“We live in a world today where we spend a lot of time in these places that are made of information instead of being a physical place.” Larry Port talks with Emily Claflin, an information architect at The Understanding Group, about structuring and organizing information in ways that are useful to people. The conversation moves from websites, intranets, and apps to enterprise environments where you cannot make the complexity go away, but you can bring clarity. Emily shares a career story that starts with history and sociology, a year of service with AmeriCorps, public libraries, a master’s in library and information science, and then an internship that became full-time work. Along the way: talk to your professors, because all sorts of opportunities open up. The conversation also touches on AI, search, browsing, and chat, as well as “garbage in, garbage out,” ethics, and navigating organizational complexity.

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Emily Claflin is an information architect with The Understanding Group. She came from library science, worked in a local public library system, and did her master’s program fully online while working full-time. She took a class in information architecture, got an internship, and then went from hourly, part-time work while finishing school to full-time work. She also talks about serving as a conference chair and selecting a theme such as “navigating complexity.”

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• What an information architect does: give structure to information, organize it, and make the most important information the easiest to find and the easiest to use
• Complex information environments: clarity, relevance, and “one kind of person with one particular goal”
• Information architecture and user experience design: a blurry line, “behind the scenes,” and “hopefully you never notice it”
• A career that was not a clear end goal: history and sociology, Spanish minor, study abroad, AmeriCorps, public libraries, and a master’s degree
• Talking to the deputy director, getting a mentor-like conversation, and planning “three or five years from now”
• Research as a prerequisite: recruiting, interviews, trade shows, and synthesizing insights into shared artifacts and models
• Who does well in the role: naturally curious, okay with ambiguity, and sees the forest and the trees at the same time
• AI, ethics, and information retrieval: search, browse, and now chat, plus “garbage in, garbage out”

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• Emily Claflin
• Larry Port
• The Understanding Group
• IA Conference
• AmeriCorps
• Facebook
• LinkedIn
• Zoom
• SharePoint
• GED classes

People trying to figure out what they wanna do for a living hear Larry Port talk with his good friend Alejandro Dao, lead product manager at Pendo.io, a very cool and innovative software company in North Carolina. Alejandro describes product management as leading the product's vision and strategy, deciding what to build next and why, and working with engineering, design, and customers.

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He compares the role to a quarterback and an orchestra director, keeping the tempo and pace of software development and making sure everybody knows what they are building and why. Alejandro shares a mix of tactical and strategic work, from sprints and steel threads to roadmap meetings, user empathy, and many conversations with customers.

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The conversation walks through his trajectory from a shy kid and Model UN to a support engineer, software developer, sales engineer, sales operations manager, MBA at Duke, an internship at Amazon, and landing at Pendo in Raleigh, North Carolina.

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👤 Guest Bio

Alejandro Dao is a lead product manager at Pendo.io in North Carolina. Originally from Venezuela, he has a background in computer science and engineering. Alejandro started as a support engineer and software developer at Rocket Matter, then moved into sales engineering, solutions engineer, and sales operations manager, owning Salesforce and sales processes.

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He completed a two-year MBA program at Duke’s Fuqua School of Business and used that to pivot into product management. After a technical product management internship at Amazon, he chose to stay in North Carolina. He joined Pendo, where he owns the guides product and spends a lot of time with engineering, design, and customers.

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📌 What We Cover

• What a product manager is, leading the vision and the strategy of the product, deciding what should be built next and why, and working with engineering, design, and customers
• Quarterback and orchestra director analogies for product management, keeping the tempo and pace of software development, so everybody knows what they are building and why
• Concrete examples from Pendo, with two big pillars, analytics and guides, and Alejandro owning the guides product and crafting what the vision of the product is going to be
• Day-to-day work that mixes tactical and strategic, from sprints, steel threads, and compromises to roadmap meetings, senior leadership, and a lot of meetings with customers about frictions, frustrations, and use cases
• Communication and empathy as critical soft skills, including stories from Rocket Matter, working with attorneys under a lot of pressure, and flexing that empathy muscle
• What it is like to work with engineers and UX designers, speaking the same language, rowing in the same direction, building prototypes together with tools like Bolt, Lovable, and V zero, and using AI as a superpower, not a replacement
• Alejandro’s path froma shy kid and Model UN, into computer science and engineering, video games, Florida Atlantic, a career fair conversation about Atlas Shrugged, and eight years at Rocket Matter in multiple roles
• Moving into sales engineering, solutions engineer, and sales operations manager, owning Salesforce integrations, automating syncs, and modernizing sales processes
• Why Alejandro wanted an MBA at Duke, filling knowledge gaps in accounting, finance, and business administration, and how the hardest part was getting in, not the...

Larry Port talks with Patrick Leary about his career in finance, bond trading and sales, work-life balance, and what this job is like on a day-to-day basis at Loop Capital on the Dream Job Cafe podcast. Patrick talks about the bond market, how bonds do not trade on an exchange like stocks, why it takes actual people to make these transactions happen, and how an old-school market still has an electronic component. They walk through market hours, inventory, and the firm's risk position, travel with clients, and take advantage of the extra credit hours that come with being successful in this industry. Patrick shares how he moved from medicine and pre-law to the business school, an internally managed stock fund, and a junior trading intern role at a bank trust company. He describes how a professor who said he would teach how the world really works changed his financial literacy, why bond trading clicked, and how AI, algorithms, bespoke products, and large language models may shape the future for young people who are curious about this path.

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Patrick Leary is the managing director and head of trading at Loop Capital, leading the firm's fixed income division. His work sits in the bond market, trading government bonds, corporate bonds, muni bonds, and mortgage-backed securities with institutional clients. Patrick manages the firm's inventory and risk position, blending sales and trading with risk management and client service. He started as a junior trading intern at a local bank trust company in St Paul, trading equities and many different types of fixed income instruments on the buy side before moving to the broker-dealer world.

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• What this job is like for a head of trading in the bond market, from market hours and being tied to the bell to lunch breaks on the desk and work-life balance across time zones.
• How sales, trading, and risk management fit together, including inventory, client warehousing risk, and the differences between institutional clients, banks, hedge funds, money managers, and public entities.
• Patrick’s path from thinking about medicine and law to pre-law, the business school, an internally managed stock fund, and a professor who said he would teach how the world really works.
• Early experience as a junior trading intern at a bank trust company in St Paul, trading equities and many different types of fixed income instruments on the buy side before moving to a broker-dealer.
• The role of salespeople has changed, from entertaining clients with ball games and great dinners to using technology tools, electronic trading, and a more sophisticated, knowledgeable sales staff.
• The future of bond trading and sales, including commoditization and electronification, algorithms and trading programs, cryptocurrencies and stable coins, and bespoke products that are not easy to commoditise.
• The temperament and skills that help in this industry, like comfort with risk, thick skin, next trade mentality, networking, internships, and using AI and large language models as a calling card for young people.

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• Larry Port