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Nathan Milford

Fault-Tolerant Byzantine General, Artisanal Emojivore, and The Willy Wonka of Distributed Systems

Nathan Milford is currently the Chief Technology Officer (CTO) at Pumpkin, a pet care company focused on pet insurance and wellness.123 He has a strong background in technology leadership, having previously held positions such as Head of Technology and Head of Engineering at Pumpkin.4

Milford is known for his expertise in:

  • Building high-performing, psychologically safe teams
  • Mentoring new managers into leadership positions
  • Managing global, remote teams
  • Executing long-term projects while meeting short-term business needs
  • Working in both startups and large public companies
  • Handling multi-million dollar budgets

His experience spans various industries, including AdTech, FinTech, and RegTech, with a focus on both direct-to-consumer and enterprise products.4 Milford has a BA in Film Production from Brooklyn College.24

Prior to joining Pumpkin, Milford held leadership positions at other companies, including:

  • SVP of Technology and VP of Engineering at PerformLine
  • Director of Engineering, Backend & Infrastructure at Shutterstock
  • Engineering Manager, US Operations at Outbrain4

At Pumpkin, Milford is part of the leadership team working to improve pet health care accessibility and affordability through innovative insurance and wellness products.3

Highlights

Aug 2 · linkedin

I love the story of the Pontiac Aztek. I always have to dig this one up every other year or so.

My Dad worked at GM while I was growing up, worked on the Pontiac Grand Prix and the Chevy Malibu at the plant in Kansas City. He'd take me on tours as a nerdy kid, I'd see the assembly line, meet all the folks from beginning to end. It was a wonderland and the people I met all loomed large in the pantheon of stories he'd tell me.

I can see and hear their motivations and experiences as quoted in this article: “I’m proud of it.” Proud of the Aztek? “Yup. That was the best program we ever did at GM. We made all our internal goals, we made the timing, and I’m really proud of the part I played in it.”

A top-down culture where a few dominant voices suppress feedback creates an environment where creativity is stifled. When your engineers are not an active participant in defining and solutioning for the problem at hand and when thier feedback is not solicited, they will happily focus that energy on execution within the narrow bounds created for them. 'Oh, my input isn't needed, I'll tie my value to output'

The Aztek serves as a cautionary tale about the importance of fostering a culture of open communication and aligning a team's internal sense of value with business outcomes, and not to the words of the loudest voices.

Aug 1 · linkedin

A Plan Is Not a Strategy!

I love this video so much and I've shared versions of it with lots of tech leads and engineering managers over the years. This is the shorter version.

For me, it's almost a comfort watch, to help orient me.

As we enter the strategic planning season, it's so easy to be seduced by the comfort of a plan, a budget, some bullet points and watch your team elegantly, and happily hit milestones, or tick off check boxes while the business struggles.

What makes a strategy both intimidating and powerful is its lack of strict guidelines. It should feel a bit uncomfortable. A plan can be restrictive and shift accountability, whereas a well-crafted strategy is generative in that it fosters agency and alignment, empowering people to solution together and independently navigate changing circumstances.

Related Questions

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Nathan Milford
Nathan Milford, photo 1
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Location

Brooklyn, New York, United States