Operator Resources

Insights from the Operators Guild community

Member Spotlight

August 19, 2026

Q&A with Darcey Bennett, OG DC member and independent operator

Get to know Darcey Bennet

Recent articles.

Member Spotlight

August 14, 2026

Q&A with Darcey Bennett, OG DC member and independent operator

The AI native operator: How to stay essential as the role changes

Build with AI: How to build AI tools for non-engineers

How to take AI builds from demo to production

How operators choose AI platforms and drive team adoption

Stablecoins for finance teams: what they are and where they create value

Building a GTM engineering function that earns its keep

OG Summit 2026 Recap: Why the next decade belongs to the operator

Member Spotlight

Q&A with Solu Nwanze, VP of Operations and Chief of Staff at Reltio and founder of Teams Who Win

How to lead from your values when scaling gets hard

Member Spotlight

Two bets and a lesson learned: A Q&A with Kevin Noble on building something of your own

Building gender equity into how your company actually operates

Member Spotlight

Why the best leaders refuse to be defined by one function with Jon Michaels

Why your AI platform is already an operating system (and how to use it like one)

Being data-driven at every stage: what actually works

The new AI cost playbook for finance and operations leaders

February 4, 2026

How AI changes the operating metrics behind modern software companies

February 2, 2026

ETA unfiltered: The risks, regrets, and realities of buying a business

January 23, 2026

Making usage-based pricing work across finance, sales, and product

December 10, 2025

How to build a feedback culture into your scaling organization

Member Spotlight

November 24, 2025

Two wins, one lesson learned, and a career built on doing the right thing with Rob Owen

November 12, 2025

Scaling teams from series A to D: what operators need to get right

Member Spotlight

November 4, 2025

Q&A with Maxwell Bonnie, co-founder of Saltbox and OG Atlanta chapter lead

October 15, 2025

Focus Session: Scaling BizOps

Member Spotlight

October 1, 2025

Q&A with Viviane Crosthwaite, VP of Operations at Esper and OG Denver Chapter Lead

Debt decoded: How operators analyze debt structures

Debt decoded: Analyzing debt structures

The three leadership mistakes that quietly break teams and what strong operators do instead

Member Spotlight

August 19, 2026

Q&A with Darcey Bennett, OG DC member and independent operator

How to lead from your values when scaling gets hard

Member Spotlight

Q&A with Solu Nwanze, VP of Operations and Chief of Staff at Reltio and founder of Teams Who Win

Member Spotlight

Two bets and a lesson learned: A Q&A with Kevin Noble on building something of your own

Building gender equity into how your company actually operates

Member Spotlight

Why the best leaders refuse to be defined by one function with Jon Michaels

January 12, 2026

The three leadership mistakes that quietly break teams and what strong operators do instead

Member Spotlight

January 9, 2026

Q&A with Maxwell Bonnie, co-founder of Saltbox and OG Atlanta chapter lead

Member Spotlight

Two wins, one lesson learned, and a career built on doing the right thing with Rob Owen

Member Spotlight

November 27, 2025

Q&A with Viviane Crosthwaite, VP of Operations at Esper and OG Denver Chapter Lead

Member Spotlight

August 19, 2026

Q&A with Darcey Bennett, OG DC member and independent operator

Member Spotlight

Q&A with Solu Nwanze, VP of Operations and Chief of Staff at Reltio and founder of Teams Who Win

Member Spotlight

Two bets and a lesson learned: A Q&A with Kevin Noble on building something of your own

Member Spotlight

Why the best leaders refuse to be defined by one function with Jon Michaels

Member Spotlight

January 9, 2026

Q&A with Maxwell Bonnie, co-founder of Saltbox and OG Atlanta chapter lead

Member Spotlight

Two wins, one lesson learned, and a career built on doing the right thing with Rob Owen

Member Spotlight

November 27, 2025

Q&A with Viviane Crosthwaite, VP of Operations at Esper and OG Denver Chapter Lead

Building a GTM engineering function that earns its keep

OG Summit 2026 Recap: Why the next decade belongs to the operator

Why your AI platform is already an operating system (and how to use it like one)

Being data-driven at every stage: what actually works

February 24, 2026

How AI changes the operating metrics behind modern software companies

February 24, 2026

ETA unfiltered: The risks, regrets, and realities of buying a business

December 10, 2025

How to build a feedback culture into your scaling organization

December 1, 2025

Scaling teams from series A to D: what operators need to get right

November 27, 2025

Focus Session: Scaling BizOps

Stablecoins for finance teams: what they are and where they create value

The new AI cost playbook for finance and operations leaders

February 24, 2026

Making usage-based pricing work across finance, sales, and product

January 12, 2026

Debt decoded: Analyzing debt structures

November 27, 2025

Debt decoded: How operators analyze debt structures

The AI native operator: How to stay essential as the role changes

August 19, 2026

Build with AI: How to build AI tools for non-engineers

How to take AI builds from demo to production

How operators choose AI platforms and drive team adoption

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