Fractional Head of Customer Success

Elevate customer satisfaction and drive retention with expert leadership. Optimise processes, build loyal relationships and maximise customer lifetime value.

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Customer Success Leadership for Growing Startups

In today's customer-centric business landscape, a robust customer success strategy is essential for sustainable growth. Many startups and growing companies need top-tier customer success leadership to drive retention and expansion, but can't justify the expense of a full-time Head of Customer Success. Our Fractional Head of Customer Success services bridges this gap, offering a solution that combines senior-level expertise with cost-effective flexibility.

Key Responsibilities of Fractional Heads of Customer Success

Our experienced Fractional Heads of Customer Success take on a wide range of critical responsibilities:

Develop and implement customer success strategies
Build and lead high-performing customer success teams
Establish customer health scores and KPIs
Optimise onboarding and engagement processes
Foster key customer relationships
Foster key customer relationships
Implement customer feedback loops and voice of customer programs
Analyse customer data to identify trends and opportunities
Develop retention and expansion strategies
Collaborate with product and sales teams to ensure a customer-centric approach
Drive product adoption and usage

The Power of Strategic Customer Success Leadership

A Fractional Head of Customer Success brings more than just operational expertise; they deliver a comprehensive vision that aligns your customer success efforts with your business objectives. Our seasoned customer success executives offer:

Data-Driven Customer Success Strategy: Leverage advanced analytics and customer insights to craft strategies that deliver measurable results.
Customer Journey Optimisation: Streamline the customer journey from onboarding to expansion.
Team Development and Coaching: Build and mentor high-performing customer success teams.
Technology Integration: Implement and optimise customer success tools and platforms.
Retention and Expansion Planning: Develop strategies to maximise customer lifetime value.

By engaging one of Shepherd's vetted Fractional Heads of Customer Success, you're partnering with a strategic leader who can transform your customer success function into a growth driver.

The Benefits of Engaging a Fractional Head of Customer Success

Cost Effective: Access senior-level customer success leadership without the financial burden of a full-time executive.
Flexible Engagement: Tailor the engagement to your specific needs and scale as your business grows.
Fresh Perspectives: Benefit from diverse experience and innovative customer success approaches.
Immediate Impact: Leverage the Fractional Head of Customer Success's experience to drive results quickly.

Who Can Benefit from Fractional Head of Customer Success Services?

Shepherd's Fractional Head of Customer Success can help address the unique challenges faced by tech startups across various growth stages:

Early-stage

Startups establishing their initial customer success processes and operations
Companies needing guidance on customer onboarding strategies
Founders seeking to build their first customer success team

Growth-stage

Startups looking to scale their customer success efforts
Companies facing challenges in customer retention and expansion
Businesses needing help with customer success automation and process scaling

Expansion-Stage

Tech companies entering new markets or launching new products
Startups requiring assistance with international customer success strategies
Businesses looking to optimise their customer success tech stack for growth

Established

Companies seeking fresh perspectives on their customer success strategies
Businesses facing increased competition and need for customer experience differentiation
Tech firms looking to revitalise their customer success approach or explore new retention strategies

By offering flexible, expert sales leadership, Shepherd's Fractional Head of Customer Success can help tech startups navigate the complex challenges of each growth phase, from initial market validation to sustained expansion and beyond.

Why Shepherd?

We speak startup

Shepherd's curated network of 150+ 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.

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Frequently Asked Questions.

Still have questions?

Get in touch and we’ll respond ASAP.

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How often will the Fractional Head of Customer Success be available?

Availability varies based on your needs, typically 10 to 20 hours per week, adjustable based on project demands.

Can a Fractional Head of Customer Success help with specific customer ops projects?

Yes, our fractional Head of Customer Success can focus on specific initiatives or provide comprehensive sales leadership, including sales team restructuring, new market entry, or sales process optimisation.

What are the typical pricing models for a Fractional CRO?

We offer three flexible pricing structures: daily rate, monthly retainer, and project-based pricing. The fractional leader will work with you to find the most suitable arrangement for your business.

Daily rate: This option is ideal for clients who need intensive, focused work on specific days.
Monthly retainer: Usually between AUD 5,000 to AUD 10,000 per month, this option provides ongoing strategic support and leadership.
Project-based: For specific product initiatives or product launch, your fractional CPO can provide a custom quote based on the scope and duration of the project.

Pricing can be customised based on the scope of work and your specific needs. We're committed to providing value and will work with you to find the most suitable arrangement for your business.

How long does a typical Fractional CRO engagement last?

Engagements can range from 3 months to over a year, depending on your company's needs and goals. Common engagement models include:

Part-time, flexible engagement: Ideal for ongoing strategic support.
Full-time, fixed engagement: Typically for 6 to 9 months, suited for time-sensitive challenges.
Project-based: For specific marketing initiatives or transformations.

Will the Fractional CRO work with our existing sales team?

Absolutely. Our Fractional CROs are experienced in collaborating with and mentoring in-house sales teams, helping to upskill your existing team while providing strategic direction.

Through regular meetings, sales reviews, and ongoing communication, your Fractional CPO will stay in sync with your team.

How do you measure the success of a Fractional CRO engagement?

Success is measured through agreed-upon KPIs and OKRs, which might include metrics like product adoption rates, user satisfaction scores, or time-to-market for new features.

Your fractional CRO will provide you with a Statement of Works at the start of the engagement, which will be reviewed and updated at every milestone and checkpoint.

Can a Fractional CRO help with our product development tools and processes?

Definitely. Our Fractional CROs are well-versed in various product development methodologies and tools, and can help optimise your product development stack and processes.

Do fractional leaders have other jobs?

Yes — most of our fractional leaders work with multiple clients. The breadth and depth of their experience is what makes them a compelling option for a startup wanting to get from A to B quickly.

Many in our network have left the 9-5 grind to intentionally work in the startup ecosystem as an independent consultant, freelance exec, and advisor. Some are also exited founders.

This means they understand the importance of prioritisation and speed-to-value, rather than getting sucked into the bureaucracy and company politicking.

Their ultimate goal is to help startups succeed, and to eventually replace themselves with someone who can take the reins, in-house.

How is Shepherd different to other talent recruitment platforms and agencies?

We're about helping you find the best fractional leader in days, not months.

Shepherd delivers a video-first matchmaking experience, enabling you to find the right match asynchronously.

We vet and meet all of the fractional leaders to ensure we can match you with the best of the best. They are all former Director+ level leaders with track records of helping startups achieve great outcomes from scratch.

No generic freelancers here —just experienced operators with passion for startups, ready to roll up their sleeves, dive deep, and make a real impact.

Shepherd is not suited for task-oriented projects with set deliverables and milestones (you've got Upwork or Expert360 for that).

Can I pause and stop at any time?

Yes — just give us 2 weeks' notice.

What's the catch?

Nope — it's free to get started.

Let's smash goals together.

Ready to drive velocity?

Great — let's get to work.

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