirit.My question for you is:1) Do you think the above is true, that product management allows you to think strategically and feel connected to multiple domains (i.e. design, data, strategy, business)?2) What is your favorite thing about product management?3) What advice would you give to someone trying to break into product management from a very different field?Thanks!
Hi there, it would be great to learn more about your work in behavioural consulting :)
I second that!
Hi Leigh! Thanks so much for the note -- and I mirror the admiration! PMs (current and former), do please feel free to interject at any point, but here's a first stab at some answers:1) Hundred percent. Product management as a discipline definitely allows for this.2) There are so many things I love about managing products, but likely the top one is that as a career path, it is so anathema to monotony. There are no two days that look the same as a PM -- every day is an adventure in creative problem-solving, rapid learning, quick (but confident) decision-making, and constant collaboration.3) The advice I would have given to someone trying to break into product management 8 years ago is very different to the advice I give now. It used to be that PMs had to jump truly through so many hoops to be even considered for a PM role. I believe the discipline has evolved (in the right way!) this last decade, however, and these the best way to break into product management these days is just by doing the work -- and by demonstrating an undeniable ability to reliably and consistently ship good products, which solve real problems and that users love. Companies/hiring managers care less about your background these days, but about a combination of demonstrated experience and your having the raw attributes that make a good product manager.