OS Consulting

Take your business to its next stage.

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

  1. Decisions start with data, and anecdotes.
  2. Simplify, standardize, scale. Then innovate.
  3. People are the business. Build trust, build reach.
  4. Strategy demands operational grounding.
  5. Now, think bigger.

What I can do for you

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.

  1. ~2 weeks Groundwork The 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.
  2. ~4 weeks First build The foundational build of your app or website, made alongside you at the controls, with the training to keep building once the engagement ends.
  3. ~4 weeks later Landfall Your 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.

Tell me your idea

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.

Tell me your idea

Decide where to play and how to win the next stage, then make it executable.

This is you if…

  • Growth has started to feel like noise instead of momentum
  • Priorities get set by whoever asked loudest, not by the plan
  • There's no cadence tying the boardroom to the front line

What I do

  • Growth thesis and prioritization; operating plans; goals that cascade from the boardroom to the front line
  • Org structure and workforce planning
  • Business diversification and long-term planning
  • Company-culture development and the executive cadence that keeps everyone rowing the same direction

Timeline Fractional or project-based, scoped to the decision in front of you

What you leave with A plan you can run, not a binder you file.

Tell me your idea

See your cash flow clearly and put every dollar where it compounds.

This is you if…

  • You have forecasts you don't fully trust
  • Cash-flow visibility is thin, and resourcing gets decided by instinct
  • Spreadsheets and gut calls have stopped scaling with the business

What I do

  • Cash-flow visibility and cash-flow management
  • Investment prioritization, resourcing and headcount planning
  • Forecasting and the financial planning (FP&A) that turns a P&L into decisions
  • So you fund what grows and starve what doesn't

Timeline Fractional or project-based, scoped to the decision in front of you

What you leave with Fund what grows, starve what doesn't: a P&L that drives decisions.

Tell me your idea

Make revenue predictable: an engine, not a mystery.

This is you if…

  • The pipeline lives in a few people's heads
  • The forecast slips every quarter
  • The CRM has become a graveyard instead of a system

What I do

  • Sales strategy and sales planning
  • Forecasting, pipeline discipline, and pipeline management
  • Territory, quota, and incentive design
  • CRM architecture and management (Salesforce), reporting, and the rhythm of business that ties it together

Timeline Fractional or project-based, scoped to the decision in front of you

What you leave with Predictable revenue, and a rhythm of business that ties selling, planning, and reporting into one loop.

Tell me your idea

Replace manual reporting with dashboards you can trust, and decisions you can defend.

This is you if…

  • Reporting is manual, late, and never quite agrees with itself
  • There's no single source of truth for how the business is doing
  • Forecasting is guesswork instead of a model

What I do

  • Dashboards and semantic models
  • Business-operations reporting and forecasting
  • The automation behind them, replacing manual reporting with self-service systems
  • Built, not just advised: at Microsoft this meant automating ~90% of the manual effort behind a global operating model

Timeline Fractional or project-based, scoped to the decision in front of you

What you leave with Durable, self-service reporting instead of manual heroics.

Tell me your idea

The infrastructure I architect

For a company with a product in market and beyond, I architect the scalable, sustainable infrastructure any function runs on, across five components.

  1. System The operating model the function runs on: how the work is structured, and how it moves.
  2. Tooling The automation and applications that do the work, so capacity comes from systems, not just headcount.
  3. Reporting One trusted source of truth: the dashboards and metrics leadership can actually act on.
  4. Review cadence The rhythm of business that turns the numbers into decisions, on a schedule that holds.
  5. People The team and the capability to run it and keep improving it after I'm gone.

Why me

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.

Track record

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.

Book a consultation