Fractional Chief Customer Officer

You've Outgrown Founder-Led Customer Success.

As healthcare SaaS companies scale, customer retention becomes harder to manage and more expensive to ignore.

I help founders reduce churn, improve net revenue retention, and build customer success systems that support the next stage of growth.

Book a Strategy Call See How I Help Growing Health Tech Companies Scale Retention
The retention challenge

Growth Creates New Retention Problems

Most founders don't realize they have a Customer Success problem until revenue starts leaking.

You may be experiencing:

  • Churn that's becoming harder to explain
  • Inconsistent onboarding experiences
  • Customers adopting slowly or not at all
  • Renewals that feel unpredictable
  • Escalations that still land on your desk
  • A CS team that's busy but struggling to move metrics
  • Limited visibility into customer health and retention risk

These issues rarely solve themselves.

Left unchecked, they become revenue problems.

What I do

Experienced Leadership. Without the Full-Time Cost.

I help healthcare technology companies build the people, processes, and systems required to scale customer retention.

Whether you're building your first formal Customer Success function or strengthening an existing team, I provide experienced leadership without the cost and commitment of a full-time executive.

How I help

Four Ways I Strengthen Customer Retention

Retention & Churn Reduction

Identify revenue risk before customers leave.

  • Churn analysis
  • Retention strategy
  • Customer health frameworks
  • Escalation management
  • Risk intervention planning
Outcome

Better visibility into retention risk and fewer surprise losses.

Customer Success Infrastructure

Build repeatable systems that scale.

  • Customer journey design
  • Segmentation strategy
  • Success plans
  • Playbooks
  • Operational workflows
Outcome

A more predictable customer experience that doesn't depend on heroics.

Leadership & Team Development

Help your team perform like a mature organization.

  • Team coaching
  • Organizational design
  • Hiring support
  • Performance management
  • Executive reporting
Outcome

A stronger team that requires less founder involvement.

Revenue Expansion

Turn Customer Success into a growth engine.

  • Expansion strategy
  • Account planning
  • Renewal management
  • Cross-functional alignment
Outcome

Higher net revenue retention and expansion opportunities.

Ways to work together

Three Engagement Models

Industry expertise

Healthcare Customer Success Is Different

Healthcare organizations buy differently.
Implementation is more complex.
Stakeholder groups are larger.
Regulatory requirements create friction.
Clinical and operational outcomes matter.

Customer Success strategies that work in generic SaaS often fail in healthcare. With experience across healthcare technology organizations, I help teams navigate these realities while building scalable customer retention programs.

Jesse Bender, Fractional Chief Customer Officer
About

Meet Jesse Bender

Fractional Chief Customer Officer

I've spent more than 15 years helping healthcare technology organizations improve customer outcomes, reduce churn, and scale customer-facing teams.

I've led Customer Success organizations through periods of rapid growth, operational transformation, and organizational change.

Today, I work directly with founders and executive teams to strengthen customer retention, build scalable systems, and create the foundation for long-term growth.

Director, Customer Success
TelePharm (acquired by a Fortune 15 healthcare company)
Built CS from scratch. Scaled ARR from $24K to $30M, achieved 135% NRR, and grew team to 11. Led the function through M&A diligence and post-acquisition integration with 100% staff retention.
Director of Product
Outcomes
Hybrid leadership role with both Product and Customer Success reporting in. Owned an $8M P&L, launched a new AI product line generating $1.6M in revenue, and held C-level relationships at Walmart, Walgreens, and other Fortune 500 pharmacy operators.
Fractional Chief Customer Officer
FractionalCS
Engagements with healthcare SaaS companies on retention strategy, CS function build-out, and operating model design. Deep expertise in healthcare technology and regulated industries with complex customer needs.
Is this the right fit?

You May Be Ready for Fractional CCO Leadership If…

✓ Churn has become a board-level concern
✓ You have Customer Success managers but no experienced CS leadership
✓ Renewals feel unpredictable
✓ Customer health scores don't exist or aren't trusted
✓ Expansion revenue is inconsistent
✓ Founders still manage customer escalations
✓ Growth is outpacing operational maturity
✓ You're preparing for fundraising or acquisition
Let's talk

Retention Problems Rarely Fix Themselves

The best time to build scalable Customer Success systems is before churn becomes a growth constraint. Let's discuss what's working, what's not, and where the biggest opportunities exist.