Your Next Move: How to Lead on the Front Lines of the AI Boom
Release Date: July 1, 2025 | Produced by Inc. and Capital One Business
In the latest episode of Your Next Move, host Mike Hoffman engages in a compelling conversation with two trailblazing female entrepreneurs: Jacqueline Samira, Founder and CEO of Howdy.com, and Isa Watson, Founder and CEO of Squad. The discussion delves into navigating leadership during the rapid advancements of the AI era, addressing challenges, opportunities, and the evolving landscape of technology and business.
1. Introducing the Innovators
Mike Hoffman (00:16):
Kicking off the episode, Mike introduces the guests, highlighting their unconventional paths into the tech industry.
Jacqueline Samira (00:46):
Howdy.com serves as an outsourced logistics hub for U.S. tech companies aiming to build software development teams in South America. From recruiting to payroll, howdy.com facilitates the entire process, operating in multiple Latin American markets including Brazil, Argentina, Chile, Peru, Colombia, Mexico, and Santiago.
Aiza Watson (01:08):
Squad is a fan engagement and data analytics platform tailored for professional sports teams, with clients spanning the NBA and WNBA.
2. The Evolving Tech Talent Landscape
Tech as an Intelligence Company (02:05 - Jacqueline Samira):
Jacqueline emphasizes that modern tech companies must evolve into intelligence companies. This shift involves:
- Vetting Technical Talent: Assessing how candidates utilize AI tools and their approach to coding and documentation.
- Adapting to AI: Evaluating candidates' ability to adopt and integrate AI technologies into their workflows.
“If they're coding the way they did six to twelve months ago, they're already outdated.” (02:40)
Importance of Documentation and Technical Debt (02:41 - Aiza Watson):
Aiza echoes Jacqueline's sentiments, stressing that strong documentation is more critical than ever to prevent technical debt accumulation. She highlights the necessity of building clean, well-documented code to maintain agility and efficiency.
“The ability to have very strong documentation... is incredibly important with how fast things are moving.” (03:20)
3. Skill Development and Mentorship
Developing Skill Sets (03:24 - Jacqueline Samira):
Jacqueline discusses the dual approach of ensuring foundational computer engineering principles and supplementing knowledge gaps through targeted training in AI tools and computer science fundamentals.
Incorporating Mentorship (04:06 - Aiza Watson):
Aiza highlights the role of mentorship in continuous skill development, pointing out that mentorship helps engineers iterate and enhance their capabilities beyond existing leadership.
“Having people like the first ten engineers at Snap... has been really, really helpful and game changing.” (04:51)
4. Leadership and Communication in Tech
Managing Tech Teams (05:12 - Aiza Watson):
Aiza outlines practical steps to foster effective tech team management:
- Regular Check-ins on Technical Debt and Documentation: Ensuring code quality and up-to-date documentation.
- Balancing Speed with Process: Implementing necessary processes to maintain code excellence without stifling agility.
Encouraging Communication (06:09 - Jacqueline Samira):
Jacqueline emphasizes that communication issues often cause discrepancies between engineering output and business expectations. She advocates for empowering employees to speak up about challenges to avoid project pitfalls.
“So much of what we've learned... is how to give people the tools to be able to communicate properly.” (07:02)
5. Product Management in the AI Era
Role of Product Managers (09:48 - Jacqueline Samira & Aiza Watson):
Both Jacqueline and Aiza discuss the heightened importance of product managers in aligning technical and business teams. Aiza notes the rise in required standards for product managers, emphasizing technical fluency and strategic thinking as essential skills.
“Product management is an alignment role... there’s a level of strategic thinking that is really, really important.” (11:45)
6. Perspectives on AI: Optimism vs. Neutrality
AI Optimism (13:19 - Jacqueline Samira):
Jacqueline shares her optimistic view on AI, drawing parallels with historical technological advancements that created new opportunities and jobs. She foresees AI as a powerful tool that can level the playing field globally.
