Take your business to its next stage.Built with you, not for you.
From a first idea to a scaling operation, OS Consulting meets you where you are. Tell me where you are and I'll take you to what fits, or browse every path below.
I'm Jack Bigelow. For over a decade I've built the revenue operations, GTM strategy, and AI systems behind high-growth cloud, SaaS, e-commerce, and devices businesses, across portfolios up to ~$200B at Microsoft, AWS, and Amazon. I build the strategies and frameworks that unlock revenue, and the AI applications, including autonomous agents, that make them run.
How I operate
Decisions start with data, and anecdotes.
Simplify, standardize, scale. Then innovate.
People are the business. Build trust, build reach.
Strategy demands operational grounding.
Now, think bigger.
Where are you?
What I can do for you
Nothing matched that path yet. .
You bring the idea. You leave with the skills, the app, and the business around it.
The cost of building just collapsed. What used to take a dev team, a year, and a funding round now takes a focused person and the right guidance. I'll teach you to build with today's AI tools, stand up the business around it, and get you submitted to the App Store, then hand you the keys so you keep building yourself.
You've had the idea for years. The quotes came back at six figures and six months; everyone said learn to code, hire a team, or raise a round first. So it sits: a note on your phone, a someday.
That wall just fell. Today's tools have cut the cost and time of building to a fraction of what the gatekeepers still quote. The bottleneck isn't money or a dev team anymore. It's knowing how to aim these tools at your idea. I know, because I did exactly this: I took my own idea, built the app, stood up the business, and I'm shipping it to the App Store. Now I'll do it with you.
~2 weeksGroundworkThe business, stood up: pricing strategy, a clear-eyed vision assessment, and a marketing plan you can actually run, plus the entity-ready setup around it.
~4 weeksFirst buildThe foundational build of your app or website, made alongside you at the controls, with the training to keep building once the engagement ends.
~4 weeks laterLandfallYour app prepared and submitted for iOS launch, with the go-to-market ready to meet it.
This is you if…
You've had the idea for years, but the quotes came back at six figures and six months
Everyone told you to learn to code, hire a team, or raise a round first
You'd rather learn to build it yourself than hand it off forever
What I do
Training to build apps and websites with today's AI tools, capability that stays with you
A foundational application or website, built alongside you
Pricing strategy, a vision assessment, and a marketing plan
A path to iOS launch, prepared and submitted to the App Store
Timeline ~10 weeks: ~2 wks Groundwork, ~4 wks First build, ~4 wks to Landfall
What you leave with A shipped app prepared and submitted to the App Store, the business stood up around it, and the capability to keep building yourself.
Ship the product on your roadmap, and leave your team able to build the next one.
This is you if…
You have a build backlog but not the team or the time to clear it
You want internal AI-build capability, not another vendor dependency
You need go-to-market ready to meet the product when it ships
What I do
Team training on building with AI tools, internal capability, not a dependency
A foundational build of your target application or website
Go-to-market: pricing, positioning, and marketing strategy
A path to iOS launch, prepared and submitted to the App Store
An optional bridge into fractional strategy, finance, and RevOps
Timeline ~10-week Landfall arc, scoped to your roadmap
What you leave with A foundational build submitted for iOS, a team that can build the next one, and go-to-market ready, with an optional bridge into the fractional practice.
For a company with a product in market and beyond, I architect the scalable, sustainable infrastructure any function runs on, across five components.
SystemThe operating model the function runs on: how the work is structured, and how it moves.
ToolingThe automation and applications that do the work, so capacity comes from systems, not just headcount.
ReportingOne trusted source of truth: the dashboards and metrics leadership can actually act on.
Review cadenceThe rhythm of business that turns the numbers into decisions, on a schedule that holds.
PeopleThe team and the capability to run it and keep improving it after I'm gone.
Why me
JB
This isn't theory. Open Shore's first product, Uki, is an app I built with these tools, stood up as a business, and am shipping to the App Store, the exact path Landfall runs with you. Behind that is a decade building the planning, finance, and revenue systems for portfolios up to ~$200B at Microsoft, AWS, and Amazon. It's a rare pairing: someone who has actually built the thing, and who knows how to build the business around it.
Redesigned the worldwide commercial sales cadence and moved revenue measurement to ARR, cutting reported volatility ~70%.
+18%YoY growth
Amazon Web Services
Principal, Global Strategy & Operations · $60B portfolio
Built the sales-planning function from near-zero during hypergrowth, structuring GTM for growth and ~74K hours/year of productivity saved.
2,000+person org
Amazon
Strategy & Planning · Chief of Staff Office
Ran executive planning rhythms and shipped a resource-allocation tool that put investment prioritization on data instead of instinct.
Built, not just advised
I don't stop at the slide. I build the tools: automation, dashboards, and AI agents that replace manual reporting with durable, self-service systems. At Microsoft that meant automating ~90% of the manual effort behind a global operating model without adding headcount. You get a plan you can run, not a binder you file.
Who I work with
Small and mid-sized companies past first traction and feeling the pull of the next stage: founders and operators who need enterprise-grade rigor without an enterprise-grade org chart. Engagements are fractional, advisory, or project-based, shaped around the problem in front of you.
Start a conversation
One email: a sentence or two on what you want to build, and whether Founders or Companies fits. I'll tell you honestly if it's a fit.