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

Strategic career skills and the job market today are the focus as Larry Port sits down with his old friend Peri Ginsberg, founder and head coach of Workforce Ready Now. Peri works heavily with college graduates, new graduates, and really early stage professionals who are navigating the workforce and feeling the pressure that the first job is going to make or break their entire career.

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Peri shares how careers are rarely linear, how any job is going to teach you something, and how her own pivots from civil and environmental engineer to management consulting, Office Depot, and entrepreneurship built the wherewithal to do what she is doing today. Larry and Peri walk through what applicant tracking systems actually are, why they are not AI or a robot, and why keyword matching and formatting can stop you from getting an interview. They talk about the seven second test for resumes, students getting ghosted after hundreds or thousands of applications, and why networking, LinkedIn outreach, and relationship building are still the secret to landing jobs right now.

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Peri Ginsberg is the founder and head coach of Workforce Ready Now and works heavily with college graduates, new graduates, and really early stage professionals in navigating the workforce. Educated as a civil and environmental engineer, she did that for a couple years, then transitioned into management consulting, which she really loved. After relocating to South Florida for family reasons and no longer being able to travel, Peri became a director in the project management office at Office Depot. Eventually she departed from the corporate lifestyle because she had that entrepreneurial bug, ran a hair salon for children, and pivoted through multiple roles that set her up for success as a coach on resumes, networking, and interviewing.

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• Why careers are rarely linear, why that first job is not going to make or break your entire career, and how any job is going to teach you something, even what you do not like.
• Peri’s own pivots from civil and environmental engineer, to management consulting, to director in the project management office at Office Depot, to entrepreneurship and Workforce Ready Now.
• What applicant tracking systems are, why the ATS is not AI, not a robot, not an evil thing that is out to get you, and how must haves, nice to haves, and keyword matching score your resume.
• How pictures, a fancy logo, text boxes, and untraditional formatting can throw off the ATS, stop the system from parsing text correctly, and stop you from getting an interview, plus why ATS compliant templates matter.
• The difference between what the ATS cares about and what a human hiring manager cares about, including headings, dates, Times New Roman, tight spacing, one page resumes for college kids, and Peri’s seven second test with strategic bold and a touch of color.
• The Wall Street Journal picture of students sending out hundreds or thousands of resumes, getting crickets and being ghosted, blaming an evil applicant tracking system, and why networking is still essential.
• Networking that scares this generation, growing up behind a phone screen, the fear of picking up a phone and saying hello, and Peri’s coaching on LinkedIn messages that simply ask for a chat and information, not “Hey, will you hire me?”
• The Florida State and MLB story of Peri’s son, customized 300 character LinkedIn messages to three people at every MLB team, a call with someone at the Tampa Bay Rays, and an advocate who made sure three hiring managers had his resume in hand.
• Peri’s...