Director of Program & Coaching Strategy
SkillHat
Canada
Posted on Jul 1, 2025
This is a remote position.
About 7-Figure Boardroom7-Figure Boardroom is a rapidly scaling high-ticket leadership network for Project Managers, Business Analysts, and Cybersecurity GRC Analysts ready to level up into Director-level roles.
We offer personalised executive coaching, hands-on leadership training, and a thriving peer community for tech professionals looking to lead and grow, not just survive.
We have proven traction and strong demand. Now we’re scaling past our supply constraints and looking for a strategic operator to lead two of our most important engines:
- Our Executive Coaching Program
- Our Monthly Masterclass Series
Your Mission
You’ll own and scale the entire delivery system of our member transformation experience, from recruiting world-class coaches, to running high-impact masterclasses, to building backend systems that drive retention, results, and referrals.
You’ll lead both strategy and execution, working directly with the founder to transform a working play book into a scalable, systems-driven program that can serve thousands of tech professionals per year.
What You'll Build & Own
Executive Coaching System
- Design a repeatable framework to source, vet, and onboard Director+ level coaches
- Launch the “Coach Playbook” + training pipeline for consistent quality
- Build a smart coach–member matching system
- Introduce group coaching pods as a scale lever without sacrificing personalisation
- Track and report on coaching impact, satisfaction, and renewals
Monthly Masterclass Engine
- Curate and coordinate live monthly sessions
- Own speaker ops: prep, content alignment, event production, and follow-up engagement
- Build a replay and resource library that compounds value over time
- Create a “Leadership Event Calendar” aligned with member career goals
Operational Scale & Impact
- Lead the rollout of progress dashboards, milestone tracking, and member accountability systems
- Collaborate with the Founder & RevOps to align coaching with revenue, retention, and referral goals
- Recommend tiering strategies, delivery automation, and strategic partnerships
- Own KPI outcomes around member experience, retention, LTV, and referral conversion
Requirements
You're a Fit If You Have...
- 4+ years building or scaling coaching, learning, or member-driven programs (Maven, Reforge, Chief, OnDeck, Monday Girl, etc.)
- Strong instincts in adult learning design, accountability systems, and coach enablement
- You’ve led or built coaching networks, learning calendars, or program operations
- You think in systems and act with urgency — you can turn a spreadsheet into a growth engine
- You’re comfortable in a founder-led, fast-paced startup where ambiguity is normal
- You believe in transforming lives and can blend empathy with operational excellence
Sample Projects in Your First 90 Days
- Recruit and onboard 5 new Director+ coaches with a defined onboarding and QA flow
- Launch group coaching pods + train coaches on pod facilitation
- Curate and execute a live Masterclass on “How to Lead High-Stakes Executive Meetings”
- Implement a coach-member tracking dashboard
- Drive 85 %+ attendance on your first 3 masterclasses and gather NPS feedback
- Recommend a tiered coaching model and identify tools to support scale
Benefits
Who You’ll Work With
- Founder – Leads brand, product vision, and overall strategy
- Revenue Ops Manager – Drives acquisition and customer funnels
- Marketing + Community Leads – Help amplify member stories and engagement
- Coaches & Speakers – You’ll be the lead recruiter, trainer, and operator for our talent bench
This is a revenue share role with upside based on program growth and retention.
We are looking for an entrepreneurial leader to help us scale to 20 new members per month by Sept 2025.
If you're successful, you’ll earn at a founder-equivalent level without founder-level risk and shape the future of tech leadership for hundreds of professionals.
This role is remote (Canada-based preferred)