“AI is an inclusive, incredibly powerful tool... I’m really excited to see what comes from that.” (14:41)
AI Neutrality (Aiza Watson):
Aiza adopts a neutral stance, acknowledging both the potential benefits and drawbacks of AI. She expresses concerns about the impact of AI on the job market and the importance of foundational engineering knowledge.
“I think from a macro perspective it is going to create a very hard job market.” (14:41)
7. Implementing AI in Organizations
Personal and Organizational Use of AI (22:15 - Jacqueline Samira & Aiza Watson):
Jacqueline shares innovative uses of AI within her company, such as an AI bot that replicates key company information to streamline internal queries and developing AI-driven performance review tools to ensure objectivity.
Aiza discusses leveraging AI for process management, including note-taking, predictive analytics for sports teams, and enhancing customer service through AI-driven solutions.
“Performance management shows people that you care about what they've done throughout the year.” (23:55)
8. Investments and Strategic Priorities
Investing in AI Education (28:25 - Jacqueline Samira):
Jacqueline details how howdy.com invests heavily in AI education for her team, offering free courses to bridge knowledge gaps and enhance productivity.
AI and Predictive Tools (30:08 - Aiza Watson):
Aiza highlights Squad’s investments in AI and predictive analytics to help sports teams enhance first-party data collection and unlock new revenue streams.
9. Funding and Entrepreneurship Challenges
Funding Experiences (42:08 - Jacqueline Samira & Aiza Watson):
Jacqueline discusses her bootstrapped journey, the pivotal role of Y Combinator in securing VC interest, and the importance of social proof in fundraising.
Aiza shares the challenges of fundraising, including facing numerous rejections and the critical role of building strategic sponsorships within Silicon Valley.
“Fundraising is actually one of the most painful things for me as a founder...” (43:26)
10. Technology Tools and Tech Stacks
Favorite Tech Tools (54:23 - Jacqueline Samira & Aiza Watson):
Jacqueline recommends tools like Fixer AI for email management, ClickUp for task organization, and Gong for sales call transcriptions.
Aiza shares her preferences for Fireflies for AI note-taking, Notion enhanced with AI for task management, and Superhuman for efficient email prioritization.
“Fixer AI is like having a personal executive assistant with you at all times.” (54:23)
Assessing Tech Stacks (56:01 - Aiza Watson & Jacqueline Samira):
Aiza emphasizes monitoring error rates and usage-driven costs, while Jacqueline focuses on cost-effectiveness and ROI when evaluating tech tools.
11. Female Leadership in Tech
Experiences as Female Founders (38:14 - Jacqueline Samira & Aiza Watson):
Jacqueline discusses the challenges of being taken seriously initially and the advantage of maintaining focus without external distractions. Aiza shares her approach to overcoming biases by projecting confidence and leveraging her technical background.
“I have to come into the room with way more than a lot of these guys.” (40:36)
12. Future Moves and Expansion
Next Steps (47:15 - Jacqueline Samira & Aiza Watson):
Jacqueline plans to continue scaling howdy.com while maintaining focus on revenue and cost metrics. Aiza aims for global expansion, targeting markets in Europe, South America, and Africa, adapting to cultural and language nuances.
Conclusion
The episode underscores the pivotal role of communication, continuous learning, and strategic investment in leading tech-driven businesses through the AI boom. Both Jacqueline and Aiza provide invaluable insights into balancing technological advancements with human-centric leadership, fostering environments where innovation thrives alongside robust operational practices.
Notable Quotes:
- “If they're coding the way they did six to twelve months ago, they're already outdated.” — Jacqueline Samira (02:40)
- “The ability to have very strong documentation... is incredibly important with how fast things are moving.” — Aiza Watson (03:20)
- “Performance management shows people that you care about what they've done throughout the year.” — Jacqueline Samira (23:55)
- “AI is an inclusive, incredibly powerful tool... I’m really excited to see what comes from that.” — Jacqueline Samira (14:41)
- “Fundraising is actually one of the most painful things for me as a founder...” — Aiza Watson (43:26)
Stay Connected:
Tune in to future episodes of Your Next Move for more conversations with industry leaders and innovators shaping the future of business and technology.