Leadership Case Study: Scaling The Ascent
Transforming a $100M+ Personal Finance Business
The Challenge
The Ascent, The Motley Fool's personal-finance affiliate business, was performing well but still had untapped growth potential. The founder wanted to step back from day-to-day operations to focus on bigger-picture strategy and expansion opportunities. The business needed leadership that could diagnose systemic bottlenecks, align cross-functional teams around clear objectives, and unlock the next phase of growth.
The Approach
Diagnostic Phase
I started with a comprehensive business audit that revealed critical insights:
- Marketing drove the lion's share of results while SEO and editorial underperformed
- Revenue concentrated dangerously among a small partner set
- Conversion rate optimization (CRO) existed only within marketing, not cross-functionally
- Individual and team goals didn't roll up to business objectives
Strategic Reorganization
Rather than treating symptoms, I restructured how teams worked together:
CRO as Cross-Functional Foundation
Elevated our single CRO practitioner from a marketing role to a cross-functional position and hired support. This meant every improvement across any team—SEO, editorial, business development—would be amplified by higher conversion rates.
OKR Implementation
Worked with each team to create objectives and key results that cascaded from business-level goals down to individual contributors. This created clear line-of-sight between daily work and business impact.
Strategic Partnerships
Collaborated with business development and the founder to identify expansion opportunities that would reduce concentration risk while capitalizing on market trends.
Team-Specific Acceleration
Partnered with SEO and editorial leads to identify both quick wins and longer-term foundational improvements, balancing immediate results with sustainable growth.
The Results
Financial Impact
Run Rate
Performance
Growth
Expansion
Revenue Growth
Grew revenue to $100M+ annual run rate
Budget Performance
Beat budget by 18% while growing 34% year-over-year—despite budget caps and headwinds in our core credit card business
Vertical Expansion
Expanded banking vertical from $750K to $44M run rate by identifying and acting on interest rate trend early
Risk Reduction
Increased high-value partners ($100K+ revenue) from 8 to 14, reducing concentration risk
Operational Excellence
Cross-Functional CRO
CRO team's cross-functional A/B testing improved conversion across all SEO pages, creating compounding returns on every traffic increase
OKR Framework
OKR framework enabled productive quarterly reviews focused on learning and refinement rather than blame
Team Alignment
Cross-team alignment eliminated siloed decision-making and accelerated execution
Leadership Lessons
This experience reinforced three principles that guide my approach:
Systems Over Heroics
The CRO elevation wasn't about working harder—it was about creating a multiplier effect where improvements in any area amplified results across the business.
Clarity Enables Speed
OKRs didn't add bureaucracy; they removed the friction of unclear priorities and misaligned incentives. Teams moved faster because they understood why their work mattered.
Strategic Preparation Creates Opportunity
Because we had identified revenue concentration as a top-level risk, teams were already watching for opportunities like the interest rate shift. When banking became attractive, the OKR alignment meant pursuing it was a natural cross-functional effort rather than a disruptive pivot—everyone understood how it served our shared goals.
Ready to Scale Your Business?
I specialize in diagnosing systemic bottlenecks and implementing frameworks that unlock sustainable growth at scale.