The decisions that cost the most arrive mid-quarter, alone, and looking routine. A contract clause. A renewal nobody wanted to cancel. A tool a team started using on a Tuesday. Leadership teams who put a standing seat against those decisions keep it: the cadence settles, the quarterly write-up becomes the running record of how technology risk is governed here, and when the board asks, the answer is already written.
The decision retainer is a standing advisory seat starting at $2,750 a month, run in 90-day cycles you can end at any cycle. It exists for the AI and security decisions that arrive mid-quarter.
Why a standing seat and not a project? Because the decisions that cost the most never arrive on a project schedule. They show up on a Tuesday, in a contract clause, a renewal quote, or a question from your largest customer. Clients who keep a standing seat tell us the value is having somewhere to send it the hour it lands, and getting a straight answer back before the meeting where they need a view. The gap between those numbers is a string of small decisions made without anyone to ask.
A set monthly fee, run in 90-day cycles, that gives your leadership team somewhere to put the question before it becomes a decision. Structured working sessions on a regular cadence, plus access in between when something lands.
Boundary, stated plainly. We advise. We do not implement, configure, resell, operate, staff, or take access to your systems. When something needs building we help you scope it and judge whoever builds it. That separation is the point.
Set by cadence and how many decision-makers are in the room. No hourly billing, no surprise invoices, and you can stop at the end of any cycle.
Cycles end on purpose. If a quarter has produced nothing worth paying for, we would rather you stop than renew out of habit.
The engagement below is real work, drawn from more than 600 AI and cybersecurity projects the people behind this firm have delivered. Names, figures and identifying details are withheld, because confidentiality does not expire when an engagement ends. Yours will get the same protection.
The setup. No CISO, no CIO — a strong IT manager and a CFO who keeps getting handed decisions shaped like technology but priced like strategy. In one quarter: a $95K security platform proposal, a major OEM's new vendor-security requirements, an AI pricing tool the sales VP wants, and a cyber insurance form with a hard deadline.
The cadence. A working session every other week, and a send-it-over channel in between. Each decision gets a straight read in days: the $95K platform overlaps two tools already owned — counter-proposal saves $60K a year; the OEM requirements map mostly to controls already in place, needing evidence rather than spend; the AI pricing tool is worth piloting, but only after the customer-data boundary is written down — which takes one page and one week.
The quarter's write-up. Every cycle ends with a written position: what changed, what did not, what next quarter should decide. When the board asks the CFO how technology risk is being governed, the answer is a document, not a shrug.
And when it should end, it ends. Cycles are 90 days. A quarter that produces nothing worth paying for is the signal to stop — we say that on the page because a retainer that cannot end is a subscription, not advice.
What this cost: this cadence — two decision-makers, biweekly sessions — sat comfortably mid-range for the cadence.
A standing advisory relationship for AI and cybersecurity decisions, billed at a set monthly fee in 90-day cycles. It covers the judgment calls that arrive between larger pieces of work.
No. Boldly Reimagined is advisory only. We do not implement, configure, resell products, provide managed services, or take access to client systems. If implementation is needed we help you scope it and evaluate whoever does it.
Related straight answers: AI governance for growing companies, incident readiness for executives, and what carriers now ask for.
It is hard to advise well on a company we have not read properly. Most relationships begin with an assessment, then continue if there is enough live work to justify it.