About Pilot & Rutter
Pilot & Rutter is a consulting firm for mid-size companies facing two problems that increasingly show up together: getting real direction on AI, and making an acquisition work after the close. We’re operators first. We’ve done this work from the inside, and we run our own firm the way we advise clients to run theirs.
The problem most leaders miss
Most leadership teams don’t lack ideas, talent, or effort. They lack a direction everyone will actually follow. So the experiments multiply, the integration drifts, and the default answer becomes more people or another big plan.
Neither fixes it. Adding headcount to a problem nobody has defined just makes it bigger. And a thick strategy is a plan nobody acts on. What moves a company is a small number of clear decisions, made by the right people, that stick.
That’s the gap we close: between strategy and the work that actually happens on Monday morning.
Where the name comes from
Beginning in the 14th century, pilots and navigators recorded their knowledge in journals known as rutters. Their enterprising spirit, combined with their rutter, let them explore uncharted seas.
We work the same way. Like those early pilots heading into unknown waters, we combine tried-and-true experience with new ideas to set direction and carry out the course today’s ever-changing world demands. As trusted advisors, we work at every level of an organization, from the boardroom to the teams doing the work, to get you where you need to go.
That’s why we believe Direction Beats Chaos™.
How we work
Operators, not observers
We’ve run the kind of work we advise on: technology, operations, and integrations inside large companies, including global retail and enterprise IT. We know what a plan looks like when it hits real people, budgets, and deadlines, because we’ve been the ones carrying it out.
Decisions, not decks
You won’t get a 300-page slide deck from us. We measure the work by the decisions it gets made: what to fund, what to stop, who owns it, and what happens next. If nothing changes on Monday, we didn’t do our job.
We test on ourselves first
Pilot & Rutter runs on its own AI agent stack. When we tell you what’s worth doing and what’s a dead end, it’s usually because we’ve already hit it ourselves. We’d rather find the sharp edges on our own work than on yours.
Leadership
Andy has spent his career at the seam where technology meets the business, from running builds and standing up the first product management function at ClickCommerce, to leading technology, supply chain, and merchandising work inside global retail and enterprise IT. At Nike, he led global fulfillment and logistics engineering. At CDW, he ran operations for an organization of more than 1,500 people, led a cloud services practice while launching new AI offerings, and worked through post-acquisition integration from the inside.
He writes Soundings, a weekly essay on why AI initiatives stall.
Selected work
Beyond AI and integration, our work has included rescuing programs and scaling delivery teams. Two examples:
Rescuing a stalled enterprise application
A footwear and apparel company built a new application for its merchandisers, and users refused to adopt it at launch. The program was $20M over budget and the team was exhausted. We went back to the users, redesigned around the gaps they named, put development leads directly with the business, and brought the most skeptical stakeholders into alpha testing. The pilot launched on schedule for the next season, and merchandisers said the application finally “works the way they think.”
Doubling revenue without doubling headcount
A business IT services company set a 100% revenue growth target and planned to hire 60 engineers to get there. We helped leadership shift from selling individual star engineers to selling team-based engagements, which opened the door to developing junior talent and made room for training and communities of practice. Revenue doubled with fewer hires than planned, and engagement improved.
See how we think
The fastest way to know whether we’re a fit is to read how we think about the problems you’re facing.