Job Coach On-Demand 

Expert Career Strategists. In Your Pocket. On Your Schedule.

Imagine this: You find a role that looks like it was written for you. Within 24 hours, you have a tailored resume, a custom cover letter, the hiring manager’s contact information, the exact messaging to reach out, and a strategic playbook that positions you to stand out. Before you even apply.

That’s not a hypothetical. That’s what happens every week when you have Kara and Jack in your corner.

The Job Coach On-Demand membership gives you direct, dedicated access to two career strategists with decades of experience. Professionals who were doing this long before AI existed, and who bring the judgment, positioning expertise, and pattern recognition that no software can replicate.

The Gap Between Great Branding and a Great Offer

Your brand is built. Your resume is strong. Your LinkedIn positions you well.

But execution is where most job searches break down. Not because you lack discipline, but because every new opportunity requires a new round of research, customization, and strategic decisions:

• Which roles are actually worth pursuing?
• How do you tailor your resume without losing your positioning?
• Who should you actually reach out to, and what do you say?
• How do you prepare for conversations that convert?
• What happens when you get stuck, stall out, or second-guess your approach?

These aren’t problems a tool can solve. They require a strategist who knows your story, understands the market, and can make the right call in real time.

What You Get

Dedicated Slack Channel with Kara & Jack

This is the core of the membership. You get a private, dedicated Slack channel with both of us: your career strategists, available when you need us.

Need a gut check on whether to apply? Ask. Want to know how to position a gap in your experience for a specific role? Ask. Not sure how to respond to a recruiter’s email? Ask.

24-hour business-day response time. Real strategic guidance from expert coaches who’ve personally supported hundreds of professionals through exactly what you’re navigating.

Up to 2 Role Strategy Packets Per Week

When you identify a role you want to pursue, submit it through our intake process. We build you a complete Role Strategy Packet: everything you need to go after that opportunity with precision.

Each Role Strategy Packet includes:

• Fully Tailored Resume - Customized to the specific role, optimized for positioning, and ready for application
• Custom Cover Letter - Written to complement your resume and connect your career to the opportunity
• 5-10 Verified Decision Makers - Hiring Managers, Recruiters, & Key Stakeholders at the target company
• Customized Outreach & Follow-Up Messaging Scripts - Personalized messaging for contacts from initial outreach to follow-up
• Company & Business Intelligence - Company overview, strategic positioning, tech stack, products, competitor landscape, and strategy so you can speak to the org intelligently
• Key Interview & Networking Touchpoints - Strategic talking points, conversation anchors, objection busters, and prepared responses for tough questions, gaps, and potential concerns

Continued Course & Interview Studio Access

Receive continued access to the Strategic Job Search Courses and continue practicing and refining your interview delivery with custom AI-powered insight within the Optimized Interview Studio to sharpen your responses and build confidence.

This is For You if...

• You’ve invested in your branding, and you’re ready to execute
• You’re confident driving your own search but want strategic backup
• You want real experts, not another AI tool, guiding your positioning
• You’re tired of spending hours customizing applications with no strategic direction
• You want to stay consistent and strategic without burning out

Frequently Asked Questions:

“Is this enough support if I’m serious about my search?”

Yes. If you’re confident executing independently, this gives you everything you need. The Slack access provides real-time strategic guidance, and 2 Role Strategy Packets per week means up to 8 fully customized opportunities each month. That’s a focused, high-quality pipeline. If you want more volume or scheduled strategy calls, check out the Executive Search Partnership.

“Do you apply for me?”

No. You submit the applications. We build the strategy, customize the materials, source the contacts, and give you everything you need to stand out. You drive the execution.

“What if I want more support or more packets?”

You can upgrade to the Executive Search Partnership at any time for up to 4 Role Strategy Packets per week plus scheduled strategy calls with Kara and Jack.

“How is this different from AI resume tools?”

AI tools generate generic output. We bring decades of experience in career strategy, hiring, and positioning. Every packet is built with human judgment: the kind that understands how a hiring manager actually reads a resume, what a recruiter is filtering for, and how to frame your story in a way that opens doors. That’s not something software can replicate.

“Can I cancel anytime?”

Yes. Monthly subscription, cancel anytime. Your service continues through the end of your billing cycle.

Stop Guessing. Start Executing:

You’ve already built your brand. Now it’s about having the right strategists behind every move you make.

The Details: 

• Designed for professionals with results-oriented personal branding in place
• Monthly subscription, cancel anytime
• Slack response within 24 business hours
• All deliverables aligned to defined weekly scope, role strategy packets are built based on roles or companies submitted by you weekly.
• Applications are submitted by you; we ensure you’re strategically positioned to stand out
• To maintain quality and responsiveness, we limit the number of members we support each month

Want More Support?

The Executive Search Partnership includes up to 4 Role Strategy Packets per week, plus 2 on-demand strategy calls per month with Jack or Kara. $997/month.