Scaling.com partners with founders and growth-stage entrepreneurs to help them scale their companies faster and more sustainably. Our Strategists are former entrepreneurs and operators who have built, scaled, and exited businesses themselves—and now guiding others through the same journey.
We are building a world-class Strategist bench, and we are looking for a senior-level recruiter who specializes in identifying, attracting, and closing former entrepreneurs to join Scaling.com as Strategists.
Role Overview
This is a senior-level, high-impact recruiting role responsible for sourcing, engaging, and hiring experienced entrepreneurs, CEOs, and senior operators to join Scaling.com as Strategists. These Strategists are client-facing advisors who work directly with our Scalers, making this role critical to both our culture and the quality of experience we deliver to our members.
This is not traditional recruiting. You will be identifying and engaging peers—individuals who have built businesses, led teams, and navigated complex growth challenges—and helping them see Scaling.com as a meaningful next chapter in their professional journey.
Success in this role requires strong communication skills, sound judgment, and a thoughtful, proactive approach to talent acquisition. You must be able to understand Scaling.com’s culture, values, and expectations at a deep level and translate that into high-quality hiring decisions. You will serve as both a brand ambassador and a trusted advisor to candidates, ensuring alignment between their experience, mindset, and our Strategist role.
This position requires exceptional relationship-building, high emotional intelligence, and the ability to confidently engage senior entrepreneurial talent in strategic conversations. You will play a key role in shaping our advisory team and directly impact the growth and success of Scaling.com by identifying individuals who can deliver world-class guidance to our Scalers.
Requirements
Key Responsibilities
- Own end-to-end recruiting strategy for entrepreneur-to-Strategist coaching talent, including sourcing approach, outreach messaging, screening criteria, and pipeline management.
- Proactively source and engage former founders, CEOs, and senior operators through direct outreach and relationship-based recruiting.
- Build and maintain a robust pipeline of high-caliber candidates across multiple industries, maintaining consistent volume without sacrificing quality.
- Lead candidate communication end-to-end through early stages: outreach, follow-up, scheduling, screening, and candidate experience management.
- Conduct high-judgment screens to evaluate entrepreneurial credibility, communication style, coaching aptitude, and alignment with Scaling.com culture—making clear recommendations on whether candidates should proceed.
- Partner closely with HR and the Strategy team to refine screening standards, calibrate on quality, and ensure consistent decision-making across the funnel.
- Collaborate with founders/leadership to define and evolve ideal Strategist profiles based on Scaling.com’s methodology and evolving client needs.
- Lead high-level discovery conversations to assess entrepreneurial track record, leadership maturity, scaling aptitude, and cultural alignment.
- Act as a trusted advisor to candidates throughout the process.
- Clearly articulate the value proposition of Strategists at Scaling.com (impact, leverage, community, income, purpose).
- Skillfully navigate the nuanced motivations, compensation expectations, and transition timelines typical of former founders and senior operators.
- Track funnel metrics, conversion rates, and quality-of-hire indicators.
Required Experience
- 8+ years of recruiting experience, with significant focus on senior, executive, or non-traditional talent.
- Direct experience recruiting former founders, entrepreneurs, CEOs, or senior operators (required).
- Proven success closing highly selective, high-agency candidates.
- Must have read The Science of Scaling
Strongly Preferred
- Experience recruiting executive coaches, operators, advisors, consultants, or fractional executives.
- Background in executive search, retained search, or high-touch internal recruiting.
- Familiarity with entrepreneurship, scaling businesses, PE/VC environments, or founder ecosystems.
Skills & Attributes
- Exceptional credibility and presence when engaging experienced entrepreneurs.
- High emotional intelligence and listening ability.
- Strong pattern recognition for entrepreneurial talent and leadership maturity.
- Comfortable operating with ambiguity and evolving role definitions.
- Persuasive storyteller who can clearly communicate mission and impact.
- Highly organized, process-oriented, and data-informed.
What Success Looks Like
- Consistently hiring high-quality former entrepreneurs who become top-performing Strategists. Initial goal is 1 per week ramping up to 2 per week over time.
- Building a repeatable, scalable recruiting engine for Strategist coaching talent.
- Strong candidate experience and high acceptance rates.
- Trusted partnership with internal leadership and strategist|strategists|strategy coachinging teams.
Why Join Scaling.com
- Help build one of the strongest entrepreneur Scaling platforms in the world.
- Work directly with elite former founders and operators.
- High autonomy and ownership over a mission-critical function.
- Meaningful impact on thousands of entrepreneurs scaling their businesses.
Benefits
Scaling.com is an equal opportunity employer. We value diversity of experience, background, and perspective—especially among those who have built and scaled companies in different ways.
