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Building partnerships w/ complex stakeholders, aligning tech debt w/ business value & decisive vs. thoughtful decision-making

with Funmi Oludaiye, Ketan Gupta, and Sasha Hall

April 22, 2025
Building partnerships w/ complex stakeholders, aligning tech debt w/ business value & decisive vs. thoughtful decision-making
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In this episode, we’re back with more insights from our local community leaders — discussing leadership insights on strategic decision-making, managing technical debt and fostering true cross-functional partnerships! Funmi Oludaiye (New York City) shares strategies for building strong cross-functional relationships between eng & business leaders. Ketan Gupta (London) breaks down the STIR framework for managing tech debt & aligning it with business value. And Sasha Hall (Toronto) works through examples of how to balance decisive (fast) vs. thoughtful (slow) decision-making. You’ll also learn some of these leaders’ best tips for diving in & getting involved with your local ELC community!

ABOUT FUNMI OLUDAIYE

Funmi is a Managing Director and the Head of the Digital Risk Office for Enterprise Partnerships at Goldman Sachs, where she is pioneering a first-of-its-kind global initiative to embed critical business, security, and engineering risk practices within the engineering organization. With nearly 15 years of experience as a software engineer, architect, and engineering manager, she has a proven track record of leading high-performing teams, delivering innovative technology solutions, and championing best practices in developer experience and productivity across large-scale engineering teams. Most recently, she was the Head of Engineering for Consumer Deposits at Marcus by Goldman Sachs, and prior to that, she led the product engineering teams that built and launched the firm's award-winning credit card partnerships with Apple and later, General Motors. Funmi is a passionate advocate for underrepresented groups in the technology industry and is committed to mentoring the next generation of engineering leaders. Her wealth of experience and dedication to driving positive change make her a sought-after speaker and advisor.

ABOUT KETAN GUPTA

Ketan is a seasoned engineering leader with 13+ years in software development, cloud, architecture, product delivery, and organizational leadership. He excels at building high-performing engineering teams and driving strategic initiatives. As an active community builder, he contributes to the Engineering Leaders Community and champions software craftsmanship.

ABOUT SASHA HALL

Sasha Hall is an Engineering Manager at Planitar Inc, makers of iGUIDE. A University of Waterloo graduate with over 5 years of leadership experience at Pegasus Aeronautics and Deep Trekker, Sasha brings valuable insights on decisive leadership, effective communication, and strategic vision in growing organizations. Their career path through underwater robotics at Deep Trekker, aerial drone systems at Pegasus Aeronautics, and spatial mapping technologies at Planitar showcases a passion for innovative hardware and sensing solutions. This diverse technical background, combined with consistent leadership dedication, has equipped Sasha with a unique perspective on navigating today's complex engineering challenges.


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SHOW NOTES:

  • Funmi discusses why successful eng leaders build true partnerships between engineering & business stakeholders (1:58)

  • Navigating the dynamics of engineering & cross-functional team partnerships (3:00)

  • Creating alignment / building relationships through fostering trust & curiosity (4:42)

  • How engaging w/ curiosity is key to building cross-functional relationships (7:21)

  • Funmi’s framework to help identify gaps in understanding (8:56)

  • Recognizing knowledge gaps and relying on subject matter experts (10:15)

  • Tips for navigating partnerships with multiple stakeholders (13:14)

  • What’s going on with ELC New York & the power of connecting with eng leaders (14:45)

  • Ketan discusses cloud transformation and AI integration (17:08)

  • Considering challenges w/ security, scalability, cost, flexibility & AI in cloud vs. hybrid migrations (18:04)

  • Explaining the impact of technical debt on organizations (20:04)

  • The STIR framework for managing tech debt during cloud migrations (21:17)

  • Translating tech debt into business value w/ STIR (24:17)

  • Separating continuous improvement / performance from tech debt (27:02)

  • Understanding team strengths & bolstering team motivation (29:24)

  • Ketan’s experience with ELC London (31:07)

  • Have fun with decision-making (33:29)

  • Sasha discusses optimizing team processes amid company growth & new hires (35:11)

  • Effective decision-making - balancing being decisive & thoughtful (37:36)

  • Examples of balancing quick decision-making w/ thoughtfulness (39:05)

  • How to refactor repetitive tasks to improve efficiency (40:32)

  • Balancing time, risk & impact in decision-making processes (42:06)

  • The value of building a network & finding mentors outside your own company (45:03)

  • Advice for jumping into ELC community events (47:41)


This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Dive in

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