You’re leaving. Or you already left. And now your old company wants to keep you around - “just in case.”
It happens all the time. Especially if you were in a senior role. You know where the bodies are buried. You kept the thing running. You solved problems no one else could quite see, let alone fix.
So they offer you a consulting arrangement. Retainer. Project work. Maybe both.
And it sounds flattering. Easy money. Minimal transition pain.
But here’s the problem: if you’re not careful, you’ll end up doing your old job again - with worse terms, no benefits, and a pile of opportunity cost.
Let’s fix that.
There are a few reasons someone sticks around after leaving a full-time role:
Each of those is fine - but you can’t price and structure them the same way.
If you’re not clear, you’ll end up doing all of it. Badly.
Your old employer will probably default to what they know: some block of hours/month. Weekly reports. Benchmarks. Time tracking.
That’s not a retainer. That’s a part-time job.
A real retainer is:
You’re not selling time. You’re renting space in your head.
You’ll be tempted. It’s familiar. It’s billable. You already know the system, the team, the product.
Don’t.
You’re not trying to become their dev shop. Or their marketing agency. Or their HR department. You’re trying to move on.
And yeah - implementation might be something you offer to other clients. That’s fine.
But this isn’t that. This is your old job. And the goal here is separation.
Even if you end up with a long-term insurance retainer, the whole point is that you’re not doing the same work you just left.
Even with clean terms, it’s easy to keep caring too much. Especially if you used to own it. That’s the trap too - not just time and money, but mindshare.
Every hour you spend delivering is:
If they want execution, help them hire or contract it out. You can provide oversight. You can review plans. You can show up to unblock them. But don’t be the one shipping the thing.
Unless you’re hungry - and even then, price it like it’s going to hurt.
If you do stay on, treat it like a bridge - not a fallback.
Structure the engagement in blocks. Three months is common. Six if they’re slow to act.
Every block should include:
No open-ended relationships. No “we’ll just see how it goes.” If they want flexibility, they can pay a premium for it.
The longer you’re available, the longer they might postpone hiring - especially if you’re still getting things done.
Most post-exit offers live somewhere between two models:
Advisory - You’re available for strategic input. You show up regularly. You help shape direction. You’re in context, but not on the hook for day-to-day.
Insurance - You’re not involved unless something breaks. They’re paying to know you’re around, not to hear from you. It’s reactive, not proactive.
In practice, many advisory retainers include both. That’s fine - especially if you’re priced at a premium.
Just be clear. If you’re offering both, define the expectations. Don’t accidentally become an on-call safety net and a standing thought partner and a silent executor.
You can do both. But do it on purpose.
Here’s what a post-exit advisory engagement might look like if I were to create it:
This package offers comprehensive advisory engagement where I’ll remain in context with your team while providing strategic guidance.
As your former CTO, I’ll maintain presence in your Slack environment, participate in regular engineering leadership meetings, and proactively identify opportunities and challenges. You’re paying for my expertise and institutional knowledge.
What’s included:
This lighter package provides the security of having my expertise available when needed.
I’ll stay familiar with your high-level direction through monthly check-ins. This allows your team to develop independently while maintaining access to my knowledge in case of emergencies.
What’s included:
I never assess an hourly or daily fee, so you don’t have to make an investment decision every time you need my assistance. This is a unique feature of my consulting practice.
Pricing (3-month commitment):
Strategic Advisory Retainer - $17,000/month
Technical Insurance Retainer - $9,000/month
A 5% discount available if paying the full 3-month term upfront.
All retainer packages include unlimited access to me via email, text, or phone, with next business day response.
Fees must be paid in advance - either monthly at the start of each month, or in full at the beginning of the 3-month term. You may change your selection at the start of any new 3-month period.
My work is guaranteed. If at any point in our first 30 days you decide I’m not meeting the standards described herein, just request a refund and I’ll send your money back - no questions asked.
Please reply to this email with your preferred option and start date, and I’ll send you an invoice. Your payment confirms acceptance of these terms.
This proposal is valid for 14 days from the date of this email.
These aren’t fixed formulas. Every slider can move - pricing, number of weekly calls (twice a week? twice a month?), quarterly reviews, even response time.
If they need weekend availability, or faster turnaround, or more active involvement? That’s fine. Just make sure the price moves with the request.
This is also how you avoid negotiating on price - you change the scope to change the price.
Credit to Jonathan Stark for his sample proposal that has been the backbone of my paperwork for years.
You don’t have to take the work. You don’t owe them a discount. You don’t have to stay in the weeds because you used to be “the person who just handled it.”
If you want to keep helping - great. But structure it like a business. Not a favor. Not a favor you’re charging hourly for. A business.
You’ve already done the hard part by leaving. Now finish it right.
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