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Chalkmark Overview & Plan

Expert-led career acceleration for ambitious young professionals

Value Proposition

Elevator Pitch

Chalkmark partners ambitious young professionals with expert mentors to master career-advancing skills and business concepts through hands-on, interactive virtual workshops.

Descriptive Pitch

Young professionals struggle to develop the skills needed to advance their careers. Chalkmark addresses this by matching them with industry experts for short, interactive online workshops where they gain hands-on perspective to tackle business problems with confidence. We handle event production and promotion so mentors can focus on facilitating interactive sessions that demonstrate their knowledge and convert participants to ongoing coaching and consulting clients.


Early career professionals often lack the skills, knowledge, and relationships they need to advance their careers. They may feel lost or unsure of where to start, and they may not have access to the right opportunities to learn and grow.
Freelancing experts and fractional executives struggle to reach ideal target customers and demonstrate value in a crowded marketplace.

Profile: Early Career Professionals


Ambitious professionals early in their career looking to develop skills, business acumen and professional connections.
Eager to learn through hands-on experiences with proven leaders able to provide tactical advice.
Seeking wisdom and perspective from those who have progressed in their fields.


Traditional learning options often lack practical, real-world application.
Difficult and often expensive to find and hire mentors and coaches that meet specific needs.
Overwhelming to identify external resources while managing other commitments.


Connect with expert mentors across industries for short-form, interactive online workshops.
Apply learning with hands-on scenarios and exercises led by seasoned professionals successful in their craft.
Gain strategic clarity, confidence and connections to propel career advancement.


Accelerated skill development through specialized sessions
Interactive, small-group learning experiences
Direct access to top industry experts and their networks
Flexible and affordable compared to formal education
Community of like-minded professionals

Profile: Seasoned Freelance Experts


Seasoned freelance/consultant/fractional expert with established acumen and leadership in a specific field and discipline.
Growing an audience (”pre-influencer”) and actively looking to build an online brand and attract more clients for product or services.
Passionate about mentorship, sharing knowledge and expertise with others.


Building an audience takes time and effort, with the added requirement of developing online marketing skills and producing content.
Difficulty with identifying, reaching and engaging ideal prospects in addition to the challenge of converting leads into sales.
Creating high-quality content and workshops can be time-consuming and require skills outside core expertise.


Turn knowledge into profit – leading workshops, attracting clients, and boosting personal brand.
Audience delivered directly; showcase passion, leadership, and capabilities to high-potential, motivated learners seeking wisdom.
Hands-on workshops demonstrate value while workshops enable lead conversion, turning participants into ongoing consulting and coaching clients.
Focus on sharing perspective and thought leadership while brand building, production, and promotion are effectively streamlined without additional work.


Increased brand awareness and visibility
Access to a highly targeted audience of potential clients
Lead generation and client acquisition
Credibility and thought leadership positioning
Develop high-quality marketing materials workshop recordings; repackaged shorts and Youtube videos
Opportunity to refine your presentation for future use (live workshops, online courses)

Business Model Analysis

List of potential revenue streams to experiment with for achieving $15,000 in revenue within 6 months of launching.

MODEL A: Charging Experts for Marketing Services

Experts pay to leverage workshop development process and promotion with opportunities for revenue sharing and content sponsorships with associated brands.
Limit to 10 experts per month
Charge per Expert: $1,500 per month
Faster adoption by experts seeking marketing reach
Easier initial validation with less complex user acquisition
Higher revenue per transaction
Build ongoing expert relationships
Smaller learner base initially might discourage expert participation
Reliant on expert buy-in, potentially limiting workshop variety
Resource intensive to recruit/manage experts
Capacity limited to number of experts

MODEL B: Freemium with Paid Features for Learners

Offer limited basic workshops for free and charge for premium workshops with higher production value, in-depth topics, or exclusive expert access.
3 free workshops
12 premium workshops with 300 paying attendees
$50 workshop price
Freemium model lowers initial commitment barrier for learners
Can offer tiered paid workshop options
Option for employee to expense to their employer
Requires attracting a critical mass of users before significant revenue generation
Need lots of free content to drive conversions
Balancing free vs. paid content needs careful design to avoid devaluing the platform

MODEL C: Subscription Model for Learners

Offer access to all workshops for a monthly or annual subscription fee.
150 subscribers
$100 monthly subscription
Allow trial for attending 1 workshop for free
Guest passes to share
Predictable revenue stream with recurring payments
Encourages learner engagement and platform loyalty
Option for employee to expense to their employer
Higher initial price barrier might deter users
Requires a strong value proposition and diverse workshop offerings
Need content libraries/platform features


Focus on one model initially and experiment with hybrid options.
Other models to explore: paid workshop & consulting engagements, sponsorships, conferences.


Based on Subscription Model (C) + Single Workshop Hybrid
Key Assumptions
150 subscribers
$100 monthly subscription
Free trial for 1 workshop attendance
Guest passes available for sharing

Phase 1: Pre-order Generation (2 weeks)

Set goals and metrics for subscriptions, churn, engagement etc.
Create landing page explaining subscription offer and benefits.
Offer 50% off for a period (1-3 months, 6-12 months) for early subscribers.
Outreach campaign to drive pre-orders.
Share subscription offer on social media and with partners.

Phase 2: First Workshops & Trials (4 weeks)

Email subscribers with workshop schedule updates.
Run 1-2 workshop trials to test formats.
Offer trial workshops for non-subscribers.
Develop referral incentives for subscribers.
Create shareable guest passes for workshops.

Phase 3: Iterate Offering & Reduce Churn

Evaluate subscriber engagement and retention rates.
Conduct user research to improve workshop experience.
Systemize workshop production process.
Test additional features like exclusive Q&As, community etc.
Develop drip campaign and re-engagement flows to reduce churn.

Why “Chalkmark”?

Around 1920, Henry Ford once balked at paying $10,000 to General Electric for work done troubleshooting a generator, and asked for an itemized bill. The engineer who performed the work, Charles Steinmetz, sent this: "Making chalk mark on generator, $1. Knowing where to make mark, $9,999." Ford paid the bill.
Note: This story may be apocryphal (but it’s too good to ignore)
Lesson: The most important step in solving a hard problem is knowing where to look.

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