Messaging An Old Boss?

This is not a sales lead. This is a high-ticket consulting opportunity, and you are looking at it all wrong.

Let’s be clear. You are correct that her formatting is “trash” and that Callisto OS can fix it. But that is a $50 problem. You are not in the business of solving $50 problems.

Your former boss does not care about content speed or scaling for clients she doesn’t have. She is in a career transition. Her current, full-time job is getting her next high-paying job. The content she is posting is a means to that end.

Her real, expensive, bleeding-neck problem is not “bad formatting.” Her problem is that she is a high-level executive who is presenting herself unprofessionally, which is undermining her authority and costing her opportunities for board seats, C-suite roles, and six-figure consulting gigs.

We are not selling her a content tool. We are selling her a “Personal Brand Operating System.” We are selling her the ability to project the same level of authority and polish in her online presence that she had in the HPE boardroom. That is a $10,000 problem.

Here is the plan.

1. The Repositioning

You are not a kid from your cousin’s basement selling a SaaS tool. You are a fellow founder and systems architect who specializes in codifying expertise. You will approach her as a peer who has observed a problem and has the specific, high-value solution.

2. The Offer: “The Executive Voice Engine”

This is not a subscription. It is a one-time, white-glove strategic package.

• Price: $7,500. This is a serious, professional price that an executive can pay without blinking if the value is there.
• The Deliverables:
  1. A “Mini Me” of Her Leadership Voice: You will conduct a 2-hour “Executive Voice” discovery session with her. You will take her post and other materials and use Callisto’s Reverse Voice Generator to deconstruct and codify her unique leadership philosophy and voice into a “Mini Me” persona.
  2. The Content Governance Engine: You will build out a set of professional formatting and structural rules in her brand configuration. This includes the “Rhythmic Readability” mandate and the “Strong Hook” mandate to ensure all her future content is sharp and impactful.
  3. The “First Strike” Content Package: You and Bohra will use the newly built “Mini Me” to generate her first month’s worth of content: four long-form LinkedIn articles based on her core ideas and 12 high-impact short-form posts.
  4. The Playbook: You will deliver a simple playbook on how she or an assistant can continue to use the system to generate on-brand content in the future.

3. The Outreach Script

You will not send a standard connection request. You will send a direct, high-status email or InMail.

Subject: A thought on your Mt. Elbert post & a proposition

[Former Boss’s Name],

I saw your recent post on the lessons from Mt. Elbert. Your insights on leadership and preparation are powerful, but the formatting on LinkedIn is actively working against your authority.

My new venture, Callisto OS, is a content operations system designed for this exact problem. We codify an executive’s unique voice and strategic insights into what we call a “Mini Me,” allowing them to produce perfectly formatted, on-brand thought leadership at scale.

This isn’t about just “making content.” It’s about ensuring a leader’s digital presence matches their real-world expertise.

I can build out your entire “Executive Voice Engine” and deliver your first month of high-impact content. The total for this one-time project is $7,500.

If you’re interested in seeing how this works, let me know.

Best,

Troy

This is how you approach this. You are not a kid asking for a sale. You are a systems expert offering a high-value solution to a problem she might not even know she has, but one that is actively costing her opportunities. You are selling her a ticket to her next six-figure job, not a content tool. That is a sale worth making.