Fractional Head of Customer Success

Turn customers into champions. Build retention engines that drive expansion revenue and word-of-mouth growth.
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Your people problems are growth problems. Solve them.

You're scaling fast but your team is fracturing. Great people are leaving. New hires aren't working out. Your culture is becoming toxic. And you're spending more time managing people drama than building your business.

Here's the thing: every hypergrowth company hits this wall. The difference between those that break through and those that crash? They get serious about people strategy before it's too late.

Enter fractional Chief People Officers: people leaders who've scaled teams from 10 to 1,000+ while maintaining the culture and performance that drives growth.

What a Fractional Chief People Officer Actually Does

Our fractional CPOs aren't HR administrators with new titles. They're strategic people leaders who:

  • Design hiring systems that scale with your growth and attract A-players
  • Build performance management that drives results without destroying morale
  • Create compensation frameworks that motivate without breaking budgets
  • Develop leadership at every level so you're not the bottleneck for every decision
  • Establish company culture that survives hypergrowth and remote work
  • Implement people analytics that predict performance and retention issues
  • Navigate complex employment law across multiple jurisdictions
  • Design equity programs that align incentives without diluting founders
  • Build diversity and inclusion strategies that actually work
  • Handle sensitive people issues before they become legal problems

When You Actually Need a Fractional Chief People Officer

You're ready if:

  • You're hiring 5+ people per month and struggling to maintain quality
  • Great employees are leaving and you don't know why
  • Management overhead is consuming founder time
  • You're scaling beyond 30-50 people and losing culture
  • Remote work is creating communication and performance challenges
  • You need proper HR processes for compliance and investor due diligence

You're not ready if:

  • Your team is under 15 people and founders can manage everything
  • You're not actively hiring or planning significant team growth
  • Your biggest people challenge is finding candidates (hire a recruiter instead)
  • You have a strong Head of People who just needs more resources

What This Actually Costs

  • Typical Engagement: 1-3 days per week, $1,000-$2,000/day depending on experience
  • Sweet Spot: $4K-12K monthly vs. $25K+ for a full-time CPO
  • ROI Timeline: People improvements typically visible within 30-90 days
  • A full-time Chief People Officer costs $200K-350K+ plus equity. The retention and performance improvements alone usually justify fractional investment.

Real Problems Fractional Chief People Officers Solve

  • "Our best people keep leaving for competitors" A fractional CPO analyses why people leave, implements retention strategies, and builds compensation and culture systems that keep top talent.
  • "Hiring is taking forever and we're still getting bad fits" They design scalable hiring processes, improve interviewing techniques, and create systems that identify cultural and performance fits quickly.
  • "Our managers don't know how to manage" They develop leadership training programs, implement proper performance management, and coach managers to become effective leaders.
  • "Our company culture is disappearing as we grow" They codify culture values, design systems that reinforce culture at scale, and ensure new hires understand and embrace company values.

Common Engagement Types

  • The Scaling Foundation (6-12 months): You're growing fast but people processes are breaking. They build hiring systems, performance management, and culture frameworks that scale with growth.
  • The Retention Recovery (3-6 months): Great people are leaving and you need to stop the bleeding. They analyze retention issues, implement fixes, and build systems that keep top performers.
  • The Leadership Development (6-9 months): Your team is growing but management skills aren't keeping up. They develop leadership programs, coach managers, and build systems that create leaders at every level.
  • The Remote Work Optimisation (3-6 months): Remote work is creating performance and culture challenges. They design remote-first processes, communication systems, and culture initiatives that work across distances.

Why Shepherd People Leaders Drive Results

  • They've scaled teams before: Our CPOs have taken companies through hypergrowth phases and know which people practices matter at each stage.
  • They're performance-focused: They measure success through business outcomes: retention, performance, hiring speed, and cultural health metrics.
  • They understand startup constraints: They build lean people systems that work with limited budgets and resources, not corporate HR bureaucracy.
  • They're strategic business partners: They align people strategy with business goals, not just HR compliance and administration.

Typical Engagement Timeline

Most engagements run 6-18 months, with many continuing as ongoing people strategy advisors. Here's what a typical engagement looks like: 

  • Month 1: People audit and immediate issue resolution
  • Month 2-3: System design and implementation
  • Month 3-6: Training and process optimisation
  • Month 6+: Strategic people leadership and culture development

Why Shepherd?

We speak startup

Shepherd's curated network of 450+ fractional leaders aren't your typical leaders, they thrive in the scrappy nature of startups. They're resourceful. They own outcomes and dive deep into the nitty-gritty alongside you.

Swipe their playbook

Imagine having access to the playbooks used to drive the go-to-market success of some of the leading tech companies. No more second-guessing whether you're doing it right. Leverage their experience to scale growth.

Bang for your buck

Tap into a diverse experience and skillset tailored to your evolving business needs—all at a fraction of the cost of a full-time hire. You get 100% brainpower without breaking your bank.

Super flexible terms

No long-term contract and fancy offices required. Start with a day or two a week, for as long as you need. Scale up or down your team as you grow, or even assemble an A-team for special projects.

Rapid deployment

You've already got enough on your plate —don't waste time sourcing and interviewing candidates. Get matched with experienced fractional operators in days, not months.

Frequently Asked Questions.

Still have questions?

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How is this different from account management?

Customer success is proactive and focused on driving customer outcomes. Account management is typically reactive and focused on maintaining relationships.

Can they work with our existing support team?

Absolutely. They typically work alongside support to create proactive customer success strategies while support handles reactive issues.

What about customer success technology and tools?

They're experts at selecting and implementing customer success platforms, health scoring systems, and automation tools.

How do they measure success?

Many specialise in high-touch enterprise customer success and understand the complexities of managing large, strategic accounts.

What about customer onboarding?

They're experts at designing onboarding experiences that get customers to value quickly and reduce early-stage churn.

Do they work directly with customers?

They typically work with customers during strategy development and training phases, then train internal teams to execute ongoing customer success activities.

What's the catch?

No catch. Just experienced customer success leaders who prefer the variety and impact of helping multiple companies build better customer relationships.

Ready to drive velocity?

Great — let's get to work.
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